TRICYCLIC COMPOUNDS AND PBK INHIBITORS CONTAINING THE SAME

Abstract
Tricyclic compounds are provided. These compounds are PBK inhibitors, and are useful for the treatment of PBK related diseases, including cancer.
Description
TECHNICAL FIELD

The present invention relates to a compound for inhibiting PBK activity, a method for the preparation thereof, and a pharmaceutical composition containing the compound as an active ingredient.


BACKGROUND ART

Previous studies revealed that PDZ binding kinase (PBK) is a serine/threonine kinase related to the dual specific mitogen-activated protein kinase kinase (MAPKK) family (Abe Y, et al., J Biol. Chem. 275: 21525-21531, 2000, Gaudet S, et al., Proc Natl Acad. Sci. 97: 5167-5172, 2000 and Matsumoto S, et al., Biochem Biophys Res Commun. 325: 997-1004, 2004). PBK was also indicated to be involved in mitosis as shown by its significant role in highly proliferating spermatocytes (Gaudet S, et al., Proc Natl Acad. Sci. 97: 5167-5172, 2000 and Fujibuchi T, et al., Dev Growth Differ. 47:637-44, 2005). In fact, abundant expression of PBK was observed in testis, while almost no PBK expression was detected in other normal organs (Park J H, et al., Cancer Res. 66: 9186-95, 2006). PBK regulates cell cycle progression. In accordance with this, its significant overexpression was detected in clinical breast cancer samples (Park J H, et al., Cancer Res. 66: 9186-95, 2006), Burkitt's lymphoma (Simons-Evelyn M, et al., Blood Cells Mol Dis. 27: 825-829, 2001) and a variety of hematologic malignancies (Nandi A, et al., Blood Cells Mol Dis. 32: 240-5, 2004).


Immunohistochemical analysis of testis revealed the expression of PBK protein around the outer region of seminiferous tubules where repeated mitosis of sperm germ cells followed by meiosis occurs (Fujibuchi T, et al., Dev Growth Differ. 47: 637-44, 2005). Especially, at prophase and metaphase, the subcellular localization of PBK was detected around the condensed chromosome in breast cancer cells (Park J H, et al., Cancer Res. 66: 9186-95, 2006). Moreover the knockdown of PBK expression with gene specific siRNAs caused dysfunction of cytokinesis and subsequently led to apoptosis of the cancer cells (Park J H, et al., Cancer Res. 66: 9186-95, 2006). These indicated the critical function of PBK at mitosis, in testicular and cancer cells.


Taken together, PBK-specific inhibitors can be used as a drug applicable for a broad spectrum of cancers. PBK is an excellent target for cancer therapy for the following reasons: i) almost no expression in normal organs (except for testis); ii) frequent overexpression in clinical cancer samples; iii) a serine/threonine kinase related to the essential function for cell mitosis.


The present inventors have found that a Tricyclic compound can selectively inhibit the activity of PBK.


SUMMARY OF INVENTION

Accordingly, it is an object of the present invention to provide a PBK inhibitor having high inhibitory activity against PBK.


It is another object of the present invention to provide a method for preparing such inhibitor.


It is a further object of the present invention to provide a pharmaceutical composition including the compound, a pharmaceutically acceptable salt, hydrate, solvate, or isomer thereof.


In accordance with one aspect of the present invention, there is provided a compound of formula (I), and a pharmaceutically acceptable salt, hydrate, solvate, or isomer thereof:


A compound represented by general formula I:




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or a pharmaceutically acceptable salt thereof,


wherein R1, R2, R3, and R4 are each independently a group selected from the group consisting of:


hydrogen,


hydroxyl,


halogen,


cyano,


nitro,


amino,


C1-C6 alkyl,


C2-C6 alkenyl,


C2-C6 alkynyl,


C3-C10 cycloalkyl,


C3-C10 cycloalkenyl,


C1-C6 alkoxy,


C6-C10 aryl,


indanyl,


heteroaryl,


3- to 8-membered heterocycloalkyl,


—OSO2CH3,
—OSO2CF3, and
—CONH2,

wherein each of the groups of R1 to R4 is optionally substituted with a substituent selected from the group consisting of substituent A below:


substituent A:

    • hydroxyl;
    • oxo (═O);
    • cyano;
    • halogen;
    • C1-C6 alkyl (wherein the C1-C6 alkyl is optionally substituted with a substituent selected from the group consisting of substituent B below);
    • C3-C10 cycloalkyl [wherein the C3-C10 cycloalkyl is optionally substituted with cyano, or C1-C6 alkyl substituted with —NR31R32 (wherein R31 and R32 each independently represent hydrogen or C1-C6 alkyl)];
    • —NR21R22 [wherein R21 and R22 each independently represent hydrogen, or C1-C6 alkyl (wherein the C1-C6 alkyl is optionally substituted with di(C1-C6 alkyl)amino, C1-C6 alkylsulfonyl (—SO2(C1-C6 alkyl)), or 3- to 8-membered heterocycloalkyl)];
    • C1-C6 alkoxy {wherein the C1-C6 alkoxy is optionally substituted with halogen, 3- to 8-membered heterocycloalkyl (wherein the 3- to 8-membered heterocycloalkyl is optionally substituted with C1-C6 alkyl), or —NR33R34 [wherein R33 and R34 each independently represent hydrogen, C1-C6 alkyl (wherein the C1-C6 alkyl is optionally substituted with C1-C6 alkylsulfonyl or di(C1-C6 alkyl)amino), or C1-C6 alkylsulfonyl]};
    • —SO2NR23R24 {wherein R23 and R24 each independently represent hydrogen, C1-C6 alkyl [wherein the C1-C6 alkyl is optionally substituted with hydroxyl, C1-C6 alkoxy, halogen, C3-C10 cycloalkyl, or —NR35R36 (wherein R35 and R36 each independently represent hydrogen or C1-C6 alkyl)], C3-C10 cycloalkyl (wherein the C3-C10 cycloalkyl is optionally substituted with C1-C6 hydroxyalkyl), or 3- to 8-membered heterocycloalkyl; or R23 and R24 may together form 3- to 8-membered heterocycloalkyl wherein the 3- to 8-membered heterocycloalkyl is optionally substituted with amino};
    • C1-C6 alkylsulfonyl (wherein the C1-C6 alkyl moiety is optionally substituted with hydroxyl);
    • C1-C6 alkylsulfonylamino (—NHSO2(C1-C6 alkyl)) [wherein the C1-C6 alkyl moiety is optionally substituted with —NR37R38 (wherein R37 and R38 each independently represent hydrogen or C1-C6 alkyl)];
    • 3- to 8-membered heterocycloalkyl {wherein the 3- to 8-membered heterocycloalkyl is optionally substituted with —NR39R40 (wherein R39 and R40 each independently represent hydrogen, C1-C6 alkyl, or C1-C6 alkylsulfonyl), C1-C6 alkyl [wherein the C1-C6 alkyl is optionally substituted with —NR41R42 (wherein R41 and R42 each independently represent hydrogen or C1-C6 alkyl)], hydroxyl, or C1-C6 alkylsulfonyl};
    • heteroaryl;
    • —COOR11 (wherein R11 represents hydrogen or C1-C6 alkyl); and
    • —COR12 [wherein R12 represents C1-C6 alkyl, C3-C10 cycloalkyl, cyanomethyl, —NR25R26 {wherein R25 and R26 each independently represent hydrogen, or C1-C6 alkyl [wherein the C1-C6 alkyl is optionally substituted with hydroxyl or —NR43R44 (wherein R43 and R44 each independently represent hydrogen or C1-C6 alkyl)]}, or 3- to 8-membered heterocycloalkyl which is optionally substituted with C1-C6 alkyl],


      substituent B:
    • halogen;
    • hydroxyl;
    • cyano;
    • 3- to 8-membered heterocycloalkyl (wherein the 3- to 8-membered heterocycloalkyl is optionally substituted with C1-C6 alkyl, hydroxyl, amino, C1-C6 aminoalkyl, or C1-C6 alkyl substituted with C2-C7 alkyloxycarbonylamino);
    • —NR51R52 {wherein R51 and R52 each independently represent hydrogen, C1-C6 alkyl [wherein the C1-C6 alkyl is optionally substituted with C1-C6 alkylsulfonyl, or 3- to 8-membered heterocycloalkyl optionally substituted with —COOR53 (wherein R53 represents hydrogen or C1-C6 alkyl)], 3- to 8-membered heterocycloalkyl, C1-C6 alkylsulfonyl, C3-C10 cycloalkyl, —COR55 (wherein R55 represents C1-C6 alkyl), —COOR56 (wherein R56 represents C1-C6 alkyl), or —CONR57R58 (wherein R57 and R58 each independently represent hydrogen or C1-C6 alkyl)}; and
    • —COOR54 (wherein R54 represents hydrogen or C1-C6 alkyl)];


      wherein R5 is hydrogen or C1-C6 alkyl; and


      wherein




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is a structure selected from the group consisting of

    • (i) —S—CR7═CR6—,
    • (ii) —CH2—CH2—CH2—,
    • (iii) —NH—CH═CCH3—, and
    • (iv) —N═CH—S—,


      wherein R6 is
    • hydrogen,
    • hydroxyl,
    • C1-C6 alkyl,
    • C6-C10 aryl (wherein the C6-C10 aryl is optionally substituted with hydroxyl), or 3- to 8-membered heterocycloalkyl [wherein the 3- to 8-membered heterocycloalkyl is optionally substituted with —NR61R62 (wherein R61 and R62 each independently represent hydrogen or C1-C6 alkyl)], and


      wherein R7 is
    • hydrogen,
    • C1-C6 alkyl (wherein the C1-C6 alkyl is optionally substituted with hydroxyl, —NR71R72 [wherein R71 and R72 each independently represent hydrogen, C1-C6 alkyl (wherein the C1-C6 alkyl is optionally substituted with dimethylamino), C3-C10 cycloalkyl (wherein the C3-C10 cycloalkyl is optionally substituted with amino), or 3- to 8-membered heterocycloalkyl], or 3- to 8-membered heterocycloalkyl (wherein the 3- to 8-membered heterocycloalkyl is optionally substituted with C1-C6 aminoalkyl)),
    • C6-C10 aryl (wherein the C6-C10 aryl is optionally substituted with hydroxyl), or
    • —COR73 {wherein R73 represents 3- to 8-membered heterocycloalkyl (wherein the 3- to 8-membered heterocycloalkyl is optionally substituted with amino), or —NR74R75 [wherein R74 and R75 each independently represent hydrogen, 3- to 8-membered heterocycloalkyl, or C3-C10 cycloalkyl (wherein the C3-C10 cycloalkyl is optionally substituted with amino)]}.


It must be noted that as used in the specification and in the appended claims, the singular forms “a”, “an”, and “the” include plural reference unless the context clearly dictates otherwise. Thus, for example, reference to “a group” is a reference to one or more groups.







DESCRIPTION OF EMBODIMENTS

In this invention, “alkyl” group refers to a straight chain or a branched chain hydrocarbon group which does not contain any hetero atoms or unsaturated carbon-carbon bonds. “C1-C6 alkyl” refers to an alkyl group which has 1-6 carbon atom(s). “C1-C4 alkyl” refers to an alkyl group which has 1-4 carbon atom(s).


Examples of “C1-C6 alkyl” include, but are not limited to, methyl, ethyl, 1-propyl, 2-propyl, 2-methyl-1-propyl, 2-methyl-2-propyl(tert-butyl(1,1-dimethyl-ethyl), 1-butyl, 2-butyl, 1-pentyl, 2-pentyl, 3-pentyl, 2-methyl-1-butyl, 3-methyl-1-butyl, 2-methyl-2-butyl, 3-methyl-2-butyl, 2,2-dimethyl-1-propyl, 1-hexyl, 2-hexyl, 3-hexyl, 2-methyl-1-pentyl, 3-methyl-1-pentyl, 4-methyl-1-pentyl, 2-methyl-2-pentyl, 3-methyl-2-pentyl, 4-methyl-2-pentyl, 2-methyl-3-pentyl, 3-methyl-3-pentyl, 2,3-dimethyl-1-butyl, 3,3-dimethyl-1-butyl, 2,2-dimethyl-1-butyl, 2-ethyl-1-butyl, 3,3-dimethyl-2-butyl, and 2,3-dimethyl-2-butyl.


In this invention, “alkenyl” group refers to a straight chain or a branched chain hydrocarbon group which contains one or more than one unsaturated carbon-carbon bond(s) and does not contain any hetero atoms. “C2-C6 alkenyl” refers to an alkenyl group which has 2-6 carbon atoms.


Examples of “C2-C6 alkenyl” include, but are not limited to, vinyl(ethenyl), 1-propenyl, 2-propenyl, 3-propenyl, 2-methyl-prop-1-en-1-yl(2-methyl-1-propenyl), 2-methyl-prop-1-en-3-yl(2-methyl-2-propenyl), but-1-en-1-yl, but-1-en-2-yl, but-1-en-3-yl, but-2-en-1-yl, but-2-en-2-yl, pent-1-en-1-yl, pent-1-en-2-yl, pent-1-en-3-yl, pent-1-en-4-yl, pent-1-en-5-yl, pent-2-en-1-yl, pent-2-en-2-yl, pent-2-en-3-yl(1-ethyl-1-propenyl), pent-2-en-4-yl, pent-2-en-5-yl, 2-methyl-but-1-en-1-yl, 2-methyl-but-1-en-2-yl, 2-methyl-but-1-en-3-yl, 2-methyl-but-1-en-4-yl, 2-methyl-but-2-en-1-yl, 2-methyl-but-2-en-3-yl, 2-methyl-but-2-en-4-yl, 3-methyl-but-1-en-1-yl, 3-methyl-but-1-en-2-yl, 3-methyl-but-1-en-3-yl, 3-methyl-but-1-en-4-yl, 2,2-dimethyl-prop-1-en-1-yl, 2,2-dimethyl-prop-1-en-2-yl, hex-1-en-1-yl, hex-1-en-2-yl, hex-1-en-3-yl, hex-1-en-4-yl, hex-1-en-5-yl, hex-1-en-6-yl, hex-2-en-1-yl, hex-2-en-2-yl, hex-2-en-3-yl, hex-2-en-4-yl, hex-2-en-5-yl, hex-2-en-6-yl, hex-3-en-1-yl, hex-3-en-2-yl, hex-3-en-3-yl, 2-methyl-pent-1-en-1-yl, 2-methyl-pent-1-en-3-yl, 2-methyl-pent-1-en-4-yl, 2-methyl-pent-1-en-5-yl, 2-methyl-pent-2-en-1-yl, 2-methyl-pent-2-en-3-yl, 2-methyl-pent-2-en-4-yl, 2-methyl-pent-2-en-5-yl, 3-methyl-pent-1-en-1-yl, 3-methyl-pent-1-en-2-yl, 3-methyl-pent-1-en-3-yl, 3-methyl-pent-1-en-4-yl, 3-methyl-pent-1-en-5-yl, 3-methyl-pent-2-en-1-yl, 3-methyl-pent-2-en-2-yl, 3-methyl-pent-2-en-4-yl, 3-methyl-pent-2-en-5-yl, 4-methyl-pent-1-en-1-yl, 4-methyl-pent-1-en-2-yl, 4-methyl-pent-1-en-3-yl, 4-methyl-pent-1-en-4-yl, 4-methyl-pent-1-en-5-yl, 4-methyl-pent-2-en-1-yl, 4-methyl-pent-2-en-2-yl, 4-methyl-pent-2-en-3-yl, 4-methyl-pent-2-en-4-yl, 4-methyl-pent-2-en-5-yl, 2,3-dimethyl-but-1-en-1-yl, 2,3-dimethyl-but-1-en-3-yl, 2,3-dimethyl-but-1-en-4-yl, 2,3-dimethyl-but-2-en-1-yl, 3,3-dimethyl-but-1-en-1-yl, 3,3-dimethyl-but-1-en-2-yl, 3,3-dimethyl-but-1-en-4-yl, 2-ethyl-but-1-en-1-yl, 2-ethyl-but-1-en-3-yl, 2-ethyl-but-1-en-4-yl, 3-ethyl-but-1-en-1-yl, 3-ethyl-but-1-en-2-yl, 3-ethyl-but-1-en-3-yl, 3-ethyl-but-1-en-4-yl, 2-ethyl-but-2-en-1-yl, 2-ethyl-but-2-en-3-yl and 2-ethyl-but-2-en-4-yl.


In this invention, “alkynyl” group refers to a straight chain or a branched chain hydrocarbon group which contains at least one triple carbon-carbon bond and does not contain any hetero atoms. “C2-C6 alkynyl” refers to an alkynyl group which has 2-6 carbon atoms.


Examples of “C2-C6 alkynyl” include, but are not limited to, ethinyl, 1-propinyl, 2-propinyl, 3-propinyl, 2-methyl-prop-1-in-1-yl, 2-methyl-prop-1-in-3-yl, but-1-in-1-yl, but-1-in-2-yl, but-1-in-3-yl, but-2-in-1-yl, but-2-in-2-yl, pent-1-in-1-yl, pent-1-in-2-yl, pent-1-in-3-yl, pent-1-in-4-yl, pent-1-in-5-yl, pent-2-in-1-yl, pent-2-in-2-yl, pent-2-in-3-yl, pent-2-in-4-yl, pent-2-in-5-yl, 2-methyl-but-1-in-1-yl, 2-methyl-but-1-in-2-yl, 2-methyl-but-1-in-3-yl, 2-methyl-but-1-in-4-yl, 2-methyl-but-2-in-1-yl, 2-methyl-but-2-in-3-yl, 2-methyl-but-2-in-4-yl, 3-methyl-but-1-in-1-yl, 3-methyl-but-1-in-2-yl, 3-methyl-but-1-in-3-yl, 3-methyl-but-1-in-4-yl, 2,2-dimethyl-prop-1-in-1-yl, 2,2-dimethyl-prop-1-in-2-yl, hex-1-in-1-yl, hex-1-in-2-yl, hex-1-in-3-yl, hex-1-in-4-yl, hex-1-in-5-yl, hex-1-in-6-yl, hex-2-in-1-yl, hex-2-in-2-yl, hex-2-in-3-yl, hex-2-in-4-yl, hex-2-in-5-yl, hex-2-in-6-yl, hex-3-in-1-yl, hex-3-in-2-yl, hex-3-in-3-yl, 2-methyl-pent-1-in-1-yl, 2-methyl-pent-1-in-3-yl, 2-methyl-pent-1-in-4-yl, 2-methyl-pent-1-in-5-yl, 2-methyl-pent-2-in-1-yl, 2-methyl-pent-2-in-3-yl, 2-methyl-pent-2-in-4-yl, 2-methyl-pent-2-in-5-yl, 3-methyl-pent-1-in-1-yl, 3-methyl-pent-1-in-2-yl, 3-methyl-pent-1-in-3-yl, 3-methyl-pent-1-in-4-yl, 3-methyl-pent-1-in-5-yl, 3-methyl-pent-2-in-1-yl, 3-methyl-pent-2-in-2-yl, 3-methyl-pent-2-in-4-yl, 3-methyl-pent-2-in-5-yl, 4-methyl-pent-1-in-1-yl, 4-methyl-pent-1-in-2-yl, 4-methyl-pent-1-in-3-yl, 4-methyl-pent-1-in-4-yl, 4-methyl-pent-1-in-5-yl, 4-methyl-pent-2-in-1-yl, 4-methyl-pent-2-in-2-yl, 4-methyl-pent-2-in-3-yl, 4-methyl-pent-2-in-4-yl, 4-methyl-pent-2-in-5-yl, 2,3-dimethyl-but-1-in-1-yl, 2,3-dimethyl-but-1-in-3-yl, 2,3-dimethyl-but-1-in-4-yl, 2,3-dimethyl-but-2-in-1-yl, 3,3-dimethyl-but-1-in-1-yl, 3,3-dimethyl-but-1-in-2-yl, 3,3-dimethyl-but-1-in-4-yl, 2-ethyl-but-1-in-1-yl, 2-ethyl-but-1-in-3-yl, 2-ethyl-but-1-in-4-yl, 3-ethyl-but-1-in-1-yl, 3-ethyl-but-1-in-2-yl, 3-ethyl-but-1-in-3-yl, 3-ethyl-but-1-in-4-yl, 2-ethyl-but-2-in-1-yl, 2-ethyl-but-2-in-3-yl and 2-ethyl-but-2-in-4-yl.


In the present invention, “alkoxy” group refers to a group represented by —OR, wherein R is alkyl.


“C1-C6 alkoxy” group refers to an alkoxy group which has 1-6 carbon atom(s). “C1-C4 alkoxy” refers to an alkoxy group which has 1-4 carbon atom(s).


Examples of “C1-C6 alkoxy” include, but are not limited to, methoxy, ethoxy, 1-propyloxy, 2-propyloxy, 2-methyl-1-propyloxy, 2-methyl-2-propyloxy, and 1-butyloxy, and 2-butyloxy.


In the present invention, “cycloalkyl” group refers to a saturated carbon ring system. “C3-C10 cycloalkyl” group refers to 3-10 membered cycloalkyl.


Examples of “C3-C10 cycloalkyl” include, but are not limited to, cyclopropyl, cyclobutyl, cyclopentyl, cyclohexyl, cycloheptanyl, cyclooctanyl, and adamantyl. For example, 3-8 membered cycloalkyl is also included in “C3-C10 cycloalkyl”.


In the present invention, “C3-C10cycloalkenyl” group refers to a cyclic unsaturated aliphatic hydrocarbon group of 3 to 10 carbon atoms with at least one double bond (two adjacent SP2 carbon atoms).


Specific examples of “C3-C10cycloalkenyl” include cyclopropenyl, cyclobutenyl, cyclopentenyl, cyclohexenyl, cycloheptenyl, and cyclooctenyl.


In the present invention, “C6-C10aryl” refers to an aromatic cyclic hydrocarbon group of 6 to 10 carbon atoms.


Specific examples of “C6-C10aryl” include phenyl, 1-naphthyl, and 2-naphthyl.


In the present invention, “halogen” refers to a fluorine atom, a chlorine atom, a bromine atom, or an iodine atom.


As used herein, “hetero atom” refers to a sulfur atom, an oxygen atom, or a nitrogen atom.


In this invention, “amino” refers to a group represented by —NH2 whose hydrogens may each be optionally substituted by a substituent.


In the present invention, “C1-C6 alkylamino” refers to an amino group bound to the C1-C6 alkyl.


Examples of “C1-C6 alkylamino” include, but are not limited to, methylamino, ethylamino, propylamino, isopropylamino, n-butylamino, s-butylamino, t-butylamino, and 2-ethylbutylamino.


In the present invention, “di(C1-C6alkyl)amino” refers to an amino group bound to two “C1-C6alkyls” defined above.


Specific examples of “di(C1-C6alkyl)amino” include dimethylamino, diethylamino, dipropylamino, diisopropylamino, di-n-butylamino, di-s-butylamino, di-t-butylamino, and di-2-ethylbutylamino.


In the present invention, “C2-C7alkyloxycarbonylamino” refers to a group represented by (C1-C6alkyl)-O—C═O—NH—, or a group in which the “C1-C6alkyl” defined above is bound to —OCONH—.


In the present invention, “C1-C6aminoalkyl” refers to a group in which an amino group is bound to the “C1-C6alkyl” defined above.


In the present invention, “C1-C6hydroxyalkyl” refers to a group in which one or more hydroxy groups are bound to the “C1-C6alkyl” defined above.


In this invention, “sulfonyl” is a group represented by —SO2—.


In this invention, “C1-C6 alkylsulfonyl” refers to R—SO2— wherein R is the C1-C6 alkyl. “C1-C4 alkylsulfonyl” refers to R—SO2— wherein R is C1-C4 alkyl.


Examples of “C1-C6 alkylsulfonyl” include, but are not limited to, methylsulfonyl, ethylsulfonyl, propylsulfonyl, isopropylsulfonyl, n-butylsulfonyl, s-butylsulfonyl, t-butylsulfonyl, and 2-ethylbutylsulfonyl.


In this invention, “C6-C10 arylsulfonyl” refers to R—SO2— wherein R is the C6-C10 aryl.


Examples of “C6-C10 arylsulfonyl” include, but are not limited to, phenylsulfonyl.


In the present invention, “C1-C6alkylsulfonylamino” refers to R—SO2—NH— wherein R is “C1-C6 alkyl”. “C1-C4 alkylsulfonylamino” refers to R—SO2—NH— wherein R is R—SO2—NH— wherein R is “C1-C4 alkyl”.


Examples of “C1-C6 alkylsulfonylamino” include, but are not limited to, methylsulfonylamino, ethylsulfonylamino, propylsulfonylamino, isopropylsulfonylamino, n-butylsulfonylamino, s-butylsulfonylamino, t-butylsulfonylamino, and 2-ethylbutylsulfonylamino.


In this invention, “sulfinyl” is a group represented by —SO—.


In this invention, “C1-C6 alkylsulfinyl” refers to R—SO— wherein R is the C1-C6 alkyl. “C1-C4 alkylsulfinyl” refers to R—SO— wherein R is C1-C4 alkyl.


Examples of “C1-C6 alkylsulfinyl” include, but are not limited to, methylsulfinyl, ethylsulfinyl, propylsulfinyl, isopropylsulfinyl, n-butylsulfinyl, s-butylsulfinyl, t-butylsulfinyl, and 2-ethylbutylsulfinyl.


In the present invention, “heteroaryl” refers to a monocyclic or fused aromatic heterocyclic group that includes at least one hetero atom selected from O, S, and N. When the aromatic heterocyclic group is a fused ring, those including a partially hydrogenated ring are also included in “heteroaryl”.


Examples of such heteroaryls include pyrazolyl, thiazolyl, isothiazolyl, thiadiazolyl, imidazolyl, furyl, thienyl, oxazolyl, isooxazolyl, pyrrolyl, imidazolyl, (1,2,3)- and (1,2,4)-triazolyl, tetrazolyl, pyranyl, pyridyl, pyrimidinyl, pyrazinyl, pyridazinyl, quinolyl, isoquinolyl, tetrahydroisoquinolyl, benzofuranyl, isobenzofuranyl, indolynyl, indolyl, isoindolyl, indazolyl, benzoimidazolyl, benzotriazolyl, benzooxazolyl, benzothiazolyl, benzo[b]thiophenyl, (1,2)- and (1,3)-benzooxathiol, chromenyl, 2-oxochromenyl, benzothiadiazolyl, quinolizinyl, phthalazinyl, naphthyridinyl, quinoxalinyl, quinazolinyl, cinnolinyl, carbazolyl, tetrahydroisoquinolyl, tetrazolyl, [1,2,4]triazo[1.5-a]pyridyl, 1H-pyrrolo[2,3-b]pyridyl, and 2,3-dihydrobenzooxazolyl.


Preferable examples include pyrazolyl, furyl, thienyl, pyridyl, pyrimidinyl, tetrahydroisoquinolyl, indolynyl, indazolyl, benzoimidazolyl, benzooxazolyl, tetrahydroisoquinolyl, tetrazolyl, [1,2,4]triazo[1.5-a]pyridyl, 1H-pyrrolo[2,3-b]pyridyl, and 2,3-dihydrobenzooxazolyl.


In the present invention, “3- to 8-membered heterocycloalkyl” refers to a non-aromatic monovalent 3- to 8-membered ring that includes 1 to 3 hetero atoms in the atoms forming the ring, and that may have a double bond within the ring.


Examples of “3- to 8-membered heterocycloalkyl” include aziridinyl, azetidinyl, pyrrolidinyl, imidazolidinyl, piperidyl, piperazinyl, azepanyl, morpholinyl, oxetanyl, and 1,2,5,6-tetrahydropyridyl.


A salt is defined as the product formed from the neutralisation reaction of acids and bases. Salts are ionic compounds composed of cations (positively charged ions) and anions (negative ions) so that the product is electrically neutral. These component ions can be inorganic as well as organic.


Hydrate is a term used in inorganic chemistry and organic chemistry to indicate that a substance contains water. Solvate refers to a molecule in a solution complexed by solvent molecules. Isomers are compounds with the same molecular formula but different structural formulae. More specifically, isomer includes geometric isomer, optical isomer, stereoisomer, tautomer of the compound, and mixtures thereof.


In a preferred embodiments, the present invention provides [1] a compound represented by formula (I) or a pharmaceutically acceptable salt thereof:




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    • or a pharmaceutically acceptable salt thereof,

    • wherein R1, R2, R3, and R4 are each independently a group selected from the group consisting of:

    • hydrogen,

    • hydroxyl,

    • halogen,

    • cyano,

    • nitro,

    • amino,

    • C1-C6 alkyl,

    • C2-C6 alkenyl,

    • C2-C6 alkynyl,

    • C3-C10 cycloalkyl,

    • C3-C10 cycloalkenyl,

    • C1-C6 alkoxy,

    • C6-C10 aryl,

    • indanyl,

    • heteroaryl,

    • 3- to 8-membered heterocycloalkyl,

    • —OSO2CH3,

    • —OSO2CF3,

    • —CONH2,

    • —OCONR101R102, wherein R101 and R102 each independently is hydrogen, C1-C6 alkyl, or R101 and R102 taken together form morpholinyl,

    • —OCOR103, wherein R103 represents C1-C6 alkyl, and

    • —OCOOR104, wherein R104 represents C1-C6 alkyl,

    • wherein R1, R2, R3, and R4 are optionally substituted with a substituent independently selected from the group consisting of substituent A;

    • wherein substituent A is independently selected from the group consisting of:
      • hydroxyl;
      • oxo (═O);
      • cyano;
      • halogen;
      • C1-C6 alkyl optionally substituted with substituent B;
      • C3-C10 cycloalkyl optionally substituted with cyano or C1-C6 alkyl substituted with —NR31R32, wherein R31 and R32 each independently represent hydrogen or C1-C6 alkyl;
      • —NR21R22, wherein R21 and R22 each independently represent hydrogen; C1-C6 alkyl optionally substituted with hydroxyl, amino, di(C1-C6 alkyl)amino, —SO2(C1-C6 alkyl), 3- to 8-membered heterocycloalkyl, or cyano; or a 3- to 8-membered heterocycloalkyl optionally substituted with —COOR105 wherein R105 represents C1-C6 alkyl;
      • C1-C6 alkoxy optionally substituted with halogen, 3- to 8-membered heterocycloalkyl optionally substituted with C1-C6 alkyl, or —NR33R34 wherein R33 and R34 each independently represent hydrogen, C1-C6 alkylsulfonyl, or C1-C6 alkyl optionally substituted with C1-C6 alkylsulfonyl or di(C1-C6 alkyl)amino;
      • —SO2NR23R24, wherein R23 and R24 each independently represent hydrogen; C1-C6 alkyl optionally substituted with hydroxyl, C1-C6 alkoxy, halogen, C3-C10 cycloalkyl, heteroaryl, or —NR35R36 wherein R35 and R36 each independently represent hydrogen or C1-C6 alkyl; C3-C10 cycloalkyl optionally substituted with C1-C6 hydroxyalkyl; 3- to 8-membered heterocycloalkyl; or R23 and R24 taken together form 3- to 8-membered heterocycloalkyl optionally substituted with amino or halogen;
      • C1-C6 alkylsulfonyl optionally substituted with hydroxyl;
      • —NHSO2(C1-C6 alkyl), wherein the carbon atoms are optionally substituted with —NR37R38 wherein R37 and R38 each independently represent hydrogen or C1-C6 alkyl;
      • 3- to 8-membered heterocycloalkyl optionally substituted with —NR39R40, wherein R39 and R40 each independently represent hydrogen, C1-C6 alkyl, or C1-C6 alkylsulfonyl; C1-C6 alkyl optionally substituted with —NR41R42, wherein R41 and R42 each independently represent hydrogen or C1-C6 alkyl; hydroxyl; or C1-C6 alkylsulfonyl;
      • aryl optionally substituted with C1-C6 alkyl optionally substituted with cyano or amino;
      • heteroaryl;
      • —COOR11, wherein R11 represents hydrogen or C1-C6 alkyl; and
      • —COR12, wherein R12 represents C1-C6 alkyl; C3-C10 cycloalkyl; cyanomethyl; aminomethyl; —NR25R26 wherein R25 and R26 each independently represent hydrogen or C1-C6 alkyl optionally substituted with hydroxyl or —NR43R44, wherein R43 and R44 each independently represent hydrogen or C1-C6 alkyl; or 3- to 8-membered heterocycloalkyl optionally substituted with C1-C6 alkyl;

    • wherein substituent B is independently selected from the group consisting of:
      • halogen;
      • hydroxyl;
      • C1-C6 alkoxy;
      • cyano;
      • cycloalkyl;
      • C6-C10 aryl optionally substituted with cyano;
      • heteroaryl;
      • 3- to 8-membered heterocycloalkyl optionally substituted with C1-C6 alkyl, hydroxyl, amino, C1-C6 aminoalkyl, or C1-C6 alkyl substituted with C2-C7 alkyloxycarbonylamino;
      • —NR51R52, wherein R51 and R52 each independently represent hydrogen; C1-C6 alkyl optionally substituted with C1-C6 alkylsulfonyl or 3- to 8-membered heterocycloalkyl optionally substituted with —COOR56 wherein R53 represents hydrogen or C1-C6 alkyl; 3- to 8-membered heterocycloalkyl; C1-C6 alkylsulfonyl; C3-C10 cycloalkyl; —COR55 wherein R55 represents C1-C6 alkyl; —COOR56 wherein R56 represents C1-C6 alkyl; or —CONR57R58 wherein R57 and R58 each independently represent hydrogen or C1-C6 alkyl;
      • —COOR54, wherein R54 represents hydrogen or C1-C6 alkyl;
      • —CONH2;
      • —SO2NR106R107, wherein R106 and R107 each independently represent hydrogen, C1-C6 alkyl, or C3-C10 cycloalkyl;
      • C1-C6 alkylsulfinyl; and
      • C1-C6 alkylsulfonyl;

    • wherein R5 is hydrogen or C1-C6 alkyl; and

    • wherein







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    •  is a structure selected from the group consisting of
      • (i) —S—CR7═CR6—,
      • (ii) —CH2—CH2—CH2—,
      • (iii) —NR108—CH═CR109—, wherein R108 represents hydrogen, or C1-C6 alkyl optionally substituted with hydroxyl, and R109 represents hydrogen, CH3, or phenyl substituted with C1-C6 aminoalkyl, and
      • (iv) —N═CH—S—,

    • wherein R6 is selected from the group consisting of:
      • hydrogen,
      • hydroxyl,
      • C1-C6 alkyl,
      • C6-C10 aryl optionally substituted with hydroxyl, and
      • 3- to 8-membered heterocycloalkyl optionally substituted with —NR61R62, wherein R61 and R62 each independently represent hydrogen or C1-C6 alkyl;

    • wherein R7 is selected from the group consisting of:
      • hydrogen;
      • halogen;
      • C1-C6 alkyl optionally substituted with hydroxyl, —NR71R72 wherein R71 and R72 each independently represent hydrogen; C1-C6 alkyl optionally substituted with dimethylamino; C3-C10 cycloalkyl optionally substituted with amino or 3- to 8-membered heterocycloalkyl; or 3- to 8-membered heterocycloalkyl optionally substituted with C1-C6 aminoalkyl;
      • C6-C10 aryl optionally substituted with hydroxyl;
      • C6-C10 arylsulfonyl; and
      • —COR73, wherein R73 represents 3- to 8-membered heterocycloalkyl optionally substituted with amino; or —NR74R75 wherein R74 and R75 each independently represent hydrogen, 3- to 8-membered heterocycloalkyl, or C3-C10 cycloalkyl optionally substituted with amino.



  • [2] The compound of [1], or a pharmaceutically acceptable salt thereof, wherein





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  •  is —S—CR7═CR6—.

  • [3] The compound of [2], or a pharmaceutically acceptable salt thereof, wherein R1 is hydrogen, cyano, C1-C6 alkyl optionally substituted with hydroxyl or halogen, C3-C10 cycloalkyl, C2-C6 alkenyl, C2-C6 alkynyl, or halogen.

  • [4] The compound of [2], or a pharmaceutically acceptable salt thereof, wherein R2 is hydrogen, hydroxyl, halogen, C1-C6 alkoxy, or C6-C10 aryl optionally substituted with hydroxyl.

  • [5] The compound of [2] or a pharmaceutically acceptable salt, wherein R2 is hydrogen, hydroxyl, halogen, C1-C6 alkoxy, or dihydroxyphenyl.

  • [6] The compound of [2], or a pharmaceutically acceptable salt thereof, wherein R3 is selected from the group consisting of: hydrogen; hydroxyl; C1-C6 alkyl optionally substituted with hydroxyl, halogen, or hydroxyethylamino; halogen; C1-C6 alkoxy optionally substituted with dimethylamino or morpholinyl; C1-C6 alkylphenyl, wherein the aliphatic carbons are optionally substituted with —NR51R52; cyano; nitro; amino; 3- to 8-membered heterocycloalkyl optionally substituted with amino; heteroaryl; —OSO2CH3; —OSO2CF3; —OCOR103, wherein R103 represents C1-C6 alkyl; —OCOOR104 wherein R104 represents C1-C6 alkyl; —OCONR101R1022 wherein R101 and R102 each independently represent hydrogen or C1-C6 alkyl, or R101 and R102 taken together form morpholinyl; and —CONH2.

  • [7] The compound of [6], or a pharmaceutically acceptable salt thereof, wherein when R3 is a 3- to 8-membered heterocycloalkyl, the 3- to 8-membered heterocycloalkyl is selected from the group consisting of piperidyl, pyrrolidinyl, morpholinyl, or piperazinyl and optionally substituted with amino; and when R3 is heteroaryl, the heteroaryl is pyridyl.

  • [8]. The compound of [2], or a pharmaceutically acceptable salt thereof, wherein R4 is selected from the group consisting of hydrogen, hydroxyl, halogen, amino, C1-C6 alkyl, C2-C6 alkenyl, C3-C10 cycloalkyl, C3-C10 cycloalkenyl, C1-C6 alkoxy, C6-C10 aryl, indanyl, heteroaryl, and 3- to 8-membered heterocycloalkyl, and R4 is optionally substituted with substituent A.

  • [9] The compound of [8], or a pharmaceutically acceptable salt thereof, wherein when R4 is heteroaryl, the heteroaryl is selected from the group consisting of pyridyl, 1H-indazolyl, 1H-tetrazolyl, [1,2,4]triazolo[1,5-a]pyridyl, benzoimidazolyl, 2,3-dihydrobenzooxazolyl, pyrazolyl, pyrrolo[2,3-b]pyridyl, pyrimidinyl, indolinyl, furyl, thienyl, and tetrahydroisoquinolyl); and wherein the 3- to 8-membered heterocycloalkyl is selected from the group consisting of aziridinyl, azetidinyl, pyrrolidinyl, imidazolidinyl, piperidyl, piperazinyl, azepanyl, morpholinyl, and 1,2,3,6-tetrahydropyridyl; wherein each of the groups of R4 is optionally substituted with substituent A-1;
    • wherein substituent A-1 is selected from the group consisting of:
    • hydroxyl;
    • oxo;
    • cyano;
    • halogen;
    • C1-C6 alkyl optionally substituted with a substituent selected from the group consisting of substituent B-1;
    • C3-C10 cycloalkyl optionally substituted with cyano, or C1-C6 alkyl substituted with —NR31R32;
    • —NR21AR22A, wherein R21A and R22A each independently represent hydrogen; C1-C6 alkyl optionally substituted with amino, di(C1-C6 alkyl)amino, —SO2 (C1-C6 alkyl), piperidyl, or cyano; or piperidyl optionally substituted with —COOR105;
    • C1-C6 alkoxy optionally substituted with halogen; a 3- to 8-membered heterocycloalkyl selected from piperidyl and piperazinyl, either of which is optionally substituted with C1-C6 alkyl; or —NR33R34;
    • —SO2NR23AR24A, wherein R23A and R24A each independently represent hydrogen, C1-C6 alkyl optionally substituted with hydroxyl, C1-C6 alkoxy, halogen, C3-C10 cycloalkyl, pyrazolyl, imidazolyl, or —NR35R36; C3-C10 cycloalkyl optionally substituted with C1-C6 hydroxyalkyl; azetidinyl; pyrrolidinyl, or R23A and R24A taken together form pyrrolidinyl optionally substituted with amino or halogen;
    • C1-C6 alkylsulfonyl optionally substituted with hydroxyl;
    • —NHSO2(C1-C6 alkyl), wherein the carbon atoms are optionally substituted with NR37R38;
    • 3- to 8-membered heterocycloalkyl selected from the group consisting of azetidinyl, pyrrolidinyl, piperidyl, piperazinyl, and tetrahydropyridyl any of which is optionally substituted with —NR39R40; C1-C6 alkyl optionally substituted with —NR41R42; hydroxyl; or C1-C6 alkylsulfonyl;
    • 1H-tetrazolyl;
    • aryl optionally substituted with C1-C6 alkyl, wherein C1-C6 is the aliphatic carbons are optionally substituted with cyano or amino;
    • —COOR11; and
    • —COR12A, wherein R12A represents piperazinyl optionally substituted with C1-C6 alkyl; C3-C10 cycloalkyl; cyanomethyl; aminomethyl; —NR25R26 wherein R25 and R26 each independently represent hydrogen or C1-C6 alkyl optionally substituted with hydroxyl or —NR43R44; or C1-C6 alkylsulfonyl;
    • wherein substituent B-1 is selected from the group consisting of:
    • halogen;
    • hydroxyl;
    • C1-C6 alkoxy;
    • cyano;
    • cycloalkyl;
    • phenyl optionally substituted with cyano;
    • heteroaryl selected from the group consisting of imidazolyl, pyrazolyl, and thiazolyl;
    • 3- to 8-membered heterocycloalkyl selected from the group consisting of pyrrolidinyl, piperidyl, piperazinyl, morpholinyl, and oxetanyl any of which are optionally substituted with hydroxyl, amino, C1-C6 aminoalkyl, or C1-C6 alkyl optionally substituted with C2-C7 alkyloxycarbonylamino;
    • —NR51AR52A, wherein R51A and R52A each independently represent hydrogen; C1-C6 alkyl optionally substituted with C1-C6 alkylsulfonyl or piperidyl optionally substituted with —COOR53; piperidyl; C1-C6 alkylsulfonyl; C3-C10 cycloalkyl; —COR55, —COOR56, or —CONR57R58;
    • —COOR54;
    • —CONH2;
    • —SO2NR106R107;
    • C1-C6 alkylsulfinyl; and
    • C1-C6 alkylysulfonyl.

  • [10] The compound of [9], or a pharmaceutically acceptable salt thereof, wherein R4 is a group selected from group (p):
    • wherein group (p) is independently selected from the group consisting of:
      • hydrogen,
      • hydroxyl,
      • halogen,
      • amino optionally substituted with a substituent selected from the group consisting of substituent (g),
      • C1-C6 alkyl optionally substituted with a substituent selected from the group consisting of substituent (a),
      • C2-C6 alkenyl optionally substituted with a substituent selected from the group consisting of substituent (b),
      • C3-C10 cycloalkyl,
      • C3-C10 cycloalkenyl,
      • C1-C6 alkoxy,
      • C6-C10 aryl optionally substituted with a substituent selected from the group consisting of substituent (c),
      • indanyl optionally substituted with a substituent selected from the group consisting of substituent (d),
      • heteroaryl selected from the group consisting of pyridyl, 1H-indazolyl, 1H-tetrazolyl, [1,2,4]triazolo[1,5-a]pyridyl, benzoimidazolyl, 2,3-dihydrobenzooxazolyl, pyrazolyl, pyrrolo[2,3-b]pyridyl, pyrimidinyl, indolinyl, furyl, thienyl, and tetrahydroisoquinolyl any of which is optionally substituted with a substituent selected from the group consisting of substituent (e); and
      • 3- to 8-membered heterocycloalkyl selected from the group consisting of pyrrolidinyl, piperidyl, piperazinyl, morpholinyl, and 1,2,3,6-tetrahydropyridyl any of which is optionally substituted with a substituent selected from the group consisting of substituent (f);
      • wherein substituent (a) is selected from the group consisting of:
        • —NR21AR22A, wherein R21A and R22A each independently represent hydrogen; C1-C6 alkyl optionally substituted with piperidyl; or piperidyl optionally substituted with —COOR105;
        • 3- to 8-membered heterocycloalkyl selected from the group consisting of pyrrolidinyl and piperidyl either of which is optionally substituted with C1-C6 alkyl optionally substituted with —NR41R42 or —NR39R40 wherein R39 and R4 each independently represent hydrogen or C1-C6 alkyl; and
        • —NHSO2(C1-C6 alkyl);
      • wherein substituent (b) is selected from the group consisting of:
        • —COOR11;
        • —NR21aR22a, wherein R21a and R22a each independently represent hydrogen, or C1-C6 alkyl optionally substituted with di(C1-C6 alkyl)amino or C1-C6 alkylsulfonyl;
        • 3- to 8-membered heterocycloalkyl selected from the group consisting of azetidinyl, pyrrolidinyl, and piperidyl any of which are optionally substituted with —NR39R40, C1-C6 alkyl optionally substituted with —NR41R42, hydroxyl, or C1-C6 alkylsulfonyl;
        • cyano; and
        • C1-C6 alkoxy;
      • wherein substituent (c) is selected from the group consisting of:
        • hydroxyl;
        • cyano;
        • halogen;
        • C1-C6 alkyl optionally substituted with a substituent selected from the group consisting of substituent B-c below;
        • C3-C10 cycloalkyl optionally substituted with cyano, or C1-C6 alkyl substituted with —NR31R32;
        • —NR21cR22c, wherein R21c and R22c each independently represent hydrogen or C1-C6 alkyl optionally substituted with amino or cyano;
        • C1-C6 alkoxy optionally substituted with halogen, 3- to 8-membered heterocycloalkyl selected from the group consisting of piperidyl and piperazinyl either of which are optionally substituted with C1-C6 alkyl, or —NR33R34;
        • —SO2NR23cR24c, wherein R23c and R24c each independently represent hydrogen, C1-C6 alkyl optionally substituted with hydroxyl, C1-C6 alkoxy, halogen, C3-C10 cycloalkyl, pyrazolyl, imidazolyl, or —NR35R36; C3-C10 cycloalkyl optionally substituted with C1-C6 hydroxyalkyl; azetidinyl, pyrrolidinyl, or wherein R23c and R24c taken together form pyrrolidinyl which is optionally substituted with amino or halogen;
        • C1-C6 alkylsulfonyl optionally substituted with hydroxyl;
        • —NHSO2(C1-C6 alkyl), wherein the carbon atoms are optionally substituted with NR37R38;
        • piperazinyl optionally substituted with C1-C6 alkyl or C1-C6 alkylsulfonyl;
        • piperidyl optionally substituted with hydroxyl;
        • 1H-tetrazolyl;
        • 1,2,3,6-tetrahydropyridyl; and
        • —COR12c, wherein R12c represents piperazinyl which is optionally substituted with C1-C6 alkyl, C3-C10 cycloalkyl, cyanomethyl, aminomethyl, —NR25R26, or C1-C6 alkyl; and
      • wherein substituent B-c is selected from the group consisting of:
        • halogen;
        • hydroxyl;
        • methoxy;
        • cyano;
        • C3-C10 cycloalkyl;
        • 3- to 8-membered heterocycloalkyl selected from the group consisting of pyrrolidinyl, piperidyl, piperazinyl, morpholinyl, and oxetanyl, any of which is optionally substituted with C1-C6 alkyl, hydroxyl, amino, C1-C6 aminoalkyl, or C1-C6 alkyl substituted with C2-C7 alkyloxycarbonylamino;
        • —NR51cR52c, wherein R51c and R52c each independently represent hydrogen; C1-C6 alkyl optionally substituted with C1-C6 alkylsulfonyl, or piperidyl optionally substituted with —COOR53; piperidyl; C1-C6alkylsulfonyl; C3-C10 cycloalkyl; —COR55; or —CONR57R58;
        • heteroaryl selected from the group consisting of imidazolyl, pyrazolyl, and thiazolyl;
        • —COOR54;
        • —CONH2;
        • —SO2NR106R107;
        • C1-C6 alkylsufinyl; and
        • C1-C6 alkylsulfonyl;
      • wherein substituent (d) is selected from the group consisting of:
        • —NR21dR22d, wherein R21d and R22d each independently represent hydrogen or C1-C6 alkyl;
      • wherein substituent (e) is selected from the group consisting of:
        • hydroxyl;
        • oxo;
        • cyano;
        • C3-C10 cycloalkyl optionally substituted with cyano;
        • —NR21eR22e, wherein R21e and R22e each independently represent hydrogen or C1-C6 alkyl optionally substituted with amino;
        • piperidyl;
        • C1-C6 alkoxy optionally substituted with —NR33R34;
        • C1-C6 alkyl optionally substituted with cyano; —NR51eR52e, wherein R51e and R52e each independently represent hydrogen, C1-C6 alkyl, or —COOR56; morpholinyl; or cyanophenyl;
        • —CONH2;
      • wherein substituent (f) is selected from the group consisting of:
        • C1-C6 alkyl optionally substituted with —NR51fR52f, wherein R51f and R52f each independently represent hydrogen, C1-C6 alkyl, or —COOR56; and C1-C6 alkylsulfonyl;
      • wherein substituent (g) is aryl optionally substituted with C1-C6 alkyl having the aliphatic carbons optionally substituted with cyano or amino.

  • [11] The compound of [2], or a pharmaceutically acceptable salt thereof, wherein R6 is hydrogen; hydroxyl; C1-C6 alkyl; phenyl optionally substituted with 1 to 3 hydroxyls; piperidyl optionally substituted with amino; or piperazinyl.

  • [12] The compound of [11], or a pharmaceutically acceptable salt thereof, wherein R7 is hydrogen; C1-C6 alkyl optionally substituted with hydroxyl or piperidyl; or halogen.

  • [13] The compound of [2], or a pharmaceutically acceptable salt thereof, wherein R7 is hydrogen;
    • C1-C6 alkyl optionally substituted with hydroxyl; —NR71AR72A wherein R71A and R72A independently represent hydrogen, C1-C6 alkyl optionally substituted with dimethylamino, C3-C10 cycloalkyl optionally substituted with amino, or piperidyl; or 3- to 8-membered heterocycloalkyl selected from the group consisting of piperidyl and morpholinyl either of which is optionally substituted with C1-C6 aminoalkyl;
    • phenyl optionally substituted with 1 to 2 hydroxyls;
    • phenylsulfonyl; or
    • —COR73A, wherein R73A represents piperidyl optionally substituted with amino, or —NR74AR75A, wherein R74A and R75A each independently represent hydrogen, piperidyl, or C3-C10 cycloalkyl optionally substituted with amino.

  • [14] The compound of [1], or a pharmaceutically acceptable salt thereof, wherein





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  •  is —CH2—CH2—CH2—.

  • [15] The compound of [14], or a pharmaceutically acceptable salt thereof, wherein R1 and R2 are hydrogen.

  • [16] The compound of [14], or a pharmaceutically acceptable salt thereof, wherein R3 is hydroxyl or methoxy.

  • [17] The compound of [14], or a pharmaceutically acceptable salt thereof, wherein R4 is hydrogen; phenyl substituted with C1-C6 alkyl substituted with —NR51AR52A, wherein R51A and R52A each independently represent hydrogen or C1-C6 alkyl, or —SO2NR53AR54A, wherein R53A and R54A each independently represent hydrogen or C1-C6 alkyl optionally substituted with halogen or hydroxy; 1,2,3,6-tetrahydropyridyl; hydroxypyridyl; or methoxypyridyl.

  • [18] The compound of [1], or a pharmaceutically acceptable salt thereof, wherein





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  •  is —NR108—CH═CR109—,
    • R1, R2, and R4 are hydrogen, and
    • R3 is hydrogen, hydroxyl or C1-C6 alkoxy.

  • [19] The compound of [1], or a pharmaceutically acceptable salt thereof, wherein





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  •  is —N═CH—S—,
    • R1, R2, and R4 are hydrogen, and
    • R3 is methoxy.



Alternatively, in some embodiments, the present invention also provides a compound represented by formula (I) or a pharmaceutically acceptable salt thereof:

  • 1. A compound represented by general formula I:




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    • or a pharmaceutically acceptable salt thereof,

    • wherein R1, R2, R3, and R4 are each independently a group selected from the group consisting of:

    • hydrogen,

    • hydroxyl,

    • halogen,

    • cyano,

    • nitro,

    • amino,

    • C1-C6 alkyl,

    • C2-C6 alkenyl,

    • C2-C6 alkynyl,

    • C3-C10 cycloalkyl,

    • C3-C10 cycloalkenyl,

    • C1-C6 alkoxy,

    • C6-C10 aryl,

    • indanyl,

    • heteroaryl,

    • 3- to 8-membered heterocycloalkyl,

    • —OSO2CH3,

    • —OSO2CF3,

    • —CONH2

    • —OCONR101R102 (wherein R101 and R102 each independently represent hydrogen or C1-C6 alkyl, or R101 and R102 together form morpholinyl),

    • —OCOR103 (wherein R103 represents C1-C6 alkyl), and

    • —OCOOR104 (wherein R104 represents C1-C6 alkyl)

    • wherein each of the groups of R1 to R4 is optionally substituted with a substituent selected from the group consisting of substituent A below:

    • substituent A:
      • hydroxyl;
      • oxo (═O);
      • cyano;
      • halogen;
      • C1-C6 alkyl (wherein the C1-C6 alkyl is optionally substituted with a substituent selected from the group consisting of substituent B below);
      • C3-C10 cycloalkyl [wherein the C3-C10 cycloalkyl is optionally substituted with cyano, or C1-C6 alkyl substituted with —NR31R32 (wherein R31 and R32 each independently represent hydrogen or C1-C6 alkyl)];
      • —NR21R22 [wherein R21 and R22 each independently represent hydrogen, C1-C6 alkyl (wherein the C1-C6 alkyl is optionally substituted with hydroxyl, amino, di(C1-C6 alkyl)amino, C1-C6 alkylsulfonyl (—SO2(C1-C6 alkyl)), 3- to 8-membered heterocycloalkyl, or cyano), or 3- to 8-membered heterocycloalkyl (wherein the 3- to 8-membered heterocycloalkyl is optionally substituted with —COOR105 (wherein R1055 represents C1-C6))];
      • C1-C6 alkoxy {wherein the C1-C6 alkoxy is optionally substituted with halogen, 3- to 8-membered heterocycloalkyl (wherein the 3- to 8-membered heterocycloalkyl is optionally substituted with C1-C6 alkyl), or —NR33R34 [wherein R33 and R34 each independently represent hydrogen, C1-C6 alkyl (wherein the C1-C6 alkyl is optionally substituted with C1-C6 alkylsulfonyl or di(C1-C6 alkyl)amino), or C1-C6 alkylsulfonyl]};
      • —SO2NR23R24 (wherein R23 and R24 each independently represent hydrogen, C1-C6 alkyl [wherein the C1-C6 alkyl is optionally substituted with hydroxyl, C1-C6 alkoxy, halogen, C3-C10 cycloalkyl, heteroaryl, or —NR35R36 (wherein R35 and R36 each independently represent hydrogen or C1-C6 alkyl)], C3-C10 cycloalkyl (wherein the C3-C10 cycloalkyl is optionally substituted with C1-C6 hydroxyalkyl), or 3- to 8-membered heterocycloalkyl; or R23 and R24 may together form 3- to 8-membered heterocycloalkyl wherein the 3- to 8-membered heterocycloalkyl is optionally substituted with amino or halogen);
      • C1-C6 alkylsulfonyl (wherein the C1-C6 alkyl moiety is optionally substituted with hydroxyl);
      • C1-C6 alkylsulfonylamino (—NHSO2(C1-C6 alkyl)) [wherein the C1-C6 alkyl moiety is optionally substituted with —NR37R38 (wherein R37 and R38 each independently represent hydrogen or C1-C6 alkyl)];
      • 3- to 8-membered heterocycloalkyl (wherein the 3- to 8-membered heterocycloalkyl is optionally substituted with —NR39R40 (wherein R39 and R40 each independently represent hydrogen, C1-C6 alkyl, or C1-C6 alkylsulfonyl), C1-C6 alkyl [wherein the C1-C6 alkyl is optionally substituted with —NR41R42 (wherein R41 and R42 each independently represent hydrogen or C1-C6 alkyl)], hydroxyl, or C1-C6 alkylsulfonyl);
      • Aryl (wherein the aryl is optionally substituted with C1-C6 alkyl[wherein C1-C6 alkyl is optionally substituted with cyano or amino]);
      • heteroaryl;
      • —COOR11 (wherein R11 represents hydrogen or C1-C6 alkyl); and
      • —COR12 [wherein R12 represents C1-C6 alkyl, C3-C10 cycloalkyl, cyanomethyl, aminomethyl, —NR25R26 {wherein R25 and R26 each independently represent hydrogen, or C1-C6 alkyl [wherein the C1-C6 alkyl is optionally substituted with hydroxyl or —NR43R44 (wherein R43 and R44 each independently represent hydrogen or C1-C6 alkyl)]}), or 3- to 8-membered heterocycloalkyl which is optionally substituted with C1-C6 alkyl],

    • substituent B:
      • halogen;
      • hydroxyl;
      • C1-C6 alkoxy;
      • cyano;
      • cycloalkyl;
      • C6-C10 aryl (wherein C6-C10 aryl is optionally substituted with cyano) heteroaryl;
      • 3- to 8-membered heterocycloalkyl (wherein the 3- to 8-membered heterocycloalkyl is optionally substituted with C1-C6 alkyl, hydroxyl, amino, C1-C6 aminoalkyl, or C1-C6 alkyl substituted with C2-C7 alkyloxycarbonylamino);
      • —NR51R52 {wherein R51 and R52 each independently represent hydrogen, C1-C6 alkyl [wherein the C1-C6 alkyl is optionally substituted with C1-C6 alkylsulfonyl, or 3- to 8-membered heterocycloalkyl optionally substituted with —COOR53 (wherein R53 represents hydrogen or C1-C6 alkyl)], 3- to 8-membered heterocycloalkyl, C1-C6 alkylsulfonyl, C3-C10 cycloalkyl, —COR55 (wherein R55 represents C1-C6 alkyl), —COOR56 (wherein R56 represents C1-C6 alkyl), or —CONR57R58 (wherein R57 and R58 each independently represent hydrogen or C1-C6 alkyl)};
      • —COOR54 (wherein R54 represents hydrogen or C1-C6 alkyl)];
      • —CONH2;
      • —SO2NR106R107 (wherein R106 and R107 each independently represent hydrogen, C1-C6 alkyl, or C3-C10 cycloalkyl)
      • C1-C6 alkylsulfinyl; and
      • C1-C6 alkylsulfonyl;

    • wherein R5 is hydrogen or C1-C6 alkyl; and

    • wherein







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    •  is a structure selected from the group consisting of
      • (i) —S—CR7═CR6—,
      • (ii)-CH2—CH2—CH2—,
      • (iii)-NR108—CH═CR109— (wherein R108 represents hydrogen, or C1-C6 alkyl that is optionally substituted with hydroxyl, and R109 represents hydrogen, CH3, or phenyl that is substituted with C1-C6 aminoalkyl, and
      • (iv) —N═CH—S—,

    • wherein R6 is
      • hydrogen,
      • hydroxyl,
      • C1-C6 alkyl,
      • C6-C10 aryl (wherein the C6-C10 aryl is optionally substituted with hydroxyl), or
      • 3- to 8-membered heterocycloalkyl [wherein the 3- to 8-membered heterocycloalkyl is optionally substituted with —NR61R62 (wherein R61 and R62 each independently represent hydrogen or C1-C6 alkyl)];

    • wherein R7 is
      • hydrogen;
      • halogen;
      • C1-C6 alkyl {wherein the C1-C6 alkyl is optionally substituted with hydroxyl, —NR71R72 [wherein R71 and R72 each independently represent hydrogen, C1-C6 alkyl (wherein the C1-C6 alkyl is optionally substituted with dimethylamino), C3-C10 cycloalkyl (wherein the C3-C10 cycloalkyl is optionally substituted with amino), or 3- to 8-membered heterocycloalkyl], or 3- to 8-membered heterocycloalkyl (wherein the 3- to 8-membered heterocycloalkyl is optionally substituted with C1-C6 aminoalkyl)},
      • C6-C10 aryl (wherein the C6-C10 aryl is optionally substituted with hydroxyl);
      • C6-C10 arylsulfonyl; or
      • —COR73 {wherein R73 represents 3- to 8-membered heterocycloalkyl (wherein the 3- to 8-membered heterocycloalkyl is optionally substituted with amino), or —NR74R75 [wherein R74 and R75 each independently represent hydrogen, 3- to 8-membered heterocycloalkyl, or C3-C10 cycloalkyl (wherein the C3-C10 cycloalkyl is optionally substituted with amino)]}.



  • 2. The compound of above 1, or a pharmaceutically acceptable salt thereof, wherein





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  •  is —S—CR7═CR6—.

  • 3. The compound of above 2, or a pharmaceutically acceptable salt thereof, wherein R1 is hydrogen, cyano, C1-C6 alkyl (wherein C1-C6 alkyl is optionally substituted with hydroxyl or halogen), C3-C10 cycloalkyl, C2-C6 alkenyl, C2-C6 alkynyl, or halogen.

  • 4. The compound of above 2, or a pharmaceutically acceptable salt thereof, wherein R2 is hydrogen, hydroxyl, halogen, C1-C6 alkoxy, or C6-C10 aryl which is optionally substituted with hydroxyl.

  • 5. The compound of above 2 or a pharmaceutically acceptable salt, wherein R2 is hydrogen, hydroxyl, halogen, C1-C6 alkoxy, or dihydroxyphenyl.

  • 6. The compound of above 2, or a pharmaceutically acceptable salt thereof, wherein R3 is hydrogen; hydroxyl; C1-C6 alkyl (wherein alkyl is optionally substituted with hydroxyl, halogen, or hydroxyethylamino); halogen; C1-C6 alkoxy optionally substituted with dimethylamino or morpholinyl; C1-C6 alkylphenyl [wherein C1-C6 alkyl of the C1-C6 alkylphenyl is optionally substituted with —NR51R52 {wherein R51 and R52 each independently represent hydrogen, C1-C6 alkyl, or —COOR56 (wherein R56 represents C1-C6 alkyl))}]; cyano; nitro; amino; 3- to 8-membered heterocycloalkyl which is optionally substituted with amino; heteroaryl; —OSO2CH3; —OSO2CF3; —OCOR103 (R103 represents C1-C6 alkyl); —OCOOR104 (wherein R104 represents C1-C6 alkyl); —OCONR101R102 (wherein R101, R102 each independently represent hydrogen or C1-C6 alkyl, or R101 and R102 together form morpholinyl); or —CONH2.

  • 7. The compound of above 2, or a pharmaceutically acceptable salt thereof, wherein R3 is hydrogen; hydroxyl; C1-C6 alkyl (wherein alkyl is optionally substituted with hydroxyl, halogen, or hydroxyethylamino); halogen; C1-C6 alkoxy that is optionally substituted with dimethylamino or morpholinyl; C1-C6 alkylphenyl (wherein C1-C6 alkyl of the C1-C6 alkylphenyl is optionally substituted with —NR51R52 (wherein R51 and R52 each independently represent hydrogen, C1-C6 alkyl, or —COOR56 (wherein R56 represents C1-C6 alkyl) cyano; nitro; amino; 3- to 8-membered heterocycloalkyl which is optionally substituted with amino (wherein the 3- to 8-membered heterocycloalkyl is piperidyl, pyrrolidinyl, morpholinyl, or piperazinyl); pyridyl; —OSO2CH3; —OSO2CF3; —OCOR103 (R103 represents C1-C6 alkyl); —OCOOR104 (wherein R104 represents C1-C6 alkyl); —OCONR101R102 (wherein R101, R102 each independently represent hydrogen or C1-C6 alkyl, or R101 and R102 together form morpholinyl); or —CONH2.

  • 8. The compound of above 2, or a pharmaceutically acceptable salt thereof, wherein R4 is a group selected from the group consisting of hydrogen, hydroxyl, halogen, amino, C1-C6 alkyl, C2-C6 alkenyl, C3-C10 cycloalkyl, C3-C10 cycloalkenyl, C1-C6 alkoxy, C6-C10 aryl, indanyl, heteroaryl, and 3- to 8-membered heterocycloalkyl, wherein each of the groups of R4 is optionally substituted with a substituent selected from the group consisting of substituent A above.

  • 9. The compound of above 2, or a pharmaceutically acceptable salt thereof, wherein R4 is a group selected from the group consisting of hydrogen, hydroxyl, halogen, amino, C1-C6 alkyl, C2-C6 alkenyl, C3-C10 cycloalkyl, C3-C10 cycloalkenyl, C1-C6 alkoxy, C6-C10 aryl, indanyl, heteroaryl (wherein the heteroaryl is selected from the group consisting of pyridyl, 1H-indazolyl, 1H-tetrazolyl, [1,2,4]triazolo[1,5-a]pyridyl, benzoimidazolyl, 2,3-dihydrobenzooxazolyl, pyrazolyl, pyrrolo[2,3-b]pyridyl, pyrimidinyl, indolinyl, furyl, thienyl, and tetrahydroisoquinolyl), and 3- to 8-membered heterocycloalkyl (wherein the 3- to 8-membered heterocycloalkyl is selected from the group consisting of aziridinyl, azetidinyl, pyrrolidinyl, imidazolidinyl, piperidyl, piperazinyl, azepanyl, morpholinyl, and 1,2,3,6-tetrahydropyridyl), wherein each of the groups of R4 is optionally substituted with a substituent selected from the group consisting of substituent A-1 below:
    • substituent A-1:
    • hydroxyl;
    • oxo;
    • cyano;
    • halogen;
    • C1-C6 alkyl (wherein the C1-C6 alkyl is optionally substituted with a substituent selected from the group consisting of substituent B-1 below);
    • C3-C10 cycloalkyl [wherein the C3-C10 cycloalkyl is optionally substituted with cyano, or C1-C6 alkyl substituted with —NR31R32 (wherein R31 and R32 each independently represent hydrogen or C1-C6 alkyl)];
    • —NR21AR22A [wherein R21A and R22A each independently represent hydrogen, C1-C6 alkyl (wherein C1-C6 alkyl is optionally substituted with amino, di(C1-C6 alkyl)amino, C1-C6 alkylsulfonyl (—SO2 (C1-C6 alkyl)), piperidyl, or cyano), or piperidyl (wherein piperidyl is optionally substituted with —COOR105 (wherein R105 represents C1-C6 alkyl))];
    • C1-C6 alkoxy {wherein the C1-C6 alkoxy is optionally substituted with 3- to 8-membered heterocycloalkyl selected from halogen, piperidyl, and piperazinyl (wherein the 3- to 8-membered heterocycloalkyl is optionally substituted with C1-C6 alkyl), or —NR33R34 [wherein R33 and R34 each independently represent hydrogen, C1-C6 alkyl (wherein the C1-C6 alkyl is optionally substituted with C1-C6 alkylsulfonyl or di(C1-C6 alkyl)amino), or C1-C6 alkylsulfonyl]};
    • —SO2NR23AR24A (wherein R23A and R24A each independently represent hydrogen, C1-C6 alkyl [wherein the C1-C6 alkyl is optionally substituted with hydroxyl, C1-C6 alkoxy, halogen, C3-C10 cycloalkyl, pyrazolyl, imidazolyl, or —NR35R36 (wherein R35 and R36 each independently represent hydrogen or C1-C6 alkyl)], C3-C10 cycloalkyl (wherein the C3-C10 cycloalkyl is optionally substituted with C1-C6 hydroxyalkyl), azetidinyl, or pyrrolidinyl, or may together form pyrrolidinyl, wherein the pyrrolidinyl is optionally substituted with amino or halogen);
    • C1-C6 alkylsulfonyl (wherein the C1-C6 alkyl moiety is optionally substituted with hydroxyl);
    • C1-C6 alkylsulfonylamino (—NHSO2 (C1-C6 alkyl)) [wherein the C1-C6 alkyl moiety is optionally substituted with —NR37R38 (wherein R37 and R38 each independently represent hydrogen or C1-C6 alkyl)];
    • 3- to 8-membered heterocycloalkyl selected from the group consisting of azetidinyl, pyrrolidinyl, piperidyl, piperazinyl, and tetrahydropyridyl {wherein the 3- to 8-membered heterocycloalkyl is optionally substituted with —NR39R40 (wherein R39 and R40 each independently represent hydrogen, C1-C6 alkyl, or C1-C6 alkylsulfonyl), C1-C6 alkyl [wherein the C1-C6 alkyl is optionally substituted with —NR41R42 (wherein R41 and R42 each independently represent hydrogen or C1-C6 alkyl)], hydroxyl, or C1-C6 alkylsulfonyl};
    • 1H-tetrazolyl;
    • aryl (wherein aryl is optionally substituted with C1-C6 alkyl [wherein C1-C6 alkyl is optionally substituted with cyano or amino])
    • —COOR11 (wherein R11 represents hydrogen or C1-C6 alkyl); and
    • —COR12A [wherein R12A represents piperazinyl which is optionally substituted with C1-C6 alkyl, C3-C10 cycloalkyl, cyanomethyl, aminomethyl, —NR25R26 {wherein R25 and R26 each independently represent hydrogen or C1-C6 alkyl [wherein the C1-C6 alkyl is optionally substituted with hydroxyl or —NR43R44 (wherein R43 and R44 each independently represent hydrogen or C1-C6 alkyl)]}, or C1-C6 alkyl];
    • substituent B-1:
    • halogen;
    • hydroxyl;
    • C1-C6 alkoxy;
    • cyano;
    • cycloalkyl;
    • phenyl (wherein phenyl is optionally substituted with cyano);
    • heteroaryl selected from the group consisting of imidazolyl, pyrazolyl, and thiazolyl
    • 3- to 8-membered heterocycloalkyl selected from the group consisting of pyrrolidinyl, piperidyl, piperazinyl, morpholinyl, and oxetanyl (wherein the 3- to 8-membered heterocycloalkyl is optionally substituted with C1-C6 alkyl, hydroxyl, amino, C1-C6 aminoalkyl, or C1-C6 alkyl substituted with C2-C7 alkyloxycarbonylamino);
    • —NR51AR52A {wherein R51A and R52A each independently represent hydrogen, C1-C6 alkyl [wherein the C1-C6 alkyl is optionally substituted with C1-C6 alkylsulfonyl, or piperidyl which is optionally substituted with, —COOR53 (wherein R53 represents hydro en or C1-C6 alkyl)], piperidyl, C1-C6 alkylsulfonyl, C3-C10 cycloalkyl, —COR55 (wherein R55 represents C1-C6 alkyl), —COOR56 (wherein R56 represents C1-C6 alkyl), or —CONR57R58 (wherein R57 and R58 each independently represent hydrogen or C1-C6 alkyl)};
    • —COOR54 (wherein R54 represents hydrogen or C1-C6 alkyl);
    • —CONH2;
    • —SO2NR106R107 (wherein R106 and R107 each independently represent hydrogen, C1-C6 alkyl, or C3-C10 cycloalkyl);
    • C1-C6 alkylsulfinyl; and
    • C1-C6 alkylysulfonyl

  • 10. The compound of above 9, or a pharmaceutically acceptable salt thereof, wherein R4 is a group selected from the group consisting of (p) below:
    • (p):
      • hydrogen,
      • hydroxyl,
      • halogen,
      • amino which is optionally substituted with a substituent selected from the group consisting of substituent (g) below,
      • C1-C6 alkyl which is optionally substituted with a substituent selected from the group consisting of substituent (a) below,
      • C2-C6 alkenyl which is optionally substituted with a substituent selected from the group consisting of substituent (b) below,
      • C3-C10 cycloalkyl,
      • C3-C10 cycloalkenyl,
      • C1-C6 alkoxy,
      • C6-C10 aryl which is optionally substituted with a substituent selected from the group consisting of substituent (c) below,
      • indanyl which is optionally substituted with a substituent selected from the group consisting of substituent (d) below,
      • heteroaryl which is optionally substituted with a substituent selected from the group consisting of substituent (e) below, and
      • 3- to 8-membered heterocycloalkyl which is optionally substituted with a substituent selected from the group consisting of substituent (f) below,
    • wherein, in the group (p),
      • the heteroaryl is selected from the group consisting of pyridyl, 1H-indazolyl, 1H-tetrazolyl, [1,2,4]triazolo[1,5-a]pyridyl, benzoimidazolyl, 2,3-dihydrobenzooxazolyl, pyrazolyl, pyrrolo[2,3-b]pyridyl, pyrimidinyl, indolinyl, furyl, thienyl, and tetrahydroisoquinolyl;
      • the 3- to 8-membered heterocycloalkyl is selected from the group consisting of pyrrolidinyl, piperidyl, piperazinyl, morpholinyl, and 1,2,3,6-tetrahydropyridyl;
      • substituent (a):
        • —NR21AR22A [wherein R21A and R22A each independently represent hydrogen, C1-C6 alkyl {wherein C1-C6 alkyl is optionally substituted with piperidyl}, or piperidyl {wherein piperidyl is optionally substituted with —COOR105 (wherein R105 represents C1-C6 alkyl)}];
        • 3- to 8-membered heterocycloalkyl selected from the group consisting of pyrrolidinyl and piperidyl {wherein the 3- to 8-membered heterocycloalkyl is optionally substituted with —NR39R40 (wherein R39 and R40 each independently represent hydrogen or C1-C6 alkyl), or C1-C6 alkyl [wherein the C1-C6 alkyl is optionally substituted with —NR41R42 (wherein R41 and R42 each independently represent hydrogen or C1-C6 alkyl)]}; and
        • C1-C6 alkylsulfonylamino (—NHSO2(C1-C6 alkyl));
      • substituent (b):
        • —COOR11 (wherein R11 represents hydrogen or C1-C6 alkyl); —NR21aR22a [wherein R21a and R22a each independently represent hydrogen, or C1-C6 alkyl (wherein the C1-C6 alkyl is optionally substituted with di(C1-C6 alkyl)amino or C1-C6 alkylsulfonyl)];
        • 3- to 8-membered heterocycloalkyl selected from the group consisting of azetidinyl, pyrrolidinyl, and piperidyl {wherein the 3- to 8-membered heterocycloalkyl is optionally substituted with —NR39R40 (wherein R39 and R40 each independently represent hydrogen, C1-C6 alkyl, or C1-C6 alkylsulfonyl), C1-C6 alkyl [wherein the C1-C6 alkyl is optionally substituted with —NR41R42 (wherein R41 and R42 each independently represent hydrogen or C1-C6 alkyl)], hydroxyl, or C1-C6 alkylsulfonyl};
        • cyano; and
        • C1-C6 alkoxy;
      • substituent (c):
        • hydroxyl;
        • cyano;
        • halogen;
        • C1-C6 alkyl (wherein the C1-C6 alkyl is optionally substituted with a substituent selected from the group consisting of substituent B-c below);
        • C3-C10 cycloalkyl [wherein the C3-C10 cycloalkyl is optionally substituted with cyano, or C1-C6 alkyl substituted with —NR31R32 (wherein R31 and R32 each independently represent hydrogen or C1-C6 alkyl)];
        • —NR21cR22c [wherein R21c and R22c each independently represent hydrogen or C1-C6 alkyl (wherein C1-C6 alkyl is optionally substituted with amino, or cyano)]];
        • C1-C6 alkoxy {wherein the C1-C6 alkoxy is optionally substituted with 3- to 8-membered heterocycloalkyl selected from halogen, piperidyl, and piperazinyl (wherein the 3- to 8-membered heterocycloalkyl is optionally substituted with C1-C6 alkyl), or —NR33R34 [wherein R33 and R34 each independently represent hydrogen, C1-C6 alkyl (wherein the C1-C6 alkyl is optionally substituted with di(C1-C6 alkyl)amino), or C1-C6 alkylsulfonyl]};
        • —SO2NR23cR24c {wherein R23c and R24c each independently represent hydrogen, C1-C6 alkyl [wherein the C1-C6 alkyl is optionally substituted with hydroxyl, C1-C6 alkoxy, halogen, C3-C10 cycloalkyl, pyrazolyl, imidazolyl, or —NR35R36 (wherein R35 and R36 each independently represent hydrogen or C1-C6 alkyl)], C3-C10cycloalkyl (wherein the C3-C10 cycloalkyl is optionally substituted with C1-C6 hydroxyalkyl), azetidinyl, or pyrrolidinyl, or wherein R23c and R24c may together form pyrrolidinyl which is optionally substituted with amino or halogen};
        • C1-C6 alkylsulfonyl (wherein the C1-C6 alkyl moiety is optionally substituted with hydroxyl);
        • C1-C6 alkylsulfonylamino (—NHSO2(C1-C6 alkyl)) [wherein the C1-C6 alkyl moiety is optionally substituted with —NR37R38 (wherein R37 and R38 each independently represent hydrogen or C1-C6 alkyl)];
        • piperazinyl {wherein the piperazinyl is optionally substituted with C1-C6 alkyl or C1-C6 alkylsulfonyl};
        • piperidyl (wherein piperidyl is optionally substituted with hydroxyl);
        • 1H-tetrazolyl;
        • 1,2,3,6-tetrahydropyridyl; and
        • —COR12c [wherein R12c represents piperazinyl which is optionally substituted with C1-C6 alkyl, C3-C10 cycloalkyl, cyanomethyl, aminomethyl, —NR25R26 {wherein R25 and R26 each independently represent hydrogen or C1-C6 alkyl [wherein the C1-C6 alkyl is optionally substituted with hydroxyl, or —NR43R44 (wherein R43 and R44 each independently represent hydrogen or C1-C6 alkyl)]}, or C1-C6 alkyl]; and
      • substituent B-c:
        • halogen;
        • hydroxyl;
        • methoxy;
        • cyano;
        • C3-C10 cycloalkyl
        • 3- to 8-membered heterocycloalkyl selected from the group consisting of pyrrolidinyl, piperidyl, piperazinyl, morpholinyl, and oxetanyl (wherein the 3- to 8-membered heterocycloalkyl is optionally substituted with C1-C6 alkyl, hydroxyl, amino, C1-C6 aminoalkyl, or C1-C6 alkyl substituted with C2-C7 alkyloxycarbonylamino); and
        • —NR51cR52c {wherein R51c and R52c each independently represent hydrogen, C1-C6 alkyl [wherein the C1-C6 alkyl is optionally substituted with C1-C6 alkylsulfonyl, or piperidyl which is optionally substituted with —COOR53 (wherein R53 represents hydrogen or C1-C6 alkyl)], piperidyl, C1-C6alkylsulfonyl, C3-C10 cycloalkyl, —COR55 (wherein R55 represents C1-C6 alkyl), or —CONR57R58 (wherein R57 and R58 each independently represent hydrogen or C1-C6 alkyl)}];
        • heteroaryl selected from the group of imidazolyl, pyrazolyl, and thiazolyl;
        • —COOR54 (wherein R54 represents hydrogen, or C1-C6 alkyl)
        • —CONH2;
        • —SO2NR106R107 wherein R106 and R107 each independently represent hydrogen, C1-C6 alkyl, or C3-C10 cycloalkyl);
        • C1-C6 alkylsufinyl; and
        • C1-C6 alkylsulfonyl;
      • substituent (d):
        • —NR21dR22d (wherein R21d and R22d each independently represent hydrogen or C1-C6 alkyl);
      • substituent (e):
        • hydroxyl;
        • oxo;
        • cyano;
        • C3-C10 cycloalkyl [wherein C3-C10 cycloalkyl is optionally substituted with cyano];
        • —NR21R22 [wherein R21 and R22 each independently represent hydrogen or C1-C6 alkyl (wherein C1-C6 alkyl is optionally substituted with amino)];
        • piperidyl;
        • C1-C6 alkoxy (wherein C1-C6 alkoxy is optionally substituted with —NR33R34 [wherein R33 and R34 each independently represent hydrogen, or C1-C6 alkyl]); and
        • C1-C6 alkyl {wherein the C1-C6 alkyl is optionally substituted with cyano, —NR51eR52e [wherein R51e and R52e each independently represent hydrogen, C1-C6 alkyl, or —COOR56 (wherein R56 represents C1-C6 alkyl)], morpholinyl, or cyanophenyl}; —CONH2;
      • substituent (f):
        • C1-C6 alkyl {wherein the C1-C6 alkyl is optionally substituted with —NR51fR52f [wherein R51f and R52f each independently represent hydrogen, C1-C6 alkyl, or —COOR56 (wherein R56 represents C1-C6 alkyl)]}; and C1-C6 alkylsulfonyl;
      • substituent (g):
      • Aryl (wherein aryl is optionally substituted with C1-C6 alkyl [wherein C1-C6 alkyl is optionally substituted with cyano or amino]).

  • 11. The compound of above 2, or a pharmaceutically acceptable salt thereof, wherein R6 is hydrogen; hydroxyl; C1-C6 alkyl; phenyl which is optionally substituted with 1 to 3 hydroxyls; piperidyl which is optionally substituted with amino; or piperazinyl.

  • 12. The compound of above 11, or a pharmaceutically acceptable salt thereof, wherein R7 is hydrogen, C1-C6 alkyl (wherein C1-C6 alkyl is optionally substituted by a substituent selected from the group comprising hydroxyl and piperidyl), or halogen.

  • 13. The compound of above 2, or a pharmaceutically acceptable salt thereof, wherein R7 is hydrogen;
    • C1-C6 alkyl {wherein the C1-C6 alkyl is optionally substituted with hydroxyl, —NR71AR72A [wherein R71A and R72A each independently represent hydrogen, C1-C6 alkyl (wherein the C1-C6 alkyl is optionally substituted with dimethylamino), C3-C10 cycloalkyl (wherein the C3-C10 cycloalkyl is optionally substituted with amino), or piperidyl], or 3- to 8-membered heterocycloalkyl selected from the group consisting of piperidyl and morpholinyl (wherein the 3- to 8-membered heterocycloalkyl is optionally substituted with C1-C6 aminoalkyl)};
    • phenyl which is optionally substituted with 1 to 2 hydroxyls;
    • phenylsulfonyl; or
    • —COR73A {wherein R73A represents piperidyl (wherein the piperidyl is optionally substituted with amino), or —NR74AR75A [wherein R74A and R75A each independently represent hydrogen, piperidyl, or C3-C10 cycloalkyl (wherein the C3-C10 cycloalkyl is optionally substituted with amino)]}.

  • 14. The compound of above 1, or a pharmaceutically acceptable salt thereof, wherein





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  •  is —CH2—CH2—CH2—.

  • 15. The compound of above 14, or a pharmaceutically acceptable salt thereof, wherein R1 and R2 are hydrogen.

  • 16. The compound of above 14, or a pharmaceutically acceptable salt thereof, wherein R3 is hydroxyl or methoxy.

  • 17. The compound of above 14, or a pharmaceutically acceptable salt thereof, wherein R4 is hydrogen, phenyl [wherein the phenyl is substituted with C1-C6 alkyl substituted with —NR51AR52A (wherein R51A and R52A each independently represent hydrogen or C1-C6 alkyl), or —SO2NR53AR54A(wherein R53A and R54A each independently represent hydrogen, or C1-C6 alkyl that is optionally substituted with halogen or hydroxyl)], 1,2,3,6-tetrahydropyridyl, hydroxypyridyl, or methoxypyridyl.

  • 18. The compound of above 1, or a pharmaceutically acceptable salt thereof, wherein





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  •  is —NR108—CH═CR109— (wherein R108 represents hydrogen, or C1-C6 alkyl that is optionally substituted with hydroxyl, and R109 represents hydrogen, CH3, or phenyl group which is substituted with C1-C6-aminoalkyl),
    • R1, R2, and R4 are hydrogen, and
    • R3 is hydrogen, hydroxyl or C1-C6alkoxy.

  • 19. The compound of above 1, or a pharmaceutically acceptable salt thereof, wherein





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  •  is —N═CH—S—,
    • R1, R2, and R4 are hydrogen, and
    • R3 is methoxy.

  • 20. A compound selected from the group consisting of:

  • (1): 8-methoxy-5-methylthieno[2,3-c]quinolin-4(5H)-one;

  • (2): 8-hydroxy-5-methylthieno[2,3-c]quinolin-4(5H)-one;

  • (3): 7,8-dihydroxythieno[2,3-c]quinolin-4(5H)-one;

  • (4): 7,8-dimethoxythieno[2,3-c]quinolin-4(5H)-one;

  • (5): 8-methoxythieno[2,3-c]quinolin-4(5H)-one;

  • (6): 7,9-dimethoxythieno[2,3-c]quinolin-4(5H)-one;

  • (7): 7,9-dihydroxythieno[2,3-c]quinolin-4(5H)-one;

  • (8): 7,8,9-trimethoxythieno[2,3-c]quinolin-4(5H)-one;

  • (9): 8-hydroxythieno[2,3-c]quinolin-4(5H)-one;

  • (10): 7,8,9-trihydroxythieno[2,3-c]quinolin-4(5H)-one;

  • (11): 9-(3-(2-aminoethyl)phenyl)-8-methoxythieno[2,3-c]quinolin-4(5H)-one;

  • (12): 8-chlorothieno[2,3-c]quinolin-4(5H)-one;

  • (13): 4-oxo-4,5-dihydrothieno[2,3-c]quinoline-8-carbonitrile;

  • (14): thieno[2,3-c]quinolin-4(5H)-one;

  • (15): 8-fluorothieno[2,3-c]quinolin-4(5H)-one;

  • (16): 8-nitrothieno[2,3-c]quinolin-4(5H)-one;

  • (17): 8-(3-aminopiperidin-1-yl)thieno[2,3-c]quinolin-4(5H)-one;

  • (18): 1-(4-hydroxyphenyl)thieno[2,3-c]quinolin-4(5H)-one;

  • (19): 1,8-dihydroxythieno[2,3-c]quinolin-4(5H)-one;

  • (20): 8-hydroxy-1-(4-hydroxyphenyl)thieno[2,3-c]quinolin-4(5H)-one;

  • (2H): (R)-8-(3-aminopyrrolidin-1-yl)thieno[2,3-c]quinolin-4(5H)-one;

  • (22): (S)-8-(3-aminopyrrolidin-1-yl)thieno[2,3-c]quinolin-4(5H)-one;

  • (23): 8-(pyridin-3-yl)thieno[2,3-c]quinolin-4(5H)-one;

  • (24): 8-(4-hydroxyphenyl)thieno[2,3-c]quinolin-4(5H)-one;

  • (25): 1-(3,4-dihydroxyphenyl)-8-hydroxythieno[2,3-c]quinolin-4(5H)-one;

  • (26): 1-(3-aminopiperidin-1-yl)-8-hydroxythieno[2,3-c]quinolin-4(5H)-one;

  • (27): 8-morpholinothieno[2,3-c]quinolin-4(5H)-one;

  • (28): 8-hydroxy-2-methylthieno[2,3-c]quinolin-4(5H)-one;

  • (29): 8-hydroxy-2-(hydroxymethyl)thieno[2,3-c]quinolin-4(5H)-one;

  • (30): 8-hydroxy-4-oxo-N-(piperidin-3-yl)-4,5-dihydrothieno[2,3-c]quinoline-2-carboxamide;

  • (31): 8-hydroxy-2-(4-hydroxyphenyl)thieno[2,3-c]quinolin-4(5H)-one;

  • (32): 8-hydroxy-1-(piperazin-1-yl)thieno[2,3-c]quinolin-4(5H)-one;

  • (33): N-((1r,4r)-4-aminocyclohexyl)-8-hydroxy-4-oxo-4,5-dihydrothieno[2,3-c]quinolin-2-carboxamide;

  • (34): 2-(3-aminopiperidine-1-carbonyl)-8-hydroxythieno[2,3-c]quinolin-4(5H)-one;

  • (35): 2-(3,4-dihydroxyphenyl)-8-hydroxythieno[2,3-c]quinolin-4(5H)-one;

  • (36): 2-(((1r,4r)-4-aminocyclohexylamino)methyl)-8-hydroxythieno[2,3-c]quinolin-4(5H)-one;

  • (37): 8-(piperazin-1-yl)thieno[2,3-c]quinolin-4(5H)-one;

  • (38): 8-hydroxy-1-methylthieno[2,3-c]quinolin-4(5H)-one;

  • (39): 2-((2-(dimethylamino)ethylamino)methyl)-8-hydroxythieno[2,3-c]quinolin-(5H)-one;

  • (40): 8-hydroxy-2-((piperidin-3-ylamino)methyl)thieno[2,3-c]quinolin-4(5H)-one;

  • (41): 7-hydroxythieno[2,3-c]quinolin-4(5H)-one;

  • (42): 9-bromo-8-hydroxythieno[2,3-c]quinolin-4(5H)-one;

  • (43): 9-(3,4-dihydroxyphenyl)-8-hydroxythieno[2,3-c]quinolin-4(5H)-one;

  • (44): 1-methyl-4-oxo-4,5-dihydrothieno[2,3-c]quinoline-8-carbonitrile;

  • (45): 7-(3,4-dihydroxyphenyl)-8-hydroxythieno[2,3-c]quinolin-4(5H)-one;

  • (46): 8-hydroxy-1-methyl-3H-pyrrolo[2,3-c]quinolin-4(5H)-one;

  • (47): 9-(3,5-dihydroxyphenyl)-8-hydroxythieno[2,3-c]quinolin-4(5H)-one;

  • (48): 8-hydroxy-9-(3-hydroxyphenyl)thieno[2,3-c]quinolin-4(5H)-one;

  • (49): 8-hydroxy-9-(4-hydroxyphenyl)thieno[2,3-c]quinolin-4(5H)-one;

  • (50): 9-(3,4-difluorophenyl)-8-methoxythieno[2,3-c]quinolin-4(5H)-one;

  • (51): (S)-8-(3-aminopyrrolidin-1-yl)-2-(4-hydroxyphenyl)thieno[2,3-c]quinolin-4(5H)-one;

  • (52): 5-(8-methoxy-4-oxo-4,5-dihydrothieno[2,3-c]quinolin-9-yl)picolinonitrile;

  • (53): 9-(6-aminopyridin-3-yl)-8-hydroxythieno[2,3-c]quinolin-4(5H)-one;

  • (54): 4-(8-hydroxy-4-oxo-4,5-dihydrothieno[2,3-c]quinolin-9-yl)benzamide;

  • (55): 9-(3-fluoro-4-hydroxyphenyl)-8-hydroxythieno[2,3-c]quinolin-4(5H)-one;

  • (56): 8-hydroxy-2-(3-hydroxyphenyl)thieno[2,3-c]quinolin-4(5H)-one;

  • (57): (R)-8-(3-aminopyrrolidin-1-yl)-2-(3,4-dihydroxyphenyl)thieno[2,3-c]quinolin-4(5H)-one;

  • (58): 9-(3,4-difluorophenyl)-8-hydroxythieno[2,3-c]quinolin-4(5H)-one;

  • (59): 9-(4-fluoro-3-hydroxyphenyl)-8-hydroxythieno[2,3-c]quinolin-4(5H)-one;

  • (60): 8-hydroxy-9-(3-hydroxy-5-(trifluoromethyl)phenyl)thieno[2,3-c]quinolin-4(5H)-one;

  • (61): 8-hydroxy-9-(1H-indazol-6-yl)thieno[2,3-c]quinolin-4(5H)-one;

  • (62): 8-hydroxy-9-(3,4,5-trihydroxyphenyl)thieno[2,3-c]quinolin-4(5H)-one;

  • (63): 9-(4-hydroxyphenyl)-8-methoxythieno[2,3-c]quinolin-4(5H)-one;

  • (64): 9-(4-(1H-tetrazol-5-yl)phenyl)-8-hydroxythieno[2,3-c]quinolin-4(5H)-one;

  • (65): 4-(8-hydroxy-4-oxo-4,5-dihydrothieno[2,3-c]quinolin-9-yl)benzenesulfonamide;

  • (66): 9-(3-chloro-4-fluorophenyl)-8-hydroxythieno[2,3-c]quinolin-4(5H)-one;

  • (67): 9-(4-chloro-3-fluorophenyl)-8-hydroxythieno[2,3-c]quinolin-4(5H)-one;

  • (68): 9-(3,4-dichlorophenyl)-8-hydroxythieno[2,3-c]quinolin-4(5H)-one;

  • (69): 9-(4-fluorophenyl)-8-hydroxythieno[2,3-c]quinolin-4(5H)-one;

  • (70): 8-hydroxy-9-phenylthieno[2,3-c]quinolin-4(5H)-one;

  • (71): 9-(4-(difluoromethoxy)phenyl)-8-methoxythieno[2,3-c]quinolin-4(5H)-one;

  • (72): 9-(4-(aminomethyl)phenyl)-8-hydroxythieno[2,3-c]quinolin-4(5H)-one;

  • (73): 9-(4-(aminomethyl)phenyl)-8-hydroxythieno[2,3-c]quinolin-4(5H)-one;

  • (74): 9-(3-aminophenyl)-8-hydroxythieno[2,3-c]quinolin-4(5H)-one;

  • (75): 3-(8-hydroxy-4-oxo-4,5-dihydrothieno[2,3-c]quinolin-9-yl)benzenesulfonamide;

  • (76): 8-hydroxy-9-(3,4,5-trifluorophenyl)thieno[2,3-c]quinolin-4(5H)-one;

  • (77): N-(4-(8-hydroxy-4-oxo-4,5-dihydrothieno[2,3-c]quinolin-9-yl)phenyl)methanesulfonamide;

  • (78): 8-methoxy-9-phenylthieno[2,3-c]quinolin-4(5H)-one;

  • (79): 8-hydroxy-9-(naphthalen-2-yl)thieno[2,3-c]quinolin-4(5H)-one;

  • (80): 8-hydroxy-9-(4-(hydroxymethyl)phenyl)thieno[2,3-c]quinolin-4(5H)-one;

  • (81): 2-(4-(8-hydroxy-4-oxo-4,5-dihydrothieno[2,3-c]quinolin-9-yl)phenyl)acetonitrile;

  • (82): 8-hydroxy-9-(4-(methylsulfonyl)phenyl)thieno[2,3-c]quinolin-4(5H)-one;

  • (83): 8-hydroxy-9-(pyridin-4-yl)thieno[2,3-c]quinolin-4(5H)-one;

  • (84): 8-hydroxy-9-(1,2,3,6-tetrahydropyridin-4-yl)thieno[2,3-c]quinolin-4(5H)-one;

  • (85): 8-hydroxy-9-(4-hydroxy-3-methoxyphenyl)thieno[2,3-c]quinolin-4(5H)-one;

  • (86): 9-(3-fluoro-4-(morpholinomethyl)phenyl)-8-hydroxythieno[2,3-c]quinolin-4(5H)-one;

  • (87): 9-(3-(aminomethyl)phenyl)-8-hydroxythieno[2,3-c]quinolin-4(5H)-one;

  • (88): 9-(4-(aminomethyl)phenyl)-8-methoxythieno[2,3-c]quinolin-4(5H)-one;

  • (89): 9-(3-(difluoromethyl)phenyl)-8-methoxythieno[2,3-c]quinolin-4(5H)-one;

  • (90): 9-(3-(aminomethyl)phenyl)-8-hydroxy-2-methylthieno[2,3-c]quinolin-4(5H)-one;

  • (91): 9-cyclohexenyl-8-methoxythieno[2,3-c]quinolin-4(5H)-one;

  • (92): 9-(3,5-difluorophenyl)-8-hydroxythieno[2,3-c]quinolin-4(5H)-one;

  • (93): 9-(4-(2-(dimethylamino)ethyl)phenyl)-8-hydroxythieno[2,3-c]quinolin-4(5H)-one;

  • (94): 9-(3-(aminomethyl)phenyl)-8-methoxythieno[2,3-c]quinolin-4(5H)-one;

  • (95): 9-(4-(aminomethyl)phenyl)-8-hydroxy-2-methylthieno[2,3-c]quinolin-4(5H)-one;

  • (96): 9-cyclopropyl-8-hydroxythieno[2,3-c]quinolin-4(5H)-one;

  • (97): 9-([1,2,4]triazolo[1,5-a]pyridin-6-yl)-8-hydroxythieno[2,3-c]quinolin-4(5H)-one;

  • (98): 8-methoxy-9-(1,2,3,6-tetrahydropyridin-4-yl)thieno[2,3-c]quinolin-4(5H)-one;

  • (99): 9-cyclohexenyl-8-hydroxythieno[2,3-c]quinolin-4(5H)-one;

  • (100): 8-methoxy-9-(4-(2-(piperidin-1-yl)ethylamino)phenyl)thieno[2,3-c]quinolin-4(5H)-one;

  • (101): 9-(4-(aminomethyl)phenyl)-8-hydroxy-2-(morpholinomethyl)thieno[2,3-c]quinolin-4(5H)-one;

  • (102): 9-(1H-benzo[d]imidazol-5-yl)-8-hydroxythieno[2,3-c]quinolin-4(5H)-one;

  • (103): 9-(4-(difluoromethyl)phenyl)-8-methoxythieno[2,3-c]quinolin-4(5H)-one;

  • (104): 9-(4-(aminomethyl)phenyl)-8-methoxy-2-(morpholinomethyl)thieno[2,3-c]quinolin-4(5H)-one;

  • (105): 8-hydroxy-9-(4-(2-(piperidin-1-yl)ethylamino)phenyl)thieno[2,3-c]quinolin-4(5H)-one;

  • (106): 8-hydroxy-9-(4-(piperazin-1-yl)phenyl)thieno[2,3-c]quinolin-4(5H)-one;

  • (107): 8-methoxy-2,3-dihydro-1H-cyclopenta[c]quinolin-4(5H)-one;

  • (108): 8-hydroxy-2,3-dihydro-1H-cyclopenta[c]quinolin-4(5H)-one;

  • (109): 5-(8-hydroxy-4-oxo-4,5-dihydrothieno[2,3-c]quinolin-9-yl)benzo[d]oxazol-2(3H)-one;

  • (110): tert-butyl 4-(2-(hydroxy-4-oxo-4,5-dihydrothieno[2,3-c]quinolin-9-yl)benzylamino)ethyl)piperidine-1-carboxylate;

  • (111): 8-methoxy-9-(4-(piperazin-1-yl)phenyl)thieno[2,3-c]quinolin-4(5H)-one;

  • (112): 8-hydroxy-9-(4-(4-(methylsulfonyl)piperazin-1-yl)phenyl)thieno[2,3-c]quinolin-4(5H)-one;

  • (113): 8-hydroxy-9-(4-((piperidin-3-ylamino)methyl)phenyl)thieno[2,3-c]quinolin-4(5H)-one;

  • (114): N-(2-(dimethylamino)ethyl)-4-(8-hydroxy-4-oxo-4,5-dihydrothieno[2,3-c]quinolin-9-yl)benzamide;

  • (115): 9-(4-(3-(dimethylamino)propoxy)phenyl)-8-methoxythieno[2,3-c]quinolin-(5H)-one;

  • (116): 8-methoxy-9-(1-(piperidin-4-yl)-1H-pyrazol-4-yl)thieno[2,3-c]quinolin-4(5H)-one;

  • (117): 8-hydroxy-9-(1-(piperidin-4-yl)-1H-pyrazol-4-yl)thieno[2,3-c]quinolin-4(5H)-one;

  • (118): 8-methoxythiazolo[4,5-c]quinolin-4(5H)-one;

  • (119): 2-((4-(aminomethyl)piperidin-1-yl)methyl)-8-hydroxythieno[2,3-c]quinolin-4(5H)-one;

  • (120): N-(2-(dimethylamino)ethyl)-4-(8-methoxy-4-oxo-4,5-dihydrothieno[2,3-c]quinolin-9-yl)benzamide;

  • (121): 9-(4-(aminomethyl)phenyl)-8-hydroxy-2,3-dihydro-1H-cyclopenta[c]quinolin-4(5H)-one;

  • (122): (E)-butyl 3-(8-hydroxy-4-oxo-4,5-dihydrothieno[2,3-c]quinolin-9-yl)acrylate;

  • (123): 8-methoxy-9-(1H-pyrrolo[2,3-b]pyridin-5-yl)thieno[2,3-c]quinolin-4(5H)-one;

  • (124): 8-hydroxy-9-(1H-pyrrolo[2,3-b]pyridin-5-yl)thieno[2,3-c]quinolin-4(5H)-one;

  • (125): N-(methoxy-4-oxo-4,5-dihydrothieno[2,3-c]quinolin-9-yl)phenethyl)acetamide;

  • (126): N-(2-aminoethyl)-4-(8-hydroxy-4-oxo-4,5-dihydrothieno[2,3-c]quinolin-9-yl)benzamide;

  • (127): N-(2-aminoethyl)-4-(8-methoxy-4-oxo-4,5-dihydrothieno[2,3-c]quinolin-9-yl)benzamide;

  • (128): N-(hydroxy-4-oxo-4,5-dihydrothieno[2,3-c]quinolin-9-yl)phenethyl)acetamide;

  • (129): 4-(8-hydroxy-4 oxo-2,3,4,5-tetrahydro-1H-cyclopenta[c]quinolin-9-yl)benzenesulfonamide;

  • (130): 8-hydroxy-9-(4-(4-methylpiperazine-1-carbonyl)phenyl)thieno[2,3-c]quinolin-4(5H)-one;

  • (131): 8-methoxy-9-(4-(4-methylpiperazine-1-carbonyl)phenyl)thieno[2,3-c]quinolin-4(5H)-one;

  • (132): 8-hydroxy-9-(4-((4-methylpiperazin-1-yl)methyl)phenyl)thieno[2,3-c]quinolin-4(5H)-one;

  • (133): 8-methoxy-9-(4-((4-methylpiperazin-1-yl)methyl)phenyl)thieno[2,3-c]quinolin-4(5H)-one;

  • (134): (E)-9-(3-(diethylamino)prop-1-enyl)-8-methoxythieno[2,3-c]quinolin-4(5H)-one;

  • (135): (E)-9-(3-(4-(aminomethyl)piperidin-1-yl)prop-1-enyl)-8-methoxythieno[2,3-c]quinolin-4(5H)-one;

  • (136): (E)-9-(3-(2-(diethylamino)ethylamino)prop-1-enyl)-8-hydroxythieno[2,3-c]quinolin-4(5H)-one;

  • (137): N-(4-(8-hydroxy-4-oxo-2,3,4,5-tetrahydro-1H-cyclopenta[c]quinolin-9-yl)phenyl)methanesulfonamide;

  • (138): 9-(2-(dimethylamino)pyrimidin-5-yl)-8-hydroxythieno[2,3-c]quinolin-4(5H)-one;

  • (139): tert-butyl(1-(methoxy-4-oxo-4,5-dihydrothieno[2,3-c]quinolin-9-yl)benzyl)piperidin-4-yl)methylcarbamate;

  • (140): 8-hydroxy-9-(4-(4-methylpiperazin-1-yl)phenyl)thieno[2,3-c]quinolin-4(5H)-one;

  • (141): 8-methoxy-9-(4-(4-methylpiperazin-1-yl)phenyl)thieno[2,3-c]quinolin-4(5H)-one;

  • (142): 8-methoxy-9-(1-(methylsulfonyl)-1,2,3,6-tetrahydropyridin-4-yl)thieno[2,3-c]quinolin-4(5H)-one;

  • (143): (E)-9-(3-(diethylamino)prop-1-enyl)-8-hydroxythieno[2,3-c]quinolin-4(5H)-one;

  • (144): 9-(3-(4-(aminomethyl)piperidin-1-yl)propyl)-8-methoxythieno[2,3-c]quinolin-4(5H)-one;

  • (145): 9-(4-(3-(2-(diethylamino)ethylamino)propoxy)phenyl)-8-methoxythieno[2,3-c]quinolin-(5H)-one;

  • (146): 9-(4-(3-(diethylamino)propoxy)phenyl)-8-methoxythieno[2,3-c]quinolin-4(5H)-one;

  • (147): 9-(4-(3-(2-(diethylamino)ethylamino)propoxy)phenyl)-8-hydroxythieno[2,3-c]quinolin-(5H)-one;

  • (148): (E)-9-(3-(4-(aminomethyl)piperidin-1-yl)prop-1-enyl)-8-hydroxythieno[2,3-c]quinolin-4(5H)-one;

  • (149): 9-(4-(3-(dimethylamino)propoxy)phenyl)-8-hydroxythieno[2,3-c]quinolin-4(5H)-one;

  • (150): 8-hydroxy-9-(4-(2-(piperidin-1-yl)ethoxy)phenyl)thieno[2,3-c]quinolin-4(5H)-one;

  • (151): 9-(4-(2-(ethylamino)ethoxy)phenyl)-8-hydroxythieno[2,3-c]quinolin-4(5H)-one;

  • (152): (E)-9-(3-(4-aminopiperidin-1-yl)prop-1-enyl)-8-methoxythieno[2,3-c]quinolin-4(5H)-one;

  • (153): 9-(1-(2-aminoethyl)-1,2,3,6-tetrahydropyridin-4-yl)-8-methoxythieno[2,3-c]quinolin-4(5H)-one;

  • (154): 9-(4-(2-(ethylamino)ethoxy)phenyl)-8-methoxythieno[2,3-c]quinolin-4(5H)-one;

  • (155): 9-(4-(2-(diethylamino)ethoxy)phenyl)-8-hydroxythieno[2,3-c]quinolin-4(5H)-one;

  • (156): 9-(4-(2-(diethylamino)ethoxy)phenyl)-8-methoxythieno[2,3-c]quinolin-4(5H)-one;

  • (157): 9-(4-(2-(dimethylamino)ethoxy)phenyl)-8-hydroxythieno[2,3-c]quinolin-4(5H)-one;

  • (158): 9-(4-(2-(dimethylamino)ethoxy)phenyl)-8-methoxythieno[2,3-c]quinolin-4(5H)-one;

  • (159): 8-methoxy-9-(4-(2-(piperidin-1-yl)ethoxy)phenyl)thieno[2,3-c]quinolin-4(5H)-one;

  • (160): 8-methoxy-9-(3-(2-(4-methylpiperazin-1-yl)ethoxy)phenyl)thieno[2,3-c]quinolin-4(5H)-one;

  • (161): 9-(3-(2-(diethylamino)ethoxy)phenyl)-8-methoxythieno[2,3-c]quinolin-4(5H)-one;

  • (162): 9-(3-(3-(diethylamino)propoxy)phenyl)-8-methoxythieno[2,3-c]quinolin-4(5H)-one;

  • (163): 9-(4-(2-(dimethylamino)ethyl)phenyl)-8-methoxythieno[2,3-c]quinolin-4(5H)-one;

  • (164): 9-(4-((dimethylamino)methyl)phenyl)-8-methoxythieno[2,3-c]quinolin-4(5H)-one;

  • (165): 9-(4-((dimethylamino)methyl)phenyl)-8-hydroxythieno[2,3-c]quinolin-4(5H)-one;

  • (166): 9-(3-(2-(diethylamino)ethoxy)phenyl)-8-hydroxythieno[2,3-c]quinolin-4(5H)-one;

  • (167): 8-hydroxy-9-(3-(2-(4-methylpiperazin-1-yl)ethoxy)phenyl)thieno[2,3-c]quinolin-4(5H)-one;

  • (168): N-ethyl-N-(2-(4-(8-methoxy-4-oxo-4,5-dihydrothieno[2,3-c]quinolin-9-yl)phenylmethoxy-4-oxo-4,5-dihydrothieno[2,3-c]quinolin-9-yl)phenoxy)ethyl)methanesulfonamide;

  • (169): 9-(4-(2-aminoethyl)phenyl)-8-methoxythieno[2,3-c]quinolin-4(5H)-one;

  • (170): 2-(3-(8-hydroxy-4-oxo-4,5-dihydrothieno[2,3-c]quinolin-9-yl)phenyl)acetonitrile;

  • (171): 2-(3-(8-methoxy-4-oxo-4,5-dihydrothieno[2,3-c]quinolin-9-yl)phenyl)acetonitrile;

  • (172): 9-(1-(2-(dimethylamino)ethyl)-1,2,3,6-tetrahydropyridin-4-yl)-8-hydroxythieno[2,3-c]quinolin-4(5H)-one;

  • (173): N-(hydroxy-4-oxo-4,5-dihydrothieno[2,3-c]quinolin-9-yl)phenethyl)methanesulfonamide;

  • (174): 9-(1-(2-(diethylamino)ethyl)-1,2,3,6-tetrahydropyridin-4-yl)-8-hydroxythieno[2,3-c]quinolin-4(5H)-one;

  • (175): 9-(4-(2-aminoethyl)phenyl)-8-hydroxythieno[2,3-c]quinolin-4(5H)-one;

  • (176): 9-(4-(2-aminoethyl)phenyl)-8-hydroxythieno[2,3-c]quinolin-4(5H)-one;

  • (177): N-(methoxy-4-oxo-4,5-dihydrothieno[2,3-c]quinolin-9-yl)phenethyl)methanesulfonamide;

  • (178): N-(methoxy-4-oxo-4,5-dihydrothieno[2,3-c]quinolin-9-yl)phenethyl)methanesulfonamide;

  • (179): N-(2-aminoethyl)-4-(8-hydroxy-4-oxo-4,5-dihydrothieno[2,3-c]quinolin-9-yl)benzensulfonamide;

  • (180): 8-hydroxy-9-(1,2,3,6-tetrahydropyridin-4-yl)-2,3-dihydro-1H-cyclopenta[c]quinolin-4(5H)-one;

  • (181): 9-(4-(1-(dimethylamino)ethyl)phenyl)-8-hydroxy-2,3-dihydro-1H-cyclopenta[c]quinolin-4(5H)-one;

  • (182): 9-(4-(2-(dimethylamino)ethyl)phenyl)-8-methoxy-2,3-dihydro-1H-cyclopenta[c]quinolin-4(5H)-one;

  • (183): 9-(4-((diethylamino)methyl)phenyl)-8-methoxythieno[2,3-c]quinolin-4(5H)-one;

  • (184): 9-(4-((diethylamino)methyl)phenyl)-8-hydroxythieno[2,3-c]quinolin-4(5H)-one;

  • (185): 9-(3-(2-(dimethylamino)ethyl)phenyl)-8-hydroxythieno[2,3-c]quinolin-4(5H)-one;

  • (186): 9-(3-(2-aminoethyl)phenyl)-8-hydroxythieno[2,3-c]quinolin-4(5H)-one;

  • (187): 8-hydroxy-9-(4-((methylamino)methyl)phenyl)thieno[2,3-c]quinolin-4(5H)-one;

  • (188): 8-methoxy-9-(4-((methylamino)methyl)phenyl)thieno[2,3-c]quinolin-4(5H)-one;

  • (189): 9-(4-amino-3-methoxyphenyl)-8-methoxythieno[2,3-c]quinolin-4(5H)-one;

  • (190): 3-(8-hydroxy-4 oxo-4,5-dihydrothieno[2,3-c]quinolin-9-yl)benzonitrile;

  • (191): 9-(4-(1-(dimethylamino)ethyl)phenyl)-8-hydroxythieno[2,3-c]quinolin-4(5H)-one;

  • (192): 9-(4-(1-(dimethylamino)ethyl)phenyl)-8-hydroxythieno[2,3-c]quinolin-4(5H)-one;

  • (193): N-(1-(4-(8-hydroxy-4-oxo-4,5-dihydrothieno[2,3-c]quinolin-9-yl)phenyl)ethyl)methanesulfonamide;

  • (194): 8-hydroxy-9-(4-(1-(pyrrolidin-1-yl)ethyl)phenyl)thieno[2,3-c]quinolin-4(5H)-one;

  • (195): 9-(4-(1-aminoethyl)phenyl)-8-hydroxythieno[2,3-c]quinolin-4(5H)-one;

  • (196): 9-(4-(1-(diethylamino)ethyl)phenyl)-8-hydroxythieno[2,3-c]quinolin-4(5H)-one;

  • (197): N-(2-aminoethyl)-4-(8-methoxy-4-oxo-4,5-dihydrothieno[2,3-c]quinolin-9-yl)benzensulfonamide;

  • (198): N-(2-(dimethylamino)ethyl)-4-(8-methoxy-4-oxo-4,5-dihydrothieno[2,3-c]quinolin-9-yl)benzenesulfonamide;

  • (199): 4-(8-hydroxy-4-oxo-4,5-dihydrothieno[2,3-c]quinolin-9-yl)-N-(pyrrolidin-3-yl)benzenesulfonamide;

  • (200): N-(azetidin-3-yl)-4-(8-hydroxy-4-oxo-4,5-dihydrothieno[2,3-c]quinolin-9-yl)benzensulfonamide;

  • (201): 9-(4-(2-(diethylamino)ethyl)phenyl)-8-hydroxythieno[2,3-c]quinolin-4(5H)-one;

  • (202): 2-amino-N-(3-(8-methoxy-4-oxo-4,5-dihydrothieno[2,3-c]quinolin-9-yl)phenyl)ethanesulfonamide;

  • (203): 4-(8-hydroxy-4-oxo-4,5-dihydrothieno[2,3-c]quinolin-9-yl)benzonitrile;

  • (204): 4-(8-methoxy-4-oxo-4,5-dihydrothieno[2,3-c]quinolin-9-yl)benzonitrile;

  • (205): (E)-9-(3-(3-aminopyrrolidin-1-yl)prop-1-enyl)-8-methoxythieno[2,3-c]quinolin-4(5H)-one;

  • (206): N-(2-hydroxyethyl)-4-(8-methoxy-4-oxo-4,5-dihydrothieno[2,3-c]quinolin-9-yl)benzenesulfonamide;

  • (207): 8-methoxy-9-(5-methoxypyridin-3-yl)thieno[2,3-c]quinolin-4(5H)-one;

  • (208): 8-methoxy-9-(5-methoxypyridin-3-yl)-2,3-dihydro-1H-cyclopenta[c]quinolin-4(5H)-one;

  • (209): 9-(4-(3-aminopyrrolidin-1-ylsulfonyl)phenyl)-8-hydroxythieno[2,3-c]quinolin-4(5H)-one;

  • (210): N-(2-bromoethyl)-4-(8-hydroxy-4-oxo-4,5-dihydrothieno[2,3-c]quinolin-9-yl)benzensulfonamide;

  • (211): 9-(4-((diisopropylamino)methyl)phenyl)-8-methoxythieno[2,3-c]quinolin-4(5H)-one;

  • (212): N-(hydroxy-4-oxo-4,5-dihydrothieno[2,3-c]quinolin-9-yl)benzyl)methanesulfonamide;

  • (213): 9-(4-((isopropylamino)methyl)phenyl)-8-methoxythieno[2,3-c]quinolin-4(5H)-one;

  • (214): 2-(dimethylamino)-N-(3-(8-hydroxy-4-oxo-4,5-dihydrothieno[2,3-c]quinolin-9-yl)phenyl)ethanesulfonamide;

  • (215): 2-amino-N-(3-(8-hydroxy-4-oxo-4,5-dihydrothieno[2,3-c]quinolin-9-yl)phenyl)ethanesulfonamide;

  • (216): 8-methoxy-9-(4-(1-(pyrrolidin-1-yl)ethyl)phenyl)thieno[2,3-c]quinolin-4(5H)-one;

  • (217): 9-(4-amino-3-hydroxyphenyl)-8-hydroxythieno[2,3-c]quinolin-4(5H)-one;

  • (218): N-(2-methoxy-4-(8-methoxy-4-oxo-4,5-dihydrothieno[2,3-c]quinolin-9-yl)phenyl)methanesulfonamide;

  • (219): 9-(3,5-difluoro-4-hydroxyphenyl)-8-methoxythieno[2,3-c]quinolin-4(5H)-one;

  • (220): N-(2-hydroxy-4-(8-hydroxy-4-oxo-4,5-dihydrothieno[2,3-c]quinolin-9-yl)phenyl)methanesulfonamide;

  • (221): 9-(4-((4-(aminomethyl)piperidin-1-yl)methyl)-3-fluorophenyl)-8-methoxythieno[2,3-c]quinolin-4(5H)-one;

  • (222): 9-(4-(2-(dimethylamino)ethyl)phenyl)-6-fluoro-8-methoxythieno[2,3-c]quinolin-4(5H)-one;

  • (223): 9-(3,5-difluoro-4-hydroxyphenyl)-8-hydroxythieno[2,3-c]quinolin-4(5H)-one;

  • (224): 6-fluoro-8-methoxy-9-(1,2,3,6-tetrahydropyridin-4-yl)thieno[2,3-c]quinolin-4(5H)-one;

  • (225): 9-(4-(1-(dimethylamino)ethyl)phenyl)-6-fluoro-8-hydroxythieno[2,3-c]quinolin-(5H)-one;

  • (226): 9-(4-((diethylamino)methyl)-3-fluorophenyl)-8-methoxythieno[2,3-c]quinolin-4(5H)-one;

  • (227): (E)-9-(3-(3-hydroxypyrrolidin-1-yl)prop-1-enyl)-8-methoxythieno[2,3-c]quinolin-4(5H)-one;

  • (228): (E)-8-hydroxy-9-(3-(3-hydroxypyrrolidin-1-yl)prop-1-enyl)thieno[2,3-c]quinolin-4(5H)-one

  • (229): 8-hydroxy-9-(4-((isopropylamino)methyl)phenyl)thieno[2,3-c]quinolin-4(5H)-one;

  • (230): (E)-9-(3-(3-aminoazetidin-1-yl)prop-1-enyl)-8-hydroxythieno[2,3-c]quinolin-4(5H)-one;

  • (231): (E)-8-methoxy-9-(3-(2-(methylsulfonyl)ethylamino)prop-1-enyl)thieno[2,3-c]quinolin-4(5H)-one;

  • (232): (S)-9-(4-(1-aminoethyl)phenyl)-8-methoxythieno[2,3-c]quinolin-4(5H)-one;

  • (233): (S)-9-(4-(1-aminoethyl)phenyl)-8-hydroxythieno[2,3-c]quinolin-4(5H)-one;

  • (234): 8-hydroxy-9-(5-hydroxypyridin-3-yl)-2,3-dihydro-1H-cyclopenta[c]quinolin-4(5H)-one;

  • (235): 9-(4-((4-(aminomethyl)piperidin-1-yl)methyl)-3-fluorophenyl)-8-hydroxythieno[2,3-c]quinolin-4(5H)-one;

  • (236): 8-methoxy-9-(4-(1-(2-(methylsulfonyl)ethylamino)ethyl)phenyl)thieno[2,3-c]quinolin-4(5H)-one;

  • (237): 9-(4-((3-aminopyrrolidin-1-yl)methyl)-3-fluorophenyl)-8-methoxythieno[2,3-c]quinolin-4(5H)-one;

  • (238): (E)-9-(3-(3-aminoazetidin-1-yl)prop-1-enyl)-8-methoxythieno[2,3-c]quinolin-4(5H)-one;

  • (239): (E)-9-(3-(ethylamino)prop-1-enyl)-8-hydroxythieno[2,3-c]quinolin-4(5H)-one;

  • (240): 9-(4-((3-aminopiperidin-1-yl)methyl)-3-fluorophenyl)-8-hydroxythieno[2,3-c]quinolin-4(5H)-one;

  • (241): 9-(4-((3-aminopyrrolidin-1-yl)methyl)-3-fluorophenyl)-8-hydroxythieno[2,3-c]quinolin-4(5H)-one;

  • (242): 9-(4-((3-aminopiperidin-1-yl)methyl)-3-fluorophenyl)-8-methoxythieno[2,3-c]quinolin-4(5H)-one;

  • (243): 8-hydroxy-9-(4-(1-(2-(methylsulfonyl)ethylamino)ethyl)phenyl)thieno[2,3-c]quinolin-4(5H)-one;

  • (244): (E)-9-(3-(3-aminopiperidin-1-yl)prop-1-enyl)-8-methoxythieno[2,3-c]quinolin-4(5H)-one;

  • (245): (E)-9-(3-(3-aminopyrrolidin-1-yl)prop-1-enyl)-8-hydroxythieno[2,3-c]quinolin-4(5H)-one;

  • (246): (E)-9-(3-(3-aminopiperidin-1-yl)prop-1-enyl)-8-hydroxythieno[2,3-c]quinolin-4(5H)-one;

  • (247): (E)-8-hydroxy-9-(3-(2-(methylsulfonyl)ethylamino)prop-1-enyl)thieno[2,3-c]quinolin-4(5H)-one;

  • (248): 8-methoxy-9-(4-(2-(2-(methylsulfonyl)ethylamino)ethyl)phenyl)thieno[2,3-c]quinolin-(5H)-one;

  • (249): 2-(2-fluoro-4-(8-methoxy-4-oxo-4,5-dihydrothieno[2,3-c]quinolin-9-yl)phenyl)acetonitrile;

  • (250): (E)-N-(1-(3-(8-methoxy-4-oxo-4,5-dihydrothieno[2,3-c]quinolin-9-yl)allyl)azetidin-3-yl)methanesulfonamide;

  • (251): 4-(8-methoxy-4-oxo-4,5-dihydrothieno[2,3-c]quinolin-9-yl)-N,N-dimethylbenzenesulfonamide;

  • (252): 4-(8-hydroxy-4-oxo-4,5-dihydrothieno[2,3-c]quinolin-9-yl)-N-methylbenzenesulfonamide;

  • (253): tert-butyl (5-(8-methoxy-4-oxo-4,5-dihydrothieno[2,3-c]quinolin-9-yl)furan-2-yl)methylcarbamate;

  • (254): N-(4-(8-hydroxy-4-oxo-4,5-dihydrothieno[2,3-c]quinolin-9-yl)-2-methylphenyl)methanesulfonamide;

  • (255): N-(4-(8-methoxy-1-oxo-4,5-dihydrothieno[2,3-c]quinolin-9-yl)-2-methylphenyl)methanesulfonamide;

  • (256): 9-(4-(aminomethyl)phenyl)-6-fluoro-8-hydroxythieno[2,3-c]quinolin-4(5H)-one;

  • (257): 9-(4-(aminomethyl)phenyl)-6-fluoro-8-methoxythieno[2,3-c]quinolin-4(5H)-one;

  • (258): 6-fluoro-8-hydroxy-9-(1,2,3,6-tetrahydropyridin-4-yl)thieno[2,3-c]quinolin-4(5H)-one;

  • (259): 9-(4-((diethylamino)methyl)-3-fluorophenyl)-8-hydroxythieno[2,3-c]quinolin-4(5H)-one;

  • (260): 8-methoxy-9-(4-(1-(piperidin-1-yl)ethyl)phenyl)thieno[2,3-c]quinolin-4(5H)-one;

  • (261): 2-(2-fluoro-4-(8-hydroxy-4-oxo-4,5-dihydrothieno[2,3-c]quinolin-9-yl)phenyl)acetonitrile;

  • (262): 8-hydroxy-9-(4-(1-(piperidin-1-yl)ethyl)phenyl)thieno[2,3-c]quinolin-4(5H)-one;

  • (263): (E)-9-(3-(3-(dimethylamino)piperidin-1-yl)prop-1-enyl)-8-hydroxythieno[2,3-c]quinolin-4(5H)-one;

  • (264): (E)-9-(3-(3-(dimethylamino)pyrrolidin-1-yl)prop-1-enyl)-8-hydroxythieno[2,3-c]quinolin-4(5H)-one;

  • (265): 9-(4-(2-aminoethyl)-3-fluorophenyl)-8-methoxythieno[2,3-c]quinolin-4(5H)-one;

  • (266): 9-(5-(aminomethyl)thiophen-2-yl)-8-hydroxythieno[2,3-c]quinolin-4(5H)-one;

  • (267): 9-(4-((ethylamino)methyl)phenyl)-8-hydroxythieno[2,3-c]quinolin-4(5H)-one;

  • (268): (E)-9-(3-(4-aminopiperidin-1-yl)prop-1-enyl)-8-hydroxythieno[2,3-c]quinolin-4(5H)-one;

  • (269): 9-(4-((ethylamino)methyl)phenyl)-8-methoxythieno[2,3-c]quinolin-4(5H)-one;

  • (270): 9-(4-(aminomethyl)phenyl)-6-bromo-8-hydroxythieno[2,3-c]quinolin-4(5H)-one;

  • (271): 9-(3-chloro-4-((diethylamino)methyl)phenyl)-8-methoxythieno[2,3-c]quinolin-4(5H)-one;

  • (272): (R)-9-(4-(1-(dimethylamino)ethyl)phenyl)-8-hydroxythieno[2,3-c]quinolin-4(5H)-one;

  • (273): 9-(4-(3-aminopropyl)phenyl)-8-hydroxythieno[2,3-c]quinolin-4(5H)-one;

  • (274): (R)-9-(4-(1-aminoethyl)phenyl)-8-methoxythieno[2,3-c]quinolin-4(5H)-one;

  • (275): (R)-9-(4-(1-aminoethyl)phenyl)-8-hydroxythieno[2,3-c]quinolin-4(5H)-one;

  • (276): 9-(4-(2-aminoethyl)-3-fluorophenyl)-8-hydroxythieno[2,3-c]quinolin-4(5H)-one;

  • (277): 9-(4-(1-amino-2-methylpropan-2-yl)phenyl)-8-hydroxythieno[2,3-c]quinolin-4(5H)-one;

  • (278): 9-(3-fluoro-4-((3-hydroxypyrrolidin-1-yl)methyl)phenyl)-8-hydroxythieno[2,3-c]quinolin-4(5H)-one;

  • (279): 9-(3-fluoro-4-((3-hydroxypyrrolidin-1-yl)methyl)phenyl)-8-methoxythieno[2,3-c]quinolin-4(5H)-one;

  • (280): 4-(8-methoxy-4-oxo-4,5-dihydrothieno[2,3-c]quinolin-9-yl)-N-(2,2,2-trifluoroethyl)benzenesulfonamide;

  • (281): 4-(8-hydroxy-4-oxo-4,5-dihydrothieno[2,3-c]quinolin-9-yl)-N-(2,2,2-trifluoroethyl)benzenesulfonamide;

  • (282): N-(2-(dimethylamino)ethyl)-4-(8-hydroxy-4-oxo-4,5-dihydrothieno[2,3-c]quinolin-9-yl)benzenesulfonamide;

  • (283): 8-hydroxy-9-(4-((2-(methylsulfonyl)ethylamino)methyl)phenyl)thieno[2,3-c]quinolin-4(5H)-one;

  • (284): 9-(3-(3-(dimethylamino)pyrrolidin-1-yl)propyl)-8-hydroxythieno[2,3-c]quinolin-4(5H)-one;

  • (285): 9-(1-(2-aminoethyl)-1H-pyrazol-4-yl)-8-methoxythieno[2,3-c]quinolin-4(5H)-one;

  • (286): 9-(3-chloro-4-((diethylamino)methyl)phenyl)-8-hydroxythieno[2,3-c]quinolin-4(5H)-one;

  • (287): 4-(7-fluoro-8-methoxy-4-oxo-4,5-dihydrothieno[2,3-c]quinolin-9-yl)-N-(2-hydroxyethyl)benzenesulfonamide;

  • (288): 9-(3-acetylphenyl)-8-methoxythieno[2,3-c]quinolin-4(5H)-one;

  • (289): 2-fluoro-4-(8-hydroxy-4-oxo-4,5-dihydrothieno[2,3-c]quinolin-9-yl)-N-(2-hydroxyethyl)benzamide;

  • (290): 3-(4-(8-hydroxy-4-oxo-4,5-dihydrothieno[2,3-c]quinolin-9-yl)phenyl)propanenitrile;

  • (291): 9-(4-acetylphenyl)-8-methoxythieno[2,3-c]quinolin-4(5H)-one;

  • (292): 2-fluoro-N-(2-hydroxyethyl)-4-(8-methoxy-4-oxo-4,5-dihydrothieno[2,3-c]quinolin-9-yl)benzamide;

  • (293): 4-(8-hydroxy-4-oxo-4,5-dihydrothieno[2,3-c]quinolin-9-yl)-N-(2-hydroxyethyl)benzamide;

  • (294): 1,1-diethyl-3-(hydroxy-4-oxo-4,5-dihydrothieno[2,3-c]quinolin-9-yl)benzyl)urea;

  • (295): N-(2-hydroxyethyl)-4-(8-methoxy-4-oxo-4,5-dihydrothieno[2,3-c]quinolin-9-yl)benzamide;

  • (296): 9-(4-acetylphenyl)-8-hydroxythieno[2,3-c]quinolin-4(5H)-one;

  • (297): N-(2-bromoethyl)-2-fluoro-4-(8-hydroxy-4-oxo-4,5-dihydrothieno[2,3-c]quinolin-9-yl)benzenesulfonamide;

  • (298): 9-(3-(3-(dimethylamino)piperidin-1-yl)propyl)-8-hydroxythieno[2,3-c]quinolin-4(5H)-one;

  • (299): N-(2-fluoro-4-(8-hydroxy-4-oxo-4,5-dihydrothieno[2,3-c]quinolin-9-yl)phenethyl)methanesulfonamide;

  • (300): 9-(3-fluoro-4-(2-(methylsulfonamido)ethyl)phenyl)-4-oxo-4,5-dihydrothieno[2,3-c]quinolin-8-yl methanesulfonate;

  • (301): (R)—N-(1-(4-(8-hydroxy-4-oxo-4,5-dihydrothieno[2,3-c]quinolin-9-yl)phenyl)ethyl)methanesulfonamide;

  • (302): (R)-9-(4-(1-(methylsulfonamido)ethyl)phenyl)-4-oxo-4,5-dihydrothieno[2,3-c]quinolin-8-yl methanesulfonate;

  • (303): 2-fluoro-N-(2-hydroxyethyl)-4-(8-methoxy-4-oxo-4,5-dihydrothieno[2,3-c]quinolin-9-yl)benzenesulfonamide;

  • (304): 4-(8-hydroxy-4-oxo-4,5-dihydrothieno[2,3-c]quinolin-9-yl)-N,N-dimethylbenzenesulfonamide;

  • (305): 9-(4-(2-(dimethylamino)ethyl)phenyl)-7-fluoro-8-methoxythieno[2,3-c]quinolin-4(5H)-one;

  • (306): N-(2-bromoethyl)-4-(7-fluoro-8-hydroxy-4-oxo-4,5-dihydrothieno[2,3-c]quinolin-9-yl)benzenesulfonamide;

  • (307): 4-(7-fluoro-8-hydroxy-4-oxo-4,5-dihydrothieno[2,3-c]quinolin-9-yl)-N-(2-hydroxyethyl)benzenesulfonamide;

  • (308): 9-(4-(1-(dimethylamino)-2-methylpropan-2-yl)phenyl)-8-hydroxythieno[2,3-c]quinolin-4(5H)-one;

  • (309): N-(2-chloro-4-(8-methoxy-4-oxo-4,5-dihydrothieno[2,3-c]quinolin-9-yl)benzyl)-N-methyl methanesulfonamide;

  • (310): 4-(8-hydroxy-4 oxo-4,5-dihydrothieno[2,3-c]quinolin-9-yl)-N-(2-methoxyethyl)benzenesulfonamide;

  • (3H): (E)-3-(8-methoxy-4-oxo-4,5-dihydrothieno[2,3-c]quinolin-9-yl)-2-methylacrylonitrile;

  • (312): N-(2-fluoro-4-(8-methoxy-4-oxo-4,5-dihydrothieno[2,3-c]quinolin-9-yl)phenethyl)methanesulfonamide;

  • (313): 8-hydroxy-9-(4-(1-hydroxyethyl)phenyl)thieno[2,3-c]quinolin-4(5H)-one;

  • (314): 9-(4-(1-(cyclopentylamino)ethyl)phenyl)-8-hydroxythieno[2,3-c]quinolin-4(5H)-one;

  • (315): 9-(4-(1-(cyclopentylamino)ethyl)phenyl)-8-methoxythieno[2,3-c]quinolin-4(5H)-one;

  • (316): 4-(8-hydroxy-4-oxo-4,5-dihydrothieno[2,3-c]quinolin-9-yl)-N-(2-hydroxyethyl)benzenesulfonamide;

  • (317): 9-(5-(aminomethyl)furan-2-yl)-8-hydroxythieno[2,3-c]quinolin-4(5H)-one;

  • (318): 9-(3-chloro-4-((methylamino)methyl)phenyl)-8-methoxythieno[2,3-c]quinolin-4(5H)-one;

  • (319): 9-(4-(2-aminopropan-2-yl)phenyl)-8-hydroxythieno[2,3-c]quinolin-4(5H)-one;

  • (320): N-(3-hydroxypropyl)-4-(8-methoxy-4-oxo-4,5-dihydrothieno[2,3-c]quinolin-9-yl)benzenesulfonamide;

  • (321): 2-fluoro-4-(8-hydroxy-4-oxo-4,5-dihydrothieno[2,3-c]quinolin-9-yl)-N-(2-hydroxyethyl)benzenesulfonamide;

  • (322): 4-(8-hydroxy-4-oxo-4,5-dihydrothieno[2,3-c]quinolin-9-yl)-N-(3-hydroxypropyl)benzensulfonamide;

  • (323): N-(3-bromopropyl)-4-(8-hydroxy-4-oxo-4,5-dihydrothieno[2,3-c]quinolin-9-yl)benzenesulfonamide;

  • (324): 2-fluoro-4-(8-hydroxy-4-oxo-4,5-dihydrothieno[2,3-c]quinolin-9-yl)-N-(2-methoxyethyl)benzenesulfonamide;

  • (325): 9-(3-chloro-4-((methylamino)methyl)phenyl)-8-hydroxythieno[2,3-c]quinolin-4(5H)-one;

  • (326): 9-(4-(aminomethyl)phenyl)-4 oxo-4,5-dihydrothieno[2,3-c]quinoline-8-carbonitrile;

  • (327): 9-(4-(2-(dimethylamino)ethyl)-3-fluorophenyl)-8-hydroxythieno[2,3-c]quinolin-(5H)-one;

  • (328): 9-(4-(aminomethyl)phenyl)-6,7-dichloro-8-hydroxythieno[2,3-c]quinolin-4(5H)-one;

  • (329): 9-(4-(aminomethyl)phenyl)-6-chloro-8-hydroxythieno[2,3-c]quinolin-4(5H)-one;

  • (330): 9-(4-(aminomethyl)phenyl)-4-oxo-4,5-dihydrothieno[2,3-c]quinolin-8-yl trifluoromethanesulfonate;

  • (331): 9-(4-(2-(dimethylamino)ethyl)phenyl)-8-methoxythieno[2,3-c]quinolin-4(5H)-one;

  • (332): N-(2-chloroethyl)-4-(8-hydroxy-4-oxo-4,5-dihydrothieno[2,3-c]quinolin-9-yl)benzenesulfonamide;

  • (333): N-(2-fluoroethyl)-4-(8-methoxy-4-oxo-4,5-dihydrothieno[2,3-c]quinolin-9-yl)benzenesulfonamide;

  • (334): 9-(4-(2-aminopropan-2-yl)phenyl)-6-chloro-8-hydroxythieno[2,3-c]quinolin-4(5H)-one;

  • (335): (S)-9-(4-(1-(dimethylamino)ethyl)phenyl)-8-hydroxythieno[2,3-c]quinolin-4(5H)-one;

  • (336): 9-(4-(1-aminopropyl)phenyl)-8-hydroxythieno[2,3-c]quinolin-4(5H)-one;

  • (337): 9-(4-(1-aminopropyl)phenyl)-8-methoxythieno[2,3-c]quinolin-4(5H)-one;

  • (338): 9-(4-(1-(diethylamino)propyl)phenyl)-8-hydroxythieno[2,3-c]quinolin-4(5H)-one;

  • (339): 9-(4-(1-(dimethylamino)propyl)phenyl)-8-hydroxythieno[2,3-c]quinolin-4(5H)-one;

  • (340): 9-amino-8-methoxythieno[2,3-c]quinolin-4(5H)-one;

  • (341): 9-(4-(1-(dimethylamino)ethyl)phenyl)-6,7-difluoro-8-hydroxythieno[2,3-c]quinolin-4(5H)-one;

  • (342): 9-(4-(1-(dimethylamino)ethyl)phenyl)-6,7-difluoro-8-methoxythieno[2,3-c]quinolin-4(5H)-one;

  • (343): N-cyclopropyl-4-(8-methoxy-4-oxo-4,5-dihydrothieno[2,3-c]quinolin-9-yl)benzenesulfonamide;

  • (344): N-cyclopropyl-4-(8-hydroxy-4-oxo-4,5-dihydrothieno[2,3-c]quinolin-9-yl)benzenesulfonamide;

  • (345): 9-(2-amino-2,3-dihydro-1H-inden-5-yl)-8-hydroxythieno[2,3-c]quinolin-4(5H)-one;

  • (346): 9-(4-(1-(dimethylamino)ethyl)phenyl)thieno[2,3-c]quinolin-4(5H)-one;

  • (347): (S)—N-(1-(4-(8-hydroxy-4-oxo-4,5-dihydrothieno[2,3-c]quinolin-9-yl)phenyl)ethyl)methanesulfonamide;

  • (348): 9-(4-(1-(aminomethyl)cyclopropyl)phenyl)-8-hydroxythieno[2,3-c]quinolin-4(5H)-one;

  • (349): 9-(4-(1-(dimethylamino)ethyl)-3-fluorophenyl)-8-hydroxythieno[2,3-c]quinolin-4(5H)-one;

  • (350): N-(1-(hydroxymethyl)cyclopentyl)-4-(8-methoxy-4-oxo-4,5-dihydrothieno[2,3-c]quinolin-9-yl)benzenesulfonamide;

  • (351): 9-(2-(diethylamino)-2,3-dihydro-1H-inden-5-yl)-8-hydroxythieno[2,3-c]quinolin-4(5H)-one;

  • (352): 9-(2-(dimethylamino)-2,3-dihydro-1H-inden-5-yl)-8-hydroxythieno[2,3-c]quinolin-4(5H)-one;

  • (353): 8-hydroxy-9-(1,2,3,4-tetrahydroisoquinolin-7-yl)thieno[2,3-c]quinolin-4(5H)-one;

  • (354): 8-methoxy-9-(1,2,3,4-tetrahydroisoquinolin-7-yl)thieno[2,3-c]quinolin-4(5H)-one;

  • (355): 3-(3-(8-hydroxy-4-oxo-4,5-dihydrothieno[2,3-c]quinolin-9-yl)phenyl)propanenitrile;

  • (356): 9-(4-(1-(diethylamino)ethyl)-3-fluorophenyl)-8-hydroxythieno[2,3-c]quinolin-4(5H)-one;

  • (357): 1-(4-(8-methoxy-4-oxo-4,5-dihydrothieno[2,3-c]quinolin-9-yl)phenyl)cyclopropanecarbonitrile;

  • (358): 9-(2-ethyl-1,2,3,4-tetrahydroisoquinolin-7-yl)-8-hydroxythieno[2,3-c]quinolin-4(5H)-one;

  • (359): 9-(4-(1-aminoethyl)-3-fluorophenyl)-8-hydroxythieno[2,3-c]quinolin-4(5H)-one;

  • (360): 3-(3-(8-methoxy-4-oxo-4,5-dihydrothieno[2,3-c]quinolin-9-yl)phenyl)propanenitrile;

  • (361): 1-(4-(8-hydroxy-4-oxo-4,5-dihydrothieno[2,3-c]quinolin-9-yl)phenyl)cyclopropanecarbonitrile;

  • (362): 9-(2-amino-2,3-dihydro-1H-inden-5-yl)-8-methoxythieno[2,3-c]quinolin-4(5H)-one;

  • (363): N-isopentyl-4-(8-methoxy-4-oxo-4,5-dihydrothieno[2,3-c]quinolin-9-yl)benzenesulfonamide;

  • (364): 9-(2-(dimethylamino)-2,3-dihydro-1H-inden-5-yl)-8-methoxythieno[2,3-c]quinolin-4(5H)-one;

  • (365): 9-(4-(1-(ethylamino)ethyl)phenyl)-8-methoxythieno[2,3-c]quinolin-4(5H)-one;

  • (366): 6-chloro-9-(4-(1-(dimethylamino)ethyl)phenyl)-8-hydroxythieno[2,3-c]quinolin-4(5H)-one;

  • (367): 9-(4-(cyclopropanecarbonyl)phenyl)-8-methoxythieno[2,3-c]quinolin-4(5H)-one;

  • (368): 9-(4-(aminomethyl)phenyl)-4-oxo-4,5-dihydrothieno[2,3-c]quinoline-8-carboxamide;

  • (369): 9-(2-aminoethyl)-8-methoxythieno[2,3-c]quinolin-4(5H)-one;

  • (370): 8-hydroxy-9-(4-(2-hydroxyethylsulfonyl)phenyl)thieno[2,3-c]quinolin-4(5H)-one;

  • (371): 9-(4-(2-hydroxyethylsulfonyl)phenyl)-8-methoxythieno[2,3-c]quinolin-4(5H)-one;

  • (372): 9-(1-ethylindolin-5-yl)-8-hydroxythieno[2,3-c]quinolin-4(5H)-one;

  • (373): 9-(4-(1-aminopropan-2-yl)phenyl)-8-methoxythieno[2,3-c]quinolin-4(5H)-one;

  • (374): 8-hydroxy-9-(2-methyl-1,2,3,4-tetrahydroisoquinolin-7-yl)thieno[2,3-c]quinolin-4(5H)-one;

  • (375): 9-(4-(1-aminoethyl)-3-fluorophenyl)-8-methoxythieno[2,3-c]quinolin-4(5H)-one;

  • (376): 8-hydroxy-9-(1-methylindolin-5-yl)thieno[2,3-c]quinolin-4(5H)-one;

  • (377): 8-hydroxy-9-(indolin-5-yl)thieno[2,3-c]quinolin-4(5H)-one;

  • (378): 9-(indolin-5-yl)-8-methoxythieno[2,3-c]quinolin-4(5H)-one;

  • (379): 9-(4-(1-((dimethylamino)methyl)cyclopropyl)phenyl)-8-hydroxythieno[2,3-c]quinolin-4(5H)-one;

  • (380): 4-(8-methoxy-4-oxo-4,5-dihydrothieno[2,3-c]quinolin-9-yl)-N-propylbenzenesulfonamide;

  • (381): N-(cyclopropylmethyl)-4-(8-methoxy-4-oxo-4,5-dihydrothieno[2,3-c]quinolin-9-yl)benzenesulfonamide;

  • (382): N-(3,3-dimethylbutyl)-4-(8-methoxy-4-oxo-4,5-dihydrothieno[2,3-c]quinolin-9-yl)benzenesulfonamide;

  • (383): 4-(8-hydroxy-4-oxo-4,5-dihydrothieno[2,3-c]quinolin-9-yl)-N-isopentylbenzenesulfonamide;

  • (384): N-(3,3-dimethylbutyl)-4-(8-hydroxy-4-oxo-4,5-dihydrothieno[2,3-c]quinolin-9-yl)benzenesulfonamide;

  • (385): 9-(4-(1-(ethylamino)ethyl)phenyl)-8-hydroxythieno[2,3-c]quinolin-4(5H)-one;

  • (386): 3-(4-(8-methoxy-4-oxo-4,5-dihydrothieno[2,3-c]quinolin-9-yl)phenyl)-3-oxopropanenitrile;

  • (387): (E)-9-(2-ethoxyvinyl)-8-methoxythieno[2,3-c]quinolin-4(5H)-one;

  • (388): N-(1-(4-(8-hydroxy-4-oxo-4,5-dihydrothieno[2,3-c]quinolin-9-yl)phenyl)ethyl)acetamide;

  • (389): 4-(8-methoxy-4-oxo-4,5-dihydrothieno[2,3-c]quinolin-9-yl)-N-(3,3,3-trifluoropropyl)benzenesulfonamide;

  • (390): 4-(8-hydroxy-4-oxo-4,5-dihydrothieno[2,3-c]quinolin-9-yl)-N-(1-(hydroxymethyl)cyclopentyl)benzenesulfonamide;

  • (391): N-(2,2-difluoroethyl)-4-(8-methoxy-4-oxo-4,5-dihydrothieno[2,3-c]quinolin-9-yl)benzenesulfonamide;

  • (1031): 8-methoxy-9-(4-(1-methoxyethyl)phenyl)thieno[2,3-c]quinolin-4(5H)-one;

  • (1032): 9-(4-(1-aminoethyl)phenyl)-6-bromo-8-hydroxythieno[2,3-c]quinolin-4(5H)-one;

  • (1033): 8-methoxy-9-(2-((piperidin-3-ylmethyl)amino)ethyl)thieno[2,3-c]quinolin-4(5H)-one;

  • (1034): 9-(2-(4-((dimethylamino)methyl)piperidin-1-yl)ethyl)-8-methoxythieno[2,3-c]quinolin-4(5H)-one;

  • (1035): tert-butyl 4-((2-(8-methoxy-4-oxo-4,5-dihydrothieno[2,3-c]quinolin-9-yl)ethyl)amino)piperidine-1-carboxylate;

  • (1036): 8-methoxy-9-(2-(piperidin-4-ylamino)ethyl)thieno[2,3-c]quinolin-4(5H)-one;

  • (1037): 4-(8-hydroxy-4-oxo-4,5-dihydrothieno[2,3-c]quinolin-9-yl)-N-(3,3,3-trifluoropropyl)benzenesulfonamide;

  • (1038): 3H-pyrrolo[2,3-c]quinolin-4(5H)-one;

  • (1039): 9-(4-(1-aminoethyl)phenyl)-6-cyclopropyl-8-hydroxythieno[2,3-c]quinolin-4(5H)-one;

  • (1040): 9-(4-(1-aminoethyl)phenyl)-8-hydroxy-4-oxo-4,5-dihydrothieno[2,3-c]quinoline-6-carbonitrile;

  • (1041): 9-(4-(1-aminoethyl)phenyl)-6-chloro-8-hydroxythieno[2,3-c]quinolin-4(5H)-one;

  • (1042): 8-hydroxy-9-(2-(4-((methylamino)methyl)piperidin-1-yl)ethyl)thieno[2,3-c]quinolin-4(5H)-one;

  • (1043): 8-methoxy-9-(2-(4-((methylamino)methyl)piperidin-1-yl)ethyl)thieno[2,3-c]quinolin-4(5H)-one;

  • (1044): 9-(2-(4-((dimethylamino)methyl)piperidin-11-yl)ethyl)-8-hydroxythieno[2,3-c]quinolin-4(5H)-one;

  • (1045): 9-(4-(1-hydroxypropyl)phenyl)-8-methoxythieno[2,3-c]quinolin-4(5H)-one;

  • (1046): (R)-8-methoxy-9-(4-(1-(methylamino)ethyl)phenyl)thieno[2,3-c]quinolin-4(5H)-one;

  • (1047): (R)-8-(4-(1-aminoethyl)phenyl)thieno[2,3-c]quinolin-4(5H)-one;

  • (1048): (R)-tert-butyl (1-(4-(4-oxo-4,5-dihydrothieno[2,3-c]quinolin-8-yl)phenyl)ethyl)carbamate;

  • (1049): 9-(4-(4-hydroxypiperidin-4-yl)phenyl)-8-methoxythieno[2,3-c]quinolin-4(5H)-one;

  • (1050): (R)-8-(4-(1-(dimethylamino)ethyl)phenyl)thieno[2,3-c]quinolin-4(5H)-one;

  • (1051): 8-hydroxy-9-(4-(1,2,3,6-tetrahydropyridin-4-yl)phenyl)thieno[2,3-c]quinolin-4(5H)-one;

  • (1052): (R)-8-hydroxy-9-(4-(1-(methylamino)ethyl)phenyl)thieno[2,3-c]quinolin-4(5H)-one;

  • (1053): 8-hydroxy-9-(4-(1-hydroxypropyl)phenyl)thieno[2,3-c]quinolin-4(5H)-one;

  • (1054): (R)-8-hydroxy-9-(4-(1-hydroxyethyl)phenyl)thieno[2,3-c]quinolin-4(5H)-one;

  • (1055): 8-hydroxy-9-(4-(4-hydroxypiperidin-4-yl)phenyl)thieno[2,3-c]quinolin-4(5H)-one;

  • (1056): (S)-8-hydroxy-9-(4-(1-hydroxyethyl)phenyl)thieno[2,3-c]quinolin-4(5H)-one;

  • (1057): N-(1-hydroxypropan-2-yl)-4-(8-methoxy-4-oxo-4,5-dihydrothieno[2,3-c]quinolin-9-yl)benzenesulfonamide;

  • (1058): 9-(4-(hydroxy(thiazol-2-yl)methyl)phenyl)-8-methoxythieno[2,3-c]quinolin-4(5H)-one;

  • (1059): 9-(6-(1-aminoethyl)pyridin-3-yl)-8-hydroxythieno[2,3-c]quinolin-4(5H)-one;

  • (1060): 9-(4-(4-hydroxybutyl)phenyl)-8-methoxythieno[2,3-c]quinolin-4(5H)-one;

  • (1061): 2-(4-(8-hydroxy-4-oxo-4,5-dihydrothieno[2,3-c]quinolin-9-yl)phenyl)-2-methylpropanamide;

  • (1062): N-(1-bromopropan-2-yl)-4-(8-hydroxy-4-oxo-4,5-dihydrothieno[2,3-c]quinolin-9-yl)benzenesulfonamide;

  • (1063): 8-hydroxy-9-(4-(hydroxy(thiazol-2-yl)methyl)phenyl)thieno[2,3-c]quinolin-4(5H)-one;

  • (1064): (S)-8-methoxy-9-(4-(1-(methylamino)ethyl)phenyl)thieno[2,3-c]quinolin-4(5H)-one;

  • (1065): 9-(6-(1-(diethylamino)ethyl)pyridin-3-yl)-8-hydroxythieno[2,3-c]quinolin-4(5H)-one;

  • (1066): 9-(4-(1-aminoethyl)phenyl)-8-hydroxy-6-methylthieno[2,3-c]quinolin-4(5H)-one;

  • (1067): 9-(6-(1-aminoethyl)pyridin-3-yl)-8-methoxythieno[2,3-c]quinolin-4(5H)-one;

  • (1068): 8-hydroxy-9-(4-(4-hydroxybutyl)phenyl)thieno[2,3-c]quinolin-4(5H)-one;

  • (1069): 9-(4-(3-amino-1-hydroxypropyl)phenyl)-8-methoxythieno[2,3-c]quinolin-4(5H)-one;

  • (1070): 9-(6-(1-(dimethylamino)ethyl)pyridin-3-yl)-8-hydroxythieno[2,3-c]quinolin-4(5H)-one;

  • (1071): 9-(6-(1-(dimethylamino)ethyl)pyridin-3-yl)-8-methoxythieno[2,3-c]quinolin-4(5H)-one;

  • (1072): 4-((4-(8-methoxy-4-oxo-4,5-dihydrothieno[2,3-c]quinolin-9-yl)-1H-pyrazol-1-yl)methyl)benzonitrile;

  • (1073): 8-aminothieno[2,3-c]quinolin-4(5H)-one;

  • (1074): 9-(4-((1H-pyrazol-1-yl)methyl)phenyl)-8-methoxythieno[2,3-c]quinolin-4(5H)-one;

  • (1075): 9-(6-(1-aminoethyl)pyridin-3-yl)-8-methoxythieno[2,3-c]quinolin-4(5H)-one;

  • (1076): 9-(4-(1-aminoethyl)phenyl)-4-oxo-4,5-dihydrothieno[2,3-c]quinolin-8-yl dimethylcarbamate;

  • (1077): 9-(4-(1-aminoethyl)phenyl)-4-oxo-4,5-dihydrothieno[2,3-c]quinolin-8-yl isopropyl carbonate;

  • (1078): 9-(4-((1H-imidazol-1-yl)methyl)phenyl)-8-methoxythieno[2,3-c]quinolin-4(5H)-one;

  • (1079): N-(2-bromopropyl)-4-(8-hydroxy-4-oxo-4,5-dihydrothieno[2,3-c]quinolin-9-yl)benzenesulfonamide;

  • (1080): (R)-9-(4-(1-aminoethyl)phenyl)-6,7-dichloro-8-hydroxythieno[2,3-c]quinolin-4(5H)-one;

  • (1081): (R)-9-(4-(1-aminoethyl)phenyl)-6-chloro-8-hydroxythieno[2,3-c]quinolin-4(5H)-one;

  • (1082): (S)-8-hydroxy-9-(4-(1-(methylamino)ethyl)phenyl)thieno[2,3-c]quinolin-4(5H)-one;

  • (1083): 9-(4-(1-aminoethyl)phenyl)-4-oxo-4,5-dihydrothieno[2,3-c]quinolin-8-yl diethylcarbamate;

  • (1084): 4-(8-hydroxy-4-oxo-4,5-dihydrothieno[2,3-c]quinolin-9-yl)-N-(2-hydroxyethyl)-N-methylbenzenesulfonamide;

  • (1085): N-(2-hydroxyethyl)-4-(8-methoxy-4-oxo-4,5-dihydrothieno[2,3-c]quinolin-9-yl)-N-methylbenzenesulfonamide;

  • (1086): 9-(4-((1H-pyrazol-1-yl)methyl)phenyl)-8-hydroxythieno[2,3-c]quinolin-4(5H)-one;

  • (1087): (S)-6-chloro-8-hydroxy-9-(4-(1-(methylamino)ethyl)phenyl)thieno[2,3-c]quinolin-4(5H)-one;

  • (1088): 9-(4-(1-aminopropyl)phenyl)-6-chloro-8-hydroxythieno[2,3-c]quinolin-4(5H)-one;

  • (1089): 9-(4-(1-aminoethyl)phenyl)-4-oxo-4,5-dihydrothieno[2,3-c]quinolin-8-yl morpholine-4-carboxylate;

  • (1090): N-(2-hydroxyethyl)-4(8-methoxy-4-oxo-2,3,4,5-tetrahydro-1H-cyclopenta[c]quinolin-9-yl)benzenesulfonamide;

  • (1091): 8-bromothieno[2,3-c]quinolin-4(5H)-one;

  • (1092): 9-(4-(2-(dimethylamino)propyl)phenyl)-8-hydroxythieno[2,3-c]quinolin-4(5H)-one;

  • (1093): 9-(4-(2-aminopropyl)phenyl)-8-methoxythieno[2,3-c]quinolin-4(5H)-one;

  • (1094): N-(2-bromoethyl)-4-(8-hydroxy-4 oxo-2,3,4,5-tetrahydro-1H-cyclopenta[c]quinolin-9-yl)benzenesulfonamide;

  • (1095): 9-(4-(2-aminopropyl)phenyl)-8-hydroxythieno[2,3-c]quinolin-4(5H)-one;

  • (1096): 8-methoxy-9-(1-(2-morpholinoethyl)-1H-pyrazol-4-yl)thieno[2,3-c]quinolin-4(5H)-one;

  • (1097): 9-(4-(2-(diethylamino)propyl)phenyl)-8-hydroxythieno[2,3-c]quinolin-4(5H)-one;

  • (1098): 9-(4-(1-aminoethyl)phenyl)-8-hydroxy-6-(hydroxymethyl)thieno[2,3-c]quinolin-4(5H)-one;

  • (1099): 9-(4-(1-aminoethyl)phenyl)-4-oxo-4,5-dihydrothieno[2,3-c]quinolin-8-yl acetate;

  • (1100): 9-(1-(1-(dimethylamino)propan-2-yl)-1H-pyrazol-4-yl)-8-methoxythieno[2,3-c]quinolin-4(5H)-one;

  • (1101): 9-(4-((1H-imidazol-1-yl)methyl)phenyl)-8-hydroxythieno[2,3-c]quinolin-4(5H)-one;

  • (1102): 9-(4-(aminomethyl)phenyl)-8-(2-morpholinoethoxy)thieno[2,3-c]quinolin-4(5H)-one;

  • (1103): 8-hydroxy-9-(1-(2-morpholinoethyl)-1H-pyrazol-4-yl)thieno[2,3-c]quinolin-4(5H)-one;

  • (1104): N-(2-(1H-pyrazol-1-yl)ethyl)-4-(8-hydroxy-4-oxo-4,5-dihydrothieno[2,3-c]quinolin-9-yl)benzenesulfonamide;

  • (1105): 8-hydroxy-9-(4-(2,2,2-trifluoro-1-hydroxyethyl)phenyl)thieno[2,3-c]quinolin-4(5H)-one;

  • (1106): 9-(4-(2-aminopropyl)phenyl)-6-chloro-8-hydroxythieno[2,3-c]quinolin-4(5H)-one;

  • (1107): N-(2-(4-(8-hydroxy-4-oxo-4,5-dihydrothieno[2,3-c]quinolin-9-yl)phenyl)-2-methylpropyl)methanesulfonamide;

  • (1108): 9-(4-(2-(dimethylamino)propyl)phenyl)-8-methoxythieno[2,3-c]quinolin-4(5H)-one;

  • (1109): 9-(4-(1-aminoethyl)phenyl)thieno[2,3-c]quinolin-4(5H)-one;

  • (1110): 9-(1-(1-(dimethylamino)propan-2-yl)-1H-pyrazol-4-yl)-8-hydroxythieno[2,3-c]quinolin-4(5H)-one;

  • (1111): 9-(4-(1-aminopropan-2-yl)phenyl)-8-hydroxythieno[2,3-c]quinolin-4(5H)-one;

  • (1112): 9-(4-(1-(dimethylamino)propan-2-yl)phenyl)-8-hydroxythieno[2,3-c]quinolin-4(5H)-one;

  • (1113): 8-methoxy-9-(4-(2,2,2-trifluoro-1-hydroxyethyl)phenyl)thieno[2,3-c]quinolin-4(5H)-one;

  • (1114): N-(2-bromoethyl)-4-(8-hydroxy-4-oxo-4,5-dihydrothieno[2,3-c]quinolin-9-yl)-N-methylbenzenesulfonamide;

  • (1115): N-(2-(1H-imidazol-1-yl)ethyl)-4-(8-hydroxy-4-oxo-4,5-dihydrothieno[2,3-c]quinolin-9-yl)benzenesulfonamide;

  • (1116): 9-(4-(1-(aminomethyl)cyclopropyl)phenyl)-6-chloro-8-hydroxythieno[2,3-c]quinolin-4(5H)-one;

  • (1117): 3-(4-(8-(2-(dimethylamino)ethoxy)-4-oxo-4,5-dihydrothieno[2,3-c]quinolin-9-yl)phenyl)propanenitrile;

  • (1118): (R)-9-(4-(1-aminopropyl)phenyl)-8-methoxythieno[2,3-c]quinolin-4(5H)-one;

  • (1119): N-(2-chloroethyl)-4-(8-hydroxy-4-oxo-4,5-dihydrothieno[2,3-c]quinolin-9-yl)-N-methylbenzenesulfonamide;

  • (1120): (S)-9-(4-(1-aminopropyl)phenyl)-8-hydroxythieno[2,3-c]quinolin-4(5H)-one;

  • (1121): (S)-9-(4-(1-aminopropyl)phenyl)-8-methoxythieno[2,3-c]quinolin-4(5H)-one;

  • (1122): (R)-9-(4-(1-aminoethyl)phenyl)-8-hydroxy-6-methylthieno[2,3-c]quinolin-4(5H)-one;

  • (1123): (R)-9-(4-(1-aminoethyl)phenyl)-6-bromo-8-hydroxythieno[2,3-c]quinolin-4(5H)-one;

  • (1124): 9-(4-(1-aminoethyl)phenyl)-4-oxo-4,5-dihydrothieno[2,3-c]quinoline-8-carbonitrile;

  • (1125): 9-(4-(1-aminoethyl)phenyl)-8-(hydroxymethyl)thieno[2,3-c]quinolin-4(5H)-one;

  • (1126): (R)-6-chloro-9-(4-(1-(dimethylamino)ethyl)phenyl)-8-hydroxythieno[2,3-c]quinolin-4(5H)-one;

  • (1127): (S)-9-(4-(1-(ethylamino)propyl)phenyl)-8-hydroxythieno[2,3-c]quinolin-4(5H)-one;

  • (1128): (S)-9-(4-(1-(dimethylamino)propyl)phenyl)-8-hydroxythieno[2,3-c]quinolin-4(5H)-one;

  • (1129): 6-chloro-9-(4-(1-(dimethylamino)propan-2-yl)phenyl)-8-hydroxythieno[2,3-c]quinolin-4(5H)-one;

  • (1130): 9-(4-(1-aminoethyl)phenyl)-6-ethynyl-8-hydroxythieno[2,3-c]quinolin-4(5H)-one;

  • (1131): (R)-9-(4-(1-aminopropyl)phenyl)-8-hydroxythieno[2,3-c]quinolin-4(5H)-one;

  • (1132): (R)-6-chloro-8-hydroxy-9-(4-(1-(methylamino)ethyl)phenyl)thieno[2,3-c]quinolin-4(5H)-one;

  • (1133): 9-(4-(2-aminoethyl)phenyl)-6-chloro-8-hydroxythieno[2,3-c]quinolin-(5H)-one;

  • (1134): 9-(4-(1-aminoethyl)phenyl)-8-(difluoromethyl)thieno[2,3-c]quinolin-4(5H)-one;

  • (1135): (R)-6-bromo-8-hydroxy-9-(4-(1-(methylamino)ethyl)phenyl)thieno[2,3-c]quinolin-4(5H)-one;

  • (1136): 9-(4-(1-aminopropan-2-yl)phenyl)-6-chloro-8-hydroxythieno[2,3-c]quinolin-4(5H)-one;

  • (1137): 9-(4-butylphenyl)-8-methoxythieno[2,3-c]quinolin-4(5H)-one;

  • (1138): 9-(4-butylphenyl)-8-hydroxythieno[2,3-c]quinolin-4(5H)-one;

  • (1139): N-(2-chloroethyl)-4-(8-methoxy-4-oxo-4,5-dihydrothieno[2,3-c]quinolin-9-yl)benzenesulfonamide;

  • (1140): 9-(4-((3-bromopyrrolidin-1-yl)sulfonyl)phenyl)-8-hydroxythieno[2,3-c]quinolin-4(5H)-one;

  • (1141): (S)-9-(4-(1-(methylsulfonamido)propyl)phenyl)-4-oxo-4,5-dihydrothieno[2,3-c]quinolin-8-yl methanesulfonate;

  • (1142): 9-(4-(2-aminoethyl)phenyl)-6-bromo-8-hydroxythieno[2,3-c]quinolin-4(5H)-one;

  • (1143): 9-(4-(3-(dimethylamino)-1-hydroxypropyl)phenyl)-8-methoxythieno[2,3-c]quinolin-4(5H)-one;

  • (1144): N-(2-bromoethyl)-4-(6-chloro-8-hydroxy-4-oxo-4,5-dihydrothieno[2,3-c]quinolin-9-yl)benzenesulfonamide;

  • (1145): N-(2-chloroethyl)-4-(8-hydroxy-4-oxo-2,3,4,5-tetrahydro-1H-cyclopenta[c]quinolin-9-yl)benzenesulfonamide;

  • (1146): N-(2-bromoethyl)-4-(5-ethyl-8-hydroxy-4-oxo-4,5-dihydrothieno[2,3-c]quinolin-9-yl)benzenesulfonamide;

  • (1147): (S)-8-methoxy-9-(4-(1-(methylamino)propyl)phenyl)thieno[2,3-c]quinolin-4(5H)-one;

  • (1148): (S)-8-hydroxy-9-(4-(1-(methylamino)propyl)phenyl)thieno[2,3-c]quinolin-4(5H)-one;

  • (1149): 9-(4-(1-aminoethyl)phenyl)-8-(((2-hydroxyethyl)amino)methyl)thieno[2,3-c]quinolin-4(5H)-one;

  • (1150): (R)-9-(4-(1-aminopropyl)phenyl)-6-bromo-8-hydroxythieno[2,3-c]quinolin-4(5H)-one;

  • (1151): (R)-9-(4-(1-(dimethylamino)propyl)phenyl)-8-hydroxythieno[2,3-c]quinolin-4(5H)-one;

  • (1152): 8-hydroxy-9-(4-pentylphenyl)thieno[2,3-c]quinolin-4(5H)-one;

  • (1153): 9-(4-(2-aminoacetyl)phenyl)-8-hydroxythieno[2,3-c]quinolin-4(5H)-one;

  • (1154): (S)-6-chloro-8-hydroxy-9-(4-(1-(methylamino)propyl)phenyl)thieno[2,3-c]quinolin-4(5H)-one;

  • (1155): 8-hydroxy-9-(4-(2-(methylamino)ethyl)phenyl)thieno[2,3-c]quinolin-4(5H)-one;

  • (1156): 8-methoxy-9-(4-(2-(methylamino)ethyl)phenyl)thieno[2,3-c]quinolin-4(5H)-one;

  • (1157): (R)-9-(4-(1-aminopropyl)phenyl)-8-hydroxy-6-methylthieno[2,3-c]quinolin-4(5H)-one;

  • (1158): (R)-9-(4-(1-aminopropyl)phenyl)-8-methoxy-6-methylthieno[2,3-c]quinolin-4(5H)-one;

  • (1159): (R)-9-(4-(1-aminopropyl)phenyl)-6-chloro-8-hydroxythieno[2,3-c]quinolin-4(5H)-one;

  • (1160): (R)-9-(4-(1-aminopropan-2-yl)phenyl)-8-hydroxythieno[2,3-c]quinolin-4(5H)-one;

  • (1161): (R)-9-(4-(1-aminopropan-2-yl)phenyl)-8-methoxythieno[2,3-c]quinolin-4(5H)-one;

  • (1162): 2-(4-(8-hydroxy-4-oxo-4,5-dihydrothieno[2,3-c]quinolin-9-yl)phenyl)butanenitrile;

  • (1163): (S)-9-(4-(1-aminopropan-2-yl)phenyl)-8-hydroxythieno[2,3-c]quinolin-4(5H)-one;

  • (1164): (S)-9-(4-(1-aminopropan-2-yl)phenyl)-8-methoxythieno[2,3-c]quinolin-4(5H)-one;

  • (1165): 6-chloro-8-hydroxy-9-(4-(2-(methylamino)ethyl)phenyl)thieno[2,3-c]quinolin-4(5H)-one;

  • (1166): (R)-9-(4-(1-aminopropan-2-yl)phenyl)-6-chloro-8-hydroxythieno[2,3-c]quinolin-4(5H)-one;

  • (1167): 9-(4-(2-aminoethyl)-3,5-difluorophenyl)-8-hydroxythieno[2,3-c]quinolin-4(5H)-one;

  • (1168): (R)-9-(4-(1-aminopropan-2-yl)phenyl)-8-hydroxy-6-methylthieno[2,3-c]quinolin-4(5H)-one

  • (1169): (R)-9-(4-(1-aminopropan-2-yl)phenyl)-8-hydroxy-6-methylthieno[2,3-c]quinolin-4(5H)-one

  • (1170): 6-chloro-8-methoxy-9-(4-(2-(methylamino)ethyl)phenyl)thieno[2,3-c]quinolin-4(5H)-one;

  • (1171): 9-(4-(2-aminoethyl)-3-chlorophenyl)-8-hydroxythieno[2,3-c]quinolin-4(5H)-one;

  • (1172): (S)-9-(4-(1-(dimethylamino)propan-2-yl)phenyl)-8-hydroxythieno[2,3-c]quinolin-4(5H)-one;

  • (1173): 6-bromo-8-methoxy-9-(4-(2-(methylamino)ethyl)phenyl)thieno[2,3-c]quinolin-4(5H)-one;

  • (1174): 9-(4-(1-aminopropan-2-yl)-3-fluorophenyl)-8-hydroxythieno[2,3-c]quinolin-4(5H)-one;

  • (1175): (R)-9-(4-(1-aminopropyl)phenyl)-6-chloro-8-methoxythieno[2,3-c]quinolin-4(5H)-one;

  • (1176): (R)-9-(4-(1-aminopropan-2-yl)phenyl)-6-bromo-8-hydroxythieno[2,3-c]quinolin-4(5H)-one;

  • (1177): 9-(4-(2-aminoethyl)-3,5-difluorophenyl)-8-methoxythieno[2,3-c]quinolin-4(5H)-one;

  • (1178): 9-(4-(2-(dimethylamino)ethyl)-3,5-difluorophenyl)-8-hydroxythieno[2,3-c]quinolin-4(5H)-one;

  • (1179): 9-(4-(1-aminopropan-2-yl)-3-fluorophenyl)-8-methoxythieno[2,3-c]quinolin-4(5H)-one;

  • (1180): (S)-9-(4-(1-aminopropan-2-yl)phenyl)-6,7-dichloro-8-methoxythieno[2,3-c]quinolin-4(5H)-one;

  • (1181): (S)-9-(4-(1-aminopropan-2-yl)phenyl)-6-chloro-8-hydroxythieno[2,3-c]quinolin-4(5H)-one;

  • (1182): (S)-6-chloro-9-(4-(1-(dimethylamino)propan-2-yl)phenyl)-8-hydroxythieno[2,3-c]quinolin-4(5H)-one;

  • (1183): 6-bromo-8-hydroxy-9-(4-(2-(methylamino)ethyl)phenyl)thieno[2,3-c]quinolin-4(5H)-one;

  • (1185): N-(2-hydroxyethyl)-4-(8-methoxy-5-methyl-4-oxo-4,5-dihydrothieno[2,3-c]quinolin-9-yl)benzenesulfonamide;

  • (1186): methyl 3-(4-(8-hydroxy-4-oxo-4,5-dihydrothieno[2,3-c]quinolin-9-yl)phenyl)propanoate;

  • (1187): (R)-8-hydroxy-9-(4-(1-(methylamino)propan-2-yl)phenyl)thieno[2,3-c]quinolin-4(5H)-one;

  • (1188): (R)-9-(4-(1-(dimethylamino)propan-2-yl)phenyl)-8-hydroxythieno[2,3-c]quinolin-4(5H)-one;

  • (1189): (R)-8-methoxy-9-(4-(1-(methylamino)propan-2-yl)phenyl)thieno[2,3-c]quinolin-4(5H)-one;

  • (1190): 9-(4-(1-aminopropan-2-yl)-3-fluorophenyl)-8-hydroxy-6-methylthieno[2,3-c]quinolin-4(5H)-one;

  • (1191): 9-(4-(2-aminoethyl)phenyl)-8-hydroxy-6-methylthieno[2,3-c]quinolin-4(5H)-one;

  • (1192): 9-(4-(2-aminoethyl)phenyl)-8-methoxy-6-methylthieno[2,3-c]quinolin-4(5H)-one;

  • (1193): 9-(4-(1-(dimethylamino)propan-2-yl)-3-fluorophenyl)-8-hydroxy-6-methylthieno[2,3-c]quinolin-4(5H)-one;

  • (1194): (S)-6-chloro-8-hydroxy-9-(4-(1-(methylamino)propan-2-yl)phenyl)thieno[2,3-c]quinolin-4(5H)-one;

  • (1195): (S)-6-chloro-9-(4-(1-(diethylamino)propan-2-yl)phenyl)-8-hydroxythieno[2,3-c]quinolin-4(5H)-one;

  • (1196): (S)-8-methoxy-9-(4-(1-(methylamino)propan-2-yl)phenyl)thieno[2,3-c]quinolin-4(5H)-one;

  • (1197): (S)-8-hydroxy-9-(4-(1-(methylamino)propan-2-yl)phenyl)thieno[2,3-c]quinolin-4(5H)-one;

  • (1198): 4-(8-hydroxy-5-methyl-4-oxo-4,5-dihydrothieno[2,3-c]quinolin-9-yl)-N-(2-hydroxyethyl)benzenesulfonamide;

  • (1199): N-(2-bromoethyl)-4-(8-hydroxy-5-methyl-4-oxo-4,5-dihydrothieno[2,3-c]quinolin-9-yl)benzenesulfonamide;

  • (1200): (R)-6-chloro-9-(4-(1-(dimethylamino)propan-2-yl)phenyl)-8-methoxythieno[2,3-c]quinolin-4(5H)-one;

  • (1201): (R)-9-(4-(1-aminopropan-2-yl)phenyl)-6-chloro-8-methoxythieno[2,3-c]quinolin-4(5H)-one;

  • (1202): 9-(4-(1-aminobutan-2-yl)phenyl)-8-methoxythieno[2,3-c]quinolin-4(5H)-one;

  • (1203): 9-(4-(2-aminopropan-2-yl)phenyl)-8-hydroxy-2-(phenylsulfonyl)thieno[2,3-c]quinolin-4(5H)-one;

  • (1204): N-(1-chloropropan-2-yl)-4-(8-hydroxy-4-oxo-4,5-dihydrothieno[2,3-c]quinolin-9-yl)benzenesulfonamide;

  • (1205): N-(1-chloropropan-2-yl)-4-(8-methoxy-4-oxo-4,5-dihydrothieno[2,3-c]quinolin-9-yl)benzenesulfonamide;

  • (1206): 9-(4-(2-aminoethyl)-3-hydroxyphenyl)-8-hydroxythieno[2,3-c]quinolin-4(5H)-one;

  • (1207): 9-(4-(2-aminoethyl)-3-methoxyphenyl)-8-methoxythieno[2,3-c]quinolin-4(5H)-one;

  • (1208): 9-(4-(2-aminoethyl)-2-chloro-5-methoxyphenyl)-8-methoxythieno[2,3-c]quinolin-4(5H)-one;

  • (1209): 9-(4-(3-(aminomethyl)pentan-3-yl)phenyl)-8-hydroxythieno[2,3-c]quinolin-4(5H)-one;

  • (1210): (R)-9-(4-(1-aminopropyl)phenyl)-8-hydroxy-5,6-dimethylthieno[2,3-c]quinolin-4(5H)-one;

  • (1211): 9-(4-(2-aminoethyl)-2-chloro-5-hydroxyphenyl)-6-chloro-8-hydroxythieno[2,3-c]quinolin-4(5H)-one;

  • (1212): 9-(4-(aminomethyl)phenyl)-8-hydroxy-6-methylthieno[2,3-c]quinolin-4(5H)-one;

  • (1213): 9-(4-(2-aminoethyl)-3-fluorophenyl)-6-bromo-8-hydroxythieno[2,3-c]quinolin-4(5H)-one;

  • (1214): 9-(4-(2-aminoethyl)-3-fluorophenyl)-6-bromo-8-methoxythieno[2,3-c]quinolin-4(5H)-one;

  • (1215): (S)-8-hydroxy-6-methyl-9-(4-(1-(methylamino)propan-2-yl)phenyl)thieno[2,3-c]quinolin-4(5H)-one;

  • (1216): 9-(4-(2-aminoethyl)-3-fluorophenyl)-8-methoxy-6-methylthieno[2,3-c]quinolin-4(5H)-one;

  • (1217): 9-(4-(2-aminoethyl)-3-fluorophenyl)-8-hydroxy-6-methylthieno[2,3-c]quinolin-4(5H)-one;

  • (1218): 9-(4-(2-aminoethyl)-3-fluorophenyl)-6-chloro-8-methoxythieno[2,3-c]quinolin-(5H)-one;

  • (1219): 9-(4-(2-aminoethyl)-3-fluorophenyl)-6-chloro-8-hydroxythieno[2,3-c]quinolin-4(5H)-one;

  • (1220): 9-(4-(2-aminoethyl)-3-fluorophenyl)-6-cyclopropyl-8-methoxythieno[2,3-c]quinolin-4(5H)-one;

  • (1221): 9-(4-(2-aminoethyl)-3-fluorophenyl)-6-cyclopropyl-8-hydroxythieno[2,3-c]quinolin-4(5H)-one;

  • (1222): (S)-8-methoxy-6-methyl-9-(4-(1-(methylamino)propan-2-yl)phenyl)thieno[2,3-c]quinolin-4(5H)-one;

  • (1223): (S)-9-(4-(1-aminopropan-2-yl)phenyl)-8-methoxy-6-methylthieno[2,3-c]quinolin-4(5H)-one;

  • (1224): 9-(4-(2-aminoethyl)-2-bromo-5-hydroxyphenyl)-8-hydroxythieno[2,3-c]quinolin-4(5H)-one;

  • (1225): (S)-9-(4-(1-aminoethyl)phenyl)-8-hydroxy-6-methylthieno[2,3-c]quinolin-4(5H)-one;

  • (1226): 3-(4-(8-hydroxy-6-methyl-4-oxo-4,5-dihydrothieno[2,3-c]quinolin-9-yl)phenyl)propanenitrile;

  • (1227): 9-(4-(1-amino-2-methylpropan-2-yl)phenyl)-8-methoxy-6-methylthieno[2,3-c]quinolin-4(5H)-one;

  • (1228): 9-(4-(1-amino-2-methylpropan-2-yl)phenyl)-8-hydroxy-6-methylthieno[2,3-c]quinolin-4(5H)-one;

  • (1229): 2-(2-fluoro-4-(8-hydroxy-6-methyl-4-oxo-4,5-dihydrothieno[2,3-c]quinolin-9-yl)phenyl)propanenitrile;

  • (1230): 6-cyclopropyl-9-(4-(2-(dimethylamino)ethyl)-3-fluorophenyl)-8-hydroxythieno[2,3-c]quinolin-4(5H)-one;

  • (1231): 6-cyclopropyl-9-(4-(2-(dimethylamino)ethyl)-3-fluorophenyl)-8-methoxythieno[2,3-c]quinolin-4(5H)-one;

  • (1232): (S)-9-(4-(1-aminopropan-2-yl)phenyl)-8-hydroxy-6-methylthieno[2,3-c]quinolin-4(5H)-one;

  • (1233): (S)-9-(4-(1-(dimethylamino)propan-2-yl)phenyl)-8-hydroxy-6-methylthieno[2,3-c]quinolin-4(5H)-one;

  • (1234): 9-(3-fluoro-4-(2-(methylamino)ethyl)phenyl)-8-methoxythieno[2,3-c]quinolin-4(5H)-one;

  • (1235): 9-(3-fluoro-4-(2-(methylamino)ethyl)phenyl)-8-hydroxythieno[2,3-c]quinolin-4(5H)-one;

  • (1236): 9-(4-(2-amino-1-cyclopentylethyl)phenyl)-8-hydroxythieno[2,3-c]quinolin-4(5H)-one;

  • (1237): 9-(4-(2-amino-1,1-dicyclopentylethyl)phenyl)-8-methoxythieno[2,3-c]quinolin-4(5H)-one;

  • (1238): 3-(4-(8-methoxy-6-methyl-4-oxo-4,5-dihydrothieno[2,3-c]quinolin-9-yl)phenyl)propanenitrile;

  • (1239): 9-(4-(2-amino-1-cyclopentylethyl)phenyl)-8-methoxythieno[2,3-c]quinolin-4(5H)-one;

  • (1240): 9-(4-(1-amino-2-methylpropan-2-yl)phenyl)-6-cyclopropyl-8-hydroxythieno[2,3-c]quinolin-4(5H)-one;

  • (1241): 9-(4-(3-aminopropyl)phenyl)-8-methoxy-6-methylthieno[2,3-c]quinolin-4(5H)-one;

  • (1242): 9-(4-(2-aminopropyl)phenyl)-8-hydroxy-6-methylthieno[2,3-c]quinolin-4(5H)-one;

  • (1243): 9-(4-(2-aminopropyl)phenyl)-8-methoxy-6-methylthieno[2,3-c]quinolin-4(5H)-one;

  • (1244): 9-(4-(1-amino-2-methylpropan-2-yl)phenyl)-6-cyclopropyl-8-methoxythieno[2,3-c]quinolin-4(5H)-one;

  • (1245): 6-bromo-9-(3-fluoro-4-(2-(methylamino)ethyl)phenyl)-8-hydroxythieno[2,3-c]quinolin-4(5H)-one;

  • (1246): 6-bromo-9-(3-fluoro-4-(2-(methylamino)ethyl)phenyl)-8-methoxythieno[2,3-c]quinolin-4(5H)-one;

  • (1247): 9-(4-(1-amino-2-methylpropan-2-yl)phenyl)-6-bromo-8-hydroxythieno[2,3-c]quinolin-4(5H)-one;

  • (1248): 9-(4-(1-amino-2-methylpropan-2-yl)phenyl)-6-bromo-8-methoxythieno[2,3-c]quinolin-4(5H)-one;

  • (1249): (R)-9-(4-(1-aminopropan-2-yl)phenyl)-6-methyl-4-oxo-4,5-dihydrothieno[2,3-c]quinolin-8-carbonitrile;

  • (1250): (R)-9-(4-(1-aminoethyl)phenyl)-8-hydroxy-6-vinylthieno[2,3-c]quinolin-4(5H)-one;

  • (1251): 9-(4-(1-(aminomethyl)cyclopropyl)phenyl)-8-methoxy-6-methylthieno[2,3-c]quinolin-4(5H)-one;

  • (1252): 9-(4-(1-amino-3-methylbutan-2-yl)phenyl)-8-hydroxythieno[2,3-c]quinolin-4(5H)-one;

  • (1253): 9-(4-(1-amino-3-methylbutan-2-yl)phenyl)-8-methoxythieno[2,3-c]quinolin-4(5H)-one;

  • (1254): 9-(4-(1-(aminomethyl)cyclopropyl)phenyl)-8-hydroxy-6-methylthieno[2,3-c]quinolin-4(5H)-one;

  • (1255): (R)-9-(4-(1-aminoethyl)phenyl)-6-ethyl-8-hydroxythieno[2,3-c]quinolin-4(5H)-one;

  • (1256): (R)-9-(4-(1-aminoethyl)phenyl)-6-(difluoromethyl)-8-hydroxythieno[2,3-c]quinolin-4(5H)-one;

  • (1257): 9-(3-fluoro-4-(2-(methylamino)ethyl)phenyl)-8-methoxy-6-methylthieno[2,3-c]quinolin-4(5H)-one;

  • (1258): 9-(3-fluoro-4-(2-(methylamino)ethyl)phenyl)-8-hydroxy-6-methylthieno[2,3-c]quinolin-4(5H)-one;

  • (1259): 6-bromo-9-(4-(1-(dimethylamino)-2-methylpropan-2-yl)phenyl)-8-hydroxythieno[2,3-c]quinolin-4(5H)-one;

  • (1260): 9-(4-(1-amino-2-methylpropan-2-yl)phenyl)-6-chloro-8-hydroxythieno[2,3-c]quinolin-4(5H)-one;

  • (1261): 9-(4-(3-aminopropyl)phenyl)-8-hydroxy-6-methylthieno[2,3-c]quinolin-4(5H)-one;

  • (1262): (R)-8-hydroxy-6-methyl-9-(4-(1-(methylamino)ethyl)phenyl)thieno[2,3-c]quinolin-4(5H)-one;

  • (1263): 9-(4-(2-aminoethyl)-3-chlorophenyl)-8-methoxy-6-methylthieno[2,3-c]quinolin-4(5H)-one;

  • (1264): 9-(4-(2-aminoethyl)-3-chlorophenyl)-8-hydroxy-6-methylthieno[2,3-c]quinolin-4(5H)-one;

  • (1265): (R)-8-methoxy-6-methyl-9-(4-(1-(methylamino)ethyl)phenyl)thieno[2,3-c]quinolin-4(5H)-one;

  • (1266): 9-(4-(2-aminopropyl)phenyl)-6-ethyl-8-hydroxythieno[2,3-c]quinolin-4(5H)-one;

  • (1267): (R)-9-(4-(1-aminoethyl)phenyl)-6-butyl-8-hydroxythieno[2,3-c]quinolin-4(5H)-one;

  • (1268): 9-(4-(2-aminoethyl)-3-chlorophenyl)-6-chloro-8-hydroxythieno[2,3-c]quinolin-(5H)-one;

  • (1269): 9-(4-(2-aminopropyl)phenyl)-6-ethyl-8-methoxythieno[2,3-c]quinolin-4(5H)-one;

  • (1270): 2-(4-(8-methoxy-4-oxo-4,5-dihydrothieno[2,3-c]quinolin-9-yl)phenyl)-2-(oxetan-3-yl)acetonitrile;

  • (1271): 9-(4-(1-amino-2-methylpropan-2-yl)-3-fluorophenyl)-8-hydroxythieno[2,3-c]quinolin-4(5H)-one;

  • (1272): (R)-6-ethyl-8-hydroxy-9-(4-(1-(methylamino)ethyl)phenyl)thieno[2,3-c]quinolin-4(5H)-one;

  • (1273): 9-(4-(1-aminopropan-2-yl)-3-fluorophenyl)-8-methoxy-6-methylthieno[2,3-c]quinolin-4(5H)-one;

  • (1274): 9-(4-(1-amino-3-methylbutan-2-yl)phenyl)-8-hydroxy-6-methylthieno[2,3-c]quinolin-4(5H)-one;

  • (1275): 9-(4-(1-aminopropan-2-yl)-3-chlorophenyl)-8-methoxy-6-methylthieno[2,3-c]quinolin-4(5H)-one;

  • (1276): 9-(4-(1-aminopropan-2-yl)-3-chlorophenyl)-8-methoxythieno[2,3-c]quinolin-4(5H)-one;

  • (1277): 9-(4-(1-aminobutan-2-yl)phenyl)-8-methoxy-6-methylthieno[2,3-c]quinolin-4(5H)-one;

  • (1278): 9-(4-(1-amino-2-methylpropan-2-yl)-3-fluorophenyl)-8-hydroxy-6-methylthieno[2,3-c]quinolin-4(5H)-one;

  • (1279): 9-(4-(1-aminopropan-2-yl)-3-chlorophenyl)-8-hydroxy-6-methylthieno[2,3-c]quinolin-4(5H)-one;

  • (1280): 9-(4-(1-aminopropan-2-yl)-3-chlorophenyl)-8-hydroxythieno[2,3-c]quinolin-4(5H)-one;

  • (1281): 9-(4-(2-amino-2-methylpropyl)phenyl)-8-methoxythieno[2,3-c]quinolin-4(5H)-one;

  • (1282): 9-(4-(2-amino-2-methylpropyl)phenyl)-8-hydroxythieno[2,3-c]quinolin-4(5H)-one;

  • (1283): 9-(4-(1-amino-3-methylbutan-2-yl)-3-fluorophenyl)-8-methoxy-6-methylthieno[2,3-c]quinolin-4(5H)-one;

  • (1284): 8-methoxy-6-methyl-9-(4-(3-methyl-1-(methylamino)butan-2-yl)phenyl)thieno[2,3-c]quinolin-4(5H)-one;

  • (1285): 8-hydroxy-6-methyl-9-(4-(3-methyl-1-(methylamino)butan-2-yl)phenyl)thieno[2,3-c]quinolin-4(5H)-one;

  • (1286): 9-(3-fluoro-4-(1-(methylamino)propan-2-yl)phenyl)-8-methoxy-6-methylthieno[2,3-c]quinolin-4(5H)-one;

  • (1287): 9-(4-(1-amino-2-methylpropan-2-yl)-3-fluorophenyl)-8-methoxythieno[2,3-c]quinolin-4(5H)-one;

  • (1288): 9-(4-(1-amino-3-methylbutan-2-yl)-3-fluorophenyl)-8-hydroxy-6-methylthieno[2,3-c]quinolin-4(5H)-one;

  • (1289): 9-(4-(2-amino-2-methylpropyl)phenyl)-6-bromo-8-methoxythieno[2,3-c]quinolin-4(5H)-one;

  • (1290): 9-(4-(1-(aminomethyl)cyclobutyl)phenyl)-8-hydroxy-6-methylthieno[2,3-c]quinolin-4(5H)-one;

  • (1291): 9-(4-(1-aminobutan-2-yl)phenyl)-8-hydroxy-6-methylthieno[2,3-c]quinolin-4(5H)-one;

  • (1292): 9-(4-(2-amino-2-methylpropyl)phenyl)-6-bromo-8-hydroxythieno[2,3-c]quinolin-4(5H)-one;

  • (1293): 9-(3-fluoro-4-(1-(methylamino)propan-2-yl)phenyl)-8-hydroxy-6-methylthieno[2,3-c]quinolin-4(5H)-one;

  • (1294): 9-(3-fluoro-4-(3-methyl-1-(methylamino)butan-2-yl)phenyl)-8-hydroxy-6-methylthieno[2,3-c]quinolin-4(5H)-one;

  • (1295): 9-(4-(1-(dimethylamino)-3-methylbutan-2-yl)phenyl)-8-methoxy-6-methylthieno[2,3-c]quinolin-4(5H)-one;

  • (1296): 9-(4-(1-(dimethylamino)-3-methylbutan-2-yl)-3-fluorophenyl)-8-hydroxy-6-methylthieno[2,3-c]quinolin-4(5H)-one;

  • (1297): 9-(4-(1-(aminomethyl)cyclobutyl)phenyl)-8-methoxy-6-methylthieno[2,3-c]quinolin-4(5H)-one;

  • (1298): (R)-8-methoxy-6-methyl-9-(4-(1-(methylamino)propan-2-yl)phenyl)thieno[2,3-c]quinolin-4(5H)-one;

  • (1299): 9-(4-(1-(aminomethyl)cyclobutyl)phenyl)-8-methoxythieno[2,3-c]quinolin-4(5H)-one;

  • (1300): 9-(4-(1-(aminomethyl)cyclobutyl)phenyl)-8-hydroxythieno[2,3-c]quinolin-4(5H)-one;

  • (1301): 8-methoxy-6-methyl-9-(4-(piperidin-3-yl)phenyl)thieno[2,3-c]quinolin-4(5H)-one;

  • (1302): 8-hydroxy-6-methyl-9-(4-(piperidin-3-yl)phenyl)thieno[2,3-c]quinolin-4(5H)-one;

  • (1303): (S)-9-(4-(1-aminopropan-2-yl)-3-fluorophenyl)-8-hydroxy-6-methylthieno[2,3-c]quinolin-4(5H)-one;

  • (1304): (S)-9-(4-(1-aminopropan-2-yl)-3-fluorophenyl)-8-hydroxy-6-methylthieno[2,3-c]quinolin-4(5H)-one;

  • (1305): (R)-9-(4-(1-aminopropan-2-yl)phenyl)-8-methoxy-6-methylthieno[2,3-c]quinolin-4(5H)-one;

  • (1306): (R)-8-hydroxy-6-methyl-9-(4-(1-(methylamino)propan-2-yl)phenyl)thieno[2,3-c]quinolin-4(5H)-one;

  • (1307): (R)-8-hydroxy-6-methyl-9-(4-(1-(methylamino)propan-2-yl)phenyl)thieno[2,3-c]quinolin-4(5H)-one;

  • (1308): 8-methoxy-3-methyl-3H-pyrrolo[2,3-c]quinolin-4(5H)-one;

  • (1309): 9-(4-(1-aminobutan-2-yl)phenyl)-8-hydroxythieno[2,3-c]quinolin-4(5H)-one;

  • (1310): (S)-9-(4-(1-aminopropan-2-yl)-3-fluorophenyl)-8-methoxy-6-methylthieno[2,3-c]quinolin-4(5H)-one;

  • (1311): (R)-9-(4-(1-(dimethylamino)propan-2-yl)-3-fluorophenyl)-8-hydroxy-6-methylthieno[2,3-c]quinolin-4(5H)-one;

  • (1312): 9-(4-(1-aminobutan-2-yl)phenyl)-6-chloro-8-hydroxythieno[2,3-c]quinolin-4(5H)-one;

  • (1313): 8-hydroxy-3-methyl-3H-pyrrolo[2,3-c]quinolin-4(5H)-one;

  • (1314): 9-amino-8-methoxy-6-methylthieno[2,3-c]quinolin-4(5H)-one;

  • (1315): (R)-9-(3-fluoro-4-(1-(methylamino)propan-2-yl)phenyl)-8-hydroxy-6-methylthieno[2,3-c]quinolin-4(5H)-one;

  • (1316): (R)-9-(3-fluoro-4-(1-(methylamino)propan-2-yl)phenyl)-8-methoxy-6-methylthieno[2,3-c]quinolin-4(5H)-one;

  • (1317): (R)-9-(4-(1-aminopropan-2-yl)-3-fluorophenyl)-8-methoxy-6-methylthieno[2,3-c]quinolin-4(5H)-one;

  • (1318): (R)-9-(4-(1-aminopropan-2-yl)-3-fluorophenyl)-8-hydroxy-6-methylthieno[2,3-c]quinolin-4(5H)-one;

  • (1319): (R)-9-(4-(1-aminopropan-2-yl)-3-fluorophenyl)-8-hydroxy-6-methylthieno[2,3-c]quinolin-4(5H)-one;

  • (1320): 9-((4-(2-aminoethyl)phenyl)amino)-8-methoxy-6-methylthieno[2,3-c]quinolin-4(5H)-one;

  • (1321): 9-(4-(1-(aminomethyl)cyclobutyl)phenyl)-6-chloro-8-methoxythieno[2,3-c]quinolin-(5H)-one;

  • (1322): (R)-1-(4-(1-aminopropan-2-yl)phenyl)-8-methoxy-3-methyl-3H-pyrrolo[2,3-c]quinolin-4(5H)-one;

  • (1323): 8-hydroxy-3-(hydroxymethyl)-3H-pyrrolo[2,3-c]quinolin-4(5H)-one;

  • (1324): (R)-9-(4-(1-(dimethylamino)propan-2-yl)phenyl)-8-hydroxy-6-methylthieno[2,3-c]quinolin-4(5H)-one;

  • (1325): 9-((4-(aminomethyl)phenyl)amino)-8-hydroxy-6-methylthieno[2,3-c]quinolin-4(5H)-one;

  • (1326): 9-((4-(aminomethyl)phenyl)amino)-8-methoxy-6-methylthieno[2,3-c]quinolin-4(5H)-one;

  • (1327): 9-((4-(1-aminopropan-2-yl)phenyl)amino)-8-methoxy-6-methylthieno[2,3-c]quinolin-4(5H)-one;

  • (1328): 9-((4-(1-aminopropan-2-yl)phenyl)amino)-8-hydroxy-6-methylthieno[2,3-c]quinolin-4(5H)-one;

  • (1329): 9-(4-(2-aminopropan-2-yl)phenyl)-8-methoxy-6-methylthieno[2,3-c]quinolin-4(5H)-one;

  • (1330): 9-(4-(2-aminopropan-2-yl)phenyl)-8-hydroxy-6-methylthieno[2,3-c]quinolin-4(5H)-one;

  • (1331): 9-(4-(3-(aminomethyl)pentan-3-yl)phenyl)-8-methoxy-6-methylthieno[2,3-c]quinolin-4(5H)-one;

  • (1332): 9-(4-((R)-1-aminopropan-2-yl)phenyl)-8-hydroxy-2-(1-hydroxyethyl)thieno[2,3-c]quinolin-4(5H)-one;

  • (1333): 9-(4-((R)-1-aminopropan-2-yl)phenyl)-2-(1-hydroxyethyl)-8-methoxythieno[2,3-c]quinolin-4(5H)-one;

  • (1334): 3-(4-((8-methoxy-6-methyl-4-oxo-4,5-dihydrothieno[2,3-c]quinolin-9-yl)amino)phenyl)propanenitrile;

  • (1335): 9-((3-(2-aminoethyl)phenyl)amino)-8-methoxy-6-methylthieno[2,3-c]quinolin-4(5H)-one;

  • (1336): 9-((4-(2-aminoethyl)phenyl)amino)-8-hydroxy-6-methylthieno[2,3-c]quinolin-4(5H)-one;

  • (1337): 9-(4-(2-(ethylamino)propyl)phenyl)-8-hydroxy-6-methylthieno[2,3-c]quinolin-4(5H)-one;

  • (1338): 9-(4-(3-(aminomethyl)pentan-3-yl)phenyl)-8-methoxythieno[2,3-c]quinolin-(5H)-one;

  • (1339): 9-(4-(3-(aminomethyl)pentan-3-yl)phenyl)-8-hydroxy-6-methylthieno[2,3-c]quinolin-4(5H)-one;

  • (1340): (R)-9-(4-(1-aminopropan-2-yl)phenyl)-8-hydroxy-2,6-dimethylthieno[2,3-c]quinolin-4(5H)-one;

  • (1341): (R)-9-(4-(1-aminopropan-2-yl)phenyl)-8-methoxy-2,6-dimethylthieno[2,3-c]quinolin-4(5H)-one;

  • (1342): 9-(4-((R)-1-aminopropan-2-yl)phenyl)-2-(1-hydroxyethyl)-8-methoxy-6-methylthieno[2,3-c]quinolin-4(5H)-one;

  • (1343): 2-((4-(8-methoxy-6-methyl-4-oxo-4,5-dihydrothieno[2,3-c]quinolin-9-yl)phenyl)amino)acetonitrile;

  • (1344): (R)-9-(4-(1-aminobutan-2-yl)phenyl)-8-methoxy-6-methylthieno[2,3-c]quinolin-4(5H)-one;

  • (1345): 9-(3-chloro-4-(2-(ethylamino)ethyl)phenyl)-8-methoxythieno[2,3-c]quinolin-4(5H)-one;

  • (1346): 9-(4-(3-((dimethylamino)methyl)pentan-3-yl)phenyl)-8-hydroxy-6-methylthieno[2,3-c]quinolin-4(5H)-one;

  • (1347): (R)-6-chloro-9-(4-(1-(dimethylamino)propan-2-yl)phenyl)-8-hydroxythieno[2,3-c]quinolin-4(5H)-one;

  • (1348): 9-(4-(2-(ethylamino)ethyl)phenyl)-8-hydroxy-6-methylthieno[2,3-c]quinolin-4(5H)-one;

  • (1349): 9-(4-(2-(ethylamino)ethyl)phenyl)-8-methoxy-6-methylthieno[2,3-c]quinolin-4(5H)-one;

  • (1350): 9-(4-(2-(ethyl(methyl)amino)propyl)phenyl)-8-hydroxy-6-methylthieno[2,3-c]quinolin-4(5H)-one;

  • (1351): 2-(hydroxy(piperidin-4-yl)methyl)-8-methoxy-6-methylthieno[2,3-c]quinolin-4(5H)-one;

  • (1352): (R)-9-(4-(1-aminobutan-2-yl)phenyl)-8-hydroxy-6-methylthieno[2,3-c]quinolin-4(5H)-one;

  • (1353): (R)-9-(4-(1-aminopropan-2-yl)phenyl)-2-chloro-8-hydroxy-6-methylthieno[2,3-c]quinolin-4(5H)-one;

  • (1354): (R)-9-(4-(1-aminopropan-2-yl)phenyl)-2-chloro-8-methoxy-6-methylthieno[2,3-c]quinolin-4(5H)-one;

  • (1355): 8-methoxy-6-methyl-9-(4-(2-(methylamino)ethyl)phenyl)thieno[2,3-c]quinolin-4(5H)-one;

  • (1356): 9-(4-(2-(ethyl(methyl)amino)ethyl)phenyl)-8-hydroxy-6-methylthieno[2,3-c]quinolin-4(5H)-one;

  • (1357): 9-(4-(3-(aminomethyl)pentan-3-yl)phenyl)-6-chloro-8-methoxythieno[2,3-c]quinolin-4(5H)-one;

  • (1358): 9-(4-(3-((dimethylamino)methyl)pentan-3-yl)phenyl)-8-hydroxythieno[2,3-c]quinolin-4(5H)-one;

  • (1359): 9-(6-(dimethylamino)pyridin-3-yl)-8-methoxy-6-methylthieno[2,3-c]quinolin-4(5H)-one;

  • (1360): (R)-9-(4-(1-(dimethylamino)butan-2-yl)phenyl)-8-hydroxy-6-methylthieno[2,3-c]quinolin-4(5H)-one;

  • (1361): (R)-8-methoxy-6-methyl-9-(4-(1-(methylamino)butan-2-yl)phenyl)thieno[2,3-c]quinolin-4(5H)-one;

  • (1362): 9-(4-(3-((diethylamino)methyl)pentan-3-yl)phenyl)-8-hydroxy-6-methylthieno[2,3-c]quinolin-4(5H)-one;

  • (1363): 9-(3-chloro-4-(2-(ethylamino)ethyl)phenyl)-8-hydroxythieno[2,3-c]quinolin-4(5H)-one;

  • (1364): 8-hydroxy-6-methyl-9-(4-(2-(methylamino)ethyl)phenyl)thieno[2,3-c]quinolin-4(5H)-one;

  • (1365): (R)-9-(4-(1-(dimethylamino)butan-2-yl)phenyl)-8-methoxy-6-methylthieno[2,3-c]quinolin-4(5H)-one;

  • (1366): (R)-9-(4-(1-(ethyl(methyl)amino)butan-2-yl)phenyl)-8-methoxy-6-methylthieno[2,3-c]quinolin-4(5H)-one;

  • (1367): (R)-9-(4-(1-(diethylamino)butan-2-yl)phenyl)-8-hydroxy-6-methylthieno[2,3-c]quinolin-4(5H)-one;

  • (1368): (R)-9-(4-(1-(ethyl(methyl)amino)butan-2-yl)phenyl)-8-hydroxy-6-methylthieno[2,3-c]quinolin-4(5H)-one;

  • (1369): 2-((4-(8-methoxy-6-methyl-4-oxo-4,5-dihydrothieno[2,3-c]quinolin-9-yl)phenyl)(methyl)amino)acetonitrile;

  • (1370): 2-((4-(8-hydroxy-6-methyl-4-oxo-4,5-dihydrothieno[2,3-c]quinolin-9-yl)phenyl)(methyl)amino)acetonitrile;

  • (1371): 9-(3-chloro-4-(2-(ethyl(methyl)amino)ethyl)phenyl)-8-hydroxythieno[2,3-c]quinolin-4(5H)-one;

  • (1372): 9-(4-(1-((dimethylamino)methyl)cyclobutyl)phenyl)-8-hydroxy-6-methylthieno[2,3-c]quinolin-4(5H)-one;

  • (1373): (R)-9-(4-(1-aminopropyl)phenyl)-6-bromo-8-methoxythieno[2,3-c]quinolin-4(5H)-one;

  • (1374): 9-(6-(2-aminoethoxy)pyridin-3-yl)-8-hydroxy-6-methylthieno[2,3-c]quinolin-4(5H)-one;

  • (1375): (R)-9-(4-(1-aminopropan-2-yl)phenyl)-2-fluoro-8-methoxy-6-methylthieno[2,3-c]quinolin-4(5H)-one;

  • (1376): 9-(6-(2-aminoethoxy)pyridin-3-yl)-8-methoxy-6-methylthieno[2,3-c]quinolin-4(5H)-one;

  • (1377): 9-(4-(1-amino-2,2,2-trifluoroethyl)phenyl)-8-hydroxy-6-methylthieno[2,3-c]quinolin-4(5H)-one;

  • (1378): 9-(4-(1-amino-2,2,2-trifluoroethyl)phenyl)-8-methoxy-6-methylthieno[2,3-c]quinolin-4(5H)-one;

  • (1379): (R)-9-(4-(1-(ethyl(methyl)amino)propan-2-yl)phenyl)-8-hydroxy-6-methylthieno[2,3-c]quinolin-4(5H)-one;

  • (1380): (R)-8-hydroxy-6-methyl-9-(4-(1-(methylamino)butan-2-yl)phenyl)thieno[2,3-c]quinolin-4(5H)-one;

  • (1381): 9-(4-(1-amino-2,2,2-trifluoroethyl)phenyl)-8-methoxythieno[2,3-c]quinolin-4(5H)-one;

  • (1382): (R)-1-(4-(1-aminopropan-2-yl)phenyl)-8-hydroxy-3-methyl-3H-pyrrolo[2,3-c]quinolin-4(5H)-one;

  • (1383): (R)-9-(4-(1-aminopropan-2-yl)phenyl)-2-fluoro-8-hydroxy-6-methylthieno[2,3-c]quinolin-4(5H)-one;

  • (1384): 9-(6-((2-aminoethyl)amino)pyridin-3-yl)-8-hydroxy-6-methylthieno[2,3-c]quinolin-4(5H)-one;

  • (1385): 9-(6-((2-aminoethyl)amino)pyridin-3-yl)-8-methoxy-6-methylthieno[2,3-c]quinolin-4(5H)-one;

  • (1386): (S)-6-chloro-9-(4-(1-(ethyl(methyl)amino)propan-2-yl)phenyl)-8-hydroxythieno[2,3-c]quinolin-4(5H)-one;

  • (1387): (S)-9-(4-(1-(dimethylamino)propan-2-yl)-3-fluorophenyl)-8-methoxy-6-methylthieno[2,3-c]quinolin-4(5H)-one;

  • (1388): (R)-9-(4-(1-(diethylamino)propan-2-yl)phenyl)-8-hydroxy-6-methylthieno[2,3-c]quinolin-4(5H)-one;

  • (1389): 9-(4-(1-amino-2,2,2-trifluoroethyl)phenyl)-8-hydroxythieno[2,3-c]quinolin-4(5H)-one;

  • (1390): 9-(4-(1-amino-2,2,2-trifluoroethyl)phenyl)-6-bromo-8-methoxythieno[2,3-c]quinolin-4(5H)-one;

  • (1391): 9-(4-(1-(aminomethyl)cyclopropyl)phenyl)-6-bromo-8-methoxythieno[2,3-c]quinolin-4(5H)-one;

  • (1392): (4-(8-hydroxy-6-methyl-4-oxo-4,5-dihydrothieno[2,3-c]quinolin-9-yl)phenyl)methanesulfonamide;

  • (1393): 8-methoxy-6-methyl-9-(4-(2-(methylsulfinyl)ethyl)phenyl)thieno[2,3-c]quinolin-4(5H)-one;

  • (1394): 8-hydroxy-6-methyl-9-(4-((methylsulfonyl)methyl)phenyl)thieno[2,3-c]quinolin-4(5H)-one;

  • (1395): (4-(8-methoxy-6-methyl-4-oxo-4,5-dihydrothieno[2,3-c]quinolin-9-yl)phenyl)methanesulfonamide;

  • (1396): 9-(4-((2-aminoethyl)(methyl)amino)phenyl)-8-methoxy-6-methylthieno[2,3-c]quinolin-4(5H)-one;

  • (1397): (R)—N-(2-(2-fluoro-4-(8-hydroxy-6-methyl-4-oxo-4,5-dihydrothieno[2,3-c]quinolin-9-yl)phenyl)propyl)methanesulfonamide;

  • (1398): (R)—N-(2-(2-fluoro-4-(8-methoxy-6-methyl-4-oxo-4,5-dihydrothieno[2,3-c]quinolin-9-yl)phenyl)propyl)methanesulfonamide;

  • (1399): (S)-9-(4-(1-(dimethylamino)propan-2-yl)-3-fluorophenyl)-8-hydroxy-6-methylthieno[2,3-c]quinolin-4(5H)-one;

  • (1400): 9-(4-((2-aminoethyl)(methyl)amino)phenyl)-8-hydroxy-6-methylthieno[2,3-c]quinolin-4(5H)-one;

  • (1401): 9-(4-(1-(aminomethyl)cyclopropyl)phenyl)-6-bromo-8-hydroxythieno[2,3-c]quinolin-4(5H)-one;

  • (1402): 2-(6-(8-methoxy-6-methyl-4-oxo-4,5-dihydrothieno[2,3-c]quinolin-9-yl)pyridin-3-yl)acetonitrile;

  • (1403): 8-hydroxy-6-methyl-9-(4-(2-(methylsulfinyl)ethyl)phenyl)thieno[2,3-c]quinolin-4(5H)-one;

  • (1404): 8-methoxy-6-methyl-9-(4-((methylsulfonyl)methyl)phenyl)thieno[2,3-c]quinolin-4(5H)-one;

  • (1405): 5-(8-methoxy-6-methyl-4-oxo-4,5-dihydrothieno[2,3-c]quinolin-9-yl)nicotinamide;

  • (1406): 2-(5-(8-hydroxy-4-oxo-4,5-dihydrothieno[2,3-c]quinolin-9-yl)pyridin-2-yl)propanenitrile;

  • (1407): 2-(4-(8-methoxy-6-methyl-4-oxo-4,5-dihydrothieno[2,3-c]quinolin-9-yl)phenyl)propanamide;

  • (1408): 9-(6-(1-aminopropan-2-yl)pyridin-3-yl)-8-methoxy-6-methylthieno[2,3-c]quinolin-4(5H)-one;

  • (1409): 2-(5-(8-methoxy-6-methyl-4-oxo-4,5-dihydrothieno[2,3-c]quinolin-9-yl)pyridin-2-yl)-2-methylpropanenitrile;

  • (1410): 2-hydroxy-2-(4-(8-hydroxy-4-oxo-4,5-dihydrothieno[2,3-c]quinolin-9-yl)phenyl)propane-1-sulfonamide;

  • (1411): N-(tert-butyl)-2-hydroxy-2-(4-(8-methoxy-4-oxo-4,5-dihydrothieno[2,3-c]quinolin-9-yl)phenyl)propane-1-sulfonamide;

  • (1412): 2-(4-(8-hydroxy-6-methyl-4-oxo-4,5-dihydrothieno[2,3-c]quinolin-9-yl)phenyl)propanamide;

  • (1413): 2-(4-(8-hydroxy-4-oxo-4,5-dihydrothieno[2,3-c]quinolin-9-yl)phenyl)propane-1-sulfonamide;

  • (1414): 9-(4-(2-amino-1-fluoroethyl)phenyl)-8-methoxy-6-methylthieno[2,3-c]quinolin-4(5H)-one;

  • (1415): 9-(6-(1-aminopropan-2-yl)pyridin-3-yl)-8-hydroxy-6-methylthieno[2,3-c]quinolin-4(5H)-one;

  • (1416): 2-(5-(8-hydroxy-6-methyl-4-oxo-4,5-dihydrothieno[2,3-c]quinolin-9-yl)pyridin-2-yl)-2-methylpropanenitrile;

  • (1417): 2-(5-(8-hydroxy-4-oxo-4,5-dihydrothieno[2,3-c]quinolin-9-yl)pyridin-2-yl)-2-methylpropanenitrile;

  • (1418): 2-(5-(8-methoxy-4-oxo-4,5-dihydrothieno[2,3-c]quinolin-9-yl)pyridin-2-yl)-2-methylpropanenitrile;

  • (1419): 2-(4-(8-hydroxy-6-methyl-4-oxo-4,5-dihydrothieno[2,3-c]quinolin-9-yl)phenyl)propane-1-sulfonamide;

  • (1420): 9-(4-(2-amino-1-hydroxyethyl)phenyl)-8-methoxy-6-methylthieno[2,3-c]quinolin-4(5H)-one;

  • (1421): 9-(6-(1-amino-2-methylpropan-2-yl)pyridin-3-yl)-8-hydroxythieno[2,3-c]quinolin-4(5H)-one;

  • (1422): N-cyclopropyl-1-(4-(8-methoxy-6-methyl-4-oxo-4,5-dihydrothieno[2,3-c]quinolin-9-yl)phenyl)methanesulfonamide;

  • (1423): 2-(5-(8-methoxy-4-oxo-4,5-dihydrothieno[2,3-c]quinolin-9-yl)pyridin-2-yl)propanenitrile;

  • (1424): (R)—N-(2-(4-(8-methoxy-6-methyl-4-oxo-4,5-dihydrothieno[2,3-c]quinolin-9-yl)phenyl)propyl)methanesulfonamide;

  • (1425): N-ethyl-1-(4-(8-methoxy-6-methyl-4-oxo-4,5-dihydrothieno[2,3-c]quinolin-9-yl)phenyl)methanesulfonamide;

  • (1426): 9-(6-(1-aminopropan-2-yl)pyridin-3-yl)-8-methoxythieno[2,3-c]quinolin-4(5H)-one;

  • (1427): N-cyclopropyl-1-(4-(8-hydroxy-6-methyl-4-oxo-4,5-dihydrothieno[2,3-c]quinolin-9-yl)phenyl)methanesulfonamide;

  • (1428): 1-(5-(8-methoxy-4-oxo-4,5-dihydrothieno[2,3-c]quinolin-9-yl)pyridin-2-yl)cyclopropanecarbonitrile;

  • (1429): N-ethyl-1-(4-(8-hydroxy-6-methyl-4-oxo-4,5-dihydrothieno[2,3-c]quinolin-9-yl)phenyl)methanesulfonamide;

  • (1430): 1-(4-(8-methoxy-6-methyl-4-oxo-4,5-dihydrothieno[2,3-c]quinolin-9-yl)phenyl)ethanesulfonamide;

  • (1431): 1-(4-(8-methoxy-4-oxo-4,5-dihydrothieno[2,3-c]quinolin-9-yl)phenyl)ethanesulfonamide;

  • (1432): (R)—N-(2-(4-(8-methoxy-4-oxo-4,5-dihydrothieno[2,3-c]quinolin-9-yl)phenyl)propyl)methanesulfonamide;

  • (1433): (R)—N-(2-(4-(8-hydroxy-4-oxo-4,5-dihydrothieno[2,3-c]quinolin-9-yl)phenyl)propyl)-N-methylmethanesulfonamide;

  • (1434): (R)—N-(2-(4-(8-hydroxy-6-methyl-4-oxo-4,5-dihydrothieno[2,3-c]quinolin-9-yl)phenyl)propyl)methanesulfonamide;

  • (1435): (R)—N-(2-(4-(8-hydroxy-4-oxo-4,5-dihydrothieno[2,3-c]quinolin-9-yl)phenyl)propyl)methanesulfonamide;

  • (1436): (R)—N-(2-(4-(8-methoxy-4-oxo-4,5-dihydrothieno[2,3-c]quinolin-9-yl)phenyl)propyl)-N-methylmethanesulfonamide;

  • (1437): (R)—N-(2-(4-(8-hydroxy-6-methyl-4-oxo-4,5-dihydrothieno[2,3-c]quinolin-9-yl)phenyl)propyl)-N-methylmethanesulfonamide;

  • (1438): (R)—N-(2-(4-(8-methoxy-6-methyl-4-oxo-4,5-dihydrothieno[2,3-c]quinolin-9-yl)phenyl)propyl)-N-methylmethanesulfonamide;
    • or a pharmaceutically acceptable salt thereof.

  • 21. A pharmaceutical composition comprising at least one compound of above 1 or 2 or a pharmaceutically acceptable salt thereof, and a pharmaceutically acceptable carrier.

  • 22. The pharmaceutical composition of above 21 which is available for preventing or treating a PBK dependent disease.

  • 23. The pharmaceutical composition of above 22, wherein the PBK dependent disease is cancer.

  • 24. A PBK inhibitor comprising at least one compound of above 1 or 2, or a pharmaceutically acceptable salt thereof.

  • 25. A method for treating a PBK dependent disease in a subject, comprising administering to said subject an effective amount of a compound or a pharmaceutically acceptable salt thereof of above 1 or 2.

  • 26. A compound or pharmaceutically acceptable salt thereof of above 1 or 2 for use in treatment of a PBK dependent disease.

  • 27. Use of a compound of above 1 or 2 or a pharmaceutically acceptable salt thereof in manufacturing a pharmaceutical composition for treating a PBK dependent disease.



Alternatively, the present invention also provides following embodiments:

  • 101. The present invention provides a compound represented by formula (I) or a pharmaceutically acceptable salt thereof:




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    • or a pharmaceutically acceptable salt thereof,

    • wherein R1, R2, R3, and R4 are each independently a group selected from the group consisting of:

    • hydrogen,

    • hydroxyl,

    • halogen,

    • cyano,

    • nitro,

    • amino,

    • C1-C6 alkyl,

    • C2-C6 alkenyl,

    • C2-C6 alkynyl,

    • C3-C10 cycloalkyl,

    • C3-C10 cycloalkenyl,

    • C1-C6 alkoxy,

    • C6-C10 aryl,

    • indanyl,

    • heteroaryl,

    • 3- to 8-membered heterocycloalkyl,

    • —OSO2CH3,

    • —OSO2CF3, and

    • —CONH2,

    • wherein each of the groups of R1 to R4 is optionally substituted with a substituent selected from the group consisting of substituent A below:

    • substituent A:
      • hydroxyl;
      • oxo (═O);
      • cyano;
      • halogen;
      • C1-C6 alkyl (wherein the C1-C6 alkyl is optionally substituted with a substituent selected from the group consisting of substituent B below);
      • C3-C10 cycloalkyl [wherein the C3-C10 cycloalkyl is optionally substituted with cyano, or C1-C6 alkyl substituted with —NR31R32 (wherein R31 and R32 each independently represent hydrogen or C1-C6 alkyl)];
      • —NR21R22 [wherein R21 and R22 each independently represent hydrogen, or C1-C6 alkyl (wherein the C1-C6 alkyl is optionally substituted with di(C1-C6 alkyl)amino, C1-C6 alkylsulfonyl (—SO2(C1-C6 alkyl)), or 3- to 8-membered heterocycloalkyl)];
      • C1-C6 alkoxy {wherein the C1-C6 alkoxy is optionally substituted with halogen, 3- to 8-membered heterocycloalkyl (wherein the 3- to 8-membered heterocycloalkyl is optionally substituted with C1-C6 alkyl), or —NR33R34 [wherein R33 and R34 each independently represent hydrogen, C1-C6 alkyl (wherein the C1-C6 alkyl is optionally substituted with C1-C6 alkylsulfonyl or di(C1-C6 alkyl)amino), or C1-C6 alkylsulfonyl]};
      • —SO2NR23R24 {wherein R23 and R24 each independently represent hydrogen, C1-C6 alkyl [wherein the C1-C6 alkyl is optionally substituted with hydroxyl, C1-C6 alkoxy, halogen, C3-C10 cycloalkyl, or —NR35R36 (wherein R35 and R36 each independently represent hydrogen or C1-C6 alkyl)], C3-C10 cycloalkyl (wherein the C3-C10 cycloalkyl is optionally substituted with C1-C6 hydroxyalkyl), or 3- to 8-membered heterocycloalkyl; or R23 and R24 may together form 3- to 8-membered heterocycloalkyl wherein the 3- to 8-membered heterocycloalkyl is optionally substituted with amino};
      • C1-C6 alkylsulfonyl (wherein the C1-C6 alkyl moiety is optionally substituted with hydroxyl);
      • C1-C6 alkylsulfonylamino (—NHSO2(C1-C6 alkyl)) [wherein the C1-C6 alkyl moiety is optionally substituted with —NR37R38 (wherein R37 and R38 each independently represent hydrogen or C1-C6 alkyl)];
      • 3- to 8-membered heterocycloalkyl {wherein the 3- to 8-membered heterocycloalkyl is optionally substituted with —NR39R40 (wherein R39 and R40 each independently represent hydrogen, C1-C6 alkyl, or C1-C6 alkylsulfonyl), C1-C6 alkyl [wherein the C1-C6 alkyl is optionally substituted with —NR41R42 (wherein R41 and R42 each independently represent hydrogen or C1-C6 alkyl)], hydroxyl, or C1-C6 alkylsulfonyl};
      • heteroaryl;
      • —COOR11 (wherein R11 represents hydrogen or C1-C6 alkyl); and
      • —COR12 [wherein R12 represents C1-C6 alkyl, C3-C10 cycloalkyl, cyanomethyl, —NR25R26 {wherein R25 and R26 each independently represent hydrogen, or C1-C6 alkyl [wherein the C1-C6 alkyl is optionally substituted with hydroxyl or —NR43R44 (wherein R43 and R44 each independently represent hydrogen or C1-C6 alkyl)]}, or 3- to 8-membered heterocycloalkyl which is optionally substituted with C1-C6 alkyl],

    • substituent B:
      • halogen;
      • hydroxyl;
      • cyano;
      • 3- to 8-membered heterocycloalkyl (wherein the 3- to 8-membered heterocycloalkyl is optionally substituted with C1-C6 alkyl, hydroxyl, amino, C1-C6 aminoalkyl, or C1-C6 alkyl substituted with C2-C7 alkyloxycarbonylamino);
      • —NR51R52 (wherein R51 and R52 each independently represent hydrogen, C1-C6 alkyl [wherein the C1-C6 alkyl is optionally substituted with C1-C6 alkylsulfonyl, or 3- to 8-membered heterocycloalkyl optionally substituted with —COOR13 (wherein R53 represents hydrogen or C1-C6 alkyl)], 3- to 8-membered heterocycloalkyl, C1-C6 alkylsulfonyl, C3-C10 cycloalkyl, —COR55 (wherein R55 represents C1-C6 alkyl), —COOR56 (wherein R56 represents C1-C6 alkyl), or —CONR57R58 (wherein R57 and R58 each independently represent hydrogen or C1-C6 alkyl)); and
      • —COOR54 (wherein R54 represents hydrogen or C1-C6 alkyl)];

    • wherein R5 is hydrogen or C1-C6 alkyl; and

    • wherein







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    •  is a structure selected from the group consisting of
      • (i) —S—CR7═CR6—,
      • (ii) —CH2—CH2—CH2—,
      • (iii) —NH—CH═CCH3—, and
      • (iv) —═CH—S—,

    • wherein R6 is
      • hydrogen,
      • hydroxyl,
      • C1-C6 alkyl,
      • C6-C10 aryl (wherein the C6-C10 aryl is optionally substituted with hydroxyl), or
      • 3- to 8-membered heterocycloalkyl [wherein the 3- to 8-membered heterocycloalkyl is optionally substituted with —NR61R62 (wherein R61 and R62 each independently represent hydrogen or C1-C6 alkyl)], and

    • wherein R7 is
      • hydrogen,
      • C1-C6 alkyl (wherein the C1-C6 alkyl is optionally substituted with hydroxyl, —NR71R72 [wherein R71 and R72 each independently represent hydrogen, C1-C6 alkyl (wherein the C1-C6 alkyl is optionally substituted with dimethylamino), C3-C10 cycloalkyl (wherein the C3-C10 cycloalkyl is optionally substituted with amino), or 3- to 8-membered heterocycloalkyl], or 3- to 8-membered heterocycloalkyl (wherein the 3- to 8-membered heterocycloalkyl is optionally substituted with C1-C6 aminoalkyl)),
      • C6-C10 aryl (wherein the C6-C10 aryl is optionally substituted with hydroxyl), or
      • —COR73 {wherein R73 represents 3- to 8-membered heterocycloalkyl (wherein the 3- to 8-membered heterocycloalkyl is optionally substituted with amino), or —NR74R75 [wherein R74 and R75 each independently represent hydrogen, 3- to 8-membered heterocycloalkyl, or C3-C10 cycloalkyl (wherein the C3-C10 cycloalkyl is optionally substituted with amino)]}.



  • 102. The compound of above 101, or a pharmaceutically acceptable salt thereof, wherein





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  •  is —S—CR7═CR6—.
    • Specifically, the compound of above 1 which have a following formula II, or a pharmaceutically acceptable salt thereof;





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  • 103. The compound of above 102, or a pharmaceutically acceptable salt thereof, wherein R1 is hydrogen or halogen.

  • 104. The compound of above 102 or 103, or a pharmaceutically acceptable salt thereof, wherein R2 is hydrogen, hydroxyl, halogen, C1-C6 alkoxy, or C6-C10 aryl which is optionally substituted with hydroxyl.

  • 105. The compound of any one of above 102-104 or a pharmaceutically acceptable salt, wherein R2 is hydrogen, hydroxyl, halogen, C1-C6 alkoxy, or dihydroxyphenyl.

  • 106. The compound of any one of above 102-105, or a pharmaceutically acceptable salt thereof, wherein R3 is hydrogen; hydroxyl; halogen; C1-C6 alkoxy; cyano; nitro; 3- to 8-membered heterocycloalkyl which is optionally substituted with amino; heteroaryl; —OSO2CH3; —OSO2CF3; or —CONH2.

  • 107. The compound of any one of above 102-106, or a pharmaceutically acceptable salt thereof, wherein R3 is hydrogen; hydroxyl; halogen; C1-C6 alkoxy; cyano; nitro; 3- to 8-membered heterocycloalkyl which is optionally substituted with amino (wherein the 3- to 8-membered heterocycloalkyl is piperidyl, pyrrolidinyl, morpholinyl, or piperazinyl); pyridyl; —OSO2CH3; —OSO2CF3; or —CONH2.

  • 108. The compound of any one of above 102-107, or a pharmaceutically acceptable salt thereof, wherein R4 is a group selected from the group consisting of hydrogen, hydroxyl, halogen, amino, C1-C6 alkyl, C2-C6 alkenyl, C3-C10 cycloalkyl, C3-C10 cycloalkenyl, C1-C6 alkoxy, C6-C10 aryl, indanyl, heteroaryl, and 3- to 8-membered heterocycloalkyl, wherein each of the groups of R4 is optionally substituted with a substituent selected from the group consisting of substituent A above.



109. The compound of any one of above 102-108, or a pharmaceutically acceptable salt thereof, wherein R4 is a group selected from the group consisting of hydrogen, hydroxyl, halogen, amino, C1-C6 alkyl, C2-C6 alkenyl, C3-C10 cycloalkyl, C3-C10 cycloalkenyl, C1-C6 alkoxy, C6-C10 aryl, indanyl, heteroaryl (wherein the heteroaryl is selected from the group consisting of pyridyl, 1H-indazolyl, 1H-tetrazolyl, [1,2,4]triazolo[1,5-a]pyridyl, benzoimidazolyl, 2,3-dihydrobenzooxazolyl, pyrazolyl, pyrrolo[2,3-b]pyridyl, pyrimidinyl, indolinyl, furyl, thienyl, and tetrahydroisoquinolyl), and 3- to 8-membered heterocycloalkyl (wherein the 3- to 8-membered heterocycloalkyl is selected from the group consisting of aziridinyl, azetidinyl, pyrrolidinyl, imidazolidinyl, piperidyl, piperazinyl, azepanyl, morpholinyl, and 1,2,3,6-tetrahydropyridyl), wherein each of the groups of R4 is optionally substituted with a substituent selected from the group consisting of substituent A-1 below:

    • substituent A-1:
    • hydroxyl;
    • oxo;
    • cyano;
    • halogen;
    • C1-C6 alkyl (wherein the C1-C6 alkyl is optionally substituted with a substituent selected from the group consisting of substituent B-1 below);
    • C3-C10 cycloalkyl [wherein the C3-C10 cycloalkyl is optionally substituted with cyano, or C1-C6 alkyl substituted with —NR31R32 (wherein R31 and R32 each independently represent hydrogen or C1-C6 alkyl)];
    • —NR21AR22A [wherein R21A and R22A each independently represent hydrogen or C1-C6 alkyl (wherein C1-C6 alkyl is optionally substituted with di(C1-C6 alkyl)amino, C1-C6 alkylsulfonyl (—SO2 (C1-C6 alkyl)), or piperidyl)];
    • C1-C6 alkoxy {wherein the C1-C6 alkoxy is optionally substituted with 3- to 8-membered heterocycloalkyl selected from halogen, piperidyl, and piperazinyl (wherein the 3- to 8-membered heterocycloalkyl is optionally substituted with C1-C6 alkyl), or —NR33R34 [wherein R33 and R34 each independently represent hydrogen, C1-C6 alkyl (wherein the C1-C6 alkyl is optionally substituted with C1-C6 alkylsulfonyl or di(C1-C6 alkyl)amino), or C1-C6 alkylsulfonyl]};
    • —SO2NR23AR24A {wherein R23A and R24A each independently represent hydrogen, C1-C6 alkyl [wherein the C1-C6 alkyl is optionally substituted with hydroxyl, C1-C6 alkoxy, halogen, C3-C10 cycloalkyl, or —NR35R36 (wherein R35 and R36 each independently represent hydrogen or C1-C6 alkyl)], C3-C10 cycloalkyl (wherein the C3-C10 cycloalkyl is optionally substituted with C1-C6 hydroxyalkyl), azetidinyl, or pyrrolidinyl, or may together form pyrrolidinyl, wherein the pyrrolidinyl is optionally substituted with amino};
    • C1-C6 alkylsulfonyl (wherein the C1-C6 alkyl moiety is optionally substituted with hydroxyl);
    • C1-C6 alkylsulfonylamino (—NHSO2 (C1-C6 alkyl)) [wherein the C1-C6 alkyl moiety is optionally substituted with —NR37R38 (wherein R37 and R38 each independently represent hydrogen or C1-C6 alkyl)];
    • 3- to 8-membered heterocycloalkyl selected from the group consisting of azetidinyl, pyrrolidinyl, piperidyl, and piperazinyl (wherein the 3- to 8-membered heterocycloalkyl is optionally substituted with —NR39R40 (wherein R39 and R40 each independently represent hydrogen, C1-C6 alkyl, or C1-C6 alkylsulfonyl), C1-C6 alkyl [wherein the C1-C6 alkyl is optionally substituted with —NR41R42 (wherein R41 and R42 each independently represent hydrogen or C1-C6 alkyl)], hydroxyl, or C1-C6 alkylsulfonyl);
    • 1H-tetrazolyl;
    • —COOR11 (wherein R11 represents hydrogen or C1-C6 alkyl); and
    • —COR12A [wherein R12A represents piperazinyl which is optionally substituted with C1-C6 alkyl, C3-C10 cycloalkyl, cyanomethyl, —NR25R26 {wherein R25 and R26 each independently represent hydrogen or C1-C6 alkyl [wherein the C1-C6 alkyl is optionally substituted with hydroxyl or —NR43R44 (wherein R43 and R44 each independently represent hydrogen or C1-C6 alkyl)]}), or C1-C6 alkyl];
    • substituent B-1:
    • halogen;
    • hydroxyl;
    • 50 cyano;
    • 3- to 8-membered heterocycloalkyl selected from the group consisting of pyrrolidinyl, piperidyl, piperazinyl, and morpholinyl (wherein the 3- to 8-membered heterocycloalkyl is optionally substituted with C1-C6 alkyl, hydroxyl, amino, C1-C6 aminoalkyl, or C1-C6 alkyl substituted with C2-C7 alkyloxycarbonylamino);
    • —NR51AR52A {wherein R51A and R52A each independently represent hydrogen, C1-C6 alkyl [wherein the C1-C6 alkyl is optionally substituted with C1-C6 alkylsulfonyl, or piperidyl which is optionally substituted with, —COOR13 (wherein R53 represents hydrogen or C1-C6 alkyl)], piperidyl, C1-C6 alkylsulfonyl, C3-C10 cycloalkyl, —COR55 (wherein R55 represents C1-C6 alkyl), —COOR56 (wherein R56 represents C1-C6 alkyl), or —CONR57R58 (wherein R57 and R58 each independently represent hydrogen or C1-C6 alkyl)}; and
    • —COOR54 (wherein R54 represents hydrogen or C1-C6 alkyl).
  • 1010. The compound of any one of above 102-109, or a pharmaceutically acceptable salt thereof, wherein R4 is a group selected from the group consisting of (p) below:
    • (p):
      • hydrogen,
      • hydroxyl,
      • halogen,
      • amino,
      • C1-C6 alkyl which is optionally substituted with a substituent selected from the group consisting of substituent (a) below,
      • C2-C6 alkenyl which is optionally substituted with a substituent selected from the group consisting of substituent (b) below,
      • C3-C10 cycloalkyl,
      • C3-C10 cycloalkenyl,
      • C1-C6 alkoxy,
      • C6-C10 aryl which is optionally substituted with a substituent selected from the group consisting of substituent (c) below,
      • indanyl which is optionally substituted with a substituent selected from the group consisting of substituent (d) below,
      • heteroaryl which is optionally substituted with a substituent selected from the group consisting of substituent (e) below, and
      • 3- to 8-membered heterocycloalkyl which is optionally substituted with a substituent selected from the group consisting of substituent (f) below, wherein, in the group (p),
      • the heteroaryl is selected from the group consisting of pyridyl, 1H-indazolyl, 1H-tetrazolyl, [1,2,4]triazolo[1,5-a]pyridyl, benzoimidazolyl, 2,3-dihydrobenzooxazolyl, pyrazolyl, pyrrolo[2,3-b]pyridyl, pyrimidinyl, indolinyl, furyl, thienyl, and tetrahydroisoquinolyl;
      • the 3- to 8-membered heterocycloalkyl is selected from the group consisting of pyrrolidinyl, piperidyl, piperazinyl, morpholinyl, and 1,2,3,6-tetrahydropyridyl;
      • substituent (a):
        • 3- to 8-membered heterocycloalkyl selected from the group consisting of pyrrolidinyl and piperidyl {wherein the 3- to 8-membered heterocycloalkyl is optionally substituted with —NR39R40 (wherein R39 and R40 each independently represent hydrogen or C1-C6 alkyl), or C1-C6 alkyl [wherein the C1-C6 alkyl is optionally substituted with —NR41R42 (wherein R41 and R42 each independently represent hydrogen or C1-C6 alkyl)]}; and
        • C1-C6 alkylsulfonylamino (—NHSO2(C1-C6 alkyl));
      • substituent (b):
        • —COOR11 (wherein R11 represents hydrogen or C1-C6 alkyl);
        • —NR21aR22a [wherein R21a and R22a each independently represent hydrogen, or C1-C6 alkyl (wherein the C1-C6 alkyl is optionally substituted with di(C1-C6 alkyl)amino or C1-C6 alkylsulfonyl)];
        • 3- to 8-membered heterocycloalkyl selected from the group consisting of azetidinyl, pyrrolidinyl, and piperidyl (wherein the 3- to 8-membered heterocycloalkyl is optionally substituted with —NR39R40 {wherein R39 and R40 each independently represent hydrogen, C1-C6 alkyl, or C1-C6 alkylsulfonyl), C1-C6 alkyl [wherein the C1-C6 alkyl is optionally substituted with —NR41R42 (wherein R41 and R42 each independently represent hydrogen or C1-C6 alkyl)], hydroxyl, or C1-C6 alkylsulfonyl};
        • cyano; and
        • C1-C6 alkoxy;
      • substituent (c):
        • hydroxyl;
        • cyano;
        • halogen;
        • C1-C6 alkyl (wherein the C1-C6 alkyl is optionally substituted with a substituent selected from the group consisting of substituent B-c below);
        • C3-C10 cycloalkyl [wherein the C3-C10 cycloalkyl is optionally substituted with cyano, or C1-C6 alkyl substituted with —NR31R32 (wherein R31 and R32 each independently represent hydrogen or C1-C6 alkyl)];
        • —NR21cR22c [wherein R21c and R22c each independently represent hydrogen or C1-C6 alkyl];
        • C1-C6 alkoxy {wherein the C1-C6 alkoxy is optionally substituted with 3- to 8-membered heterocycloalkyl selected from halogen, piperidyl, and piperazinyl (wherein the 3- to 8-membered heterocycloalkyl is optionally substituted with C1-C6 alkyl), or —NR33R34 [wherein R33 and R34 each independently represent hydrogen, C1-C6 alkyl (wherein the C1-C6 alkyl is optionally substituted with di(C1-C6 alkyl)amino), or C1-C6 alkylsulfonyl]};
        • —SO2NR23cR24c {wherein R23c and R24c each independently represent hydrogen, C1-C6 alkyl [wherein the C1-C6 alkyl is optionally substituted with hydroxyl, C1-C6 alkoxy, halogen, C3-C10 cycloalkyl, or —NR35R36 (wherein R35 and R36 each independently represent hydrogen or C1-C6 alkyl)], C3-C10cycloalkyl (wherein the C3-C10 cycloalkyl is optionally substituted with C1-C6 hydroxyalkyl), azetidinyl, or pyrrolidinyl, or wherein R23c and R24c may together form pyrrolidinyl which is optionally substituted with amino};
        • C1-C6 alkylsulfonyl (wherein the C1-C6 alkyl moiety is optionally substituted with hydroxyl);
        • C1-C6 alkylsulfonylamino (—NHSO2(C1-C6 alkyl)) [wherein the C1-C6 alkyl moiety is optionally substituted with —NR37R38 (wherein R37 and R38 each independently represent hydrogen or C1-C6 alkyl)];
        • piperazinyl {wherein the piperazinyl is optionally substituted with C1-C6 alkyl or C1-C6 alkylsulfonyl};
        • 1H-tetrazolyl; and
        • —COR12c [wherein R12c represents piperazinyl which is optionally substituted with C1-C6 alkyl, C3-C10 cycloalkyl, cyanomethyl, —NR25R26 {wherein R25 and R26 each independently represent hydrogen or C1-C6 alkyl [wherein the C1-C6 alkyl is optionally substituted with hydroxyl, or —NR43R44 (wherein R43 and R44 each independently represent hydrogen or C1-C6 alkyl)]}), or C1-C6 alkyl]; and
      • substituent B-c:
        • halogen;
        • hydroxyl;
        • cyano;
        • 3- to 8-membered heterocycloalkyl selected from the group consisting of pyrrolidinyl, piperidyl, piperazinyl, and morpholinyl (wherein the 3- to 8-membered heterocycloalkyl is optionally substituted with C1-C6 alkyl, hydroxyl, amino, C1-C6 aminoalkyl, or C1-C6 alkyl substituted with C2-C7 alkyloxycarbonylamino); and
        • —NR51cR52c {wherein R51c and R52c each independently represent hydrogen, C1-C6 alkyl [wherein the C1-C6 alkyl is optionally substituted with C1-C6 alkylsulfonyl, or piperidyl which is optionally substituted with —COOR53 (wherein R53 represents hydrogen or C1-C6 alkyl)], piperidyl, C1-C6alkylsulfonyl, C3-C10cycloalkyl, —COR55 (wherein R55 represents C1-C6 alkyl), or —CONR57R58 (wherein R57 and R58 each independently represent hydrogen or C1-C6 alkyl)}];
      • substituent (d):
        • —NR21dR22d (wherein R21d and R22d each independently represent hydrogen or C1-C6 alkyl);
      • substituent (e):
        • hydroxyl;
        • oxo;
        • cyano;
        • —NR21R22 [wherein R21 and R22 each independently represent hydrogen or C1-C6 alkyl];
        • piperidyl;
        • C1-C6 alkoxy; and
        • C1-C6 alkyl {wherein the C1-C6 alkyl is optionally substituted with —NR51eR52e [wherein R51e and R52e each independently represent hydrogen or —COOR56 (wherein R56 represents C1-C6 alkyl)]}); and
      • substituent (f):
        • C1-C6 alkyl {wherein the C1-C6 alkyl is optionally substituted with —NR51fR52f [wherein R51f and R52f each independently represent hydrogen, C1-C6 alkyl, or —COOR56 (wherein R56 represents C1-C6 alkyl)]}; and
        • C1-C6 alkylsulfonyl.
  • 111. The compound of any one of above 102-110, or a pharmaceutically acceptable salt thereof, wherein R6 is hydrogen; hydroxyl; C1-C6 alkyl; phenyl which is optionally substituted with 1 to 3 hydroxyls; piperidyl which is optionally substituted with amino; or piperazinyl.
  • 112. The compound of above 111, or a pharmaceutically acceptable salt thereof, wherein R7 is hydrogen.
  • 113. The compound of any one of above 102-111, or a pharmaceutically acceptable salt thereof, wherein R7 is
    • hydrogen;
    • C1-C6 alkyl (wherein the C1-C6 alkyl is optionally substituted with hydroxyl, —NR71AR72A [wherein R71A and R72A each independently represent hydrogen, C1-C6 alkyl (wherein the C1-C6 alkyl is optionally substituted with dimethylamino), C3-C10 cycloalkyl (wherein the C3-C10 cycloalkyl is optionally substituted with amino), or piperidyl], or 3- to 8-membered heterocycloalkyl selected from the group consisting of piperidyl and morpholinyl (wherein the 3- to 8-membered heterocycloalkyl is optionally substituted with C1-C6 aminoalkyl));
    • phenyl which is optionally substituted with 1 to 2 hydroxyls; or
    • —COR73A {wherein R73A represents piperidyl (wherein the piperidyl is optionally substituted with amino), or —NR74AR75A [wherein R74A and R75A each independently represent hydrogen, piperidyl, or C3-C10 cycloalkyl (wherein the C3-C10 cycloalkyl is optionally substituted with amino)]}.
  • 114. The compound of above 101, or a pharmaceutically acceptable salt thereof, wherein




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  •  is —CH2—CH2—CH2—.
    • Specifically, the compound of above 1 which have a following formula III, or a pharmaceutically acceptable salt thereof:





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  • 115. The compound of above 114, or a pharmaceutically acceptable salt thereof, wherein R1, R2 and R5 are hydrogen.

  • 116. The compound of above 114 or 115, or a pharmaceutically acceptable salt thereof, wherein R3 is hydroxyl or methoxy.

  • 117. The compound of any one of above 114-116, or a pharmaceutically acceptable salt thereof, wherein R4 is hydrogen, phenyl [wherein the phenyl is substituted with C1-C6 alkyl substituted with —NR51AR52A (wherein R51A and R52A each independently represent hydrogen or C1-C6 alkyl), or —SO2NH2], 1,2,3,6-tetrahydropyridyl, hydroxypyridyl, or methoxypyridyl.

  • 118. The compound of above 101, or a pharmaceutically acceptable salt thereof, wherein





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  •  is —NH—CH═CCH3—,
    • R1, R2, R4 and R5 are hydrogen, and
    • R3 is hydroxyl.

  • 119. The compound of above 101, or a pharmaceutically acceptable salt thereof, wherein





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  •  is —N═CH—S—,
    • R1, R2, R4 and R5 are hydrogen, and
    • R3 is methoxy.

  • 120. A compound selected from the group consisting of:

  • (1): 8-methoxy-5-methylthieno[2,3-c]quinolin-4(5H)-one;

  • (2): 8-hydroxy-5-methylthieno[2,3-c]quinolin-4(5H)-one;

  • (3): 7,8-dihydroxythieno[2,3-c]quinolin-4(5H)-one;

  • (4): 7,8-dimethoxythieno[2,3-c]quinolin-4(5H)-one;

  • (5): 8-methoxythieno[2,3-c]quinolin-4(5H)-one;

  • (6): 7,9-dimethoxythieno[2,3-c]quinolin-4(5H)-one;

  • (7): 7,9-dihydroxythieno[2,3-c]quinolin-4(5H)-one;

  • (8): 7,8,9-trimethoxythieno[2,3-c]quinolin-4(5H)-one;

  • (9): 8-hydroxythieno[2,3-c]quinolin-4(5H)-one;

  • (10): 7,8,9-trihydroxythieno[2,3-c]quinolin-4(5H)-one;

  • (11): 9-(3-(2-aminoethyl)phenyl)-8-methoxythieno[2,3-c]quinolin-4(5H)-one;

  • (12): 8-chlorothieno[2,3-c]quinolin-4(5H)-one;

  • (13): 4-oxo-4,5-dihydrothieno[2,3-c]quinoline-8-carbonitrile;

  • (14): thieno[2,3-c]quinolin-4(5H)-one;

  • (15): 8-fluorothieno[2,3-c]quinolin-4(5H)-one;

  • (16): 8-nitrothieno[2,3-c]quinolin-4(5H)-one;

  • (17): 8-(3-aminopiperidin-1-yl)thieno[2,3-c]quinolin-4(5H)-one;

  • (18): 1-(4-hydroxyphenyl)thieno[2,3-c]quinolin-4(5H)-one;

  • (19): 1,8-dihydroxythieno[2,3-c]quinolin-4(5H)-one;

  • (20): 8-hydroxy-1-(4-hydroxyphenyl)thieno[2,3-c]quinolin-4(5H)-one;

  • (2H): (R)-8-(3-aminopyrrolidin-1-yl)thieno[2,3-c]quinolin-4(5H)-one;

  • (22): (S)-8-(3-aminopyrrolidin-1-yl)thieno[2,3-c]quinolin-4(5H)-one;

  • (23): 8-(pyridin-3-yl)thieno[2,3-c]quinolin-4(5H)-one;

  • (24): 8-(4-hydroxyphenyl)thieno[2,3-c]quinolin-4(5H)-one;

  • (25): 1-(3,4-dihydroxyphenyl)-8-hydroxythieno[2,3-c]quinolin-4(5H)-one;

  • (26): 1-(3-aminopiperidin-1-yl)-8-hydroxythieno[2,3-c]quinolin-4(5H)-one;

  • (27): 8-morpholinothieno[2,3-c]quinolin-4(5H)-one;

  • (28): 8-hydroxy-2-methylthieno[2,3-c]quinolin-4(5H)-one;

  • (29): 8-hydroxy-2-(hydroxymethyl)thieno[2,3-c]quinolin-4(5H)-one;

  • (30): 8-hydroxy-4-oxo-N-(piperidin-3-yl)-4,5-dihydrothieno[2,3-c]quinoline-2-carboxamide;

  • (31): 8-hydroxy-2-(4-hydroxyphenyl)thieno[2,3-c]quinolin-4(5H)-one;

  • (32): 8-hydroxy-1-(piperazin-1-yl)thieno[2,3-c]quinolin-4(5H)-one;

  • (33): N-((1r,4r)-4-aminocyclohexyl)-8-hydroxy-4-oxo-4,5-dihydrothieno[2,3-c]quinolin-2-carboxamide;

  • (34): 2-(3-aminopiperidine-1-carbonyl)-8-hydroxythieno[2,3-c]quinolin-4(5H)-one;

  • (35): 2-(3,4-dihydroxyphenyl)-8-hydroxythieno[2,3-c]quinolin-4(5H)-one;

  • (36): 2-(((1r,4r)-4-aminocyclohexylamino)methyl)-8-hydroxythieno[2,3-c]quinolin-4(5H)-one;

  • (37): 8-(piperazin-1-yl)thieno[2,3-c]quinolin-4(5H)-one;

  • (38): 8-hydroxy-1-methylthieno[2,3-c]quinolin-4(5H)-one;

  • (39): 2-((2-(dimethylamino)ethylamino)methyl)-8-hydroxythieno[2,3-c]quinolin-4(5H)-one;

  • (40): 8-hydroxy-2-((piperidin-3-ylamino)methyl)thieno[2,3-c]quinolin-4(5H)-one;

  • (41): 7-hydroxythieno[2,3-c]quinolin-4(5H)-one;

  • (42): 9-bromo-8-hydroxythieno[2,3-c]quinolin-4(5H)-one;

  • (43): 9-(3,4-dihydroxyphenyl)-8-hydroxythieno[2,3-c]quinolin-4(5H)-one;

  • (44): 1-methyl-4-oxo-4,5-dihydrothieno[2,3-c]quinoline-8-carbonitrile;

  • (45): 7-(3,4-dihydroxyphenyl)-8-hydroxythieno[2,3-c]quinolin-4(5H)-one;

  • (46): 8-hydroxy-1-methyl-3H-pyrrolo[2,3-c]quinolin-4(5H)-one;

  • (47): 9-(3,5-dihydroxyphenyl)-8-hydroxythieno[2,3-c]quinolin-4(5H)-one;

  • (48): 8-hydroxy-9-(3-hydroxyphenyl)thieno[2,3-c]quinolin-4(5H)-one;

  • (49): 8-hydroxy-9-(4-hydroxyphenyl)thieno[2,3-c]quinolin-4(5H)-one;

  • (50): 9-(3,4-difluorophenyl)-8-methoxythieno[2,3-c]quinolin-4(5H)-one;

  • (51): (S)-8-(3-aminopyrrolidin-1-yl)-2-(4-hydroxyphenyl)thieno[2,3-c]quinolin-4(5H)-one;

  • (52): 5-(8-methoxy-4-oxo-4,5-dihydrothieno[2,3-c]quinolin-9-yl)picolinonitrile;

  • (53): 9-(6-aminopyridin-3-yl)-8-hydroxythieno[2,3-c]quinolin-4(5H)-one;

  • (54): 4-(8-hydroxy-4-oxo-4,5-dihydrothieno[2,3-c]quinolin-9-yl)benzamide;

  • (55): 9-(3-fluoro-4-hydroxyphenyl)-8-hydroxythieno[2,3-c]quinolin-4(5H)-one;

  • (56): 8-hydroxy-2-(3-hydroxyphenyl)thieno[2,3-c]quinolin-4(5H)-one;

  • (57): (R)-8-(3-aminopyrrolidin-1-yl)-2-(3,4-dihydroxyphenyl)thieno[2,3-c]quinolin-4(5H)-one;

  • (58): 9-(3,4-difluorophenyl)-8-hydroxythieno[2,3-c]quinolin-4(5H)-one;

  • (59): 9-(4-fluoro-3-hydroxyphenyl)-8-hydroxythieno[2,3-c]quinolin-4(5H)-one;

  • (60): 8-hydroxy-9-(3-hydroxy-5-(trifluoromethyl)phenyl)thieno[2,3-c]quinolin-4(5H)-one;

  • (61): 8-hydroxy-9-(1H-indazol-6-yl)thieno[2,3-c]quinolin-4(5H)-one;

  • (62): 8-hydroxy-9-(3,4,5-trihydroxyphenyl)thieno[2,3-c]quinolin-4(5H)-one;

  • (63): 9-(4-hydroxyphenyl)-8-methoxythieno[2,3-c]quinolin-4(5H)-one;

  • (64): 9-(4-(1H-tetrazol-5-yl)phenyl)-8-hydroxythieno[2,3-c]quinolin-4(5H)-one;

  • (65): 4-(8-hydroxy-4-oxo-4,5-dihydrothieno[2,3-c]quinolin-9-yl)benzenesulfonamide;

  • (66): 9-(3-chloro-4-fluorophenyl)-8-hydroxythieno[2,3-c]quinolin-4(5H)-one;

  • (67): 9-(4-chloro-3-fluorophenyl)-8-hydroxythieno[2,3-c]quinolin-4(5H)-one;

  • (68): 9-(3,4-dichlorophenyl)-8-hydroxythieno[2,3-c]quinolin-4(5H)-one;

  • (69): 9-(4-fluorophenyl)-8-hydroxythieno[2,3-c]quinolin-4(5H)-one;

  • (70): 8-hydroxy-9-phenylthieno[2,3-c]quinolin-4(5H)-one;

  • (71): 9-(4-(difluoromethoxy)phenyl)-8-methoxythieno[2,3-c]quinolin-4(5H)-one;

  • (72): 9-(4-(aminomethyl)phenyl)-8-hydroxythieno[2,3-c]quinolin-4(5H)-one;

  • (73): 9-(4-(aminomethyl)phenyl)-8-hydroxythieno[2,3-c]quinolin-4(5H)-one;

  • (74): 9-(3-aminophenyl)-8-hydroxythieno[2,3-c]quinolin-4(5H)-one;

  • (75): 3-(8-hydroxy-4-oxo-4,5-dihydrothieno[2,3-c]quinolin-9-yl)benzenesulfonamide;

  • (76): 8-hydroxy-9-(3,4,5-trifluorophenyl)thieno[2,3-c]quinolin-4(5H)-one;

  • (77): N-(4-(8-hydroxy-4-oxo-4,5-dihydrothieno[2,3-c]quinolin-9-yl)phenyl)methanesulfonamide;

  • (78): 8-methoxy-9-phenylthieno[2,3-c]quinolin-4(5H)-one;

  • (79): 8-hydroxy-9-(naphthalen-2-yl)thieno[2,3-c]quinolin-4(5H)-one;

  • (80): 8-hydroxy-9-(4-(hydroxymethyl)phenyl)thieno[2,3-c]quinolin-4(5H)-one;

  • (81): 2-(4-(8-hydroxy-4-oxo-4,5-dihydrothieno[2,3-c]quinolin-9-yl)phenyl)acetonitrile;

  • (82): 8-hydroxy-9-(4-(methylsulfonyl)phenyl)thieno[2,3-c]quinolin-4(5H)-one;

  • (83): 8-hydroxy-9-(pyridin-4-yl)thieno[2,3-c]quinolin-4(5H)-one;

  • (84): 8-hydroxy-9-(1,2,3,6-tetrahydropyridin-4-yl)thieno[2,3-c]quinolin-4(5H)-one;

  • (85): 8-hydroxy-9-(4-hydroxy-3-methoxyphenyl)thieno[2,3-c]quinolin-4(5H)-one;

  • (86): 9-(3-fluoro-4-(morpholinomethyl)phenyl)-8-hydroxythieno[2,3-c]quinolin-4(5H)-one;

  • (87): 9-(3-(aminomethyl)phenyl)-8-hydroxythieno[2,3-c]quinolin-4(5H)-one;

  • (88): 9-(4-(aminomethyl)phenyl)-8-methoxythieno[2,3-c]quinolin-4(5H)-one;

  • (89): 9-(3-(difluoromethyl)phenyl)-8-methoxythieno[2,3-c]quinolin-4(5H)-one;

  • (90): 9-(3-(aminomethyl)phenyl)-8-hydroxy-2-methylthieno[2,3-c]quinolin-4(5H)-one;

  • (91): 9-cyclohexenyl-8-methoxythieno[2,3-c]quinolin-4(5H)-one;

  • (92): 9-(3,5-difluorophenyl)-8-hydroxythieno[2,3-c]quinolin-4(5H)-one;

  • (93): 9-(4-(2-(dimethylamino)ethyl)phenyl)-8-hydroxythieno[2,3-c]quinolin-4(5H)-one;

  • (94): 9-(3-(aminomethyl)phenyl)-8-methoxythieno[2,3-c]quinolin-4(5H)-one;

  • (95): 9-(4-(aminomethyl)phenyl)-8-hydroxy-2-methylthieno[2,3-c]quinolin-4(5H)-one;

  • (96): 9-cyclopropyl-8-hydroxythieno[2,3-c]quinolin-4(5H)-one;

  • (97): 9-([1,2,4]triazolo[1,5-a]pyridin-6-yl)-8-hydroxythieno[2,3-c]quinolin-4(5H)-one;

  • (98): 8-methoxy-9-(1,2,3,6-tetrahydropyridin-4-yl)thieno[2,3-c]quinolin-4(5H)-one;

  • (99): 9-cyclohexenyl-8-hydroxythieno[2,3-c]quinolin-4(5H)-one;

  • (100): 8-methoxy-9-(4-(2-(piperidin-1-yl)ethylamino)phenyl)thieno[2,3-c]quinolin-4(5H)-one;

  • (101): 9-(4-(aminomethyl)phenyl)-8-hydroxy-2-(morpholinomethyl)thieno[2,3-c]quinolin-4(5H)-one;

  • (102): 9-(1H-benzo[d]imidazol-5-yl)-8-hydroxythieno[2,3-c]quinolin-4(5H)-one;

  • (103): 9-(4-(difluoromethyl)phenyl)-8-methoxythieno[2,3-c]quinolin-4(5H)-one;

  • (104): 9-(4-(aminomethyl)phenyl)-8-methoxy-2-(morpholinomethyl)thieno[2,3-c]quinolin-4(5H)-one;

  • (105): 8-hydroxy-9-(4-(2-(piperidin-1-yl)ethylamino)phenyl)thieno[2,3-c]quinolin-4(5H)-one;

  • (106): 8-hydroxy-9-(4-(piperazin-1-yl)phenyl)thieno[2,3-c]quinolin-4(5H)-one;

  • (107): 8-methoxy-2,3-dihydro-1H-cyclopenta[c]quinolin-4(5H)-one;

  • (108): 8-hydroxy-2,3-dihydro-1H-cyclopenta[c]quinolin-4(5H)-one;

  • (109): 5-(8-hydroxy-4-oxo-4,5-dihydrothieno[2,3-c]quinolin-9-yl)benzo[d]oxazol-2(3H)-one;

  • (110): tert-butyl 4-(2-(hydroxy-4-oxo-4,5-dihydrothieno[2,3-c]quinolin-9-yl)benzylamino)ethyl)piperidin-1-carboxylate;

  • (111): 8-methoxy-9-(4-(piperazin-1-yl)phenyl)thieno[2,3-c]quinolin-4(5H)-one;

  • (112): 8-hydroxy-9-(4-(4-(methylsulfonyl)piperazin-1-yl)phenyl)thieno[2,3-c]quinolin-4(5H)-one;

  • (113): 8-hydroxy-9-(4-((piperidin-3-ylamino)methyl)phenyl)thieno[2,3-c]quinolin-4(5H)-one;

  • (114): N-(2-(dimethylamino)ethyl)-4-(8-hydroxy-4-oxo-4,5-dihydrothieno[2,3-c]quinolin-9-yl)benzamide;

  • (115): 9-(4-(3-(dimethylamino)propoxy)phenyl)-8-methoxythieno[2,3-c]quinolin-(5H)-one;

  • (116): 8-methoxy-9-(1-(piperidin-4-yl)-1H-pyrazol-4-yl)thieno[2,3-c]quinolin-4(5H)-one;

  • (117): 8-hydroxy-9-(1-(piperidin-4-yl)-1H-pyrazol-4-yl)thieno[2,3-c]quinolin-4(5H)-one;

  • (118): 8-methoxythiazolo[4,5-c]quinolin-4(5H)-one;

  • (119): 2-((4-(aminomethyl)piperidin-1-yl)methyl)-8-hydroxythieno[2,3-c]quinolin-4(5H)-one;

  • (120): N-(2-(dimethylamino)ethyl)-4-(8-methoxy-4-oxo-4,5-dihydrothieno[2,3-c]quinolin-9-yl)benzamide;

  • (121): 9-(4-(aminomethyl)phenyl)-8-hydroxy-2,3-dihydro-1H-cyclopenta[c]quinolin-4(5H)-one;

  • (122): (E)-butyl 3-(8-hydroxy-4-oxo-4,5-dihydrothieno[2,3-c]quinolin-9-yl)acrylate;

  • (123): 8-methoxy-9-(1H-pyrrolo[2,3-b]pyridin-5-yl)thieno[2,3-c]quinolin-4(5H)-one;

  • (124): 8-hydroxy-9-(1H-pyrrolo[2,3-b]pyridin-5-yl)thieno[2,3-c]quinolin-4(5H)-one;

  • (125): N-(methoxy-4-oxo-4,5-dihydrothieno[2,3-c]quinolin-9-yl)phenethyl)acetamide;

  • (126): N-(2-aminoethyl)-4-(8-hydroxy-4-oxo-4,5-dihydrothieno[2,3-c]quinolin-9-yl)benzamide;

  • (127): N-(2-aminoethyl)-4-(8-methoxy-4-oxo-4,5-dihydrothieno[2,3-c]quinolin-9-yl)benzamide;

  • (128): N-(hydroxy-4-oxo-4,5-dihydrothieno[2,3-c]quinolin-9-yl)phenethyl)acetamide;

  • (129): 4-(8-hydroxy-4-oxo-2,3,4,5-tetrahydro-1H-cyclopenta[c]quinolin-9-yl)benzenesulfonamide;

  • (130): 8-hydroxy-9-(4-(4-methylpiperazine-1-carbonyl)phenyl)thieno[2,3-c]quinolin-4(5H)-one;

  • (131): 8-methoxy-9-(4-(4-methylpiperazine-1-carbonyl)phenyl)thieno[2,3-c]quinolin-4(5H)-one;

  • (132): 8-hydroxy-9-(4-((4-methylpiperazin-1-yl)methyl)phenyl)thieno[2,3-c]quinolin-4(5H)-one;

  • (133): 8-methoxy-9-(4-((4-methylpiperazin-1-yl)methyl)phenyl)thieno[2,3-c]quinolin-4(5H)-one;

  • (134): (E)-9-(3-(diethylamino)prop-1-enyl)-8-methoxythieno[2,3-c]quinolin-4(5H)-one;

  • (135): (E)-9-(3-(4-(aminomethyl)piperidin-1-yl)prop-1-enyl)-8-methoxythieno[2,3-c]quinolin-4(5H)-one;

  • (136): (E)-9-(3-(2-(diethylamino)ethylamino)prop-1-enyl)-8-hydroxythieno[2,3-c]quinolin-4(5H)-one;

  • (137): N-(4-(8-hydroxy-4-oxo-2,3,4,5-tetrahydro-1H-cyclopenta[c]quinolin-9-yl)phenyl)methanesulfonamide;

  • (138): 9-(2-(dimethylamino)pyrimidin-5-yl)-8-hydroxythieno[2,3-c]quinolin-4(5H)-one;

  • (139): tert-butyl (1-(methoxy-4-oxo-4,5-dihydrothieno[2,3-c]quinolin-9-yl)benzyl)piperidin-4-yl)methylcarbamate;

  • (140): 8-hydroxy-9-(4-(4-methylpiperazin-1-yl)phenyl)thieno[2,3-c]quinolin-4(5H)-one;

  • (141): 8-methoxy-9-(4-(4-methylpiperazin-1-yl)phenyl)thieno[2,3-c]quinolin-4(5H)-one;

  • (142): 8-methoxy-9-(1-(methylsulfonyl)-1,2,3,6-tetrahydropyridin-4-yl)thieno[2,3-c]quinolin-4(5H)-one;

  • (143): (E)-9-(3-(diethylamino)prop-1-enyl)-8-hydroxythieno[2,3-c]quinolin-4(5H)-one;

  • (144): 9-(3-(4-(aminomethyl)piperidin-1-yl)propyl)-8-methoxythieno[2,3-c]quinolin-4(5H)-one;

  • (145): 9-(4-(3-(2-(diethylamino)ethylamino)propoxy)phenyl)-8-methoxythieno[2,3-c]quinolin-4(5H)-one;

  • (146): 9-(4-(3-(diethylamino)propoxy)phenyl)-8-methoxythieno[2,3-c]quinolin-4(5H)-one;

  • (147): 9-(4-(3-(2-(diethylamino)ethylamino)propoxy)phenyl)-8-hydroxythieno[2,3-c]quinolin-4(5H)-one;

  • (148): (E)-9-(3-(4-(aminomethyl)piperidin-1-yl)prop-1-enyl)-8-hydroxythieno[2,3-c]quinolin-4(5H)-one;

  • (149): 9-(4-(3-(dimethylamino)propoxy)phenyl)-8-hydroxythieno[2,3-c]quinolin-4(5H)-one;

  • (150): 8-hydroxy-9-(4-(2-(piperidin-1-yl)ethoxy)phenyl)thieno[2,3-c]quinolin-4(5H)-one;

  • (151): 9-(4-(2-(ethylamino)ethoxy)phenyl)-8-hydroxythieno[2,3-c]quinolin-(5H)-one;

  • (152): (E)-9-(3-(4-aminopiperidin-1-yl)prop-1-enyl)-8-methoxythieno[2,3-c]quinolin-4(5H)-one;

  • (153): 9-(1-(2-aminoethyl)-1,2,3,6-tetrahydropyridin-4-yl)-8-methoxythieno[2,3-c]quinolin-4(5H)-one;

  • (154): 9-(4-(2-(ethylamino)ethoxy)phenyl)-8-methoxythieno[2,3-c]quinolin-4(5H)-one;

  • (155): 9-(4-(2-(diethylamino)ethoxy)phenyl)-8-hydroxythieno[2,3-c]quinolin-4(5H)-one;

  • (156): 9-(4-(2-(diethylamino)ethoxy)phenyl)-8-methoxythieno[2,3-c]quinolin-4(5H)-one;

  • (157): 9-(4-(2-(dimethylamino)ethoxy)phenyl)-8-hydroxythieno[2,3-c]quinolin-4(5H)-one;

  • (158): 9-(4-(2-(dimethylamino)ethoxy)phenyl)-8-methoxythieno[2,3-c]quinolin-4(5H)-one;

  • (159): 8-methoxy-9-(4-(2-(piperidin-1-yl)ethoxy)phenyl)thieno[2,3-c]quinolin-4(5H)-one;

  • (160): 8-methoxy-9-(3-(2-(4-methylpiperazin-1-yl)ethoxy)phenyl)thieno[2,3-c]quinolin-4(5H)-one;

  • (161): 9-(3-(2-(diethylamino)ethoxy)phenyl)-8-methoxythieno[2,3-c]quinolin-4(5H)-one;

  • (162): 9-(3-(3-(diethylamino)propoxy)phenyl)-8-methoxythieno[2,3-c]quinolin-4(5H)-one;

  • (163): 9-(4-(2-(dimethylamino)ethyl)phenyl)-8-methoxythieno[2,3-c]quinolin-4(5H)-one;

  • (164): 9-(4-((dimethylamino)methyl)phenyl)-8-methoxythieno[2,3-c]quinolin-4(5H)-one;

  • (165): 9-(4-((dimethylamino)methyl)phenyl)-8-hydroxythieno[2,3-c]quinolin-4(5H)-one;

  • (166): 9-(3-(2-(diethylamino)ethoxy)phenyl)-8-hydroxythieno[2,3-c]quinolin-4(5H)-one;

  • (167): 8-hydroxy-9-(3-(2-(4-methylpiperazin-1-yl)ethoxy)phenyl)thieno[2,3-c]quinolin-4(5H)-one;

  • (168): N-ethyl-N-(2-(4-(8-methoxy-4-oxo-4,5-dihydrothieno[2,3-c]quinolin-9-yl)phenylmethoxy-4-oxo-4,5-dihydrothieno[2,3-c]quinolin-9-yl)phenoxy)ethyl)methanesulfonamide;

  • (169): 9-(4-(2-aminoethyl)phenyl)-8-methoxythieno[2,3-c]quinolin-4(5H)-one;

  • (170): 2-(3-(8-hydroxy-4-oxo-4,5-dihydrothieno[2,3-c]quinolin-9-yl)phenyl)acetonitrile;

  • (171): 2-(3-(8-methoxy-4-oxo-4,5-dihydrothieno[2,3-c]quinolin-9-yl)phenyl)acetonitrile;

  • (172): 9-(1-(2-(dimethylamino)ethyl)-1,2,3,6-tetrahydropyridin-4-yl)-8-hydroxythieno[2,3-c]quinolin-4(5H)-one;

  • (173): N-(hydroxy-4-oxo-4,5-dihydrothieno[2,3-c]quinolin-9-yl)phenethyl)methanesulfonamide;

  • (174): 9-(1-(2-(diethylamino)ethyl)-1,2,3,6-tetrahydropyridin-4-yl)-8-hydroxythieno[2,3-c]quinolin-4(5H)-one;

  • (175): 9-(4-(2-aminoethyl)phenyl)-8-hydroxythieno[2,3-c]quinolin-4(5H)-one;

  • (176): 9-(4-(2-aminoethyl)phenyl)-8-hydroxythieno[2,3-c]quinolin-4(5H)-one;

  • (177): N-(methoxy-4-oxo-4,5-dihydrothieno[2,3-c]quinolin-9-yl)phenethyl)methanesulfonamide;

  • (178): N-(methoxy-4-oxo-4,5-dihydrothieno[2,3-c]quinolin-9-yl)phenethyl)methanesulfonamide;

  • (179): N-(2-aminoethyl)-4-(8-hydroxy-4-oxo-4,5-dihydrothieno[2,3-c]quinolin-9-yl)benzenesulfonamide;

  • (180): 8-hydroxy-9-(1,2,3,6-tetrahydropyridin-4-yl)-2,3-dihydro-1H-cyclopenta[c]quinolin-4(5H)-one;

  • (181): 9-(4-(1-(dimethylamino)ethyl)phenyl)-8-hydroxy-2,3-dihydro-1H-cyclopenta[c]quinolin-4(5H)-one;

  • (182): 9-(4-(2-(dimethylamino)ethyl)phenyl)-8-methoxy-2,3-dihydro-1H-cyclopenta[c]quinolin-4(5H)-one;

  • (183): 9-(4-((diethylamino)methyl)phenyl)-8-methoxythieno[2,3-c]quinolin-4(5H)-one;

  • (184): 9-(4-((diethylamino)methyl)phenyl)-8-hydroxythieno[2,3-c]quinolin-4(5H)-one;

  • (185): 9-(3-(2-(dimethylamino)ethyl)phenyl)-8-hydroxythieno[2,3-c]quinolin-4(5H)-one;

  • (186): 9-(3-(2-aminoethyl)phenyl)-8-hydroxythieno[2,3-c]quinolin-4(5H)-one;

  • (187): 8-hydroxy-9-(4-((methylamino)methyl)phenyl)thieno[2,3-c]quinolin-4(5H)-one;

  • (188): 8-methoxy-9-(4-((methylamino)methyl)phenyl)thieno[2,3-c]quinolin-4(5H)-one;

  • (189): 9-(4-amino-3-methoxyphenyl)-8-methoxythieno[2,3-c]quinolin-4(5H)-one;

  • (190): 3-(8-hydroxy-4 oxo-4,5-dihydrothieno[2,3-c]quinolin-9-yl)benzonitrile;

  • (191): 9-(4-(1-(dimethylamino)ethyl)phenyl)-8-hydroxythieno[2,3-c]quinolin-4(5H)-one;

  • (192): 9-(4-(1-(dimethylamino)ethyl)phenyl)-8-hydroxythieno[2,3-c]quinolin-4(5H)-one;

  • (193): N-(1-(4-(8-hydroxy-4-oxo-4,5-dihydrothieno[2,3-c]quinolin-9-yl)phenyl)ethyl)methanesulfonamide;

  • (194): 8-hydroxy-9-(4-(1-(pyrrolidin-1-yl)ethyl)phenyl)thieno[2,3-c]quinolin-4(5H)-one;

  • (195): 9-(4-(1-aminoethyl)phenyl)-8-hydroxythieno[2,3-c]quinolin-4(5H)-one;

  • (196): 9-(4-(1-(diethylamino)ethyl)phenyl)-8-hydroxythieno[2,3-c]quinolin-4(5H)-one;

  • (197): N-(2-aminoethyl)-4-(8-methoxy-4-oxo-4,5-dihydrothieno[2,3-c]quinolin-9-yl)benzenesulfonamide;

  • (198): N-(2-(dimethylamino)ethyl)-4-(8-methoxy-4-oxo-4,5-dihydrothieno[2,3-c]quinolin-9-yl)benzenesulfonamide;

  • (199): 4-(8-hydroxy-4-oxo-4,5-dihydrothieno[2,3-c]quinolin-9-yl)-N-(pyrrolidin-3-yl)benzenesulfonamide;

  • (200): N-(azetidin-3-yl)-4-(8-hydroxy-4-oxo-4,5-dihydrothieno[2,3-c]quinolin-9-yl)benzenesulfonamide;

  • (201): 9-(4-(2-(diethylamino)ethyl)phenyl)-8-hydroxythieno[2,3-c]quinolin-4(5H)-one;

  • (202): 2-amino-N-(3-(8-methoxy-4-oxo-4,5-dihydrothieno[2,3-c]quinolin-9-yl)phenyl)ethanesulfonamide;

  • (203): 4-(8-hydroxy-4 oxo-4,5-dihydrothieno[2,3-c]quinolin-9-yl)benzonitrile;

  • (204): 4-(8-methoxy-4 oxo-4,5-dihydrothieno[2,3-c]quinolin-9-yl)benzonitrile;

  • (205): (E)-9-(3-(3-aminopyrrolidin-1-yl)prop-1-enyl)-8-methoxythieno[2,3-c]quinolin-4(5H)-one;

  • (206): N-(2-hydroxyethyl)-4-(8-methoxy-4-oxo-4,5-dihydrothieno[2,3-c]quinolin-9-yl)benzensulfonamide;

  • (207): 8-methoxy-9-(5-methoxypyridin-3-yl)thieno[2,3-c]quinolin-4(5H)-one;

  • (208): 8-methoxy-9-(5-methoxypyridin-3-yl)-2,3-dihydro-1H-cyclopenta[c]quinolin-4(5H)-one;

  • (209): 9-(4-(3-aminopyrrolidin-1-ylsulfonyl)phenyl)-8-hydroxythieno[2,3-c]quinolin-4(5H)-one;

  • (210): N-(2-bromoethyl)-4-(8-hydroxy-4-oxo-4,5-dihydrothieno[2,3-c]quinolin-9-yl)benzensulfonamide;

  • (211): 9-(4-((diisopropylamino)methyl)phenyl)-8-methoxythieno[2,3-c]quinolin-4(5H)-one;

  • (212): N-(hydroxy-4-oxo-4,5-dihydrothieno[2,3-c]quinolin-9-yl)benzyl)methanesulfonamide;

  • (213): 9-(4-((isopropylamino)methyl)phenyl)-8-methoxythieno[2,3-c]quinolin-4(5H)-one;

  • (214): 2-(dimethylamino)-N-(3-(8-hydroxy-4-oxo-4,5-dihydrothieno[2,3-c]quinolin-9-yl)phenyl)ethanesulfonamide;

  • (215): 2-amino-N-(3-(8-hydroxy-4-oxo-4,5-dihydrothieno[2,3-c]quinolin-9-yl)phenyl)ethanesulfonamide;

  • (216): 8-methoxy-9-(4-(1-(pyrrolidin-1-yl)ethyl)phenyl)thieno[2,3-c]quinolin-4(5H)-one;

  • (217): 9-(4-amino-3-hydroxyphenyl)-8-hydroxythieno[2,3-c]quinolin-4(5H)-one;

  • (218): N-(2-methoxy-4-(8-methoxy-4-oxo-4,5-dihydrothieno[2,3-c]quinolin-9-yl)phenyl)methanesulfonamide;

  • (219): 9-(3,5-difluoro-4-hydroxyphenyl)-8-methoxythieno[2,3-c]quinolin-4(5H)-one;

  • (220): N-(2-hydroxy-4-(8-hydroxy-4-oxo-4,5-dihydrothieno[2,3-c]quinolin-9-yl)phenyl)methanesulfonamide;

  • (221): 9-(4-((4-(aminomethyl)piperidin-1-yl)methyl)-3-fluorophenyl)-8-methoxythieno[2,3-c]quinolin-4(5H)-one;

  • (222): 9-(4-(2-(dimethylamino)ethyl)phenyl)-6-fluoro-8-methoxythieno[2,3-c]quinolin-4(5H)-one;

  • (223): 9-(3,5-difluoro-4-hydroxyphenyl)-8-hydroxythieno[2,3-c]quinolin-4(5H)-one;

  • (224): 6-fluoro-8-methoxy-9-(1,2,3,6-tetrahydropyridin-4-yl)thieno[2,3-c]quinolin-4(5H)-one;

  • (225): 9-(4-(1-(dimethylamino)ethyl)phenyl)-6-fluoro-8-hydroxythieno[2,3-c]quinolin-(5H)-one;

  • (226): 9-(4-((diethylamino)methyl)-3-fluorophenyl)-8-methoxythieno[2,3-c]quinolin-4(5H)-one;

  • (227): (E)-9-(3-(3-hydroxypyrrolidin-1-yl)prop-1-enyl)-8-methoxythieno[2,3-c]quinolin-4(5H)-one;

  • (228): (E)-8-hydroxy-9-(3-(3-hydroxypyrrolidin-1-yl)prop-1-enyl)thieno[2,3-c]quinolin-4(5H)-one

  • (229): 8-hydroxy-9-(4-((isopropylamino)methyl)phenyl)thieno[2,3-c]quinolin-4(5H)-one;

  • (230): (E)-9-(3-(3-aminoazetidin-1-yl)prop-1-enyl)-8-hydroxythieno[2,3-c]quinolin-4(5H)-one;

  • (231): (E)-8-methoxy-9-(3-(2-(methylsulfonyl)ethylamino)prop-1-enyl)thieno[2,3-c]quinolin-4(5H)-one;

  • (232): (S)-9-(4-(1-aminoethyl)phenyl)-8-methoxythieno[2,3-c]quinolin-4(5H)-one;

  • (233): (S)-9-(4-(1-aminoethyl)phenyl)-8-hydroxythieno[2,3-c]quinolin-4(5H)-one;

  • (234): 8-hydroxy-9-(5-hydroxypyridin-3-yl)-2,3-dihydro-1H-cyclopenta[c]quinolin-4(5H)-one;

  • (235): 9-(4-((4-(aminomethyl)piperidin-1-yl)methyl)-3-fluorophenyl)-8-hydroxythieno[2,3-c]quinolin-4(5H)-one;

  • (236): 8-methoxy-9-(4-(1-(2-(methylsulfonyl)ethylamino)ethyl)phenyl)thieno[2,3-c]quinolin-4(5H)-one;

  • (237): 9-(4-((3-aminopyrrolidin-1-yl)methyl)-3-fluorophenyl)-8-methoxythieno[2,3-c]quinolin-4(5H)-one;

  • (238): (E)-9-(3-(3-aminoazetidin-1-yl)prop-1-enyl)-8-methoxythieno[2,3-c]quinolin-4(5H)-one;

  • (239): (E)-9-(3-(ethylamino)prop-1-enyl)-8-hydroxythieno[2,3-c]quinolin-4(5H)-one;

  • (240): 9-(4-((3-aminopiperidin-1-yl)methyl)-3-fluorophenyl)-8-hydroxythieno[2,3-c]quinolin-4(5H)-one;

  • (241): 9-(4-((3-aminopyrrolidin-1-yl)methyl)-3-fluorophenyl)-8-hydroxythieno[2,3-c]quinolin-4(5H)-one;

  • (242): 9-(4-((3-aminopiperidin-1-yl)methyl)-3-fluorophenyl)-8-methoxythieno[2,3-c]quinolin-4(5H)-one;

  • (243): 8-hydroxy-9-(4-(1-(2-(methylsulfonyl)ethylamino)ethyl)phenyl)thieno[2,3-c]quinolin-4(5H)-one;

  • (244): (E)-9-(3-(3-aminopiperidin-1-yl)prop-1-enyl)-8-methoxythieno[2,3-c]quinolin-4(5H)-one;

  • (245): (E)-9-(3-(3-aminopyrrolidin-1-yl)prop-1-enyl)-8-hydroxythieno[2,3-c]quinolin-4(5H)-one;

  • (246): (E)-9-(3-(3-aminopiperidin-1-yl)prop-1-enyl)-8-hydroxythieno[2,3-c]quinolin-4(5H)-one;

  • (247): (E)-8-hydroxy-9-(3-(2-(methylsulfonyl)ethylamino)prop-1-enyl)thieno[2,3-c]quinolin-4(5H)-one;

  • (248): 8-methoxy-9-(4-(2-(2-(methylsulfonyl)ethylamino)ethyl)phenyl)thieno[2,3-c]quinolin-(5H)-one;

  • (249): 2-(2-fluoro-4-(8-methoxy-4-oxo-4,5-dihydrothieno[2,3-c]quinolin-9-yl)phenyl)acetonitrile;

  • (250): (E)-N-(1-(3-(8-methoxy-4-oxo-4,5-dihydrothieno[2,3-c]quinolin-9-yl)allyl)azetidin-3-yl)methanesulfonamide;

  • (251): 4-(8-methoxy-4-oxo-4,5-dihydrothieno[2,3-c]quinolin-9-yl)-N,N-dimethylbenzenesulfonamide;

  • (252): 4-(8-hydroxy-4-oxo-4,5-dihydrothieno[2,3-c]quinolin-9-yl)-N-methylbenzenesulfonamide;

  • (253): tert-butyl (5-(8-methoxy-4-oxo-4,5-dihydrothieno[2,3-c]quinolin-9-yl)furan-2-yl)methylcarbamate;

  • (254): N-(4-(8-hydroxy-4-oxo-4,5-dihydrothieno[2,3-c]quinolin-9-yl)-2-methylphenyl)methanesulfonamide;

  • (255): N-(4-(8-methoxy-4-oxo-4,5-dihydrothieno[2,3-c]quinolin-9-yl)-2-methylphenyl)methanesulfonamide;

  • (256): 9-(4-(aminomethyl)phenyl)-6-fluoro-8-hydroxythieno[2,3-c]quinolin-4(5H)-one;

  • (257): 9-(4-(aminomethyl)phenyl)-6-fluoro-8-methoxythieno[2,3-c]quinolin-4(5H)-one;

  • (258): 6-fluoro-8-hydroxy-9-(1,2,3,6-tetrahydropyridin-4-yl)thieno[2,3-c]quinolin-4(5H)-one;

  • (259): 9-(4-((diethylamino)methyl)-3-fluorophenyl)-8-hydroxythieno[2,3-c]quinolin-4(5H)-one;

  • (260): 8-methoxy-9-(4-(1-(piperidin-1-yl)ethyl)phenyl)thieno[2,3-c]quinolin-4(5H)-one;

  • (261): 2-(2-fluoro-4-(8-hydroxy-4-oxo-4,5-dihydrothieno[2,3-c]quinolin-9-yl)phenyl)acetonitrile;

  • (262): 8-hydroxy-9-(4-(1-(piperidin-1-yl)ethyl)phenyl)thieno[2,3-c]quinolin-4(5H)-one;

  • (263): (E)-9-(3-(3-(dimethylamino)piperidin-1-yl)prop-1-enyl)-8-hydroxythieno[2,3-c]quinolin-4(5H)-one;

  • (264): (E)-9-(3-(3-(dimethylamino)pyrrolidin-1-yl)prop-1-enyl)-8-hydroxythieno[2,3-c]quinolin-4(5H)-one;

  • (265): 9-(4-(2-aminoethyl)-3-fluorophenyl)-8-methoxythieno[2,3-c]quinolin-4(5H)-one;

  • (266): 9-(5-(aminomethyl)thiophen-2-yl)-8-hydroxythieno[2,3-c]quinolin-4(5H)-one;

  • (267): 9-(4-((ethylamino)methyl)phenyl)-8-hydroxythieno[2,3-c]quinolin-4(5H)-one;

  • (268): (E)-9-(3-(4-aminopiperidin-1-yl)prop-1-enyl)-8-hydroxythieno[2,3-c]quinolin-4(5H)-one;

  • (269): 9-(4-((ethylamino)methyl)phenyl)-8-methoxythieno[2,3-c]quinolin-4(5H)-one;

  • (270): 9-(4-(aminomethyl)phenyl)-6-bromo-8-hydroxythieno[2,3-c]quinolin-4(5H)-one;

  • (271): 9-(3-chloro-4-((diethylamino)methyl)phenyl)-8-methoxythieno[2,3-c]quinolin-4(5H)-one;

  • (272): (R)-9-(4-(1-(dimethylamino)ethyl)phenyl)-8-hydroxythieno[2,3-c]quinolin-4(5H)-one;

  • (273): 9-(4-(3-aminopropyl)phenyl)-8-hydroxythieno[2,3-c]quinolin-4(5H)-one;

  • (274): (R)-9-(4-(1-aminoethyl)phenyl)-8-methoxythieno[2,3-c]quinolin-4(5H)-one;

  • (275): (R)-9-(4-(1-aminoethyl)phenyl)-8-hydroxythieno[2,3-c]quinolin-4(5H)-one;

  • (276): 9-(4-(2-aminoethyl)-3-fluorophenyl)-8-hydroxythieno[2,3-c]quinolin-4(5H)-one;

  • (277): 9-(4-(1-amino-2-methylpropan-2-yl)phenyl)-8-hydroxythieno[2,3-c]quinolin-4(5H)-one;

  • (278): 9-(3-fluoro-4-((3-hydroxypyrrolidin-1-yl)methyl)phenyl)-8-hydroxythieno[2,3-c]quinolin-4(5H)-one;

  • (279): 9-(3-fluoro-4-((3-hydroxypyrrolidin-1-yl)methyl)phenyl)-8-methoxythieno[2,3-c]quinolin-4(5H)-one;

  • (280): 4-(8-methoxy-4-oxo-4,5-dihydrothieno[2,3-c]quinolin-9-yl)-N-(2,2,2-trifluoroethyl)benzenesulfonamide;

  • (281): 4-(8-hydroxy-4-oxo-4,5-dihydrothieno[2,3-c]quinolin-9-yl)-N-(2,2,2-trifluoroethyl)benzene sulfonamide;

  • (282): N-(2-(dimethylamino)ethyl)-4-(8-hydroxy-4-oxo-4,5-dihydrothieno[2,3-c]quinolin-9-yl)benzenesulfonamide;

  • (283): 8-hydroxy-9-(4-((2-(methylsulfonyl)ethylamino)methyl)phenyl)thieno[2,3-c]quinolin-4(5H)-one;

  • (284): 9-(3-(3-(dimethylamino)pyrrolidin-1-yl)propyl)-8-hydroxythieno[2,3-c]quinolin-4(5H)-one;

  • (285): 9-(1-(2-aminoethyl)-1H-pyrazol-4-yl)-8-methoxythieno[2,3-c]quinolin-4(5H)-one;

  • (286): 9-(3-chloro-4-((diethylamino)methyl)phenyl)-8-hydroxythieno[2,3-c]quinolin-4(5H)-one;

  • (287): 4-(7-fluoro-8-methoxy-4-oxo-4,5-dihydrothieno[2,3-c]quinolin-9-yl)-N-(2-hydroxyethyl)benzenesulfonamide;

  • (288): 9-(3-acetylphenyl)-8-methoxythieno[2,3-c]quinolin-4(5H)-one;

  • (289): 2-fluoro-4-(8-hydroxy-4-oxo-4,5-dihydrothieno[2,3-c]quinolin-9-yl)-N-(2-hydroxyethyl)benzamide;

  • (290): 3-(4-(8-hydroxy-4-oxo-4,5-dihydrothieno[2,3-c]quinolin-9-yl)phenyl)propanenitrile;

  • (291): 9-(4-acetylphenyl)-8-methoxythieno[2,3-c]quinolin-4(5H)-one;

  • (292): 2-fluoro-N-(2-hydroxyethyl)-4-(8-methoxy-4-oxo-4,5-dihydrothieno[2,3-c]quinolin-9-yl)benzamide;

  • (293): 4-(8-hydroxy-4-oxo-4,5-dihydrothieno[2,3-c]quinolin-9-yl)-N-(2-hydroxyethyl)benzamide;

  • (294): 1,1-diethyl-3-(hydroxy-4-oxo-4,5-dihydrothieno[2,3-c]quinolin-9-yl)benzyl)urea;

  • (295): N-(2-hydroxyethyl)-4-(8-methoxy-4-oxo-4,5-dihydrothieno[2,3-c]quinolin-9-yl)benzamide;

  • (296): 9-(4-acetylphenyl)-8-hydroxythieno[2,3-c]quinolin-4(5H)-one;

  • (297): N-(2-bromoethyl)-2-fluoro-4-(8-hydroxy-4-oxo-4,5-dihydrothieno[2,3-c]quinolin-9-yl)benzenesulfonamide;

  • (298): 9-(3-(3-(dimethylamino)piperidin-1-yl)propyl)-8-hydroxythieno[2,3-c]quinolin-4(5H)-one;

  • (299): N-(2-fluoro-4-(8-hydroxy-4-oxo-4,5-dihydrothieno[2,3-c]quinolin-9-yl)phenethyl)methanesulfonamide;

  • (300): 9-(3-fluoro-4-(2-(methylsulfonamido)ethyl)phenyl)-4-oxo-4,5-dihydrothieno[2,3-c]quinolin-8-yl methanesulfonate;

  • (301): (R)—N-(1-(4-(8-hydroxy-4-oxo-4,5-dihydrothieno[2,3-c]quinolin-9-yl)phenyl)ethyl)methanesulfonamide;

  • (302): (R)-9-(4-(1-(methylsulfonamido)ethyl)phenyl)-4-oxo-4,5-dihydrothieno[2,3-c]quinolin-8-yl methanesulfonate;

  • (303): 2-fluoro-N-(2-hydroxyethyl)-4-(8-methoxy-4-oxo-4,5-dihydrothieno[2,3-c]quinolin-9-yl)benzenesulfonamide;

  • (304): 4-(8-hydroxy-4-oxo-4,5-dihydrothieno[2,3-c]quinolin-9-yl)-N,N-dimethylbenzenesulfonamide;

  • (305): 9-(4-(2-(dimethylamino)ethyl)phenyl)-7-fluoro-8-methoxythieno[2,3-c]quinolin-4(5H)-one;

  • (306): N-(2-bromoethyl)-4-(7-fluoro-8-hydroxy-4-oxo-4,5-dihydrothieno[2,3-c]quinolin-9-yl)benzenesulfonamide;

  • (307): 4-(7-fluoro-8-hydroxy-4-oxo-4,5-dihydrothieno[2,3-c]quinolin-9-yl)-N-(2-hydroxyethyl)benzenesulfonamide;

  • (308): 9-(4-(1-(dimethylamino)-2-methylpropan-2-yl)phenyl)-8-hydroxythieno[2,3-c]quinolin-4(5H)-one;

  • (309): N-(2-chloro-4-(8-methoxy-4-oxo-4,5-dihydrothieno[2,3-c]quinolin-9-yl)benzyl)-N-methyl methanesulfonamide;

  • (310): 4-(8-hydroxy-4 oxo-4,5-dihydrothieno[2,3-c]quinolin-9-yl)-N-(2-methoxyethyl)benzenesulfonamide;

  • (3H): (E)-3-(8-methoxy-4-oxo-4,5-dihydrothieno[2,3-c]quinolin-9-yl)-2-methylacrylonitrile;

  • (312): N-(2-fluoro-4-(8-methoxy-4-oxo-4,5-dihydrothieno[2,3-c]quinolin-9-yl)phenethyl)methanesulfonamide;

  • (313): 8-hydroxy-9-(4-(1-hydroxyethyl)phenyl)thieno[2,3-c]quinolin-4(5H)-one;

  • (314): 9-(4-(1-(cyclopentylamino)ethyl)phenyl)-8-hydroxythieno[2,3-c]quinolin-4(5H)-one;

  • (315): 9-(4-(1-(cyclopentylamino)ethyl)phenyl)-8-methoxythieno[2,3-c]quinolin-4(5H)-one;

  • (316): 4-(8-hydroxy-4-oxo-4,5-dihydrothieno[2,3-c]quinolin-9-yl)-N-(2-hydroxyethyl)benzenesulfonamide;

  • (317): 9-(5-(aminomethyl)furan-2-yl)-8-hydroxythieno[2,3-c]quinolin-4(5H)-one;

  • (318): 9-(3-chloro-4-((methylamino)methyl)phenyl)-8-methoxythieno[2,3-c]quinolin-4(5H)-one;

  • (319): 9-(4-(2-aminopropan-2-yl)phenyl)-8-hydroxythieno[2,3-c]quinolin-4(5H)-one;

  • (320): N-(3-hydroxypropyl)-4-(8-methoxy-4-oxo-4,5-dihydrothieno[2,3-c]quinolin-9-yl)benzenesulfonamide;

  • (321): 2-fluoro-4-(8-hydroxy-4-oxo-4,5-dihydrothieno[2,3-c]quinolin-9-yl)-N-(2-hydroxyethyl)benzenesulfonamide;

  • (322): 4-(8-hydroxy-4-oxo-4,5-dihydrothieno[2,3-c]quinolin-9-yl)-N-(3-hydroxypropyl)benzenesulfonamide;

  • (323): N-(3-bromopropyl)-4-(8-hydroxy-4-oxo-4,5-dihydrothieno[2,3-c]quinolin-9-yl)benzenesulfonamide;

  • (324): 2-fluoro-4-(8-hydroxy-4-oxo-4,5-dihydrothieno[2,3-c]quinolin-9-yl)-N-(2-methoxyethyl)benzenesulfonamide;

  • (325): 9-(3-chloro-4-((methylamino)methyl)phenyl)-8-hydroxythieno[2,3-c]quinolin-4(5H)-one;

  • (326): 9-(4-(aminomethyl)phenyl)-4 oxo-4,5-dihydrothieno[2,3-c]quinoline-8-carbonitrile;

  • (327): 9-(4-(2-(dimethylamino)ethyl)-3-fluorophenyl)-8-hydroxythieno[2,3-c]quinolin-(5H)-one;

  • (328): 9-(4-(aminomethyl)phenyl)-6,7-dichloro-8-hydroxythieno[2,3-c]quinolin-4(5H)-one;

  • (329): 9-(4-(aminomethyl)phenyl)-6-chloro-8-hydroxythieno[2,3-c]quinolin-4(5H)-one;

  • (330): 9-(4-(aminomethyl)phenyl)-4-oxo-4,5-dihydrothieno[2,3-c]quinolin-8-yl trifluoromethanesulfonate;

  • (331): 9-(4-(2-(dimethylamino)ethyl)phenyl)-8-methoxythieno[2,3-c]quinolin-4(5H)-one;

  • (332): N-(2-chloroethyl)-4-(8-hydroxy-4-oxo-4,5-dihydrothieno[2,3-c]quinolin-9-yl)benzenesulfonamide;

  • (333): N-(2-fluoroethyl)-4-(8-methoxy-4-oxo-4,5-dihydrothieno[2,3-c]quinolin-9-yl)benzenesulfonamide;

  • (334): 9-(4-(2-aminopropan-2-yl)phenyl)-6-chloro-8-hydroxythieno[2,3-c]quinolin-4(5H)-one;

  • (335): (S)-9-(4-(1-(dimethylamino)ethyl)phenyl)-8-hydroxythieno[2,3-c]quinolin-4(5H)-one;

  • (336): 9-(4-(1-aminopropyl)phenyl)-8-hydroxythieno[2,3-c]quinolin-4(5H)-one;

  • (337): 9-(4-(1-aminopropyl)phenyl)-8-methoxythieno[2,3-c]quinolin-4(5H)-one;

  • (338): 9-(4-(1-(diethylamino)propyl)phenyl)-8-hydroxythieno[2,3-c]quinolin-4(5H)-one;

  • (339): 9-(4-(1-(dimethylamino)propyl)phenyl)-8-hydroxythieno[2,3-c]quinolin-4(5H)-one;

  • (340): 9-amino-8-methoxythieno[2,3-c]quinolin-4(5H)-one;

  • (341): 9-(4-(1-(dimethylamino)ethyl)phenyl)-6,7-difluoro-8-hydroxythieno[2,3-c]quinolin-4(5H)-one;

  • (342): 9-(4-(1-(dimethylamino)ethyl)phenyl)-6,7-difluoro-8-methoxythieno[2,3-c]quinolin-4(5H)-one;

  • (343): N-cyclopropyl-4-(8-methoxy-4-oxo-4,5-dihydrothieno[2,3-c]quinolin-9-yl)benzenesulfonamide;

  • (344): N-cyclopropyl-4-(8-hydroxy-4-oxo-4,5-dihydrothieno[2,3-c]quinolin-9-yl)benzenesulfonamide;

  • (345): 9-(2-amino-2,3-dihydro-1H-inden-5-yl)-8-hydroxythieno[2,3-c]quinolin-4(5H)-one;

  • (346): 9-(4-(1-(dimethylamino)ethyl)phenyl)thieno[2,3-c]quinolin-4(5H)-one;

  • (347): (S)—N-(1-(4-(8-hydroxy-4-oxo-4,5-dihydrothieno[2,3-c]quinolin-9-yl)phenyl)ethyl)methanesulfonamide;

  • (348): 9-(4-(1-(aminomethyl)cyclopropyl)phenyl)-8-hydroxythieno[2,3-c]quinolin-4(5H)-one;

  • (349): 9-(4-(1-(dimethylamino)ethyl)-3-fluorophenyl)-8-hydroxythieno[2,3-c]quinolin-4(5H)-one;

  • (350): N-(1-(hydroxymethyl)cyclopentyl)-4-(8-methoxy-4-oxo-4,5-dihydrothieno[2,3-c]quinolin-9-yl)benzenesulfonamide;

  • (351): 9-(2-(diethylamino)-2,3-dihydro-1H-inden-5-yl)-8-hydroxythieno[2,3-c]quinolin-4(5H)-one

  • (352): 9-(2-(dimethylamino)-2,3-dihydro-1H-inden-5-yl)-8-hydroxythieno[2,3-c]quinolin-4(5H)-one;

  • (353): 8-hydroxy-9-(1,2,3,4-tetrahydroisoquinolin-7-yl)thieno[2,3-c]quinolin-4(5H)-one;

  • (354): 8-methoxy-9-(1,2,3,4-tetrahydroisoquinolin-7-yl)thieno[2,3-c]quinolin-4(5H)-one;

  • (355): 3-(3-(8-hydroxy-4-oxo-4,5-dihydrothieno[2,3-c]quinolin-9-yl)phenyl)propanenitrile;

  • (356): 9-(4-(1-(diethylamino)ethyl)-3-fluorophenyl)-8-hydroxythieno[2,3-c]quinolin-4(5H)-one;

  • (357): 1-(4-(8-methoxy 4-oxo-4,5-dihydrothieno[2,3-c]quinolin-9-yl)phenyl)cyclopropanecarbonitrile;

  • (358): 9-(2-ethyl-1,2,3,4-tetrahydroisoquinolin-7-yl)-8-hydroxythieno[2,3-c]quinolin-4(5H)-one;

  • (359): 9-(4-(1-aminoethyl)-3-fluorophenyl)-8-hydroxythieno[2,3-c]quinolin-4(5H)-one;

  • (360): 3-(3-(8-methoxy-4-oxo-4,5-dihydrothieno[2,3-c]quinolin-9-yl)phenyl)propanenitrile;

  • (361): 1-(4-(8-hydroxy-4-oxo-4,5-dihydrothieno[2,3-c]quinolin-9-yl)phenyl)cyclopropanecarbonitrile;

  • (362): 9-(2-amino-2,3-dihydro-1H-inden-5-yl)-8-methoxythieno[2,3-c]quinolin-4(5H)-one;

  • (363): N-isopentyl-4-(8-methoxy-4-oxo-4,5-dihydrothieno[2,3-c]quinolin-9-yl)benzenesulfonamide;

  • (364): 9-(2-(dimethylamino)-2,3-dihydro-1H-inden-5-yl)-8-methoxythieno[2,3-c]quinolin-4(5H)-one;

  • (365): 9-(4-(1-(ethylamino)ethyl)phenyl)-8-methoxythieno[2,3-c]quinolin-4(5H)-one;

  • (366): 6-chloro-9-(4-(1-(dimethylamino)ethyl)phenyl)-8-hydroxythieno[2,3-c]quinolin-4(5H)-one;

  • (367): 9-(4-(cyclopropanecarbonyl)phenyl)-8-methoxythieno[2,3-c]quinolin-4(5H)-one;

  • (368): 9-(4-(aminomethyl)phenyl)-4-oxo-4,5-dihydrothieno[2,3-c]quinoline-8-carboxamide;

  • (369): 9-(2-aminoethyl)-8-methoxythieno[2,3-c]quinolin-4(5H)-one;

  • (370): 8-hydroxy-9-(4-(2-hydroxyethylsulfonyl)phenyl)thieno[2,3-c]quinolin-4(5H)-one;

  • (371): 9-(4-(2-hydroxyethylsulfonyl)phenyl)-8-methoxythieno[2,3-c]quinolin-4(5H)-one;

  • (372): 9-(1-ethylindolin-5-yl)-8-hydroxythieno[2,3-c]quinolin-4(5H)-one;

  • (373): 9-(4-(1-aminopropan-2-yl)phenyl)-8-methoxythieno[2,3-c]quinolin-4(5H)-one;

  • (374): 8-hydroxy-9-(2-methyl-1,2,3,4-tetrahydroisoquinolin-7-yl)thieno[2,3-c]quinolin-4(5H)-one;

  • (375): 9-(4-(1-aminoethyl)-3-fluorophenyl)-8-methoxythieno[2,3-c]quinolin-4(5H)-one;

  • (376): 8-hydroxy-9-(1-methylindolin-5-yl)thieno[2,3-c]quinolin-4(5H)-one;

  • (377): 8-hydroxy-9-(indolin-5-yl)thieno[2,3-c]quinolin-4(5H)-one;

  • (378): 9-(indolin-5-yl)-8-methoxythieno[2,3-c]quinolin-4(5H)-one;

  • (379): 9-(4-(1-((dimethylamino)methyl)cyclopropyl)phenyl)-8-hydroxythieno[2,3-c]quinolin-4(5H)-one;

  • (380): 4-(8-methoxy-4 oxo-4,5-dihydrothieno[2,3-c]quinolin-9-yl)-N-propylbenzenesulfonamide;

  • (381): N-(cyclopropylmethyl)-4-(8-methoxy-4-oxo-4,5-dihydrothieno[2,3-c]quinolin-9-yl)benzene sulfonamide;

  • (382): N-(3,3-dimethylbutyl)-4-(8-methoxy-4-oxo-4,5-dihydrothieno[2,3-c]quinolin-9-yl)benzenesulfonamide;

  • (383): 4-(8-hydroxy-4-oxo-4,5-dihydrothieno[2,3-c]quinolin-9-yl)-N-isopentylbenzenesulfonamide;

  • (384): N-(3,3-dimethylbutyl)-4-(8-hydroxy-4-oxo-4,5-dihydrothieno[2,3-c]quinolin-9-yl)benzenesulfonamide;

  • (385): 9-(4-(1-(ethylamino)ethyl)phenyl)-8-hydroxythieno[2,3-c]quinolin-4(5H)-one;

  • (386): 3-(4-(8-methoxy-4-oxo-4,5-dihydrothieno[2,3-c]quinolin-9-yl)phenyl)-3-oxopropanenitrile;

  • (387): (E)-9-(2-ethoxyvinyl)-8-methoxythieno[2,3-c]quinolin-4(5H)-one;

  • (388): N-(1-(4-(8-hydroxy-4-oxo-4,5-dihydrothieno[2,3-c]quinolin-9-yl)phenyl)ethyl)acetamide;

  • (389): 4-(8-methoxy-4-oxo-4,5-dihydrothieno[2,3-c]quinolin-9-yl)-N-(3,3,3-trifluoropropyl)benzenesulfonamide;

  • (390): 4-(8-hydroxy-4-oxo-4,5-dihydrothieno[2,3-c]quinolin-9-yl)-N-(1-(hydroxymethyl)cyclopentyl)benzenesulfonamide;

  • (391): N-(2,2-difluoroethyl)-4-(8-methoxy-4-oxo-4,5-dihydrothieno[2,3-c]quinolin-9-yl)benzenesulfonamide;
    • or a pharmaceutically acceptable salt thereof.

  • 121. A pharmaceutical composition comprising at least one compound of any one of above 101-120 or a pharmaceutically acceptable salt thereof, and a pharmaceutically acceptable carrier.

  • 122. The pharmaceutical composition of above 121 which is available for preventing or treating a PBK dependent disease.

  • 123. The pharmaceutical composition of above 122, wherein the PBK dependent disease is cancer.

  • 124. A PBK inhibitor comprising at least one compound of any one of above 101-120, or a pharmaceutically acceptable salt thereof.

  • 125. A method for treating a PBK dependent disease in a subject, comprising administering to said subject an effective amount of a compound or a pharmaceutically acceptable salt thereof of any one of above 101-120.

  • 126. A compound or a pharmaceutically acceptable salt thereof of any one of above 101-120 for use in a treatment of a PBK dependent disease.

  • 127. Use of a compound of any one of above 101-120 or a pharmaceutically acceptable salt thereof in manufacturing a pharmaceutical composition for treating a PBK dependent disease.



Preferred compounds include those selected from the group consisting of: Example Nos. 1-391 listed in Table 1 below; and the pharmaceutically acceptable salts, prodrugs, hydrates and solvates of the forgoing compounds.









TABLE 1







(Examples 1-391)









Example
Structure
Name





1


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8-methoxy-5-methylthieno[2,3-c] quinolin-4(5H)-one





2


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8-hydroxy-5-methylthieno[2,3-c] quinolin-4(5H)-one





3


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7,8-dihydroxythieno[2,3-c] quinolin-4(5H)-one





4


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7,8-dimethoxythieno[2,3-c] quinolin-4(5H)-one





5


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8-methoxythieno[2,3-c] quinolin-4(5H)-one





6


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7,9-dimethoxythieno[2,3-c] quinolin-4(5H)-one





7


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7,9-dihydroxythieno[2,3-c] quinolin-4(5H)-one





8


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7,8,9-trimethoxythieno[2,3-c] quinolin-4(5H)-one





9


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8-hydroxythieno[2,3-c] quinolin-4(5H)-one





10


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7,8,9-trihydroxythieno[2,3-c] quinolin-4(5H)-one





11


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9-(3-(2-aminoethyl)phenyl)-8- methoxythieno[2,3-c] quinolin-4(5H)-one





12


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8-chlorothieno[2,3-c] quinolin-4(5H)-one





13


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4-oxo-4,5-dihydrothieno[2,3-c] quinoline-8-carbonitrile





14


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thieno[2,3-c]quinolin-4(5H)-one





15


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8-fluorothieno[2,3-c]quinolin- 4(5H)-one





16


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8-nitrothieno[2,3-c]quinolin- 4(5H)-one





17


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8-(3-aminopiperidin-1-yl)thieno [2,3-c]quinolin-4(5H)-one





18


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l-(4-hydroxyphenyl)thieno[2,3-c] quinolin-4(5H)-one





19


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1,8-dihydroxythieno[2,3-c] quinolin-4(5H)-one





20


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8-hydroxy-1-(4-hydroxyphenyl) thieno[2,3-c]quinolin-4(5H)-one





21


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(R)-8-(3-aminopyrrolidin-1-yl)thieno [2,3-c]quinolin-4(5H)-one





22


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(S)-8-(3-aminopyrrolidin-1-yl)thieno [2,3-c]quinolin-4(5H)-one





23


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8-(pyridin-3-yl)thieno[2,3-c] quinolin-4(5H)-one





24


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8-(4-hydroxyphenyl)thieno[2,3-c] quinolin-4(5H)-one





25


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1-(3,4-dihydroxyphenyl)-8-hydroxy thieno[2,3-c]quinolin-4(5H)-one





26


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1-(3-aminopiperidin-1-yl)-8-hydroxy thieno[2,3-c]quinolin-4(5H)-one





27


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8-morpholinothieno[2,3-c]quinolin- 4(5H)-one hydrochloride





28


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8-hydroxy-2-methylthieno[2,3-c] quinolin-4(5H)-one





29


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8-hydroxy-2-(hydroxymethyl)thieno [2,3-c]quinolin-4(5H)-one





30


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8-hydroxy-4-oxo-N-(piperidin-3-yl)- 4,5-dihydrothieno[2,3-c]quinoline-2- carboxamide





31


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8-hydroxy-2-(4-hydroxyphenyl) thieno[2,3-c]quinolin-4(5H)-one





32


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8-hydroxy-1-(piperazin-1-yl)thieno [2,3-c]quinolin-4(5H)-one





33


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N-((1R,4R)-4-aminocyclohexyl)-8- hydroxy-4-oxo-4,5-dihydrothieno[2,3-c] quinoline-2-carboxamide





34


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2-(3-aminopiperidine-1-carbonyl)-8- hydroxythieno[2,3-c]quinolin- 4(5H)-one





35


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2-(3,4-dihydroxyphenyl)-8-hydroxy thieno[2,3-c]quinolin-4(5H)-one





36


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2-(((1R,4R)-4-aminocyclohexylamino) methyl)-8-hydroxythieno[2,3-c] quinolin-4(5H)-one





37


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8-(piperazin-1-yl)thieno[2,3-c] quinolin-4(5H)-one dihydrochloride





38


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8-hydroxy-1-methylthieno[2,3-c] quinolin-4(5H)-one





39


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2-((2-(dimethylamino)ethylamino) methyl)-8-hydroxythieno[2,3-c] quinolin-4(5H)-one





40


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8-hydroxy-2-((piperidin-3-ylamino) methyl)thieno[2,3-c]quinolin- 4(5H)-one





41


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7-hydroxythieno[2,3-c]quinolin- 4(5H)-one





42


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9-bromo-8-hydroxythieno[2,3-c] quinolin-4(5H)-one





43


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9-(3,4-dihydroxyphenyl)-8- hydroxythieno[2,3-c]quinolin-4(5H)-one





44


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1-methyl-4-oxo-4,5-dihydrothieno [2,3-c]quinoline-8-carbonitrile





45


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7-(3,4-dihydroxyphenyl)-8-hydroxy thieno[2,3-c]quinolin-4(5H)-one





46


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8-hydroxy-1-methyl-3H-pyrrolo [2,3-c]quinolin-4(5H)-one





47


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9-(3,5-dihydroxyphenyl)-8-hydroxy thieno[2,3-c]quinolin-4(5H)-one





48


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8-hydroxy-9-(3-hydroxyphenyl) thieno[2,3-c]quinolin-4(5H)-one





49


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8-hydroxy-9-(4-hydroxyphenyl) thieno[2,3-c]quinolin-4(5H)-one





50


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9-(3,4-difluorophenyl)-8-methoxy thieno[2,3-c]quinolin-4(5H)-one





51


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(S)-8-(3-aminopyrrolidin-1-yl)-2-(4- hydroxyphenyl)thieno[2,3-c]quinolin- 4(5H)-one dihydrochloride





52


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5-(8-methoxy-4-oxo-4,5-dihydro thieno[2,3-c]quinolin-9-yl) picolinonitrile





53


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9-(6-aminopyridin-3-yl)-8-hydroxy thieno[2,3-c]quinolin-4(5H)-one





54


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4-(8-hydroxy-4-oxo-4,5-dihydro thieno[2,3-c]quinolin-9-yl)benzamide





55


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9-(3-fluoro-4-hydroxyphenyl)-8- hydroxythieno[2,3-c]quinolin- 4(5H)-one





56


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8-hydroxy-2-(3-hydroxyphenyl) thieno[2,3-c]quinolin-4(5H)-one





57


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(R)-8-(3-aminopyrrolidin-1-yl)-2-(3,4- dihydroxyphenyl)thieno[2,3-c] quinolin-4(5H)-one dihydrochloride





58


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9-(3,4-difluorophenyl)-8-hydroxy thieno[2,3-c]quinolin-4(5H)-one





59


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9-(4-fluoro-3-hydroxyphenyl)-8- hydroxythieno[2,3-c]quinolin- 4(5H)-one





60


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8-hydroxy-9-(3-hydroxy-5-(trifluoro methyl)phenyl)thieno[2,3-c] quinolin-4(5H)-one





61


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8-hydroxy-9-(1H-indazol-6-yl)thieno [2,3-c]quinolin-4(5H)-one





62


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8-hydroxy-9-(3,4,5-trihydroxy phenyl)thieno[2,3-c]quinolin- 4(5H)-one





63


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9-(4-hydroxyphenyl)-8-methoxy thieno[2,3-c]quinolin-4(5H)-one





64


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9-(4-(1H-tetrazol-5-yl)phenyl)-8- hydroxythieno[2,3-c] quinolin-4(5H)-one





65


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4-(8-hydroxy-4-oxo-4,5-dihydro thieno[2,3-c]quinolin-9-yl) benzenesulfonamide





66


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9-(3-chloro-4-fluorophenyl)-8- hydroxythieno[2,3-c] quinolin-4(5H)-one





67


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9-(4-chloro-3-fluorophenyl)-8- hydroxythieno[2,3-c] quinolin-4(5H)-one





68


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9-(3,4-dichlorophenyl)-8-hydroxy thieno[2,3-c]quinolin-4(5H)-one





69


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9-(4-fluorophenyl)-8-hydroxythieno [2,3-c]quinolin-4(5H)-one





70


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8-hydroxy-9-phenylthieno[2,3-c] quinolin-4(5H)-one





71


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9-(4-(difluoromethoxy)phenyl)-8- methoxythieno[2,3-c] quinolin-4(5H)-one





72


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9-(4-(aminomethyl)phenyl)-8- hydroxythieno[2,3-c] quinolin-4(5H)-one





73


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9-(4-(aminomethyl)phenyl)-8- hydroxythieno[2,3-c] quinolin-4(5H)-one hydrochloride





74


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9-(3-aminophenyl)-8-hydroxythieno [2,3-c]quinolin-4(5H)-one





75


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3-(8-hydroxy-4-oxo-4,5-dihydro thieno[2,3-c]quinolin-9-yl) benzenesulfonamide





76


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8-hydroxy-9-(3,4,5-trifluorophenyl) thieno[2,3-c]quinolin-4(5H)-one





77


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N-(4-(8-hydroxy-4-oxo-4,5-dihydro thieno[2,3-c]quinolin-9-yl)phenyl) methanesulfonamide





78


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8-methoxy-9-phenylthieno[2,3-c] quinolin-4(5H)-one





79


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8-hydroxy-9-(naphthalen-2-yl)thieno [2,3-c]quinolin-4(5H)-one





80


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8-hydroxy-9-(4-(hydroxymethyl) phenyl)thieno[2,3-c]quinolin- 4(5H)-one





81


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2-(4-(8-hydroxy-4-oxo-4,5-dihydro thieno[2,3-c]quinolin-9- yl)phenyl)acetonitrile





82


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8-hydroxy-9-(4-(methylsulfonyl) phenyl)thieno[2,3-c]quinolin- 4(5H)-one





83


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8-hydroxy-9-(pyridin-4-yl)thieno [2,3-c]quinolin-4(5H)-one





84


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8-hydroxy-9-(1,2,3,6-tetrahydro pyridin-4-yl)thieno[2,3-c] quinolin-4(5H)-one





85


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8-hydroxy-9-(4-hydroxy-3-methoxy phenyl)thieno[2,3-c]quinolin- 4(5H)-one





86


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9-(3-fluoro-4-(morpholinomethyl) phenyl)-8-hydroxythieno[2,3-c] quinolin-4(5H)-one





87


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9-(3-(aminomethyl)phenyl)-8- hydroxythieno[2,3-c]quinolin- 4(5H)-one





88


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9-(4-(aminomethyl)phenyl)-8- methoxythieno[2,3-c]quinolin- 4(5H)-one





89


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9-(3-(difluoromethyl)phenyl)-8- methoxythieno[2,3-c]quinolin- 4(5H)-one





90


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9-(3-(aminomethyl)phenyl)-8- hydroxy-2-methylthieno[2,3-c] quinolin-4(5H)-one





91


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9-cyclohexenyl-8-methoxythieno [2,3-c]quinolin-4(5H)-one





92


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9-(3,5-difluorophenyl)-8-hydroxy thieno[2,3-c]quinolin-4(5H)-one





93


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9-(4-(2-(dimethylamino)ethyl) phenyl)-8-hydroxythieno[2,3-c] quinolin-4(5H)-one





94


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9-(3-(aminomethyl)phenyl)-8- methoxythieno[2,3-c]quinolin- 4(5H)-one





95


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9-(4-(aminomethyl)phenyl)-8- hydroxy-2-methylthieno[2,3-c] quinolin-4(5H)-one





96


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9-cyclopropyl-8-hydroxythieno [2,3-c]quinolin-4(5H)-one





97


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9-([1,2,4]triazolo[1,5-a]pyridin-6-yl)- 8-hydroxythieno[2,3-c]quinolin- 4(5H)-one





98


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8-methoxy-9-(1,2,3,6-tetrahydro pyridin-4-yl)thieno[2,3-c] quinolin-4(5H)-one





99


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9-cyclohexenyl-8-hydroxythieno [2,3-c]quinolin-4(5H)-one





100


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8-methoxy-9-(4-(2-(piperidin-1-yl) ethylamino)phenyl)thieno[2,3-c] quinolin-4(5H)-one





101


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9-(4-(aminomethyl)phenyl)-8- hydroxy-2-(morpholinomethyl) thieno[2,3-c]quinolin-4(5H)-one





102


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9-(1H-benzo[d]imidazol-5-yl)-8- hydroxythieno[2,3-c]quinolin- 4(5H)-one





103


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9-(4-(difluoromethyl)phenyl)-8- methoxythieno[2,3-c]quinolin- 4(5H)-one





104


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9-(4-(aminomethyl)phenyl)-8- methoxy-2-(morpholinomethyl) thieno[2,3-c]quinolin-4(5H)-one





105


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8-hydroxy-9-(4-(2-(piperidin-1-yl) ethylamino)phenyl)thieno[2,3-c] quinolin-4(5H)-one





106


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8-hydroxy-9-(4-(piperazin-1-yl) phenyl)thieno[2,3-c]quinolin- 4(5H)-one





107


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8-methoxy-2,3-dihydro-1H-cyclo penta[c]quinolin-4(5H)-one





108


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8-hydroxy-2,3-dihydro-1H-cyclo penta[c]quinolin-4(5H)-one





109


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5-(8-hydroxy-4-oxo-4,5-dihydro thieno[2,3-c]quinolin-9-yl)benzo [d]oxazol-2(3H)-one





110


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tert-butyl 4-(2-(hydroxy-4-oxo-4,5- dihydrothieno[2,3-c]quinolin-9-yl) benzylamino)ethyl)piperidine- 1-carboxylate





111


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8-methoxy-9-(4-(piperazin-1-yl) phenyl)thieno[2,3-c]quinolin- 4(5H)-one





112


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8-hydroxy-9-(4-(4-(methylsulfonyl) piperazin-1-yl)phenyl)thieno[2,3-c] quinolin-4(5H)-one





113


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8-hydroxy-9-(4-((piperidin-3-yl amino)methyl)phenyl)thieno [2,3-c]quinolin-4(5H)-one





114


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N-(2-(dimethylamino)ethyl)-4-(8- hydroxy-4-oxo-4,5-dihydrothieno [2,3-c]quinolin-9-yl)benzamide





115


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9-(4-(3-(dimethylamino)propoxy) phenyl)-8-methoxythieno[2,3-c] quinolin-4(5H)-one





116


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8-methoxy-9-(1-(piperidin-4-yl)-1H- pyrazol-4-yl)thieno[2,3-c] quinolin-4(5H)-one





117


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8-hydroxy-9-(1-(piperidin-4-yl)-1H- pyrazol-4-yl)thieno[2,3-c] quinolin-4(5H)-one





118


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8-methoxythiazolo[4,5-c]quinolin- 4(5H)-one





119


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2-((4-(aminomethyl)piperidin-1-yl) methyl)-8-hydroxythieno[2,3-c] quinolin-4(5H)-one





120


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N-(2-(dimethylamino)ethyl)-4-(8- methoxy-4-oxo-4,5-dihydrothieno [2,3-c]quinolin-9-yl)benzamide





121


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9-(4-(aminomethyl)phenyl)-8- hydroxy-2,3-dihydro-1H-cyclopenta [c]quinolin-4(5H)-one hydrochloride





122


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(E)-butyl 3-(8-hydroxy-4-oxo-4,5- dihydrothieno[2,3-c]quinolin- 9-yl)acrylate





123


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8-methoxy-9-(1H-pyrrolo[2,3-b] pyridin-5-yl)thieno[2,3-c]quinolin- 4(5H)-one





124


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8-hydroxy-9-(1H-pyrrolo[2,3-b] pyridin-5-yl)thieno[2,3-c]quinolin- 4(5H)-one





125


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N-(methoxy-4-oxo-4,5-dihydrothieno [2,3-c]quinolin-9-yl)phenethyl) acetamide





126


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N-(2-aminoethyl)-4-(8-hydroxy-4- oxo-4,5-dihydrothieno[2,3-c]quinolin- 9-yl)benzamide





127


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N-(2-aminoethyl)-4-(8-methoxy-4- oxo-4,5-dihydrothieno[2,3-c]quinolin- 9-yl)benzamide





128


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N-(hydroxy-4-oxo-4,5-dihydrothieno [2,3-c]quinolin-9-yl)phenethyl) acetamide





129


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4-(8-hydroxy-4-oxo-2,3,4,5-tetra hydro-1H-cyclopenta[c]quinolin- 9-yl)benzenesulfonamide





130


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8-hydroxy-9-(4-(4-methylpiperazine- 1-carbonyl)phenyl)thieno[2,3-c] quinolin-4(5H)-one





131


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8-methoxy-9-(4-(4-methylpiperazine- 1-carbonyl)phenyl)thieno[2,3-c] quinolin-4(5H)-one





132


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8-hydroxy-9-(4-((4-methylpiperazin- 1-yl)methyl)phenyl)thieno[2,3-c] quinolin-4(5H)-one





133


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8-methoxy-9-(4-((4-methylpiperazin- 1-yl)methyl)phenyl)thieno[2,3-c] quinolin-4(5H)-one





134


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(E)-9-(3-(diethylamino)prop-1-enyl)- 8-methoxythieno[2,3-c]quinolin- 4(5H)-one





135


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(E)-9-(3-(4-(aminomethyl)piperidin-1- yl)prop-1-enyl)-8-methoxythieno [2,3-c]quinolin-4(5H)-one





136


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(E)-9-(3-(2-(diethylamino)ethyl amino)prop-1-enyl)-8-hydroxy thieno[2,3-c]quinolin-4(5H)-one





137


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N-(4-(8-hydroxy-4-oxo-2,3,4,5-tetra hydro-1H-cyclopenta[c]quinolin- 9-yl)phenyl)methanesulfonamide





138


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9-(2-(dimethylamino)pyrimidin-5-yl)- 8-hydroxythieno[2,3-c]quinolin- 4(5H)-one





139


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tert-butyl (1-(methoxy-4-oxo-4,5- dihydrothieno[2,3-c]quinolin-9-yl) benzyl)piperidin-4-yl)methyl carbamate





140


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8-hydroxy-9-(4-(4-methylpiperazin-1- yl)phenyl)thieno[2,3-c]quinolin- 4(5H)-one





141


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8-methoxy-9-(4-(4-methylpiperazin-1- yl)phenyl)thieno[2,3-c]quinolin- 4(5H)-one diydrochloride





142


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8-methoxy-9-(1-(methylsulfonyl)-1,2, 3,6-tetrahydropyridin-4-yl)thieno [2,3-c]quinolin-4(5H)-one





143


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(E)-9-(3-(diethylamino)prop-1-enyl)- 8-hydroxythieno[2,3-c]quinolin- 4(5H)-one





144


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9-(3-(4-(aminomethyl)piperidin-1-yl) propyl)-8-methoxythieno[2,3-c] quinolin-4(5H)-one





145


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9-(4-(3-(2-(diethylamino)ethylamino) propoxy)phenyl)-8-methoxythieno [2,3-c]quinolin-4(5H)-one





146


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9-(4-(3-diethylamino)propoxy) phenyl)-8-methoxythieno[2,3-c] quinolin-4(5H)-one





147


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9-(4-(3-(2-(diethylamino)ethylamino) propoxy)phenyl)-8-hydroxythieno [2,3-c]quinolin-4(5H)-one





148


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(E)-9-(3-(4-(aminomethyl)piperidin-1- yl)prop-1-enyl)-8-hydroxythieno [2,3-c]quinolin-4(5H)-one





149


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9-(4-(3-(dimethylamino)propoxy) phenyl)-8-hydroxythieno[2,3-c]quinolin- 4(5H)-one





150


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8-hydroxy-9-(4-(2-(piperidin-1-yl) ethoxy)phenyl)thieno[2,3-c] quinolin-4(5H)-one





151


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9-(4-(2-(ethylamino)ethoxy)phenyl)- 8-hydroxythieno[2,3-c]quinolin- 4(5H)-one





152


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(E)-9-(3-(4-aminopiperidin-1-yl) prop-1-enyl)-8-methoxythieno[2,3-c] quinolin-4(5H)-one





153


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9-(1-(2-aminoethyl)-1,2,3,6-tetra hydropyridin-4-yl)-8-methoxythieno [2,3-c]quinolin-4(5H)-one





154


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9-(4-(2-(ethylamino)ethoxy)phenyl)- 8-methoxythieno[2,3-c]quinolin- 4(5H)-one





155


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9-(4-(2-(diethylamino)ethoxy)phenyl)- 8-hydroxythieno[2,3-c]quinolin- 4(5H)-one





156


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9-(4-(2-(diethylamino)ethoxy)phenyl)- 8-methoxythieno[2,3-c]quinolin- 4(5H)-one





157


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9-(4-(2-(dimethylamino)ethoxy) phenyl)-8-hydroxythieno[2,3-c] quinolin-4(5H)-one





158


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9-(4-(2-(dimethylamino)ethoxy) phenyl)-8-methoxythieno[2,3-c] quinolin-4(5H)-one





159


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8-methoxy-9-(4-(2-(piperidin-1-yl) ethoxy)phenyl)thieno[2,3-c] quinolin-4(5H)-one





160


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8-methoxy-9-(3-(2-(4-methyl piperazin-1-yl)ethoxy)phenyl) thieno[2,3-c]quinolin-4(5H)-one





161


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9-(3-(2-(diethylamino)ethoxy)phenyl)- 8-methoxythieno[2,3-c]quinolin- 4(5H)-one





162


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9-(3-(3-(diethylamino)propoxy)phenyl)- 8-methoxythieno[2,3-c]quinolin- 4(5H)-one





163


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9-(4-(2-(dimethylamino)ethyl)phenyl)- 8-methoxythieno[2,3-c]quinolin- 4(5H)-one





164


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9-(4-((dimethylamino)methyl)phenyl)- 8-methoxythieno[2,3-c]quinolin- 4(5H)-one





165


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9-(4-((dimethylamino)methyl)phenyl)- 8-hydroxythieno[2,3-c]quinolin- 4(5H)-one





166


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9-(3-(2-(diethylamino)ethoxy)phenyl)- 8-hydroxythieno[2,3-c]quinolin- 4(5H)-one





167


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8-hydroxy-9-(3-(2-(4-methylpiperazin- 1-yl)ethoxy)phenyl)thieno[2,3-c] quinolin-4(5H)-one





168


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N-ethyl-N-(2-(4-(8-methoxy-4-oxo-4, 5-dihydrothieno[2,3-c]quinolin-9-yl) phenylmethoxy-4-oxo-4,5-dihydro thieno[2,3-c]quinolin-9-yl)phenoxy) ethyl)methanesulfonamide





169


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9-(4-(2-aminoethyl)phenyl)-8- methoxythieno[2,3-c]quinolin- 4(5H)-one





170


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2-(3-(8-hydroxy-4-oxo-4,5-dihydro thieno[2,3-c]quinolin-9-yl)phenyl) acetonitrile





171


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2-(3-(8-methoxy-4-oxo-4,5-dihydro thieno[2,3-c]quinolin-9-yl)phenyl) acetonitrile





172


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9-(1-(2-(dimethylamino)ethyl)-1,2,3, 6-tetrahydropyridin-4-yl)-8-hydroxy thieno[2,3-c]quinolin-4(5H)-one





173


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N-(hydroxy-4-oxo-4,5-dihydrothieno [2,3-c]quinolin-9-yl)phenethyl) methanesulfonamide





174


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9-(1-(2-(diethylamino)ethyl)-1,2,3,6- tetrahydropyridin-4-yl)-8-hydroxy thieno[2,3-c]quinolin- 4(5H)-one





175


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9-(4-(2-aminoethyl)phenyl)-8- hydroxythieno[2,3-c]quinolin- 4(5H)-one





176


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9-(4-(2-aminoethyl)phenyl)-8- hydroxythieno[2,3-c]quinolin- 4(5H)-one hydrochloride





177


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N-(methoxy-4-oxo-4,5-dihydrothieno [2,3-c]quinolin-9-yl)phenethyl) methanesulfonamide





178


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N-(methoxy-4-oxo-4,5-dihydrothieno [2,3-c]quinolin-9-yl)phenethyl) methanesulfonamide





179


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N-(2-aminoethyl)-4-(8-hydroxy-4- oxo-4,5-dihydrothieno[2,3-c]quinolin- 9-yl)benzenesulfonamide hydrochloride





180


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8-hydroxy-9-(1,2,3,6-tetrahydro pyridin-4-yl)-2,3-dihydro-1H-cyclo penta[c]quinolin-4(5H)-one hydrochloride





181


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9-(4-(1-(dimethylamino)ethyl)phenyl)- 8-hydroxy-2,3-dihydro-1H-cyclo penta[c]quinolin-4(5H)-one hydrochloride





182


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9-(4-(2-(dimethylamino)ethyl)phenyl)- 8-methoxy-2,3-dihydro-1H-cyclo penta[c]quinolin-4(5H)-one





183


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9-(4-((diethylamino)methyl)phenyl)- 8-methoxythieno[2,3-c]quinolin- 4(5H)-one





184


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9-(4-((diethylamino)methyl)phenyl)- 8-hydroxythieno[2,3-c]quinolin- 4(5H)-one





185


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9-(3-(2-(dimethylamino)ethyl)phenyl)- 8-hydroxythieno[2,3-c]quinolin- 4(5H)-one





186


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9-(3-(2-aminoethyl)phenyl)-8- hydroxythieno[2,3-c]quinolin-4(5H)- one





187


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8-hydroxy-9-(4-((methylamino) methyl)phenyl)thieno[2,3-c]quinolin- 4(5H)-one





188


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8-methoxy-9-(4-((methylamino) methyl)phenyl)thieno[2,3-c]quinolin- 4(5H)-one





189


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9-(4-amino-3-methoxyphenyl)-8- methoxythieno[2,3-c]quinolin- 4(5H)-one hydrochloride





190


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3-(8-hydroxy-4-oxo-4,5-dihydro thieno[2,3-c]quinolin-9-yl) benzonitrile





191


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9-(4-(1-(dimethylamino)ethyl) phenyl)-8-hydroxythieno[2,3-c] quinolin-4(5H)-one





192


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9-(4-(1-(dimethylamino)ethyl) phenyl)-8-hydroxythieno[2,3-c] quinolin-4(5H)-one hydrochloride





193


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N-(1-(4-(8-hydroxy-4-oxo-4,5- dihydrothieno[2,3-c]quinolin-9-yl) phenyl)ethyl)methanesulfonamide





194


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8-hydroxy-9-(4-(1-(pyrrolidin-1-yl) ethyl)phenyl)thieno[2,3-c]quinolin- 4(5H)-one hydrochloride





195


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9-(4-(1-aminoethyl)phenyl)-8- hydroxythieno[2,3-c]quinolin- 4(5H)-one hydrochloride





196


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9-(4-(1-(diethylamino)ethyl)phenyl)- 8-hydroxythieno[2,3-c]quinolin- 4(5H)-one hydrochloride





197


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N-(2-aminoethyl)-4-(8-methoxy-4- oxo-4,5-dihydrothieno[2,3-c]quinolin- 9-yl)benzenesulfonamide hydrochloride





198


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N-(2-(dimethylamino)ethyl)-4-(8- methoxy-4-oxo-4,5-dihydrothieno [2,3-c]quinolin-9-yl) benzenesulfonamide hydrochloride





199


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4-(8-hydroxy-4-oxo-4,5-dihydro thieno[2,3-c]quinolin-9-yl)- N-(pyrrolidin-3-yl)benzenesulfonamide hydrochloride





200


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N-(azetidin-3-yl)-4-(8-hydroxy-4- oxo-4,5-dihydrothieno[2,3-c]quinolin- 9-yl)benzenesulfonamide hydrochloride





201


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9-(4-(2-(diethylamino)ethyl)phenyl)- 8-hydroxythieno[2,3-c]quinolin- 4(5H)-one hydrochloride





202


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2-amino-N-(3-(8-methoxy-4-oxo-4,5- dihydrothieno[2,3-c]quinolin-9-yl) phenyl)ethanesulfonamide hydrochloride





203


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4-(8-hydroxy-4-oxo-4,5-dihydro thieno[2,3-c]quinolin-9-yl) benzonitrile





204


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4-(8-methoxy-4-oxo-4,5-dihydro thieno[2,3-c]quinolin-9-yl) benzonitrile





205


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(E)-9-(3-(3-aminopyrrolidin-1-yl) prop-1-enyl)-8-methoxythieno[2,3-c] quinolin-4(5H)-one dihydrochloride





206


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N-(2-hydroxyethyl)-4-(8-methoxy-4- oxo-4,5-dihydrothieno[2,3-c]quinolin- 9-yl)benzenesulfonamide





207


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8-methoxy-9-(5-methoxypyridin-3- yl)thieno[2,3-c]quinolin-4(5H)-one hydrochloride





208


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N-methoxy-9-(5-methoxypyridin-3- yl)-2,3-dihydro-1H-cyclopenta[c] quinolin-4(5H)-one hydrochloride





209


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9-(4-(3-aminopyrrolidin-1-ylsulfonyl) phenyl)-8-hydroxythieno[2,3-c] quinolin-4(5H)-one hydrochloride





210


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N-(2-bromoethyl)-4-(8-hydroxy-4- oxo-4,5-dihydrothieno[2,3-c]quinolin- 9-yl)benzenesulfonamide





211


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9-(4-((diisopropylamino)methyl) phenyl)-8-methoxythieno[2,3-c] quinolin-4(5H)-one hydrochloride





212


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N-(hydroxy-4-oxo-4,5-dihydrothieno [2,3-c]quinolin-9-yl)benzyl)methane sulfonamide





213


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9-(4-((isopropylamino)methyl)phenyl)- 8-methoxythieno[2,3-c]quinolin- 4(5H)-one hydrochloride





214


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2-(dimethylamino)-N-(3-(8-hydroxy- 4-oxo-4,5-dihydrothieno[2,3-c] quinolin-9-yl)phenyl)ethane sulfonamide hydrochloride





215


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2-amino-N-(3-(8-hydroxy-4-oxo-4,5- dihydrothieno[2,3-c]quinolin-9-yl) phenyl)ethanesulfonamide hydrochloride





216


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8-methoxy-9-(4-(1-(pyrrolidin-1-yl) ethyl)phenyl)thieno[2,3-c]quinolin- 4(5H)-one hydrochloride





217


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9-(4-amino-3-hydroxyphenyl)-8- hydroxythieno[2,3-c]quinolin- 4(5H)-one hydrochloride





218


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N-(2-methoxy-4-(8-methoxy-4-oxo-4, 5-dihydrothieno[2,3-c]quinolin-9-yl) phenyl)methanesulfonamide





219


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9-(3,5-difluoro-4-hydroxyphenyl)-8- methoxythieno[2,3-c]quinolin- 4(5H)-one





220


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N-(2-hydroxy-4-(8-hydroxy-4-oxo-4, 5-dihydrothieno[2,3-c]quinolin-9-yl) phenyl)methanesulfonamide





221


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9-(4-((4-(aminomethyl)piperidin-1- yl)methyl)-3-fluorophenyl)-8- methoxythieno[2,3-c]quinolin- 4(5H)-one dihydrochloride





222


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9-(4-(2-(dimethylamino)ethyl)phenyl)- 6-fluoro-8-methoxythieno[2,3-c] quinolin-4(5H)-one hydrochloride





223


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9-(3,5-difluoro-4-hydroxyphenyl)-8- hydroxythieno[2,3-c]quinolin- 4(5H)-one





224


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6-fluoro-8-methoxy-9-(1,2,3,6-tetra hydropyridin-4-yl)thieno[2,3-c] quinolin-4(5H)-one hydrochloride





225


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9-(4-(1-(dimethylamino)ethyl)phenyl)- 6-fluoro-8-hydroxythieno[2,3-c] quinolin-4(5H)-one





226


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9-(4-((diethylamino)methyl)-3-fluoro phenyl)-8-methoxythieno[2,3-c] quinolin-4(5H)-one hydrochloride





227


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(E)-9-(3-(3-hydroxypyrrolidin-1-yl) prop-1-enyl)-8-methoxythieno[2,3-c] quinolin-4(5H)-one





228


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(E)-8-hydroxy-9-(3-(3-hydroxy pyrrolidin-1-yl)prop-1-enyl)thieno [2,3-c]quinolin-4(5H)-one





229


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8-hydroxy-9-(4-((isopropylamino) methyl)phenyl)thieno[2,3-c]quinolin- 4(5H)-one hydrochloride





230


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(E)-9-(3-(3-aminoazetidin-1-yl) prop-1-enyl)-8-hydroxythieno[2,3-c] quinolin-4(5H)-one dihydrochloride





231


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(E)-8-methoxy-9-(3-(2-(methyl sulfonyl)ethylamino)prop-1-enyl) thieno[2,3-c]quinolin-4(5H)-one hydrochloride





232


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(S)-9-(4-(1-aminoethyl)phenyl)-8- methoxythieno[2,3-c]quinolin-4(5H)- one hydrochloride





233


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(S)-9-(4-(1-aminoethyl)phenyl)-8- hydroxythieno[2,3-c]quinolin-4(5H)- one hydrochloride





234


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8-hydroxy-9-(5-hydroxypyridin-3-yl)- 2,3-dihydro-1H-cyclopenta[c] quinolin-4(5H)-one hydrochloride





235


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9-(4-((4-(aminomethyl)piperidin-1-yl) methyl)-3-fluorophenyl)-8-hydroxy thieno[2,3-c]quinolin-4(5H)-one





236


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8-methoxy-9-(4-(1-(2-(methyl sulfonyl)ethylamino)ethyl)phenyl) thieno[2,3-c]quinolin-4(5H)-one hydrochloride





237


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9-(4-((3-aminopyrrolidin-1-yl)methyl)- 3-fluorophenyl)-8-methoxythieno [2,3-c]quinolin-4(5H)-one dihydrochloride





238


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(E)-9-(3-(3-aminoazetidin-1-yl) prop-1-enyl)-8-methoxythieno[2,3-c] quinolin-4(5H)-one dihydrochloride





239


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(E)-9-(3-(ethylamino)prop-1-enyl)-8- hydroxythieno[2,3-c]quinolin-4(5H)- one hydrochloride





240


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9-(4-((3-aminopiperidin-1-yl)methyl)- 3-fluorophenyl)-8-hydroxythieno[2,3- c]quinolin-4(5H)-one dihydrochloride





241


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9-(4-((3-aminopyrrolidin-1-yl)methyl)- 3-fluorophenyl)-8-hydroxythieno[2, 3-c]quinolin-4(5H)-one dihydrochloride





242


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9-(4-((3-aminopiperidin-1-yl)methyl)- 3-fluorophenyl)-8-methoxythieno[2, 3-c]quinolin-4(5H)-one dihydrochloride





243


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8-hydroxy-9-(4-(1-(2-(methylsulfonyl) ethylamino)ethyl)phenyl)thieno[2,3- c]quinolin-4(5H)-one hydrochloride





244


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(E)-9-(3-(3-aminopiperidin-1-yl)prop- 1-enyl)-8-methoxythieno[2,3-c] quinolin-4(5H)-one dihydrochloride





245


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(E)-9-(3-(3-aminopyrrolidin-1-yl) prop-1-enyl)-8-hydroxythieno[2,3-c] quinolin-4(5H)-one dihydrochloride





246


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(E)-9-(3-(3-aminopiperidin-1-yl)prop- 1-enyl)-8-hydroxythieno[2,3-c] quinolin-4(5H)-one dihydrochloride





247


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(E)-8-hydroxy-9-(3-(2-(methyl sulfonyl)ethylamino)prop-1-enyl) thieno[2,3-c]quinolin-4(5H)-one hydrochloride





248


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8-methoxy-9-(4-(2-(2-(methyl sulfonyl)ethylamino)ethyl)phenyl) thieno[2,3-c]quinolin-4(5H)-one hydrochloride





249


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2-(2-fluoro-4-(8-methoxy-4-oxo-4,5- dihydrothieno[2,3-c]quinolin-9-yl) phenyl)acetonitrile





250


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(E)-N-(1-(3-(8-methoxy-4-oxo-4,5- dihydrothieno[2,3-c]quinolin-9-yl)allyl) azetidin-3-yl)methanesulfonamide hydrochloride





251


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4-(8-methoxy-4-oxo-4,5-dihydro thieno[2,3-c]quinolin-9-yl)-N,N- dimethylbenzenesulfonamide





252


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4-(8-hydroxy-4-oxo-4,5-dihydro thieno[2,3-c]quinolin-9-yl)-N-methyl benzenesulfonamide





253


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tert-butyl (5-(8-methoxy-4-oxo-4,5-dihydro thieno[2,3-c]quinolin-9-yl)furan-2-yl) methylcarbamate





254


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N-(4-(8-hydroxy-4-oxo-4,5-dihydro thieno[2,3-c]quinolin-9-yl)-2-methyl phenyl)methanesulfonamide





255


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N-(4-(8-methoxy-4-oxo-4,5-dihydro thieno[2,3-c]quinolin-9-yl)-2-methyl phenyl)methanesulfonamide





256


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9-(4-(aminomethyl)phenyl)-6-fluoro- 8-hydroxythieno[2,3-c]quinolin-4(5H)- one hydrochloride





257


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9-(4-(aminomethyl)phenyl)-6-fluoro- 8-methoxythieno[2,3-c]quinolin-4(5H)- one hydrochloride





258


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6-fluoro-8-hydroxy-9-(1,2,3,6-tetra hydropyridin-4-yl)thieno[2,3-c] quinolin-4(5H)-one





259


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9-(4-((diethylamino)methyl)-3-fluoro phenyl)-8-hydroxythieno[2,3-c] quinolin-4(5H)-one





260


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8-methoxy-9-(4-(1-(piperidin-1-yl) ethyl(phenyl)thieno[2,3-c]quinolin- 4(5H)-one hydrochloride





261


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2-(2-fluoro-4-(8-hydroxy-4-oxo-4,5- dihydrothieno[2,3-c]quinolin-9-yl) phenyl)acetonitrile





262


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8-hydroxy-9-(4-(1-(piperidin-1-yl) ethyl)phenyl)thieno[2,3-c]quinolin- 4(5H)-one hydrochloride





263


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(E)-9-(3-(3-(dimethylamino)piperidin- 1-yl)prop-1-enyl)-8-hydroxythieno[2, 3-c]quinolin-4(5H)-one dihydrochloride





264


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(E)-9-(3-(3-(dimethylamino) pyrrolidin-1-yl)prop-1-enyl)-8- hydroxythieno[2,3-c]quinolin- 4(5H)-one dihydrochloride





265


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9-(4-(2-aminoethyl)-3-fluorophenyl)- 8-methoxythieno[2,3-c]quinolin- 4(5H)-one hydrochloride





266


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9-(5-(aminomethyl)thiophen-2-yl)-8- hydroxythieno[2,3-c]quinolin- 4(5H)-one





267


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9-(4-((ethylamino)methyl)phenyl)-8- hydroxythieno[2,3-c]quinolin- 4(5H)-one hydrochloride





268


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(E)-9-(3-(4-aminopiperidin-1-yl) prop-1-enyl)-8-hydroxythieno[2,3-c] quinolin-4(5H)-one dihydrochloride





269


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9-(4-((ethylamino)methyl)phenyl)-8- methoxythieno[2,3-c]quinolin- 4(5H)-one hydrochloride





270


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9-(4-(aminomethyl)phenyl)-6-bromo- 8-hydroxythieno[2,3-c]quinolin- 4(5H)-one hydrochloride





271


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9-(3-chloro-4-((diethylamino)methyl) phenyl)-8-methoxythieno[2,3-c] quinolin-4(5H)-one hydrochloride





272


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(R)-9-(4-(1-(dimethylamino)ethyl) phenyl)-8-hydroxythieno[2,3-c] quinolin-4(5H)-one hydrochloride





273


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9-(4-(3-aminopropyl)phenyl)-8- hydroxythieno[2,3-c]quinolin- 4(5H)-one hydrochloride





274


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(R)-9-(4-(1-aminoethyl)phenyl)-8- methoxythieno[2,3-c]quinolin-4(5H)- one hydrochloride





275


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(R)-9-(4-(1-aminoethyl)phenyl)-8- hydroxythieno[2,3-c]quinolin-4(5H)- one hydrochloride





276


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9-(4-(2-aminoethyl)-3-fluorophenyl)- 8-hydroxythieno[2,3-c]quinolin- 4(5H)-one hydrochloride





277


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9-(4-(1-amino-2-methylpropan-2-yl) phenyl)-8-hydroxythieno[2,3-c] quinolin-4(5H)-one hydrochloride





278


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9-(3-fluoro-4-((3-hydroxypyrrolidin- 1-yl)methyl)phenyl)-8-hydroxythieno [2,3-c]quinolin-4(5H)-one hydrochloride





279


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9-(3-fluoro-4-((3-hydroxypyrrolidin- 1-yl)methyl)phenyl)-8-methoxythieno [2,3-c]quinolin-4(5H)-one hydrochloride





280


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4-(8-methoxy-4-oxo-4,5-dihydro thieno[2,3-c]quinolin-9-yl)-N-(2,2,2- trifluoroethyl)benzenesulfonamide





281


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4-(8-hydroxy-4-oxo-4,5-dihydro thieno[2,3-c]quinolin-9-yl)-N-(2,2,2- trifluoroethyl)benzenesulfonamide





282


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N-(2-(dimethylamino)ethyl)-4-(8- hydroxy-4-oxo-4,5-dihydrothieno[2,3- c]quinolin-9-yl)benzenesulfonamide





283


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8-hydroxy-9-(4-((2-(methylsulfonyl) ethylamino)methyl)phenyl)thieno[2,3- c]quinolin-4(5H)-one





284


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9-(3-(3-(dimethylamino)pyrrolidin-1- yl)propyl)-8-hydroxythieno[2,3-c] quinolin-4(5H)-one dihydrochloride





285


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9-(1-(2-aminoethyl)-1H-pyrazol-4-yl)- 8-methoxythieno[2,3-c]quinolin- 4(5H)-one dihydrochloride





286


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9-(3-chloro-4-((diethylamino)methyl) phenyl)-8-hydroxythieno[2,3-c] quinolin-4(5H)-one hydrochloride hydrochloride





287


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4-(7-fluoro-8-methoxy-4-oxo-4,5- dihydrothieno[2,3-c]quinolin-9-yl)-N-(2- hydroxyethyl)benzenesulfonamide





288


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9-(3-acetylphenyl)-8-methoxythieno [2,3-c]quinolin-4(5H)-one





289


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2-fluoro-4-(8-hydroxy-4-oxo-4,5- dihydrothieno[2,3-c]quinolin-9-yl)- N-(2-hydroxyethyl)benzamide





290


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3-(4-(8-hydroxy-4-oxo-4,5-dihydro thieno[2,3-c]quinolin-9-yl)phenyl) propanenitrile





291


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9-(4-acetylphenyl)-8-methoxythieno [2,3-c]quinolin-4(5H)-one





292


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2-fluoro-N-(2-hydroxyethyl)-4-(8- methoxy-4-oxo-4,5-dihydrothieno[2, 3-c]quinolin-9-yl)benzamide





293


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4-(8-hydroxy-4-oxo-4,5-dihydro thieno[2,3-c]quinolin-9-yl)-N-(2- hydroxyethyl)benzamide





294


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1,1-diethyl-3-(hydroxy-4-oxo-4,5- dihydrothieno[2,3-c]quinolin-9-yl) benzyl)urea





295


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N-(2-hydroxyethyl)-4-(8-methoxy-4- oxo-4,5-dihydrothieno[2,3-c]quinolin- 9-yl)benzamide





296


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9-(4-acetylphenyl)-8-hydroxythieno [2,3-c]quinolin-4(5H)-one





297


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N-(2-bromoethyl)-2-fluoro-4-(8- hydroxy-4-oxo-4,5-dihydrothieno[2,3- c]quinolin-9-yl)benzenesulfonamide





298


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9-(3-(3-(dimethylamino)piperidin-1- yl)propyl)-8-hydroxythieno[2,3-c] quinolin-4(5H)-one dihydrochloride





299


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N-(2-fluoro-4-(8-hydroxy-4-oxo-4,5- dihydrothieno[2,3-c]quinolin-9-yl) phenethyl)methanesulfonamide





300


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9-(3-fluoro-4-(2-(methylsulfonamido) ethyl)phenyl)-4-oxo-4,5-dihydro thieno[2,3-c]quinolin-8-yl methanesulfonate





301


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(R)-N-(1-(4-(8-hydroxy-4-oxo-4,5- dihydrothieno[2,3-c]quinolin-9-yl) phenyl)ethyl)methanesulfonamide





302


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(R)-9-(4-(1-(methylsulfonamido) ethyl)phenyl)-4-oxo-4,5-dihydro thieno[2,3-c]quinolin-8-yl methanesulfonate





303


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2-fluoro-N-(2-hydroxyethyl)-4-(8- methoxy-4-oxo-4,5-dihydrothieno[2, 3-c]quinolin-9-yl)benzene sulfonamide





304


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4-(8-hydroxy-4-oxo-4,5-dihydro thieno[2,3-c]quinolin-9-yl)-N,N- dimethylbenzenesulfonamide





305


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9-(4-(2-(dimethylamino)ethyl)phenyl)- 7-fluoro-8-methoxythieno[2,3-c] quinolin-4(5H)-one hydrochloride





306


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N-(2-bromoethyl)-4-(7-fluoro-8- hydroxy-4-oxo-4,5-dihydrothieno[2,3- c]quinolin-9-yl)benzenesulfonamide





307


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4-(7-fluoro-8-hydroxy-4-oxo-4,5- dihydrothieno[2,3-c]quinolin-9-yl)-N- (2-hydroxy ethyl)benzene sulfonamide





308


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9-(4-(1-(dimethylamino)-2- methylpropan-2-yl)phenyl)-8-hydroxy thieno[2,3-c]quinolin-4(5H)-one hydrochloride





309


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N-(2-chloro-4-(8-methoxy-4-oxo-4,5- dihydrothieno[2,3-c]quinolin-9-yl) benzyl)-N-methylmethane sulfonamide





310


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4-(8-hydroxy-4-oxo-4,5-dihydro thieno[2,3-c]quinolin-9-yl)-N-(2- methoxyethyl)benzenesulfonamide





311


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(E)-3-(8-methoxy-4-oxo-4,5-dihydro thieno[2,3-c]quinolin-9-yl)-2-methyl acrylonitrile





312


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N-(2-fluoro-4-(8-methoxy-4-oxo-4,5- dihydrothieno[2,3-c]quinolin-9-yl) phenethyl)methanesulfonamide





313


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8-hydroxy-9-(4-(1-hydroxyethyl) phenyl)thieno[2,3-c]quinolin- 4(5H)-one





314


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9-(4-(1-(cyclopentylamino)ethyl) phenyl)-8-hydroxythieno[2,3-c] quinolin-4(5H)-one hydrochloride





315


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9-(4-(1-(cyclopentylamino)ethyl) phenyl)-8-methoxythieno[2,3-c] quinolin-4(5H)-one hydrochloride





316


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4-(8-hydroxy-4-oxo-4,5-dihydro thieno[2,3-c]quinolin-9-yl)-N-(2- hydroxyethyl)benzenesulfonamide





317


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9-(5-(aminomethyl)furan-2-yl)-8- hydroxythieno[2,3-c]quinolin-4(5H)- one hydrochloride





318


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9-(3-chloro-4-((methylamino)methyl) phenyl)-8-methoxythieno[2,3-c] quinolin-4(5H)-one hydrochloride





319


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9-(4-(2-aminopropan-2-yl)phenyl)-8- hydroxythieno[2,3-c]quinolin- 4(5H)-one hydrochloride





320


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N-(3-hydroxypropyl)-4-(8-methoxy-4- oxo-4,5-dihydrothieno[2,3-c] quinolin-9-yl)benzenesulfonamide





321


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2-fluoro-4-(8-hydroxy-4-oxo-4,5- dihydrothieno[2,3-c]quinolin-9-yl)-N- (2-hydroxyethyl)benzenesulfonamide





322


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4-(8-hydroxy-4-oxo-4,5-dihydro thieno[2,3-c]quinolin-9-yl)-N-(3- hydroxypropyl)benzenesulfonamide





323


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N-(3-bromopropyl)-4-(8-hydroxy-4- oxo-4,5-dihydrothieno[2,3-c]quinolin- 9-yl)benzenesulfonamide





324


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2-fluoro-4-(8-hydroxy-4-oxo-4,5- dihydrothieno[2,3-c]quinolin-9-yl)-N- (2-methoxyethyl)benzenesulfonamide





325


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9-(3-chloro-4-((methylamino)methyl) phenyl)-8-hydroxythieno[2,3-c] quinolin-4(5H)-one hydrochloride





326


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9-(4-(aminomethyl)phenyl)-4-oxo-4,5- dihydrothieno[2,3-c]quinoline-8- carbonitrile hydrochloride





327


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9-(4-(2-(dimethylamino)ethyl)-3- fluorophenyl)-8-hydroxythieno[2,3-c] quinolin-4(5H)-one hydrochloride





328


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9-(4-(aminomethyl)phenyl)-6,7- dichloro-8-hydroxythieno[2,3-c] quinolin-4(5H)-one hydrochloride





329


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9-(4-(aminomethyl)phenyl)-6-chloro- 8-hydroxythieno[2,3-c]quinolin- 4(5H)-one hydrochloride





330


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9-(4-(aminomethyl)phenyl)-4-oxo-4,5- dihydrothieno[2,3-c]quinolin-8-yl trifluoromethanesulfonate hydrochloride





331


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9-(4-(2-(dimethylamino)ethyl)phenyl)- 8-methoxythieno[2,3-c]quinolin- 4(5H)-one hydrochloride





332


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N-(2-chloroethyl)-4-(8-hydroxy-4- oxo-4,5-dihydrothieno[2,3-c]quinolin- 9-yl)benzenesulfonamide





333


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N-(2-fluoroethyl)-4-(8-methoxy-4- oxo-4,5-dihydrothieno[2,3-c]quinolin- 9-yl)benzenesulfonamide





334


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9-(4-(2-aminopropan-2-yl)phenyl)-6- chloro-8-hydroxythieno[2,3-c] quinolin-4(5H)-one hydrochloride





335


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(S)-9-(4-(1-(dimethylamino)ethyl) phenyl)-8-hydroxythieno[2,3-c] quinolin-4(5H)-one hydrochloride





336


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9-(4-(1-aminopropyl)phenyl)-8- hydroxythieno[2,3-c]quinolin- 4(5H)-one hydrochloride





337


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9-(4-(1-aminopropyl)phenyl)-8- methoxythieno[2,3-c]quinolin- 4(5H)-one hydrochloride





338


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9-(4-(1-(diethylamino)propyl)phenyl)- 8-hydroxythieno[2,3-c]quinolin- 4(5H)-one hydrochloride





339


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9-(4-(1-(dimethylamino)propyl) phenyl)-8-hydroxythieno[2,3-c] quinolin-4(5H)-one hydrochloride





340


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9-amino-8-methoxythieno[2,3-c] quinolin-4(5H)-one





341


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9-(4-(1-(dimethylamino)ethyl)phenyl)- 6,7-difluoro-8-hydroxythieno[2,3-c] quinolin-4(5H)-one hydrochloride





342


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9-(4-(1-(dimethylamino)ethyl)phenyl)- 6,7-difluoro-8-methoxythieno[2,3- c]quinolin-4(5H)-one hydrochloride





343


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N-cyclopropyl-4-(8-methoxy-4-oxo-4, 5-dihydrothieno[2,3-c]quinolin-9-yl) benzenesulfonamide





344


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N-cyclopropyl-4-(8-hydroxy-4-oxo-4, 5-dihydrothieno[2,3-c]quinolin-9-yl) benzenesulfonamide





345


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9-(2-amino-2,3-dihydro-1H-inden-5- yl)-8-hydroxythieno[2,3-c]quinolin-4 (5H)-one hydrochloride





346


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9-(4-(1-(dimethylamino)ethyl)phenyl) thieno[2,3-c]quinolin-4(5H)-one





347


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(S)-N-(1-(4-(8-hydroxy-4-oxo-4,5- dihydrothieno[2,3-c]quinolin-9-yl) phenyl)ethyl)methanesulfonamide





348


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9-(4-(1-(aminomethyl)cyclopropyl) phenyl)-8-hydroxythieno[2,3-c]quinolin- 4(5H)-one hydrochloride





349


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9-(4-(1-(dimethylamino)ethyl)-3- fluorophenyl)-8-hydroxythieno[2,3-c] quinolin-4(5H)-one hydrochloride





350


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N-(1-(hydroxymethyl)cyclopentyl)-4- (8-methoxy-4-oxo-4,5-dihydrothieno [2,3-c]quinolin-9-yl)benzene sulfonamide





351


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9-(2-(diethylamino)-2,3-dihydro-1H- inden-5-yl)-8-hydroxythieno[2,3-c] quinolin-4(5H)-one hydrochloride





352


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9-(2-(dimethylamino)-2,3-dihydro-1H- inden-5-yl)-8-hydroxythieno[2,3-c] quinolin-4(5H)-one hydrochloride





353


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8-hydroxy-9-(1,2,3,4-tetrahydroiso quinolin-7-yl)thieno[2,3-c]quinolin-4 (5H)-one hydrochloride





354


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8-methoxy-9-(1,2,3,4-tetrahydroiso quinolin-7-yl)thieno[2,3-c]quinolin- 4(5H)-one hydrochloride





355


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3-(3-(8-hydroxy-4-oxo-4,5-dihydro thieno[2,3-c]quinolin-9-yl)phenyl) propanenitrile





356


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9-(4-(1-(diethylamino)ethyl)-3-fluoro phenyl)-8-hydroxythieno[2,3-c] quinolin-4(5H)-one hydrochloride





357


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1-(4-(8-methoxy-4-oxo-4,5-dihydro thieno[2,3-c]quinolin-9-yl)phenyl) cyclopropanecarbonitrile





358


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9-(2-ethyl-1,2,3,4-tetrahydroiso quinolin-7-yl)-8-hydroxythieno[2,3-c] quinolin-4(5H)-one hydrochloride





359


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9-(4-(1-aminoethyl)-3-fluorophenyl)- 8-hydroxythieno[2,3-c]quinolin- 4(5H)-one hydrochloride





360


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3-(3-(8-methoxy-4-oxo-4,5-dihydro thieno[2,3-c]quinolin-9-yl)phenyl) propanenitrile





361


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1-(4-(8-hydroxy-4-oxo-4,5-dihydro thieno[2,3-c]quinolin-9-yl)phenyl) cyclopropanecarbonitrile





362


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9-(2-amino-2,3-dihydro-1H-inden-5- yl)-8-methoxythieno[2,3-c]quinolin-4 (5H)-one hydrochloride





363


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N-isopentyl-4-(8-methoxy-4-oxo-4,5- dihydrothieno[2,3-c]quinolin-9-yl) benzenesulfonamide





364


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9-(2-(dimethylamino)-2,3-dihydro-1H- inden-5-yl)-8-methoxythieno[2,3-c] quinolin-4(5H)-one hydrochloride





365


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9-(4-(1-(ethylamino)ethyl)phenyl)-8- methoxythieno[2,3-c]quinolin-4(5H)- one hydrochloride





366


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6-chloro-9-(4-(1-(dimethylamino) ethyl)phenyl)-8-hydroxythieno[2,3-c] quinolin-4(5H)-one hydrochloride





367


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9-(4-(cyclopropanecarbonyl)phenyl)- 8-methoxythieno[2,3-c]quinolin- 4(5H)-one





368


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9-(4-(aminomethyl)phenyl)-4-oxo-4,5- dihydrothieno[2,3-c]quinoline-8- carboxamide hydrochloride





369


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9-(2-aminoethyl)-8-methoxythieno[2, 3-c]quinolin-4(5H)-one





370


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8-hydroxy-9-(4-(2-hydroxyethylsulfonyl) phenyl)thieno[2,3-c]quinolin- 4(5H)-one





371


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9-(4-(2-hydroxyethylsulfonyl)phenyl)- 8-methoxythieno[2,3-c]quinolin- 4(5H)-one





372


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9-(1-ethylindolin-5-yl)-8-hydroxy thieno[2,3-c]quinolin-4(5H)-one hydrochloride





373


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9-(4-(1-aminopropan-2-yl)phenyl)-8- methoxythieno[2,3-c]quinolin- 4(5H)-one hydrochloride





374


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8-hydroxy-9-(2-methyl-1,2,3,4-tetra hydroisoquinolin-7-yl)thieno[2,3-c] quinolin-4(5H)-one hydrochloride





375


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9-(4-(1-aminoethyl)-3-fluorophenyl)- 8-methoxythieno[2,3-c]quinolin- 4(5H)-one hydrochloride





376


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8-hydroxy-9-(1-methylindolin-5-yl) thieno[2,3-c]quinolin-4(5H)-one hydrochloride





377


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8-hydroxy-9-(indolin-5-yl)thieno[2,3- c]quinolin-4(5H)-one hydrochloride





378


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9-(indolin-5-yl)-8-methoxythieno[2,3- c]quinolin-4(5H)-one hydrochloride





379


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9-(4-(1-((dimethylamino)methyl) cyclopropyl)phenyl)-8-hydroxythieno [2,3-c]quinolin-4(5H)-one hydrochloride





380


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4-(8-methoxy-4-oxo-4,5-dihydro thieno[2,3-c]quinolin-9-yl)-N-propyl benzenesulfonamide





381


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N-(cyclopropylmethyl)-4-(8-methoxy- 4-oxo-4,5-dihydrothieno[2,3-c] quinolin-9-yl)benzenesulfonamide





382


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N-(3,3-dimethylbutyl)-4-(8-methoxy- 4-oxo-4,5-dihydrothieno[2,3-c] quinolin-9-yl)benzenesulfonamide





383


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4-(8-hydroxy-4-oxo-4,5-dihydrothieno [2,3-c]quinolin-9-yl)-N-isopentyl benzenesulfonamide





384


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N-(3,3-dimethylbutyl)-4-(8-hydroxy- 4-oxo-4,5-dihydrothieno[2,3-c] quinolin-9-yl)benzenesulfonamide





385


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9-(4-(1-(ethylamino)ethyl)phenyl)-8- hydroxythieno[2,3-c]quinolin- 4(5H)-one hydrochloride





386


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3-(4-(8-methoxy-4-oxo-4,5-dihydro thieno[2,3-c]quinolin-9-yl)phenyl)-3- oxopropanenitrile





387


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(E)-9-(2-ethoxyvinyl)-8-methoxy thieno[2,3-c]quinolin-4(5H)-one





388


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N-(1-(4-(8-hydroxy-4-oxo-4,5- dihydrothieno[2,3-c]quinolin- 9-yl)phenyl)ethyl)acetamide





389


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4-(8-methoxy-4-oxo-4,5-dihydro thieno[2,3-c]quinolin-9-yl)-N-(3,3,3- trifluoropropyl)benzenesulfonamide





390


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4-(8-hydroxy-4-oxo-4,5-dihydro thieno[2,3-c]quinolin-9-yl)-N-(1- (hydroxymethyl)cyclopentyl) benzenesulfonamide





391


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N-(2,2-difluoroethyl)-4-(8-methoxy-4- oxo-4,5-dihydrothieno[2,3-c] quinolin-9-yl)benzenesulfonamide










(Examples 1031-1438)









No.
Molecule
Name





1031


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8-methoxy-9-(4-(1-methoxyethyl) phenyl)thieno[2,3-c]quinolin- 4(5H)-one





1032


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9-(4-(1-aminoethyl)phenyl)-6- bromo-8-hydroxythieno[2,3-c] quinolin-4(5H)-one





1033


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8-methoxy-9-(2-((piperidin-3- ylmethyl)amino)ethyl)thieno[2,3- c]quinolin-4(5H)-one





1034


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9-(2-(4-((dimethylamino)methyl) piperidin-1-yl)ethyl)-8- methoxythieno[2,3-c]quinolin- 4(5H)-one





1035


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tert-butyl 4-((2-(8-methoxy-4-oxo-4,5- dihydrothieno[2,3-c]quinolin-9- yl)ethyl)amino)piperidine-1- carboxylate





1036


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8-methoxy-9-(2-(piperidin-4-yl amino)ethyl)thieno[2,3-c] quinolin-4(5H)-one





1037


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4-(8-hydroxy-4-oxo-4,5- dihydrothieno[2,3-c]quinolin- 9-yl)-N-(3,33-trifluoropropyl) benzenesulfonamide





1038


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3H-pyrrolo[2,3-c]quinolin- 4(5H)-one





1039


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9-(4-(1-aminoethyl)phenyl)-6- cyclopropyl-8-hydroxythieno[2, 3-c]quinolin-4(5H)-one





1040


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9-(4-(1-aminoethyl)phenyl)-8- hydroxy-4-oxo-4,5-dihydrothieno [2,3-c]quinoline-6-carbonitrile





1041


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9-(4-(1-aminoethyl)phenyl)-6- chloro-8-hydroxythieno[2,3-c] quinolin-4(5H)-one





1042


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8-hydroxy-9-(2-(4-((methylamino) methyl)piperidin-1-yl)ethyl) thieno[2,3-c]quinolin-4(5H)-one





1043


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8-methoxy-9-(2-(4-((methylamino) methyl)piperidin-1-yl)ethyl) thieno[2,3-c]quinolin-4(5H)-one





1044


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9-(2-(4-((dimethylamino)methyl) piperidin-1-yl)ethyl)-8- hydroxythieno[2,3-c] quinolin-4(5H)-one





1045


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9-(4-(1-hydroxypropyl)phenyl)- 8-methoxythieno[2,3-c] quinolin-4(5H)-one





1046


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(R)-8-methoxy-9-(4-(1-(methyl amino)ethyl)phenyl)thieno[2,3- c]quinolin-4(5H)-one





1047


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(R)-8-(4-(1-aminoethyl)phenyl) thieno[2,3-c]quinolin-4(5H)-one





1048


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(R)-tert-butyl (1-(4-(4-oxo-4,5-dihydrothieno [2,3-c]quinolin-8-yl)phenyl) ethyl)carbamate





1049


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9-(4-(4-hydroxypiperidin-4-yl) phenyl)-8-methoxythieno[2,3- c]quinolin-4(5H)-one





1050


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(R)-8-(4-(1-(dimethylamino) ethyl)phenyl)thieno[2,3- c]quinolin-4(5H)-one





1051


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8-hydroxy-9-(4-(1,2,3,6- tetrahydropyridin-4-yl) phenyl)thieno[2,3-c] quinolin-4(5H)-one





1052


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(R)-8-hydroxy-9-(4-(1-(methyl amino)ethyl)phenyl)thieno[2,3- c]quinolin-4(5H)-one





1053


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8-hydroxy-9-(4-(1- hydroxypropyl)phenyl)thieno [2,3-c]quinolin-4(5H)-one





1054


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(R)-8-hydroxy-9-(4-(1-hydroxy ethyl)phenyl)thieno[2,3-c] quinolin-4(5H)-one





1055


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8-hydroxy-9-(4-(4- hydroxypiperidin-4- yl)phenyl)thieno[2,3-c] quinolin-4(5H)-one





1056


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(S)-8-hydroxy-9-(4-(1-hydroxy ethyl)phenyl)thieno[2,3-c] quinolin-4(5H)-one





1057


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N-(1-hydroxypropan-2-yl)-4-(8- methoxy-4-oxo-4,5-dihydrothieno [2,3-c]quinolin-9-yl) benzenesulfonamide





1058


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9-(4-(hydroxy(thiazol-2-yl) methyl)phenyl)-8-methoxythieno [2,3-c]quinolin-4(5H)-one





1059


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9-(6-(1-aminoethyl)pyridin-3- yl)-8-hydroxythieno[2,3-c] quinolin-4(5H)-one





1060


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9-(4-(4-hydroxybutyl)phenyl)-8- methoxythieno[2,3-c]quinolin- 4(5H)-one





1061


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2-(4-(8-hydroxy-4-oxo-4,5- dihydrothieno[2,3-c]quinolin-9- yl)phenyl)-2-methylpropanamide





1062


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N-(1-bromopropan-2-yl)-4-(8- hydroxy-4-oxo-4,5-dihydrothieno [2,3-c]quinolin-9-yl) benzenesulfonamide





1063


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8-hydroxy-9-(4-(hydroxy (thiazol-2-yl)methyl)phenyl) thieno[2,3-c]quinolin-4(5H)-one





1064


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(S)-8-methoxy-9-(4-(1-(methyl amino)ethyl)phenyl)thieno[2,3- c]quinolin-4(5H)-one





1065


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9-(6-(1-(diethylamino)ethyl) pyridin-3-yl)-8-hydroxythieno [2,3-c]quinolin-4(5H)-one





1066


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9-(4-(1-aminoethyl)phenyl)-8- hydroxy-6-methylthieno[2,3-c] quinolin-4(5H)-one





1067


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9-(6-(1-aminoethyl)pyridin-3- yl)-8-methoxythieno[2,3-c] quinolin-4(5H)-one





1068


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8-hydroxy-9-(4-(4-hydroxybutyl) phenyl)thieno[2,3-c]quinolin- 4(5H)-one





1069


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9-(4-(3-amino-1-hydroxypropyl) phenyl)-8-methoxythieno[2,3- c]quinolin-4(5H)-one





1070


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9-(6-(1-(dimethylamino)ethyl) pyridin-3-yl)-8-hydroxythieno[2, 3-c]quinolin-4(5H)-one





1071


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9-(6-(1-(dimethylamino)ethyl) pyridin-3-yl)-8-methoxythieno [2,3-c]quinolin-4(5H)-one





1072


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4-((4-(8-methoxy-4-oxo-4,5- dihydrothieno[2,3-c]quinolin-9- yl)-1H-pyrazol-1-yl)methyl) benzonitrile





1073


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8-aminothieno[2,3-c]quinolin- 4(5H)-one





1074


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9-(4-((1H-pyrazol-1-yl)methyl) phenyl)-8-methoxythieno[2,3- c]quinolin-4(5H)-one





1075


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9-(6-(1-aminoethyl)pyridin-3- yl)-8-methoxythieno[2,3-c] quinolin-4(5H)-one





1076


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9-(4-(1-aminoethyl)phenyl)-4- oxo-4,5-dihydrothieno[2,3-c] quinolin-8-yl dimethylcarbamate





1077


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9-(4-(1-aminoethyl)phenyl)-4- oxo-4,5-dihydrothieno[2,3-c] quinolin-8-yl isopropyl carbonate





1078


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9-(4-((1H-imidazol-1-yl)methyl) phenyl)-8-methoxythieno[2,3- c]quinolin-4(5H)-one





1079


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N-(2-bromopropyl)-4-(8- hydroxy-4-oxo-4,5-dihydrothieno [2,3-c]quinolin-9-yl) benzenesulfonamide





1080


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(R)-9-(4-(1-aminoethyl)phenyl)- 6,7-dichloro-8-hydroxythieno [2,3-c]quinolin-4(5H)-one





1081


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(R)-9-(4-(1-aminoethyl)phenyl)- 6-chloro-8-hydroxythieno[2,3- c]quinolin-4(5H)-one





1082


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(S)-8-hydroxy-9-(4-(1- (methylamino)ethyl)phenyl) thieno[2,3-c]quinolin- 4(5H)-one





1083


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9-(4-(1-aminoethyl)phenyl)-4- oxo-4,5-dihydrothieno[2,3-c] quinolin-8-yl diethylcarbamate





1084


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4-(8-hydroxy-4-oxo-4,5- dihydrothieno[2,3-c]quinolin- 9-yl)-N-(2-hydroxyethyl)- N-methylbenzenesulfonamide





1085


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N-(2-hydroxyethyl)-4-(8- methoxy-4-oxo-4,5-dihydrothieno [2,3-c]quinolin-9-yl)-N- methylbenzenesulfonamide





1086


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9-(4-((1H-pyrazol-1-yl(methyl) phenyl)-8-hydroxythieno[2,3-c] quinolin-4(5H)-one





1087


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(S)-6-chloro-8-hydroxy-9-(4-(1- (methylamino)ethyl)phenyl) thieno[2,3-c]quinolin-4(5H)-one





1088


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9-(4-(1-aminopropyl)phenyl)-6- chloro-8-hydroxythieno[2,3-c] quinolin-4(5H)-one





1089


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9-(4-(1-aminoethyl)phenyl)-4- oxo-4,5-dihydrothieno[2,3-c] quinolin-8-yl morpholine-4-carboxylate





1090


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N-(2-hydroxyethyl)-4-(8- methoxy-4-oxo-2,3,4,5- tetrahydro-1H-cyclopenta [c]quinolin-9-yl) benzenesulfonamide





1091


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8-bromothieno[2,3-c]quinolin- 4(5H)-one





1092


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9-(4-(2-(dimethylamino)propyl) phenyl)-8-hydroxythieno[2,3-c] quinolin-4(5H)-one





1093


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9-(4-(2-aminopropyl)phenyl)-8- methoxythieno[2,3-c]quinolin- 4(5H)-one





1094


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N-(2-bromoethyl)-4-(8-hydroxy- 4-oxo-2,3,4,5-tetrahydro-1H- cyclopenta[c]quinolin-9-yl) benzenesulfonamide





1095


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9-(4-(2-aminopropyl)phenyl)-8- hydroxythieno[2,3-c]quinolin- 4(5H)-one





1096


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8-methoxy-9-(1-(2-morpholino ethyl)-1H-pyrazol-4-yl)thieno [2,3-c]quinolin-4(5H)-one





1097


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9-(4-(2-(diethylamino)propyl) phenyl)-8-hydroxythieno[2,3-c] quinolin-4(5H)-one





1098


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9-(4-(1-aminoethyl)phenyl)-8- hydroxy-6-(hydroxymethyl) thieno[2,3-c]quinolin-4(5H)-one





1099


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9-(4-(1-aminoethyl)phenyl)-4- oxo-4,5-dihydrothieno[2,3-c] quinolin-8-yl acetate





1100


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9-(1-(1-(dimethylamino)propan- 2-yl)-1H-pyrazol-4-yl)-8- methoxythieno[2,3-c]quinolin- 4(5H)-one





1101


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9-(4-((1H-imidazol-1-yl)methyl) phenyl)-8-hydroxythieno[2,3- c]quinolin-4(5H)-one





1102


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9-(4-(aminomethyl)phenyl)-8- (2-morpholinoethoxy)thieno[2,3- c]quinolin-4(5H)-one





1103


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8-hydroxy-9-(1-(2- morpholinoethyl)-1H-pyrazol- 4-yl)thieno[2,3-c]quinolin- 4(5H)-one





1104


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N-(2-(1H-pyrazol-1-yl)ethyl)- 4-(8-hydroxy-4-oxo-4,5- dihydrothieno[2,3-c]quinolin-9- yl)benzenesulfonamide





1105


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8-hydroxy-9-(4-(2,2,2-trifluoro- 1-hydroxyethyl)phenyl)thieno [2,3-c]quinolin-4(5H)-one





1106


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9-(4-(2-aminopropyl)phenyl)-6- chloro-8-hydroxythieno[2,3-c] quinolin-4(5H)-one





1107


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N-(2-(4-(8-hydroxy-4-oxo-4,5- dihydrothieno[2,3-c]quinolin-9- yl)phenyl)-2-methylpropyl) methanesulfonamide





1108


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9-(4-(2-(dimethylamino)propyl) phenyl)-8-methoxythieno[2,3- c]quinolin-4(5H)-one





1109


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9-(4-(1-aminoethyl)phenyl) thieno[2,3-c]quinolin-4(5H)-one





1110


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9-(1-(1-(dimethylamino)propan- 2-yl)-1H-pyrazol-4-yl)-8- hydroxythieno[2,3-c]quinolin- 4(5H)-one





1111


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9-(4-(1-aminopropan-2-yl) phenyl)-8-hydroxythieno[2,3-c] quinolin-4(5H)-one





1112


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9-(4-(1-(dimethylamino)propan- 2-yl)phenyl)-8-hydroxythieno [2,3-c]quinolin-4(5H)-one





1113


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8-methoxy-9-(4-(2,2,2-trifluoro- 1-hydroxyethyl)phenyl)thieno [2,3-c]quinolin-4(5H)-one





1114


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N-(2-bromoethyl)-4-(8-hydroxy- 4-oxo-4,5-dihydrothieno[2,3- c]quinolin-9-yl)-N- methylbenzenesulfonamide





1115


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N-(2-(1H-imidazol-1-yl)ethyl)- 4-(8-hydroxy-4-oxo-4,5- dihydrothieno[2,3-c]quinolin-9-yl) benzenesulfonamide





1116


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9-(4-(1-(aminomethyl) cyclopropyl)phenyl)-6-chloro-8- hydroxythieno[2,3-c]quinolin- 4(5H)-one





1117


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3-(4-(8-(2-(dimethylamino) ethoxy)-4-oxo-4,5-dihydrothieno [2,3-c]quinolin-9-yl)phenyl) propanenitrile





1118


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(R)-9-(4-(1-aminopropyl) phenyl)-8-methoxythieno[2,3-c] quinolin-4(5H)-one





1119


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N-(2-chloroethyl)-4-(8-hydroxy- 4-oxo-4,5-dihydrothieno[2,3- c]quinolin-9-yl)-N- methylbenzenesulfonamide





1120


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(S)-9-(4-(1-aminopropyl) phenyl)-8-hydroxythieno[2,3- c]quinolin-4(5H)-one





1121


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(S)-9-(4-(1-aminopropyl) phenyl)-8-methoxythieno[2,3- c]quinolin-4(5H)-one





1122


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(R)-9-(4-(1-aminoethyl)phenyl)- 8-hydroxy-6-methylthieno[2,3- c]quinolin-4(5H)-one





1123


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(R)-9-(4-(1-aminoethyl)phenyl)- 6-bromo-8-hydroxythieno[2,3- c]quinolin-4(5H)-one





1124


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9-(4-(1-aminoethyl)phenyl)-4- oxo-4,5-dihydrothieno[2,3-c] quinoline-8-carbonitrile





1125


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9-(4-(1-aminoethyl)phenyl)-8- (hydroxymethyl)thieno[2,3-c] quinolin-4(5H)-one





1126


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(R)-6-chloro-9-(4-(1- (dimethylamino)ethyl)phenyl)- 8-hydroxythieno[2,3-c] quinolin-4(5H)-one





1127


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(S)-9-(4-(1-(ethylamino)propyl) phenyl)-8-hydroxythieno[2,3-c] quinolin-4(5H)-one





1128


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(S)-9-(4-(1-(dimethylamino) propyl)phenyl)-8-hydroxythieno[2, 3-c]quinolin-4(5H)-one





1129


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6-chloro-9-(4-(1-(dimethylamino) propan-2-yl)phenyl)-8- hydroxythieno[2,3-c]quinolin- 4(5H)-one





1130


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9-(4-(1-aminoethyl)phenyl)-6- ethynyl-8-hydroxythieno[2,3-c] quinolin-4(5H)-one





1131


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(R)-9-(4-(1-aminopropyl) phenyl)-8-hydroxythieno[2,3-c] quinolin-4(5H)-one





1132


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(R)-6-chloro-8-hydroxy-9-(4-(1- (methylamino)ethyl)phenyl) thieno[2,3-c]quinolin-4(5H)-one





1133


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9-(4-(2-aminoethyl)phenyl)-6- chloro-8-hydroxythieno[2,3-c] quinolin-4(5H)-one





1134


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9-(4-(1-aminoethyl)phenyl)-8- (difluoromethyl)thieno[2,3-c] quinolin-4(5H)-one





1135


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(R)-6-bromo-8-hydroxy-9-(4- (1-(methylamino)ethyl)phenyl) thieno[2,3-c]quinolin-4(5H)-one





1136


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9-(4-(1-aminopropan-2-yl) phenyl)-6-chloro-8-hydroxythieno [2,3-c]quinolin-4(5H)-one





1137


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9-(4-butylphenyl)-8-methoxythieno [2,3-c]quinolin-4(5H)-one





1138


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9-(4-butylphenyl)-8-hydroxythieno [2,3-c]quinolin-4(5H)-one





1139


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N-(2-chloroethyl)-4-(8-methoxy- 4-oxo-4,5-dihydrothieno[2,3- c]quinolin-9-yl) benzenesulfonamide





1140


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9-(4-((3-bromopyrrolidin-1-yl) sulfonyl)phenyl)-8-hydroxythieno [2,3-c]quinolin-4(5H)-one





1141


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(S)-9-(4-(1-(methylsulfonamido) propyl)phenyl)-4-oxo-4,5- dihydrothieno[2,3-c]quinolin-8-yl methanesulfonate





1142


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9-(4-(2-aminoethyl)phenyl)-6- bromo-8-hydroxythieno[2,3-c] quinolin-4(5H)-one





1143


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9-(4-(3-(dimethylamino)-1- hydroxypropyl)phenyl)-8- methoxythieno[2,3-c]quinolin- 4(5H)-one





1144


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N-(2-bromoethyl)-4-(6-chloro- 8-hydroxy-4-oxo-4,5- dihydrothieno[2,3-c]quinolin- 9-yl)benzenesulfonamide





1145


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N-(2-chloroethyl)-4-(8-hydroxy- 4-oxo-2,3,4,5-tetrahydro-1H- cyclopenta[c]quinolin-9-yl) benzenesulfonamide





1146


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N-(2-bromoethyl)-4-(5-ethyl-8- hydroxy-4-oxo-4,5-dihydrothieno [2,3-c]quinolin-9-yl) benzenesulfonamide





1147


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(S)-8-methoxy-9-(4-(1-(methyl amino)propyl)phenyl)thieno[2, 3-c]quinolin-4(5H)-one





1148


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(S)-8-hydroxy-9-(4-(1- (methylamino)propyl)phenyl) thieno[2,3-c]quinolin-4(5H)-one





1149


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9-(4-(1-aminoethyl)phenyl)-8- (((2-hydroxyethyl)amino)methyl) thieno[2,3-c]quinolin-4(5H)- one





1150


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(R)-9-(4-(1-aminopropyl)phenyl)- 6-bromo-8-hydroxythieno[2, 3-c]quinolin-4(5H)-one





1151


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(R)-9-(4-(1-(dimethylamino) propyl)phenyl)-8-hydroxythieno [2,3-c]quinolin-4(5H)-one





1152


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8-hydroxy-9-(4-pentylphenyl) thieno[2,3-c]quinolin-4(5H)-one





1153


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9-(4-(2-aminoacetyl)phenyl)-8- hydroxythieno[2,3-c]quinolin- 4(5H)-one





1154


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(S)-6-chloro-8-hydroxy-9-(4-(1- (methylamino)propyl)phenyl) thieno[2,3-c]quinolin-4(5H)-one





1155


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8-hydroxy-9-(4-(2-(methylamino) ethyl)phenyl)thieno[2,3-c] quinolin-4(5H)-one





1156


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8-methoxy-9-(4-(2-(methylamino) ethyl)phenyl)thieno[2,3-c] quinolin-4(5H)-one





1157


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(R)-9-(4-(1-aminopropyl)phenyl)- 8-hydroxy-6-methylthieno[2, 3-c]quinolin-4(5H)-one





1158


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(R)-9-(4-(1-aminopropyl)phenyl)- 8-methoxy-6-methylthieno[2, 3-c]quinolin-4(5H)-one





1159


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(R)-9-(4-(1-aminopropyl)phenyl)- 6-chloro-8-hydroxythieno[2, 3-c]quinolin-4(5H)-one





1160


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(R)-9-(4-(1-aminopropan-2-yl) phenyl)-8-hydroxythieno[2,3-c] quinolin-4(5H)-one





1161


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(R)-9-(4-(1-aminopropan-2-yl) phenyl)-8-methoxythieno[2,3-c] quinolin-4(5H)-one





1162


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2-(4-(8-hydroxy-4-oxo-4,5- dihydrothieno[2,3-c]quinolin-9-yl) phenyl)butanenitrile





1163


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(S)-9-(4-(1-aminopropan-2-yl) phenyl)-8-hydroxythieno[2,3-c] quinolin-4(5H)-one





1164


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(S)-9-(4-(1-aminopropan-2-yl) phenyl)-8-methoxythieno[2,3-c] quinolin-4(5H)-one





1165


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6-chloro-8-hydroxy-9-(4-(2- (methylamino)ethyl)phenyl)thieno [2,3-c]quinolin-4(5H)-one





1166


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(R)-9-(4-(1-aminopropan-2-yl) phenyl)-6-chloro-8-hydroxythieno [2,3-c]quinolin-4(5H)-one





1167


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9-(4-(2-aminoethyl)-3,5- difluorophenyl)-8-hydroxythieno [2,3-c]quinolin-4(5H)-one





1168


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(R)-9-(4-(1-aminopropan-2-yl) phenyl)-8-hydroxy-6-methylthieno [2,3-c]quinolin-4(5H)-one





1169


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(R)-9-(4-(1-aminopropan-2-yl) phenyl)-8-hydroxy-6-methylthieno [2,3-c]quinolin-4(5H)-one





1170


embedded image


6-chloro-8-methoxy-9-(4-(2- (methylamino)ethyl)phenyl)thieno [2,3-c]quinolin-4(5H)-one





1171


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9-(4-(2-aminoethyl)-3- chlorophenyl)-8-hydroxythieno [2,3-c]quinolin-4(5H)-one





1172


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(S)-9-(4-(1-(dimethylamino) propan-2-yl)phenyl)-8-hydroxythieno [2,3-c]quinolin-4(5H)-one





1173


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6-bromo-8-methoxy-9-(4-(2- (methylamino)ethyl)phenyl)thieno [2,3-c]quinolin-4(5H)-one





1174


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9-(4-(1-aminopropan-2-yl)-3- fluorophenyl)-8-hydroxythieno [2,3-c]quinolin-4(5H)-one





1175


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(R)-9-(4-(1-aminopropyl)phenyl)- 6-chloro-8-methoxythieno[2, 3-c]quinolin-4(5H)-one





1176


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(R)-9-(4-(1-aminopropan-2-yl) phenyl)-6-bromo-8-hydroxythieno [2,3-c]quinolin-4(5H)-one





1177


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9-(4-(2-aminoethyl)-3,5- difluorophenyl)-8-methoxythieno [2,3-c]quinolin-4(5H)-one





1178


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9-(4-(2-(dimethylamino)ethyl)- 3,5-difluorophenyl)-8- hydroxythieno[2,3-c]quinolin- 4(5H)-one





1179


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9-(4-(1-aminopropan-2-yl)-3- fluorophenyl)-8-methoxythieno [2,3-c]quinolin-4(5H)-one





1180


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(S)-9-(4-(1-aminopropan-2-yl) phenyl)-6,7-dichloro-8- methoxythieno[2,3-c]quinolin- 4(5H)-one





1181


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(S)-9-(4-(1-aminopropan-2-yl) phenyl)-6-chloro-8-hydroxythieno [2,3-c]quinolin-4(5H)-one





1182


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(S)-6-chloro-9-(4-(1-(dimethylamino) propan-2-yl)phenyl)-8- hydroxythieno[2,3-c]quinolin- 4(5H)-one





1183


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6-bromo-8-hydroxy-9-(4-(2- (methylamino)ethyl)phenyl)thieno [2,3-c]quinolin-4(5H)-one





1185


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N-(2-hydroxyethyl)-4-(8-methoxy- 5-methyl-4-oxo-4,5-dihydro thieno[2,3-c]quinolin-9-yl) benzenesulfonamide





1186


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methyl 3-(4-(8-hydroxy-4-oxo-4,5- dihydrothieno[2,3-c]quinolin-9-yl) phenyl)propanoate





1187


embedded image


(R)-8-hydroxy-9-(4-(1-(methyl amino)propan-2-yl)phenyl) thieno[2,3-c]quinolin-4(5H)-one





1188


embedded image


(R)-9-(4-(1-(dimethylamino) propan-2-yl)phenyl)-8-hydroxythieno [2,3-c]quinolin-4(5H)-one





1189


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(R)-8-methoxy-9-(4-(1-(methyl amino)propan-2-yl)phenyl) thieno[2,3-c]quinolin-4(5H)-one





1190


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9-(4-(1-aminopropan-2-yl)-3- fluorophenyl)-8-hydroxy-6- methylthieno[2,3-c]quinolin- 4(5H)-one





1191


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9-(4-(2-aminoethyl)phenyl)-8- hydroxy-6-methylthieno[2,3-c] quinolin-4(5H)-one





1192


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9-(4-(2-aminoethyl)phenyl)-8- methoxy-6-methylthieno[2,3-c] quinolin-4(5H)-one





1193


embedded image


9-(4-(1-(dimethylamino)propan- 2-yl)-3-fluorophenyl)-8- hydroxy-6-methylthieno[2,3-c] quinolin-4(5H)-one





1194


embedded image


(S)-6-chloro-8-hydroxy-9-(4-(1- (methylamino)propan-2-yl) phenyl)thieno[2,3-c]quinolin- 4(5H)-one





1195


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(S)-6-chloro-9-(4-(1-(diethylamino) propan-2-yl)phenyl)-8- hydroxythieno[2,3-c]quinolin- 4(5H)-one





1196


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(S)-8-methoxy-9-(4-(1-(methyl amino)propan-2-yl)phenyl) thieno[2,3-c]quinolin-4(5H)-one





1197


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(S)-8-hydroxy-9-(4-(1- (methylamino)propan-2-yl) phenyl)thieno[2,3-c]quinolin- 4(5H)-one





1198


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4-(8-hydroxy-5-methyl-4-oxo-4, 5-dihydrothieno[2,3-c]quinolin- 9-yl)-N-(2-hydroxyethyl) benzenesulfonamide





1199


embedded image


N-(2-bromoethyl)-4-(8-hydroxy- 5-methyl-4-oxo-4,5-dihydrothieno [2,3-c]quinolin-9-yl) benzenesulfonamide





1200


embedded image


(R)-6-chloro-9-(4-(1-(dimethyl amino)propan-2-yl)phenyl)-8- methoxythieno[2,3-c]quinolin- 4(5H)-one





1201


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(R)-9-(4-(1-aminopropan-2-yl) phenyl)-6-chloro-8-methoxythieno [2,3-c]quinolin-4(5H)-one





1202


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9-(4-(1-aminobutan-2-yl)phenyl)- 8-methoxythieno[2,3-c] quinolin-4(5H)-one





1203


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9-(4-(2-aminopropan-2-yl) phenyl)-8-hydroxy-2-(phenylsulfonyl) thieno[2,3-c]quinolin-4(5H)-one





1204


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N-(1-chloropropan-2-yl)-4-(8- hydroxy-4-oxo-4,5-dihydrothieno [2,3-c]quinolin-9-yl) benzenesulfonamide





1205


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N-(1-chloropropan-2-yl)-4-(8- methoxy-4-oxo-4,5-dihydrothieno [2,3-c]quinolin-9-yl) benzenesulfonamide





1206


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9-(4-(2-aminoethyl)-3-hydroxy phenyl)-8-hydroxythieno[2,3-c] quinolin-4(5H)-one





1207


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9-(4-(2-aminoethyl)-3-methoxy phenyl)-8-methoxythieno[2,3-c] quinolin-4(5H)-one





1208


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9-(4-(2-aminoethyl)-2-chloro-5- methoxyphenyl)-8-methoxythieno [2,3-c]quinolin-4(5H)-one





1209


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9-(4-(3-(aminomethyl)pentan- 3-yl)phenyl)-8-hydroxythieno[2, 3-c]quinolin-4(5H)-one





1210


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(R)-9-(4-(1-aminopropy)phenyl)- 8-hydroxy-5,6-dimethylthieno [2,3-c]quinolin-4(5H)-one





1211


embedded image


9-(4-(2-aminoethyl)-2-chloro-5- hydroxyphenyl)-6-chloro-8- hydroxythieno[2,3-c]quinolin- 4(5H)-one





1212


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9-(4-(aminomethyl)phenyl)-8- hydroxy-6-methylthieno[2,3-c] quinolin-4(5H)-one





1213


embedded image


9-(4-(2-aminoethyl)-3- fluorophenyl)-6-bromo-8- hydroxythieno[2,3-c] quinolin-4(5H)-one





1214


embedded image


9-(4-(2-aminoethyl)-3- fluorophenyl)-6-bromo- 8-methoxythieno [2,3-c]quinolin-4(5H)-one





1215


embedded image


(S)-8-hydroxy-6-methyl-9-(4-(1- (methylamino)propan-2-yl) phenyl)thieno[2,3-c]quinolin- 4(5H)-one





1216


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9-(4-(2-aminoethyl)-3- fluorophenyl)-8-methoxy- 6-methylthieno[2,3-c] quinolin-4(5H)-one





1217


embedded image


9-(4-(2-aminoethyl)-3- fluorophenyl)-8-hydroxy- 6-methylthieno [2,3-c]quinolin-4(5H)-one





1218


embedded image


9-(4-(2-aminoethyl)-3- fluorophenyl)-6-chloro- 8-methoxythieno [2,3-c]quinolin-4(5H)-one





1219


embedded image


9-(4-(2-aminoethyl)-3- fluorophenyl)-6-chloro-8- hydroxythieno[2,3-c] quinolin-4(5H)-one





1220


embedded image


9-(4-(2-aminoethyl)-3-fluorophenyl)- 6-cyclopropyl-8-methoxy thieno[2,3-c]quinolin-4(5H)-one





1221


embedded image


9-(4-(2-aminoethyl)-3- fluorophenyl)-6-cyclopropyl- 8-hydroxythieno[2,3-c] quinolin-4(5H)-one





1222


embedded image


(S)-8-methoxy-6-methyl-9-(4- (1-(methylamino)propan-2-yl) phenyl)thieno[2,3-c]quinolin- 4(5H)-one





1223


embedded image


(S)-9-(4-(1-aminopropan-2-yl) phenyl)-8-methoxy-6-methylthieno [2,3-c]quinolin-4(5H)-one





1224


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9-(4-(2-aminoethyl)-2-bromo-5- hydroxyphenyl)-8-hydroxythieno [2,3-c]quinolin-4(5H)-one





1225


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(S)-9-(4-(1-aminoethyl)phenyl)- 8-hydroxy-6-methylthieno[2,3- c]quinolin-4(5H)-one





1226


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3-(4-(8-hydroxy-6-methyl-4- oxo-4,5-dihydrothieno[2,3-c] quinolin-9-yl)phenyl)propanenitrile





1227


embedded image


9-(4-(1-amino-2-methylpropan- 2-yl)phenyl)-8-methoxy-6- methylthieno[2,3-c]quinolin-4(5H)- one





1228


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9-(4-(1-amino-2-methylpropan- 2-yl)phenyl)-8-hydroxy-6- methylthieno[2,3-c]quinolin-4(5H)- one





1229


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2-(2-fluoro-4-(8-hydroxy-6- methyl-4-oxo-4,5-dihydrothieno[2, 3-c]quinolin-9-yl)phenyl) propanenitrile





1230


embedded image


6-cyclopropyl-9-(4-(2- (dimethylamino)ethyl)-3- fluorophenyl)-8-hydroxythieno [2,3-c]quinolin-4(5H)-one





1231


embedded image


6-cyclopropyl-9-(4-(2- (dimethylamino)ethyl)-3- fluorophenyl)-8-methoxythieno [2,3-c]quinolin-4(5H)-one





1232


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(S)-9-(4-(1-aminopropan-2-yl) phenyl)-8-hydroxy-6-methylthieno [2,3-c]quinolin-4(5H)-one





1233


embedded image


(S)-9-(4-(1-(dimethylamino) propan-2-yl)phenyl)-8-hydroxy-6- methylthieno[2,3-c]quinolin- 4(5H)-one





1234


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9-(3-fluoro-4-(2-(methylamino) ethyl)phenyl)-8-methoxythieno [2,3-c]quinolin-4(5H)-one





1235


embedded image


9-(3-fluoro-4-(2-(methylamino) ethyl)phenyl)-8-hydroxythieno [2,3-c]quinolin-4(5H)-one





1236


embedded image


9-(4-(2-amino-1-cyclopentylethyl) phenyl)-8-hydroxythieno[2, 3-c]quinolin-4(5H)-one





1237


embedded image


9-(4-(2-amino-1,1- dicyclopentylethyl)phenyl)- 8-methoxythieno [2,3-c]quinolin-4(5H)-one





1238


embedded image


3-(4-(8-methoxy-6-methyl-4- oxo-4,5-dihydrothieno[2,3-c] quinolin-9-yl)phenyl)propanenitrile





1239


embedded image


9-(4-(2-amino-1-cyclopentylethyl) phenyl)-8-methoxythieno[2, 3-c]quinolin-4(5H)-one





1240


embedded image


9-(4-(1-amino-2-methylpropan- 2-yl)phenyl)-6-cyclopropyl-8- hydroxythieno[2,3-c]quinolin- 4(5H)-one





1241


embedded image


9-(4-(3-aminopropyl)phenyl)-8- methoxy-6-methylthieno[2,3-c] quinolin-4(5H)-one





1242


embedded image


9-(4-(2-aminopropyl)phenyl)-8- hydroxy-6-methylthieno[2,3-c] quinolin-4(5H)-one





1243


embedded image


9-(4-(2-aminopropyl)phenyl)-8- methoxy-6-methylthieno[2,3-c] quinolin-4(5H)-one





1244


embedded image


9-(4-(1-amino-2-methylpropan- 2-yl)phenyl)-6-cyclopropyl-8- methoxythieno[2,3-c]quinolin- 4(5H)-one





1245


embedded image


6-bromo-9-(3-fluoro-4-(2- (methylamino)ethyl)phenyl)-8- hydroxythieno[2,3-c]quinolin- 4(5H)-one





1246


embedded image


6-bromo-9-(3-fluoro-4-(2- (methylamino)ethyl)phenyl)- 8-methoxythieno[2,3-c]quinolin- 4(5H)-one





1247


embedded image


9-(4-(1-amino-2-methylpropan- 2-yl)phenyl)-6-bromo-8-hydroxy thieno[2,3-c]quinolin-4(5H)- one





1248


embedded image


9-(4-(1-amino-2-methylpropan- 2-yl)phenyl)-6-bromo-8- methoxythieno[2,3-c]quinolin- 4(5H)-one





1249


embedded image


(R)-9-(4-(1-aminopropan-2-yl) phenyl)-6-methyl-4-oxo-4,5- dihydrothieno[2,3-c]quinoline- 8-carbonitrile





1250


embedded image


(R)-9-(4-(1-aminoethyl)phenyl)- 8-hydroxy-6-vinylthieno[2,3- c]quinolin-4(5H)-one





1251


embedded image


9-(4-(1-(aminomethyl) cyclopropyl)phenyl)-8-methoxy- 6-methylthieno[2,3-c]quinolin- 4(5H)-one





1252


embedded image


9-(4-(1-amino-3-methylbutan-2- yl)phenyl)-8-hydroxythieno[2, 3-c]quinolin-4(5H)-one





1253


embedded image


9-(4-(1-amino-3-methylbutan-2- yl)phenyl)-8-methoxythieno[2, 3-c]quinolin-4(5H)-one





1254


embedded image


9-(4-(1-(aminomethyl) cyclopropyl)phenyl)-8-hydroxy- 6-methylthieno[2,3-c]quinolin- 4(5H)-one





1255


embedded image


(R)-9-(4-(1-aminoethyl)phenyl)- 6-ethyl-8-hydroxythieno[2,3- c]quinolin-4(5H)-one





1256


embedded image


(R)-9-(4-(1-aminoethyl)phenyl)- 6-(difluoromethyl)-8- hydroxythieno[2,3-c]quinolin- 4(5H)-one





1257


embedded image


9-(3-fluoro-4-(2-(methylamino) ethyl)phenyl)-8-methoxy-6- methylthieno[2,3-c]quinolin- 4(5H)-one





1258


embedded image


9-(3-fluoro-4-(2-(methylamino) ethyl)phenyl)-8-hydroxy-6- methylthieno[2,3-c]quinolin- 4(5H)-one





1259


embedded image


6-bromo-9-(4-(1-(dimethylamino)- 2-methylpropan-2-yl)phenyl)- 8-hydroxythieno[2,3-c] quinolin-4(5H)-one





1260


embedded image


9-(4-(1-amino-2-methylpropan- 2-yl)phenyl)-6-chloro-8- hydroxythieno[2,3-c]quinolin- 4(5H)-one





1261


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9-(4-(3-aminopropyl)phenyl)-8- hydroxy-6-methylthieno[2,3-c] quinolin-4(5H)-one





1262


embedded image


(R)-8-hydroxy-6-methyl-9-(4- (1-(methylamino)ethyl)phenyl) thieno[2,3-c]quinolin-4(5H)-one





1263


embedded image


9-(4-(2-aminoethyl)-3- chlorophenyl)-8-methoxy-6- methylthieno[2,3-c]quinolin- 4(5H)-one





1264


embedded image


9-(4-(2-aminoethyl)-3- chlorophenyl)-8-hydroxy-6- methylthieno[2,3-c]quinolin- 4(5H)-one





1265


embedded image


(R)-8-methoxy-6-methyl-9-(4- (1-(methylamino)ethyl)phenyl) thieno[2,3-c]quinolin-4(5H)-one





1266


embedded image


9-(4-(2-aminopropyl)phenyl)-6- ethyl-8-hydroxythieno[2,3-c] quinolin-4(5H)-one





1267


embedded image


(R)-9-(4-(1-aminoethyl)phenyl)- 6-butyl-8-hydroxythieno[2,3- c]quinolin-4(5H)-one





1268


embedded image


9-(4-(2-aminoethyl)-3- chlorophenyl)-6-chloro-8- hydroxythieno[2,3-c]quinolin- 4(5H)-one





1269


embedded image


9-(4-(2-aminopropyl)phenyl)-6- ethyl-8-methoxythieno[2,3-c] quinolin-4(5H)-one





1270


embedded image


2-(4-(8-methoxy-4-oxo-4,5- dihydrothieno[2,3-c]quinolin-9-yl) phenyl)-2-(oxetan-3-yl) acetonitrile





1271


embedded image


9-(4-(1-amino-2-methylpropan- 2-yl)-3-fluorophenyl)-8- hydroxythieno[2,3-c]quinolin- 4(5H)-one





1272


embedded image


(R)-6-ethyl-8-hydroxy-9-(4-(1- (methylamino)ethyl)phenyl) thieno[2,3-c]quinolin-4(5H)-one





1273


embedded image


9-(4-(1-aminopropan-2-yl)-3- fluorophenyl)-8-methoxy-6- methylthieno[2,3-c]quinolin- 4(5H)-one





1274


embedded image


9-(4-(1-amino-3-methylbutan-2- yl)phenyl)-8-hydroxy-6- methylthieno[2,3-c]quinolin- 4(5H)-one





1275


embedded image


9-(4-(1-aminopropan-2-yl)-3- chlorophenyl)-8-methoxy-6- methylthieno[2,3-c]quinolin- 4(5H)-one





1276


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9-(4-(1-aminopropan-2-yl)-3- chlorophenyl)-8-methoxythieno[2, 3-c]quinolin-4(5H)-one





1277


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9-(4-(1-aminobutan-2-yl)phenyl)- 8-methoxy-6-methylthieno[2, 3-c]quinolin-4(5H)-one





1278


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9-(4-(1-amino-2-methylpropan- 2-yl)-3-fluorophenyl)-8- hydroxy-6-methylthieno[2,3- c]quinolin-4(5H)-one





1279


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9-(4-(1-aminopropan-2-yl)-3- chlorophenyl)-8-hydroxy-6- methylthieno[2,3-c]quinolin- 4(5H)-one





1280


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9-(4-(1-aminopropan-2-yl)-3- chlorophenyl)-8-hydroxythieno[2, 3-c]quinolin-4(5H)-one





1281


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9-(4-(2-amino-2-methylpropyl) phenyl)-8-methoxythieno[2,3- c]quinolin-4(5H)-one





1282


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9-(4-(2-amino-2-methylpropyl) phenyl)-8-hydroxythieno[2,3-c] quinolin-4(5H)-one





1283


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9-(4-(1-amino-3-methylbutan- 2-yl)-3-fluorophenyl)-8-methoxy- 6-methylthieno[2,3-c]quinolin- 4(5H)-one





1284


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8-methoxy-6-methyl-9-(4-(3- methyl-1-(methylamino)butan-2- yl)phenyl)thieno[2,3-c]quinolin- 4(5H)-one





1285


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8-hydroxy-6-methyl-9-(4-(3- methyl-1-(methylamino)butan-2- yl)phenyl)thieno[2,3-c]quinolin- 4(5H)-one





1286


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9-(3-fluoro-4-(1-(methylamino) propan-2-yl)phenyl)-8-methoxy- 6-methylthieno[2,3-c]quinolin- 4(5H)-one





1287


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9-(4-(1-amino-2-methylpropan- 2-yl)-3-fluorophenyl)-8- methoxythieno[2,3-c]quinolin- 4(5H)-one





1288


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9-(4-(1-amino-3-methylbutan- 2-yl)-3-fluorophenyl)-8-hydroxy- 6-methylthieno[2,3-c]quinolin- 4(5H)-one





1289


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9-(4-(2-amino-2-methylpropyl) phenyl)-6-bromo-8-methoxythieno [2,3-c]quinolin-4(5H)-one





1290


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9-(4-(1-(aminomethyl)cyclobutyl) phenyl)-8-hydroxy-6-methyl thieno[2,3-c]quinolin- 4(5H)-one





1291


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9-(4-(1-aminobutan-2-yl) phenyl)-8-hydroxy-6-methylthieno [2,3-c]quinolin-4(5H)-one





1292


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9-(4-(2-amino-2-methylpropyl) phenyl)-6-bromo-8-hydroxythieno [2,3-c]quinolin-4(5H)-one





1293


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9-(3-fluoro-4-(1-(methylamino) propan-2-yl)phenyl)-8-hydroxy- 6-methylthieno[2,3-c]quinolin- 4(5H)-one





1294


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9-(3-fluoro-4-(3-methyl-1- (methylamino)butan-2-yl) phenyl)-8-hydroxy-6-methylthieno [2,3-c]quinolin-4(5H)-one





1295


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9-(4-(1-(dimethylamino)-3- methylbutan-2-yl)phenyl)-8- methoxy-6-methylthieno[2,3- c]quinolin-4(5H)-one





1296


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9-(4-(1-(dimethylamino)-3- methylbutan-2-yl)-3-fluorophenyl)- 8-hydroxy-6-methylthieno[2,3- c]quinolin-4(5H)-one





1297


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9-(4-(1-(aminomethyl)cyclobutyl) phenyl)-8-methoxy-6-methyl thieno[2,3-c]quinolin- 4(5H)-one





1298


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(R)-8-methoxy-6-methyl-9-(4- (1-(methylamino)propan-2-yl) phenyl)thieno[2,3-c]quinolin- 4(5H)-one





1299


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9-(4-(1-(aminomethyl)cyclobutyl) phenyl)-8-methoxythieno[2, 3-c]quinolin-4(5H)-one





1300


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9-(4-(1-(aminomethyl)cyclobutyl) phenyl)-8-hydroxythieno[2,3- c]quinolin-4(5H)-one





1301


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8-methoxy-6-methyl-9-(4- (piperidin-3-yl)phenyl)thieno[2,3-c] quinolin-4(5H)-one





1302


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8-hydroxy-6-methyl-9-(4- (piperidin-3-yl)phenyl)thieno[2,3- c]quinolin-4(5H)-one





1303


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(S)-9-(4-(1-aminopropan-2-yl)- 3-fluorophenyl)-8-hydroxy-6- methylthieno[2,3-c]quinolin- 4(5H)-one





1304


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(S)-9-(4-(1-aminopropan-2-yl)- 3-fluorophenyl)-8-hydroxy-6- methylthieno[2,3-c]quinolin- 4(5H)-one





1305


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(R)-9-(4-(1-aminopropan-2-yl) phenyl)-8-methoxy-6-methylthieno [2,3-c]quinolin-4(5H)-one





1306


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(R)-8-hydroxy-6-methyl-9-(4- (1-(methylamino)propan-2-yl) phenyl)thieno[2,3-c]quinolin- 4(5H)-one





1307


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(R)-8-hydroxy-6-methyl-9-(4- (1-(methylamino)propan-2-yl) phenyl)thieno[2,3-c]quinolin- 4(5H)-one





1308


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8-methoxy-3-methyl-3H-pyrrolo [2,3-c]quinolin-4(5H)-one





1309


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9-(4-(1-aminobutan-2-yl)phenyl)- 8-hydroxythieno[2,3-c] quinolin-4(5H)-one





1310


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(S)-9-(4-(1-aminopropan-2-yl)- 3-fluorophenyl)-8-methoxy-6- methylthieno[2,3-c]quinolin- 4(5H)-one





1311


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(R)-9-(4-(1-(dimethylamino) propan-2-yl)-3-fluorophenyl)- 8-hydroxy-6-methylthieno[2,3-c] quinolin-4(5H)-one





1312


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9-(4-(1-aminobutan-2-yl)phenyl)- 6-chloro-8-hydroxythieno[2, 3-c]quinolin-4(5H)-one





1313


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8-hydroxy-3-methyl-3H-pyrrolo [2,3-c]quinolin-4(5H)-one





1314


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9-amino-8-methoxy-6-methylthieno [2,3-c]quinolin-4(5H)-one





1315


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(R)-9-(3-fluoro-4-(1-(methylamino) propan-2-yl)phenyl)-8- hydroxy-6-methylthieno[2, 3-c]quinolin-4(5H)-one





1316


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(R)-9-(3-fluoro-4-(1-(methylamino) propan-2-yl)phenyl)-8- methoxy-6-methylthieno[2,3- c]quinolin-4(5H)-one





1317


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(R)-9-(4-(1-aminopropan-2-yl)- 3-fluorophenyl)-8-methoxy-6- methylthieno[2,3-c]quinolin- 4(5H)-one





1318


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(R)-9-(4-(1-aminopropan-2-yl)- 3-fluorophenyl)-8-hydroxy-6- methylthieno[2,3-c]quinolin- 4(5H)-one





1319


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(R)-9-(4-(1-aminopropan-2-yl)- 3-fluorophenyl)-8-hydroxy-6- methylthieno[2,3-c]quinolin- 4(5H)-one





1320


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9-((4-(2-aminoethyl)phenyl) amino)-8-methoxy-6-methylthieno [2,3-c]quinolin-4(5H)-one





1321


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9-(4-(1-(aminomethyl)cyclobutyl) phenyl)-6-chloro-8-methoxythieno [2,3-c]quinolin-4(5H)-one





1322


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(R)-1-(4-(1-aminopropan-2-yl) phenyl)-8-methoxy-3-methyl- 3H-pyrrolo[2,3-c]quinolin-4(5H)- one





1323


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8-hydroxy-3-(hydroxymethyl)- 3H-pyrrolo[2,3-c]quinolin- 4(5H)-one





1324


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(R)-9-(4-(1-(dimethylamino) propan-2-yl)phenyl)-8-hydroxy- 6-methylthieno[2,3-c]quinolin- 4(5H)-one





1325


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9-((4-(aminomethyl)phenyl) amino)-8-hydroxy-6-methylthieno [2,3-c]quinolin-4(5H)-one





1326


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9-((4-(aminomethyl)phenyl) amino)-8-methoxy-6-methylthieno [2,3-c]quinolin-4(5H)-one





1327


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9-((4-(1-aminopropan-2-yl) phenyl)amino)-8-methoxy-6- methylthieno[2,3-c]quinolin- 4(5H)-one





1328


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9-((4-(1-aminopropan-2-yl) phenyl)amino)-8-hydroxy-6- methylthieno[2,3-c]quinolin- 4(5H)-one





1329


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9-(4-(2-aminopropan-2-yl) phenyl)-8-methoxy-6-methylthieno [2,3-c]quinolin-4(5H)-one





1330


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9-(4-(2-aminopropan-2-yl)phenyl)- 8-hydroxy-6-methylthieno [2,3-c]quinolin-4(5H)-one





1331


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9-(4-(3-(aminomethyl)pentan- 3-yl)phenyl)-8-methoxy-6- methylthieno[2,3-c]quinolin- 4(5H)-one





1332


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9-(4-((R)-1-aminopropan-2-yl) phenyl)-8-hydroxy-2-(1- hydroxyethyl)thieno[2,3-c] quinolin-4(5H)-one





1333


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9-(4-((R)-1-aminopropan-2-yl) phenyl)-2-(1-hydroxyethyl)-8- methoxythieno[2,3-c]quinolin- 4(5H)-one





1334


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3-(4-((8-methoxy-6-methyl-4- oxo-4,5-dihydrothieno[2,3-c] quinolin-9-yl)amino)phenyl) propanenitrile





1335


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9-((3-(2-aminoethyl)phenyl) amino)-8-methoxy-6-methylthieno [2,3-c]quinolin-4(5H)-one





1336


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9-((4-(2-aminoethyl)phenyl) amino)-8-hydroxy-6-methylthieno [2,3-c]quinolin-4(5H)-one





1337


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9-(4-(2-(ethylamino)propyl) phenyl)-8-hydroxy-6-methylthieno [2,3-c]quinolin-4(5H)-one





1338


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9-(4-(3-(aminomethyl)pentan- 3-yl)phenyl)-8-methoxythieno[2, 3-c]quinolin-4(5H)-one





1339


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9-(4-(3-(aminomethyl)pentan-3- yl)phenyl)-8-hydroxy-6- methylthieno[2,3-c]quinolin- 4(5H)-one





1340


embedded image


(R)-9-(4-(1-aminopropan-2-yl) phenyl)-8-hydroxy-2,6- dimethylthieno[2,3-c]quinolin- 4(5H)-one





1341


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(R)-9-(4-(1-aminopropan-2-yl) phenyl)-8-methoxy-2,6- dimethylthieno[2,3-c]quinolin- 4(5H)-one





1342


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9-(4-((R)-1-aminopropan-2-yl) phenyl)-2-(1-hydroxyethyl)-8- methoxy-6-methylthieno[2,3-c] quinolin-4(5H)-one





1343


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2-((4-(8-methoxy-6-methyl-4- oxo-4,5-dihydrothieno[2,3-c] quinolin-9-yl)phenyl)amino) acetonitrile





1344


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(R)-9-(4-(1-aminobutan-2-yl) phenyl)-8-methoxy-6-methylthieno [2,3-c]quinolin-4(5H)-one





1345


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9-(3-chloro-4-(2-(ethylamino) ethyl)phenyl)-8-methoxythieno [2,3-c]quinolin-4(5H)-one





1346


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9-(4-(3-((dimethylamino)methyl) pentan-3-yl)phenyl)-8-hydroxy- 6-methylthieno[2,3-c] quinolin-4(5H)-one





1347


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(R)-6-chloro-9-(4-(1- (dimethylamino)propan-2- yl)phenyl)-8-hydroxythieno[2, 3-c]quinolin-4(5H)-one





1348


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9-(4-(2-(ethylamino)ethyl)phenyl)- 8-hydroxy-6-methylthieno [2,3-c]quinolin-4(5H)-one





1349


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9-(4-(2-(ethylamino)ethyl) phenyl)-8-methoxy-6-methylthieno [2,3-c]quinolin-4(5H)-one





1350


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9-(4-(2-(ethyl(methyl)amino) propyl)phenyl)-8-hydroxy-6- methylthieno[2,3-c]quinolin- 4(5H)-one





1351


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2-(hydroxy(piperidin-4-yl) methyl)-8-methoxy-6-methylthieno [2,3-c]quinolin-4(5H)-one





1352


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(R)-9-(4-(1-aminobutan-2-yl) phenyl)-8-hydroxy-6-methylthieno [2,3-c]quinolin-4(5H)-one





1353


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(R)-9-(4-(1-aminopropan-2-yl) phenyl)-2-chloro-8-hydroxy-6- methylthieno[2,3-c]quinolin- 4(5H)-one





1354


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(R)-9-(4-(1-aminopropan-2-yl) phenyl)-2-chloro-8-methoxy-6- methylthieno[2,3-c]quinolin- 4(5H)-one





1355


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8-methoxy-6-methyl-9-(4-(2- (methylamino)ethyl)phenyl) thieno[2,3-c]quinolin-4(5H)-one





1356


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9-(4-(2-(ethyl(methyl)amino) ethyl)phenyl)-8-hydroxy-6- methylthieno[2,3-c]quinolin- 4(5H)-one





1357


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9-(4-(3-(aminomethyl)pentan- 3-yl)phenyl)-6-chloro-8- methoxythieno[2,3-c] quinolin-4(5H)-one





1358


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9-(4-(3-((dimethylamino)methyl) pentan-3-yl)phenyl)-8- hydroxythieno[2,3-c]quinolin- 4(5H)-one





1359


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9-(6-(dimethylamino)pyridin- 3-yl)-8-methoxy-6-methylthieno [2,3-c]quinolin-4(5H)-one





1360


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(R)-9-(4-(1-(dimethylamino) butan-2-yl)phenyl)-8-hydroxy- 6-methylthieno[2,3-c]quinolin- 4(5H)-one





1361


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(R)-8-methoxy-6-methyl-9-(4- (1-(methylamino)butan-2-yl) phenyl)thieno[2,3-c]quinolin- 4(5H)-one





1362


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9-(4-(3-((diethylamino)methyl) pentan-3-yl)phenyl)-8-hydroxy- 6-methylthieno[2,3-c]quinolin- 4(5H)-one





1363


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9-(3-chloro-4-(2-(ethylamino) ethyl)phenyl)-8-hydroxythieno[2, 3-c]quinolin-4(5H)-one





1364


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8-hydroxy-6-methyl-9-(4-(2- (methylamino)ethyl)phenyl) thieno[2,3-c]quinolin-4(5H)-one





1365


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(R)-9-(4-(1-(dimethylamino) butan-2-yl)phenyl)-8-methoxy-6- methylthieno[2,3-c]quinolin- 4(5H)-one





1366


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(R)-9-(4-(1-(ethyl(methyl) amino)butan-2-yl)phenyl)-8- methoxy-6-methylthieno[2,3- c]quinolin-4(5H)-one





1367


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(R)-9-(4-(1-(diethylamino) butan-2-yl)phenyl)-8-hydroxy- 6-methylthieno[2,3-c] quinolin-4(5H)-one





1368


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(R)-9-(4-(1-(ethyl(methyl) amino)butan-2-yl)phenyl)-8- hydroxy-6-methylthieno[2,3- c]quinolin-4(5H)-one





1369


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2-((4-(8-methoxy-6-methyl-4- oxo-4,5-dihydrothieno[2,3-c] quinolin-9-yl)phenyl)(methyl) amino)acetonitrile





1370


embedded image


2-((4-(8-hydroxy-6-methyl-4- oxo-4,5-dihydrothieno[2,3-c] quinolin-9-yl)phenyl)(methyl) amino)acetonitrile





1371


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9-(3-chloro-4-(2-(ethyl(methyl) amino)ethyl)phenyl)-8- hydroxythieno[2,3-c]quinolin- 4(5H)-one





1372


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9-(4-(1-((dimethylamino)methyl) cyclobutyl)phenyl)-8-hydroxy- 6-methylthieno[2,3-c]quinolin- 4(5H)-one





1373


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(R)-9-(4-(1-aminopropyl) phenyl)-6-bromo-8-methoxythieno [2,3-c]quinolin-4(5H)-one





1374


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9-(6-(2-aminoethoxy)pyridin-3- yl)-8-hydroxy-6-methylthieno [2,3-c]quinolin-4(5H)-one





1375


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(R)-9-(4-(1-aminopropan-2-yl) phenyl)-2-fluoro-8-methoxy-6- methylthieno[2,3-c]quinolin- 4(5H)-one





1376


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9-(6-(2-aminoethoxy)pyridin-3- yl)-8-methoxy-6-methylthieno [2,3-c]quinolin-4(5H)-one





1377


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9-(4-(1-amino-2,2,2-trifluoroethyl) phenyl)-8-hydroxy-6-methylthieno [2,3-c]quinolin-4(5H)-one





1378


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9-(4-(1-amino-2,2,2-trifluoroethyl) phenyl)-8-methoxy-6-methylthieno [2,3-c]quinolin-4(5H)-one





1379


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(R)-9-(4-(1-(ethyl(methyl) amino)propan-2-yl)phenyl)-8- hydroxy-6-methylthieno[2,3- c]quinolin-4(5H)-one





1380


embedded image


(R)-8-hydroxy-6-methyl-9-(4- (1-(methylamino)butan-2-yl) phenyl)thieno[2,3-c]quinolin- 4(5H)-one





1381


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9-(4-(1-amino-2,2,2-trifluoroethyl) phenyl)-8-methoxythieno [2,3-c]quinolin-4(5H)-one





1382


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(R)-1-(4-(1-aminopropan-2-yl) phenyl)-8-hydroxy-3-methyl- 3H-pyrrolo[2,3-c]quinolin-4(5H)-one





1383


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(R)-9-(4-(1-aminopropan-2-yl) phenyl)-2-fluoro-8-hydroxy-6- methylthieno[2,3-c]quinolin- 4(5H)-one





1384


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9-(6-((2-aminoethyl)amino) pyridin-3-yl)-8-hydroxy-6-methylthieno [2,3-c]quinolin-4(5H)-one





1385


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9-(6-((2-aminoethyl)amino) pyridin-3-yl)-8-methoxy-6-methylthieno [2,3-c]quinolin-4(5H)-one





1386


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(S)-6-chloro-9-(4-(1-(ethyl (methyl)amino)propan-2-yl) phenyl)-8-hydroxythieno[2,3- c]quinolin-4(5H)-one





1387


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(S)-9-(4-(1-(dimethylamino) propan-2-yl)-3-fluorophenyl)- 8-methoxy-6-methylthieno[2,3- c]quinolin-4(5H)-one





1388


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(R)-9-(4-(1-(diethylamino) propan-2-yl)phenyl)-8-hydroxy- 6-methylthieno[2,3-c]quinolin- 4(5H)-one





1389


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9-(4-(1-amino-2,2,2-trifluoroethyl) phenyl)-8-hydroxythieno[2, 3-c]quinolin-4(5H)-one





1390


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9-(4-(1-amino-2,2,2-trifluoroethyl) phenyl)-6-bromo-8-methoxythieno [2,3-c]quinolin-4(5H)-one





1391


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9-(4-(1-(aminomethyl)cyclopropyl) phenyl)-6-bromo-8-methoxythieno [2,3-c]quinolin-4(5H)-one





1392


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(4-(8-hydroxy-6-methyl-4-oxo- 4,5-dihydrothieno[2,3-c] quinolin-9-yl)phenyl) methanesulfonamide





1393


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8-methoxy-6-methyl-9-(4-(2- (methylsulfinyl)ethyl)phenyl) thieno[2,3-c]quinolin-4(5H)-one





1394


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8-hydroxy-6-methyl-9-(4- ((methylsulfonyl)methyl)phenyl) thieno[2,3-c]quinolin-4(5H)-one





1395


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(4-(8-methoxy-6-methyl-4-oxo- 4,5-dihydrothieno[2,3-c] quinolin-9-yl)phenyl) methanesulfonamide





1396


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9-(4-((2-aminoethyl)(methyl) amino)phenyl)-8-methoxy-6- methylthieno[2,3-c]quinolin- 4(5H)-one





1397


embedded image


(R)-N-(2-(2-fluoro-4-(8-hydroxy- 6-methyl-4-oxo-4,5-dihydrothieno [2,3-c]quinolin-9-yl) phenyl)propyl)methanesulfonamide





1398


embedded image


(R)-N-(2-(2-fluoro-4-(8-methoxy- 6-methyl-4-oxo-4,5-dihydrothieno [2,3-c]quinolin-9-yl) phenyl)propyl)methanesulfonamide





1399


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(S)-9-(4-(1-(dimethylamino)propan- 2-yl)-3-fluorophenyl)-8- hydroxy-6-methylthieno[2,3- c]quinolin-4(5H)-one





1400


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9-(4-((2-aminoethyl)(methyl) amino)phenyl)-8-hydroxy-6- methylthieno[2,3-c]quinolin- 4(5H)-one





1401


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9-(4-(1-(aminomethyl)cyclopropyl) phenyl)-6-bromo-8-hydroxythieno [2,3-c]quinolin-4(5H)-one





1402


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2-(6-(8-methoxy-6-methyl-4- oxo-4,5-dihydrothieno[2,3-c] quinolin-9-yl)pyridin-3-yl) acetonitrile





1403


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8-hydroxy-6-methyl-9-(4-(2- (methylsulfinyl)ethyl)phenyl) thieno[2,3-c]quinolin-4(5H)-one





1404


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8-methoxy-6-methyl-9-(4- ((methylsulfonyl)methyl)phenyl) thieno[2,3-c]quinolin-4(5H)-one





1405


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5-(8-methoxy-6-methyl-4-oxo- 4,5-dihydrothieno[2,3-c] quinolin-9-yl)nicotinamide





1406


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2-(5-(8-hydroxy-4-oxo-4,5- dihydrothieno[2,3-c]quinolin-9-yl) pyridin-2-yl)propanenitrile





1407


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2-(4-(8-methoxy-6-methyl-4- oxo-4,5-dihydrothieno[2,3-c] quinolin-9-yl)phenyl)propanamide





1408


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9-(6-(1-aminopropan-2-yl) pyridin-3-yl)-8-methoxy-6- methylthieno[2,3-c]quinolin- 4(5H)-one





1409


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2-(5-(8-methoxy-6-methyl-4- oxo-4,5-dihydrothieno[2,3-c] quinolin-9-yl)pyridin-2-yl)-2- methylpropanenitrile





1410


embedded image


2-hydroxy-2-(4-(8-hydroxy-4- oxo-4,5-dihydrothieno[2,3-c] quinolin-9-yl)phenyl)propane- 1-sulfonamide





1411


embedded image


N-(tert-butyl)-2-hydroxy-2-(4- (8-methoxy-4-oxo-4,5-dihydrothieno [2,3-c]quinolin-9-yl)phenyl) propane-1-sulfonamide





1412


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2-(4-(8-hydroxy-6-methyl-4- oxo-4,5-dihydrothieno[2,3-c] quinolin-9-yl)phenyl)propanamide





1413


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2-(4-(8-hydroxy-4-oxo-4,5- dihydrothieno[2,3-c]quinolin-9-yl) phenyl)propane-1-sulfonamide





1414


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9-(4-(2-amino-1-fluoroethyl) phenyl)-8-methoxy-6-methylthieno [2,3-c]quinolin-4(5H)-one





1415


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9-(6-(1-aminopropan-2-yl) pyridin-3-yl)-8-hydroxy-6- methylthieno[2,3-c]quinolin- 4(5H)-one





1416


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2-(5-(8-hydroxy-6-methyl-4- oxo-4,5-dihydrothieno[2,3-c] quinolin-9-yl)pyridin-2-yl)-2- methylpropanenitrile





1417


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2-(5-(8-hydroxy-4-oxo-4,5- dihydrothieno[2,3-c]quinolin-9-yl) pyridin-2-yl)-2- methylpropanenitrile





1418


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2-(5-(8-methoxy-4-oxo-4,5- dihydrothieno[2,3-c]quinolin-9-yl) pyridin-2-yl)-2- methylpropanenitrile





1419


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2-(4-(8-hydroxy-6-methyl-4- oxo-4,5-dihydrothieno[2,3-c] quinolin-9-yl)phenyl)propane- 1-sulfonamide





1420


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9-(4-(2-amino-1-hydroxyethyl) phenyl)-8-methoxy-6-methylthieno [2,3-c]quinolin-4(5H)-one





1421


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9-(6-(1-amino-2-methylpropan- 2-yl)pyridin-3-yl)-8-hydroxythieno [2,3-c]quinolin-4(5H)-one





1422


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N-cyclopropyl-1-(4-(8-methoxy- 6-methyl-4-oxo-4,5-dihydrothieno [2,3-c]quinolin-9-yl)phenyl) methanesulfonamide





1423


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2-(5-(8-methoxy-4-oxo-4,5- dihydrothieno[2,3-c]quinolin-9-yl) pyridin-2-yl)propanenitrile





1424


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(R)-N-(2-(4-(8-methoxy-6- methyl-4-oxo-4,5-dihydrothieno[2, 3-c]quinolin-9-yl)phenyl) propyl)methanesulfonamide





1425


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N-ethyl-1-(4-(8-methoxy-6- methyl-4-oxo-4,5-dihydrothieno[2, 3-c]quinolin-9-yl)phenyl) methanesulfonamide





1426


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9-(6-(1-aminopropan-2-yl) pyridin-3-yl)-8-methoxythieno [2,3-c]quinolin-4(5H)-one





1427


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N-cyclopropyl-1-(4-(8-hydroxy- 6-methyl-4-oxo-4,5-dihydrothieno [2,3-c]quinolin-9-yl)phenyl) methanesulfonamide





1428


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1-(5-(8-methoxy-4-oxo-4,5- dihydrothieno[2,3-c]quinolin-9-yl) pyridin-2-yl) cyclopropanecarbonitrile





1429


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N-ethyl-1-(4-(8-hydroxy-6-methyl- 4-oxo-4,5-dihydrothieno[2, 3-c]quinolin-9-yl)phenyl) methanesulfonamide





1430


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1-(4-(8-methoxy-6-methyl-4- oxo-4,5-dihydrothieno[2,3-c] quinolin-9-yl)phenyl) ethanesulfonamide





1431


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1-(4-(8-methoxy-4-oxo-4,5- dihydrothieno[2,3-c]quinolin-9-yl) phenyl)ethanesulfonamide





1432


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(R)-N-(2-(4-(8-methoxy-4-oxo- 4,5-dihydrothieno[2,3-c] quinolin-9-yl)phenyl)propyl) methanesulfonamide





1433


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(R)-N-(2-(4-(8-hydroxy-4-oxo- 4,5-dihydrothieno[2,3-c] quinolin-9-yl)phenyl)propyl)- N-methylmethanesulfonamide





1434


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(R)-N-(2-(4-(8-hydroxy-6- methyl-4-oxo-4,5-dihydrothieno [2,3-c]quinolin-9-yl)phenyl)propyl) methanesulfonamide





1435


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(R)-N-(2-(4-(8-hydroxy-4-oxo- 4,5-dihydrothieno[2,3-c] quinolin-9-yl)phenyl)propyl) methanesulfonamide





1436


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(R)-N-(2-(4-(8-methoxy-4-oxo- 4,5-dihydrothieno[2,3-c] quinolin-9-yl)phenyl)propyl)- N-methylmethanesulfonamide





1437


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(R)-N-(2-(4-(8-hydroxy-6-methyl- 4-oxo-4,5-dihydrothieno[2,3-c] quinolin-9-yl)phenyl)propyl)- N-methylmethanesulfonamide





1438


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(R)-N-(2-(4-(8-methoxy-6- methyl-4-oxo-4,5-dihydrothieno[2, 3-c]quinolin-9-yl)phenyl)propyl)- N-methylmethanesulfonamide







text missing or illegible when filed








The compound of formula (I) of the present invention may be in the form of a pharmaceutically acceptable salt derived from an inorganic or organic acid. Representative examples of the pharmaceutically acceptable salt derived from an inorganic or organic acid include salts obtained by adding to the compound of formula (I) an inorganic acid including, but not limited to hydrochloric acid, hydrobromic acid, phosphoric acid or sulfonic acid, or organic carboxylic acids such as acetic acid, trifluoroacetic acid, citric acid, formic acid, maleic acid, oxalic acid, succinic acid, benzoic acid, tartaric acid, fumaric acid, mandelic acid, ascorbic acid or malic acid, methanesulfonic acid, or para toluenesulfonic acid, which do not limit its scope. Such acids may be prepared by the conventional processes, and other acids, which themselves are not pharmaceutically acceptable, including oxalic acid may be employed in the preparation of the salts.


Alternatively, the compound of formula (I) of the present invention may also be in the form of a pharmaceutically acceptable salt derived from an inorganic or organic base include salts obtained by adding an inorganic or organic base. For example, alkalis including sodium hydroxide or potassium hydroxide, or alkaline earth metal hydroxides including calcium hydroxide, magnesium hydroxide, aluminum hydroxide or ammonium hydroxide may be used for the preparation of inorganic salt of the compound. Further, organic bases including triethylamine or diisopropylethylamine may also be used for the preparation of organic salt of the compound.


The compounds of formula (I) may be prepared as in Scheme (I) and (II).




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A variety of acids A whose structure is defined by the cycles (Cy1-3) shown in Scheme I, were converted to the corresponding acid chloride and then coupled with the requisite aniline to afford coupled products B. In the case where R5=H, the amide was protected to obtain intermediates C which subsequently underwent the key intramolecular Heck cyclization using bis-tri-t-butyl phosphine as the catalyst of choice. This provided tricycles D which included some compounds of Formula I, II and III. In some instances tricycles D were brominated using NBS or nitrated using potassium nitrate and trifluoroacetic anhydride to provide products E (Scheme I).




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The aryl bromides F were either purchased or prepared and then converted to the corresponding boronic acids or boronate esters G via standard conditions. Bromides E underwent Suzuki or Buchwald type cross-coupling reactions with the requisite boronate esters or boronic acids G to afford compounds H some of which are compounds of Formula I, II and III. In cases where R3=OCH3, treatment of compounds H (via path i) with boron tribromide or aluminum chloride provided the de-methylated compounds I which includes compounds of Formula I, II and III (Scheme II). Additionally, treatment of compounds H (via path ii) with NCS or NBS afforded compounds I containing a halogen at R1. These halogenated compounds were treated with boron tribromide or aluminum chloride to provide the de-methylated compounds I. Finally, compounds with R1=Br were reacted with trimethylboroxine and palladium catalyst to afford compounds J of formula I, II and III where R1=CH3. Treatment of these compounds with boron tribromide afforded compounds of formula I, II and III.


A salt, hydrate, solvate and isomer of the inventive compound of formula (I) or (II) may be prepared by employing any of the known methods. The inventive compound of formula (I) or (II), or a salt, hydrate, solvate or isomer thereof, may be used for the treatment of PBK-dependent diseases such as cancer. The treatment of PBK-dependent diseases can be accomplished by way of inhibiting PBK activity. The inventive compound typically have an IC50 value (micro M) in the range of 0.0001 to 100, for example 0.001 to 50, preferably 0.001 to 10, more preferably 0.001 to 5.


Accordingly, the present invention includes a pharmaceutical composition that includes a therapeutically effective amount of the compound of formula (I) or (II), a salt, hydrate, solvate or isomer thereof as an active ingredient and a pharmaceutically acceptable carrier. The pharmaceutical composition of the present invention can be used to treat or prevent PBK-dependent diseases.


A pharmaceutical formulation may be prepared in accordance with any of the conventional procedures. In preparing the formulation, the active ingredient is preferably admixed or diluted with a carrier, or enclosed within a carrier, sachet or other container. The carrier may be a solid, semi-solid or liquid material acting as a vehicle, excipient or medium for the active ingredient. The formulations may be in the form of a tablet, pill, powder, sachet, elixir, suspension, emulsion, solution, syrup, aerosol, soft and hard gelatin capsule, sterile injectable solution, sterile packaged powder and the like.


Examples of suitable carriers, excipients, and diluents are lactose, dextrose, sucrose, sorbitol, mannitol, calcium silicate, cellulose, methyl cellulose, microcrystalline cellulose, polyvinylpyrrolidone, water, and mineral oil. The formulations may additionally include fillers, antiemulsifiers, preservatives and the like. The compositions of the invention may be formulated to provide immediate, sustained or delayed release of the active ingredient after their administration to a mammal by employing any of the procedures well known in the art.


The pharmaceutical composition of the present invention can be administered via various routes including oral, transdermal, subcutaneous, intravenous and intramuscular administration.


In addition to the above, the present composition may contain other pharmaceutical active ingredients so long as they do not inhibit the in vivo function of the compound of the present invention. The compounds as disclosed herein can be co-administered with a second therapeutic agent, such as a chemotherapeutic agent. The term “co-administer” means to administer more than one active agent, such that the duration of physiological effect of one active agent overlaps with the physiological effect of a second active agent. For systematic agents, the term co-administer means that more than one active agent is present in the bloodstream during at least one time point. Co-administration includes administering two active agents simultaneously, approximately simultaneously, or sequentially in any order. In some embodiments, co-administration can be accomplished by co-formulation, i.e., preparing a single dosage unit including both active agents.


“Treating” the disease includes one or more of: addressing a physiological cause of the disease, addressing a physiological cause of a disease symptom, reducing the severity of the disease, ameliorating a symptom of the disease, and shortening the duration of the disease. “Preventing” the disease includes eliminating or delaying the onset of a disease or its symptoms.


The compounds disclosed herein can be used to treat or prevent PBK-dependent diseases, including cancer. It has been shown that PBK is a target for treating cancers, such as breast cancer (Example 504 of the present specification), bladder cancer (WO2006/085684), and small cell lung cancer (WO2007/013665). Accordingly, cancers to be targeted include, but are not limited to, breast cancer, bladder cancer, and small cell lung cancer. For example, the present invention provides methods for treating or preventing PBK-dependent diseases, including cancer, in a subject by administering to said subject the compounds disclosed herein.


In a preferred embodiment, such compound can be administered to the subject in the form of pharmaceutical composition including the compound of the present invention and pharmaceutically or physiologically acceptable carrier. The pharmaceutical composition of the present invention can be administered via various routes including oral, transdermal, subcutaneous, intravenous and intramuscular introduction for treating PBK dependent diseases, including cancer, in a subject.


In another embodiment, the present invention also provides the use of the compound of the present invention in manufacturing a pharmaceutical composition for treating a PBK dependent diseases including cancer. For example, the present invention relates to a use of the compound of the present invention for manufacturing a pharmaceutical composition for treating PBK dependent diseases, including cancer. In another embodiment, the compounds of the present invention can be used in treating PBK dependent diseases, including cancer.


In another embodiment, the present invention also provides a method or process for manufacturing a pharmaceutical composition for treating a PBK dependent diseases including cancer, wherein the method or process includes a step for admixing an active ingredient with a pharmaceutically or physiologically acceptable carrier, wherein the active ingredient is the compound of the present invention.


The dosage and method of administration vary according to the body weight, age, and symptoms of the patient; however, one skilled in the art can suitably select them.


For example, the dose is generally about 0.1 mg to about 100 mg per day, preferably about 1.0 mg to about 50 mg per day and more preferably about 1.0 mg to about 20 mg per day, when administered orally to a normal adult human (weight 60 kg).


When administering the compound parenterally, in the form of an injection to a normal adult human (weight 60 kg), although there are some differences according to the patient, target organ, symptoms and method of administration, it is convenient to intravenously inject a dose of about 0.01 mg to about 30 mg per day, preferably about 0.1 to about 20 mg per day and more preferably about 0.1 to about 10 mg per day. In the case of other animals, the appropriate dosage amount may be routinely calculated by converting to 60 kg of body weight.


EXAMPLES

The following examples are intended to further illustrate the present invention without limiting its scope.


General Procedure A (Scheme I):

Step 1: To a suspension of the requisite carboxylic acid A (1 mol) in CH2Cl2 (0.1-0.5 M) at room temperature was added (COCl)2 (2 mol) followed by the addition of catalytic DMF. The reaction mixture was stirred at room temperature for 18 h, concentrated and dried under high vacuum to obtain the intermediate acid chloride. The acid chloride was dissolved in CH2Cl2 (0.1-0.3 M) followed by the addition of Et3N (1.5-2 mol) and the requisite aniline (1.1 mol) and the reaction was stirred at room temperature for 18 h. The reaction mixture was concentrated, triturated with an appropriate solvent or purified by flash chromatography to obtain amide B as a solid.


Step 2: To a solution of amide B (1 mol) in THF (0.1-0.3 M) at 0° C. was added NaH (1.2 mol) and the reaction was warmed up to 45° C. for 15 min and cooled to 0° C. followed by the addition of (Boc)2O (2 mol). The reaction mixture was warmed to room temperature and stirred for 18 h. The reaction mixture was quenched by slowly pouring it into a stirred solution of water and satd aq NaHCO3 at 0° C. The mixture was extracted with ethyl acetate and the combined organic layers were washed with brine, dried over Na2SO4 and concentrated. The residue was triturated with an appropriate solvent or purified by flash chromatography to obtain C as a solid.


Step 3: Intermediate C (1 mol), bis(tri-tert-butylphosphine)palladium (5 mol %) and potassium acetate (4 mol) were added to a Parr pressure reactor followed by the addition of dimethyl acetamide (0.3 M). The reaction mixture was sparged with nitrogen for 30 min followed by heating at 140-150° C. for 4 h. The reaction mixture was cooled and quenched by pouring into brine at 0° C. The resulting precipitate was filtered and the filter cake was washed with water and ether to obtain crude D as a solid.


Step 4: To a solution of crude D (1 mol) in CH2Cl2:AcOH (1:1) was added NBS (1 mol) and the reaction mixture was stirred at room temperature for 18 h. The reaction mixture was quenched by pouring slowly into a stirred solution of ice and satd aq Na2CO3. Once the aqueous layer was at pH 8 the layers were separated and the CH2Cl2 layer was concentrated, triturated with acetonitrile and filtered to obtain E as solid.


Example 392
4-(tert-Butyldimethylsilyloxy)aniline



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To a solution of 4-aminophenol (11 g, 100 mmol) and imidazole (10 g, 150 mmol) in THF (250 mL) was added tert-butyldimethylsilyl chloride (18 g, 120 mmol) and the reaction was stirred at room temperature for 18 h. The reaction mixture was poured into water and extracted with diethyl ether. The combined organic layers were dried over Na2SO4, filtered, concentrated and the residue was purified by column chromatography to afford the desired product (15 g, 67%): ESI MS m/z 224 [C12H21NOSi+H]+.


Example 393
3-Bromo-N-[4-(tert-butyldimethylsilyloxy)phenyl]thiophene-2-carboxamide



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Following Step 1 from General Procedure A, 5-bromothiophene-2-carboxylic acid (3.0 g, 14 mmol) was reacted with 4-(tert-butyldimethylsilyloxy)aniline (4.2 g, 19 mmol) to afford the desired product (4.4 g, 73%) as a solid: ESI MS m/z 413 [C17H22BrNO2SSi+H]+.


Example 394
tert-Butyl 3-Bromothiophene-2-carbonyl[4-(tert-butyldimethylsilyloxy)phenyl]carbamate



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Following Step 2 from General Procedure A, 3-bromo-N-[4-(tert-butyldimethylsilyloxy)phenyl]thiophene-2-carboxamide (4.4 g, 11 mmol) was reacted with di-tert-butyl dicarbonate (4.6 g, 21 mmol) to afford the desired product (1.5 g, 28%) as a solid: ESI MS m/z 513 [C22H30BrNO4SSi+H]+.


Example 395
8-(tert-Butyldimethylsilyloxy)thieno[2,3-c]quinolin-4(5H)-one



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Following Step 3 from General Procedure A, tert-butyl 3-bromothiophene-2-carbonyl[4-(tert-butyldimethylsilyloxy)phenyl]carbamate (1.0 g, 2.0 mmol) was reacted with bis(tri-tert-butylphosphine)palladium (50 mg, 0.098 mmol) to afford the desired product (740 mg, quant.) as a solid: ESI MS m/z 332 [C17H21NO2SSi+H]+.


Example 396
9-Bromo-8-(tert-butyldimethylsilyloxy)thieno[2,3-c]quinolin-4(5H)-one



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Following Step 4 from General Procedure A, 8-(tert-butyldimethylsilyloxy)thieno[2,3-c]quinolin-4(5H)-one (740 mg, 2.2 mmol) was reacted with N-bromosuccinimide (480 mg, 2.7 mmol) to afford the desired product (340 mg, 37%) as a brown solid: ESI MS m/z 411 [C17H20BrNO2SSi+H]+.


Example 397
N-(2-Bromo-4-methoxyphenyl)-5-methyl-N-(5-methylthiophene-2-carbonyl)thiophene-2-carboxamide



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Following Step 1 from General Procedure A, 5-methylthiophene-2-carboxylic acid (8.5 g, 60 mmol) was reacted with 2-bromo-4-methoxyaniline (6.7 g, 30 mmol) to afford the desired product (5.0 g, 57%) as a solid: ESI MS m/z 327 [C13H12BrNO2S+H]+.


Example 398
8-Methoxy-2-methylthieno[2,3-c]quinolin-4(5H)-one



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Following Step 3 from General Procedure A, N-(2-bromo-4-methoxyphenyl)-5-methyl-N-(5-methylthiophene-2-carbonyl)thiophene-2-carboxamide (500 mg, 1.1 mmol) was reacted with bis(tri-tert-butylphosphine)palladium (45 mg, 0.089 mmol) to afford the desired product (1.3 g, 48%) as a green solid: ESI MS m/z 246 [C13H11NO2S+H]+.


Example 399
9-Bromo-8-methoxy-2-methylthieno[2,3-c]quinolin-4(5H)-one



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Following Step 4 from General Procedure A, 8-methoxy-2-methylthieno[2,3-c]quinolin-4(5H)-one (1.4 g, 5.7 mmol) was reacted with N-bromosuccinimide (1.2 g, 6.9 mmol) to afford the desired product (740 mg, 40%) as a brown solid: ESI MS m/z 325 [C13H10BrNO2S+H]+.


Example 400
3-bromo-N-(2-fluoro-4-methoxyphenyl)thiophene-2-carboxamide



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Following Step 1 from General Procedure A, 3-bromothiophene-2-carboxylic acid (7.3 g, 35 mmol) was reacted with 2-fluoro-4-methoxyaniline (5.0 g, 35 mmol) to afford the desired product (10 g, 90%) as an orange solid: ESI MS m/z 331 [C12H1FNO2S+H]+.


Example 401
tert-butyl 3-bromothiophene-2-carbonyl(2-fluoro-4-methoxyphenyl)carbamate



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Following Step 2 from General Procedure A, 3-bromo-N-(2-fluoro-4-methoxyphenyl)thiophene-2-carboxamide (12 g, 35 mmol) was reacted with di-tert-butyl dicarbonate (12 g, 53 mmol) to afford the desired product (14 g, >99%) as an orange solid: ESI MS m/z 331 [C12H10FNO2S+H]+.


Example 402
6-Fluoro-8-methoxythieno[2,3-c]quinolin-4(5H)-one



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Following Step 3 from General Procedure A, tert-butyl 3-bromothiophene-2-carbonyl(2-fluoro-4-methoxyphenyl)carbamate (2.0 g, 4.6 mmol) was reacted with bis(tri-tert-butylphosphine)palladium (100 mg, 0.20 mmol) to afford the desired product (950 mg, 80%) as a dark brown solid: ESI MS m/z 250 [C12H8FNO2S+H]+.


Example 403
9-Bromo-6-fluoro-8-methoxythieno[2,3-c]quinolin-4(5H)-one



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Following Step 4 from General Procedure A, 6-fluoro-8-methoxythieno[2,3-c]quinolin-4(5H)-one (1.0 g, 4.0 mmol) was reacted with N-bromosuccinimide (570 mg, 4.8 mmol) to afford the desired product (800 mg, 61%) as a brown solid: ESI MS m/z 329 [C12H7BrFNO2S+H]+.


Example 404
3-Bromo-N-(2,3-difluoro-4-methoxyphenyl)thiophene-2-carboxamide



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Following Step 1 from General Procedure A, 3-bromothiophene-2-carboxylic acid (1.3 g, 6.3 mmol) was reacted with 2,3-difluoro-4-methoxyaniline (960 mg, 7.5 mmol) to afford the desired product (2.2 g, >99%): ESI MS m/z 349 [Cl2HsBrF2NO2S+H]+.


Example 405
tert-Butyl 3-Bromothiophene-2-carbonyl(2,3-difluoro-4-methoxyphenyl)carbamate



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Following Step 2 from General Procedure A, 3-bromo-N-(2,3-difluoro-4-methoxyphenyl)thiophene-2-carboxamide (2.4 g, 7.00 mmol) was reacted with di-tert-butyl dicarbonate (330 mg, 14 mmol) to afford the desired product (2.1 g, 67%) as a white solid: ESI MS m/z 448 [C17H16BrF2NO4S+H]+.


Example 406
6,7-Difluoro-8-methoxythieno[2,3-c]quinolin-4(5H)-one



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Following Step 3 from General Procedure A, tert-butyl 3-bromothiophene-2-carbonyl(2,3-difluoro-4-methoxyphenyl)carbamate (1.4 g, 3.1 mmol) was reacted with bis(tri-tert-butylphosphine)palladium (80 mg, 0.15 mmol) to afford the desired product (58 mg, 65%) as a brown solid: ESI MS m/z 268 [C12H7F2NO2S+H]+.


Example 407
9-Bromo-6,7-difluoro-8-methoxythieno[2,3-c]quinolin-4(5H)-one



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Following Step 4 from General Procedure A, 6,7-difluoro-8-methoxythieno[2,3-c]quinolin-4(5H)-one (300 mg, 1.1 mmol) was reacted with N-bromosuccinimide (400 mg, 2.2 mmol) to afford the desired product (200 mg, 57%) as a yellow solid: ESI MS m/z 347 [C12H6BrF2NO2S+H]+.


Example 510
3-bromo-N-(4-methoxy-2-methylphenyl)thiophene-2-carboxamide



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Following Step 1 from General Procedure A, 3-bromothiophene-2-carboxylic acid (6.7 g, 49 mol) was reacted with 2-methyl-4-methoxyaniline (12 g, 53 mmol) to afford the desired product (13 g, 80%) as an orange solid: ESI MS m/z 331 [C12H10FNO2S+H]+.


Example 511
tert-butyl 3-bromothiophene-2-carbonyl(4-methoxy-2-methylphenyl)carbamate



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Following Step 2 from General Procedure A, 3-bromo-N-(4-methoxy-2-methylphenyl)thiophene-2-carboxamide (12 g, 37 mmol) was reacted with di-tert-butyl dicarbonate (9.6 g, 44 mmol) to afford the desired product (15 g, 96%) as an orange solid: ESI MS m/z 331 [C12H10FNO2S+H]+.


Example 512
8-methoxy-6-methylthieno[2,3-c]quinolin-4(5H)-one



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Following Step 3 from General Procedure A, tert-butyl 3-bromothiophene-2-carbonyl(4-methoxy-2-methylphenyl)carbamate (14 g, 33 mmol) was reacted with bis(tri-tert-butylphosphine)palladium (750 mg, 1.5 mmol) to afford the desired product (7.0 g, 85%) as a dark brown solid: ESI MS m/z 250 [C12H8FNO2S+H]+.


Example 513
9-bromo-8-methoxy-6-methylthieno[2,3-c]quinolin-4(5H)-one



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Following Step 4 from General Procedure A, 8-methoxy-6-methylthieno[2,3-c]quinolin-4(5H)-one (6.4 g, 26 mmol) was reacted with N-bromosuccinimide (5.0 g, 26 mmol) to afford the desired product (7.0 g, 82%) as a brown solid: ESI MS m/z 329 [C12H7BrFNO2S+H]+.


Example 514
3-Bromo-N-(4-methoxyphenyl)thiophene-2-carboxamide



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Following Step 1 from General Procedure A, 5-bromothiophene-2-carboxylic acid (75 g, 360 mmol) was reacted with 4-methoxyaniline (54 g, 430 mmol) to afford the desired product (110 g, 93%) as a solid: ESI MS m/z 313 [C12H10BrNO2S+H]+.


Example 515
tert-Butyl 3-bromothiophene-2-carbonyl(4-methoxyphenyl)carbamate



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Following Step 2 from General Procedure A, 3-Bromo-N-(4-methoxyphenyl)thiophene-2-carboxamide (60 g, 190 mmol) was reacted with di-tert-butyl dicarbonate (83 g, 380 mmol) to afford the desired product (65 g, 82%) as a solid: ESI MS m/z 413 [C17H18BrNO4S+H]+.


Example 516
8-Methoxythieno[2,3-c]quinolin-4(5H)-one



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Following Step 3 from General Procedure A, tert-butyl 3-bromothiophene-2-carbonyl (4-methoxyphenyl)carbamate (62 g, 150 mmol) was reacted with bis(tri-tert-butylphosphine) palladium (3.7 g, 5 mol %) to afford the crude desired product (26 g) as a grey-brown solid: ESI MS m/z 232 [C2H9NO2S+H]+.


Example 517
9-Bromo-8-methoxythieno[2,3-c]quinolin-4(5H)-one



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General Procedure B (Scheme II):

To a solution of bromides E (1 mmol) in DMF was added Cs2CO3 (3 mmol), Pd(dppf)Cl2 (0.1 mmol) and boronate esters or acids G (1-2 mmol) and the reaction was heated at 80° C. for 18 h. The reaction mixture was cooled, concentrated and the residue was purified by column chromatography (silica, ethyl acetate/hexanes gradient) or preparatory HPLC (C18 silica, acetonitrile/water with 0.05% TFA gradient) to obtain the desired products H. In some instances the desired product was dissolved in aqueous HCl, concentrated and dried under high vacuum to afford the desired product as a hydrochloride salt.


General Procedure C (Scheme II):

The compound from General Procedure B (1 mmol) was dissolved in TFA (10 mmol) and stirred at room temperature for 2 h and concentrated. The residue was eluted through an ion-exchange column (using methanol and 7 N methanol in ammonia) to obtain the desired product as the free base. In some instances the desired product was dissolved in aqueous HCl, concentrated and dried under high vacuum to afford the desired product as a hydrochloride salt.


General Procedure D-1 (Scheme II):

The requisite compound (1 mmol) was dissolved in methanol followed by the addition of 2 N HCl in diethylether (100 mmol). The reaction mixture was stirred at room temperature for 2 h and filtered or concentrated to obtain the desired product as the hydrochloride salt.


General Procedure D-2 (Scheme II):

The requisite compound was dissolved in aqueous HCl, concentrated and dried under high vacuum to afford the desired product as a hydrochloride salt.


General Procedure D-3 (Scheme II):

The requisite compound (1 mmol) was dissolved in aqueous HCl (100 mmol) and stirred concentrated at room temperature for 2 h, concentrated and dried under high vacuum to afford the desired product as a hydrochloride salt.


General Procedure E—One Pot (Scheme II):

To a solution of aryl bromides F (1 mmol) in dioxane was added KOAc (2 mmol), Pd(dppf)Cl2 (0.1 mmol) and bis(pinacolato)diboron (1.5 mmol) and the reaction was heated at 90° C. until the aryl bromide was consumed. To the reaction mixture was added Cs2CO3 (2 mmol) and bromides E (0.5 mmol) and heating was continued for 18 h. The reaction mixture was cooled, concentrated and purified by chromatography (silica, ethyl acetate/hexanes gradient) or preparatory HPLC (C18 silica, acetonitrile/water with 0.05% TFA gradient) to obtain the desired products I. In some instances the desired product was dissolved in aqueous HCl, concentrated and dried under high vacuum to afford the desired product as a hydrochloride salt.


General Procedure F (Scheme II):

To a solution or suspension of compounds H, I, or J (R3═OCH3) (1 mmol) in CH2Cl2 at 0° C. was added BBr3 (6-10 mmol) and the reaction was warmed to room temperature for 18 h or until the starting material disappeared by LCMS analysis. The reaction was quenched by pouring onto ice-water and the resulting mixture was concentrated and purified by preparatory HPLC (C18 silica, acetonitrile/water (with 0.05% TFA) gradient). The desired fractions were combined, concentrated and eluted through an ion-exchange column (using methanol and 7 N methanol in ammonia) to obtain the desired product. In some instances the desired product was dissolved in aqueous HCl, concentrated and dried under high vacuum to afford the desired product as a hydrochloride salt.


General Procedure G (Scheme II):

To a solution of aryl bromides F (1 mmol) in dioxane was added KOAc (2 mmol), Pd(dppf)Cl2 (0.1 mmol) and bis(pinacolato)diboron (1.5 mmol) and the reaction was heated at 90° C. for 18 h. The reaction mixture was cooled, concentrated and the residue was purified by column chromatography (silica, ethyl acetate/hexanes gradient) to obtain the desired product.


General Procedure H (Scheme II):

To a solution requisite compound H (1.0 mmol) in DMF was added N-chlorosuccinimide (1.2 mmol) and the reaction was stirred at room temperature for 30 min and heated at 60° C. for 2 h. The reaction mixture was concentrated and the residue purified by column chromatography (silica, 0-30% ethyl acetate/heptane) to afford the desired product I.


General Procedure I (Scheme II):

To a solution requisite compound H (1.0 mmol) in DMF was added N-bromosuccinimide (1.2 mmol) and the reaction was stirred at room temperature for 30 min and heated at 50° C. for 2 h. The reaction mixture was concentrated and the residue purified by column chromatography (silica, 0-30% ethyl acetate/heptane) to afford the desired product I.


General Procedure J (Scheme II):

To a solution requisite compound I (1.0 mmol) in toluene, was added tripotassium phosphate (4.0 mmol), trimethylboroxine (3.0 mmol), water (0.60 M) and Pd(PPh3)4 (0.10 mmol) the reaction mixture degassed and heated at 120° C. for 2 hr. The reaction mixture was cooled, concentrated and the residue was purified by column chromatography (silica, ethyl acetate/hexanes gradient) to afford the desired product J.


Example 518
(S)-tert-Butyl 1-(4-(8-methoxy-4-oxo-4,5-dihydrothieno[2,3-c]quinolin-9-yl)phenyl)propyl(methyl)carbamate



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Following General Procedure B, 9-bromo-8-methoxythieno[2,3-c]quinolin-4(5H-1)-one (670 mg, 2.2 mmol) was reacted with (S)-tert-butyl methyl(1-(4-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)phenyl)propyl)carbamate (1.3 g, 3.4 mmol) to afford the desired product (700 mg, 48%) as a light brown solid: ESI MS m/z 479 [C27H30N2O4S+H]+.


Example 519
(S)-tert-Butyl 2-(4-(8-methoxy-4-oxo-4,5-dihydrothieno[2,3-c]quinolin-9-yl)phenyl)propylcarbamate



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Following General Procedure B, 9-bromo-8-methoxythieno[2,3-c]quinolin-4(5H)-one (240 mg, 0.32 mmol) was reacted with (S)-tert-butyl 2-(4-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)phenyl)propylcarbamate (3.5 g, 9.7 mmol) to afford the desired product (1.4 g, 32%) as a light brown solid: ESI MS m/z 465 [C26H28N2O4S+H]+.


Example 520
tert-Butyl(1-(4-(8-methoxy-4-oxo-4,5-dihydrothieno[2,3-c]quinolin-9-yl)phenyl)cyclopropyl)methylcarbamate



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Following General Procedure B, 9-bromo-8-methoxythieno[2,3-c]quinolin-4(5H)-one (830 mg, 2.7 mmol) was reacted with tert-butyl(1-(4-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)phenyl)cyclopropyl)methylcarbamate (1.5 g, 4.0 mmol) to afford the desired product (670 mg, 52%) as a light brown solid: ESI MS m/z 477 [C27H28N2O4S+H]+.


Example 521
tert-Butyl (1-(4-(8-methoxy-6-methyl-4-oxo-4,5-dihydrothieno[2,3-c]quinolin-9-yl)phenyl)cyclopropyl)methylcarbamate



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Following General Procedure B, 9-bromo-8-met oxy-6-methylthieno[2,3-c]quinolin-4(5H)-one (150 mg, 0.46 mmol) was reacted with tert-butyl(1-(4-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)phenyl)cyclopropyl)methylcarbamate (260 mg, 0.69 mmol) to afford the desired product (150 mg, 68%) as a light brown solid: ESI MS m/z 491 [C28H30N2O4S+H]+.


Example 522
(S)-tert-Butyl 2-(4-(8-methoxy-4-oxo-4,5-dihydrothieno[2,3-c]quinolin-9-yl)phenyl)propyl(methyl)carbamate



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Following General Procedure B, 9-bromo-8-methoxythieno[2,3-c]quinolin-4(5H)-one (2.5 g, 8.1 mmol) was reacted with (S)-tert-butylmethyl(2-(4-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)phenyl)propyl)carbamate (4.6 g, 12 mmol) to afford the desired product (1.9 g, 50%) as a light brown solid: ESI MS m/z 47 [C27H30N2O4S+H]+.


Example 523
(S)-tert-Butyl 2-(4-(8-methoxy-6-methyl-4-oxo-4,5-dihydrothieno[2,3-c]quinolin-9-yl)phenyl)propylcarbamate



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Following General Procedure B, 9-bromo-8-methoxy-6-methylthieno[2,3-c]quinolin-4(5H)-one (150 mg, 0.46 mmol) was reacted with (S)-tert-butyl-2-(4-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)phenyl)propylcarbamate (251 mg, 0.69 mmol) to afford the desired product (140 mg, 62%) as a light brown solid: ESI MS m/z 479 [C27H30N2O4S+H]+.


Example 524
(S)-tert-Butyl 2-(4-(8-methoxy-6-methyl-4-oxo-4,5-dihydrothieno[2,3-c]quinolin-9-yl)phenyl)propylcarbamate



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Following General Procedure B, 9-bromo-8-methoxy-6-methylthieno[2,3-c]quinolin-4(5H)-one (150 mg, 0.46 mmol) was reacted with (S)-tert-butyl2-(4-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)phenyl)propylcarbamate (251 mg, 0.69 mmol) to afford the desired product (135 mg, 62%) as a light brown solid: ESI MS m/z 479 [C27H30N2O4S+H]+.


Example 525
tert-Butyl 2-chloro-44-(8-methoxy-4-oxo-4,5-dihydrothieno[2,3-c]quinolin-9-yl)phenethylcarbamate



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Following General Procedure B, 9-bromo-8-methoxythieno[2,3-c]quinolin-4(5H)-one (3.0 g, 9.7 mmol) was reacted with tert-butyl 2-chloro-4-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)phenethylcarbamate (5.53 g, 14.5 mmol) to afford the desired product (2.65 g, 57%) as a light brown solid. ESI MS m/z 485 [C25H25ClN2O4S+H]+.


Example 526
(R)-tert-Butyl 1-(4-(8-methoxy-6-methyl-4-oxo-4,5-dihydrothieno[2,3-c]quinolin-9-yl)phenyl)ethyl(methyl)carbamate



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Following General Procedure B, 9-bromo-8-methoxy-6-methylthieno[2,3-c]quinolin-4(5H)-one (150 mg, 0.46 mmol) was reacted with (R)-tert-butylmethyl(1-(4-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)phenyl)ethyl)carbamate (250 mg, 0.69 mmol to afford the desired product (145 mg, 66%) as a light brown solid: ESI MS m/z 479 [C27H30N2O4S+H]+.


Example 527
(R)-tert-Butyl 1-(4-(8-methoxy-4-oxo-4,5-dihydrothieno[2,3-c]quinolin-9-yl)phenyl)ethyl(methyl)carbamate



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Following General Procedure B, 9-bromo-8-methoxythieno[2,3-c]quinolin-4(5H)-one 1.4 g, 4.4 mmol) was reacted with (R)-tert-butylmethyl(1-(4-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)phenyl)ethyl)carbamate (2.4 g, 6.6 mmol) to afford the desired product (1.4 g, 66%) as a light brown solid: ESI MS m/z 465 [C26H28N2O4S+H]+.


Example 528
tert-Butyl 2-(2-fluoro-4-(8-methoxy-1-oxo-4,5-dihydrothieno[2,3-c]quinolin-9-yl)phenyl)-2-methylpropylcarbamate



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Following General Procedure B, 9-bromo-8-methoxythieno[2,3-c]quinolin-4(5H)-one (1.4 g, 4.3 mmol) was reacted with tert-butyl2-(2-fluoro-4-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)phenyl)-2-methylpropylcarbamate (2.5 g, 6.4 mmol) to afford the desired product (1.7 g, 79%) as a light brown solid. ESI MS m/z 497 [C27H21FN2O4S+H]+.


Example 529
tert-Butyl 2-(2-fluoro-4-(8-methoxy-6-methyl-4-oxo-4,5-dihydrothieno[2,3-c]quinolin-9-yl)phenyl)-2-methylpropylcarbamate



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Following General Procedure B, 9-bromo-8-methoxy-6-methylthieno[2,3-c]quinolin-4(5H)-one (150 mg, 0.46 mmol) was reacted with tert-butyl 2-(2-fluoro-4-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)phenyl)-2-methylpropylcarbamate (270 mg, 0.64 mmol) to afford the desired product (130 mg, 56%) as a light brown solid: ESI MS m/z 511 [C28H31FN2O4S+H]+.


Example 530
tert-Butyl 2-(4-(8-methoxy-6-methyl-4-oxo-4,5-dihydrothieno[2,3-c]quinolin-9-yl)phenyl)butylcarbamate



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Following General Procedure B, 9-brom-8-methoxy-6-methylthieno[2,3-c]quinolin-4(5H)-one (150 mg, 0.46 mmol) was reacted with tert-butyl 2-(4-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)phenyl)butylcarbamate (240 mg, 0.64 mmol) to afford the desired product (75 mg, 33%) as a light brown solid: ESI MS m/z 493 [C28H12N2O4S+H]+.


Example 531
(S)-tert-Butyl 1-(4-(8-Methoxy-4-oxo-4,5-dihydrothieno[2,3-c]quinolin-9-yl)phenyl)propylcarbamate



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Following General Procedure B, 9-bromo-8-methoxythieno[2,3-c]quinolin-4(5H)-one (640 mg, 2.1 mmol) was reacted with (S)-tert-butyl 1-(4-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)phenyl)propylcarbamate (1.13 g, 3.12 mmol) to afford the desired product (680 mg, 71%) as a light brown solid: ESI MS m/z 465 [C26H28N2O4S+H]+.


Example 532
tert-Butyl(1-(4-(8-methoxy-6-methyl-4-oxo-4,5-dihydrothieno[2,3-c]quinolin-9-yl)phenyl)cyclobutyl)methylcarbamate



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Following General Procedure B, 9-bromo-8-methoxy-6-methylthieno[2,3-c]quinolin-4(5H)-one (150 mg, 0.46 mmol) was reacted with tert-butyl (1-(4-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)phenyl)cyclobutyl)methylcarbamate (270 mg, 0.70 mmol to afford the desired product (105 mg, 45%) as a light brown solid: ESI MS m/z 505 [C29H32N2O4S+H]+.


Example 533
tert-Butyl(1-(4-(8-methoxy-4-oxo-4,5-dihydrothieno[2,3-c]quinolin-9-yl)phenyl)cyclobutyl)methylcarbamate



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Following General Procedure B, 9-bromo-8-methoxythieno[2,3-c]quinolin-4(5H)-one (1.9 g, 6.0 mmol) was reacted with tert-butyl (1-(4-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)phenyl)cyclobutyl)methylcarbamate (3.5 g, 9.0 mmol) to afford the desired product (1.5 g, 33%) as a light brown solid: ESI MS m/z 491 [C28H30N2O4S+H]+.


Example 534
tert-Butyl 2-(4-(8-methoxy-4-oxo-4,5-dihydrothieno[2,3-c]quinolin-9-yl)phenyl)butylcarbamate



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Following General Procedure B, 9-bromo-8-methoxythieno[2,3-c]quinolin-4(5H)-one (840 mg, 2.7 mmol) was reacted with tert-butyl 2-(4-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)phenyl)butylcarbamate (1.5 g, 4.0 mmol) to afford the desired product (820 mg, 43%) as a light brown solid: ESI MS m/z 479 [C27H30N2O4S+H]+.


Example 535
tert-Butyl ethyl(1-((8-methoxy-4-oxo-4,5-dihydrothieno[2,3-c]quinolin-9-yl)phenyl)ethyl)carbamate



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Following General Procedure B, 9-bromo-8-methoxythieno[2,3-c]quinolin-4(5H)-one (770 mg, 2.5 mmol) was reacted with tert-butyl ethyl(1-(4-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)phenyl)ethyl)carbamate (1.4 g, 3.7 mmol) to afford the desired product (450 mg, 40%) as a light brown solid: ESI MS m/z 479 [C27H30N2O4S+H]+.


Example 536
tert-Butyl4-(8-methoxy-4-oxo-4,5-dihydrothieno[2,3-c]quinolin-9-yl)phenethyl(methyl)carbamate



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Following General Procedure B, 9-bromo-8-methoxythieno[2,3-c]quinolin-4(5H)-one (2.4 g, 7.6 mmol) was reacted with tert-butyl methyl(4-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)phenethyl)carbamate (4.2 g, 11 mmol) to afford the desired product (2.1 g, 40%) as a light brown solid: ESI MS m/z 465 [C26H28N2O4S+H]+.


Example 537
(S)-tert-Butyl 2-(4-(8-methoxy-4-oxo-4,5-dihydrothieno[2,3-c]quinolin-9-yl)phenyl)propyl(methyl)carbamate



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Following General Procedure B, 9-bromo-8-methoxythieno[2,3-c]quinolin-4(5H)-one (2.6 g, 8.2 mmol) was reacted with (S)-tert-butyl methyl(2-(4-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)phenyl)propyl)carbamate (4.6 g, 12 mmol) to afford the desired product (1.9 g, 50%) as a light brown solid: ESI MS m/z 479 [C27H30N2O4S+H]+.


Example 538
(S)-tert-Butyl 2-(2-fluoro-4-(8-methoxy-6-methyl-4-oxo-4,5-dihydrothieno[2,3-c]quinolin-9-yl)phenyl)propylcarbamate



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Following General Procedure B, 9-bromo-8-methoxy-6-methylthieno[2,3-c]quinolin-4(5H)-one) (380 mg, 1.2 mmol) was reacted with (S)-tert-butyl2-(2-fluoro-4-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)phenyl)propylcarbamate (400 mg, 1.1 mmol) to afford the desired product (190 mg, 36%) as a yellow solid: ESI MS m/z 497 [C27H29FN2O4S+H]+.


Example 539
tert-Butyl 2-(4-(8-methoxy-4-oxo-4,5-dihydrothieno[2,3-c]quinolin-9-yl)phenyl)-3-methylbutylcarbamate



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Following General Procedure B, 9-bromo-8-methoxy-thieno[2,3-c]quinolin-4(5H)-one) (800 mg, 2.58 mmol) was reacted with tert-butyl 3-methyl-2-(4-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)phenyl)butylcarbamate (1.2 g, 3.09 mmol) to afford the desired product (250 mg, 20%) as a yellow solid: ESI MS m % z 493 [C28H32N2O4S+H]+.


Example 540
tert-Butyl 2-(4-(8-methoxy-6-methyl-4-oxo-4,5-dihydrothieno[2,3-c]quinolin-9-yl)phenyl)-3-methylbutylcarbamate



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Following General Procedure B, 9-bromo-8-methoxy-6-methylthieno[2,3-c]quinolin-4(5H)-one) (500 mg, 1.54 mmol) was reacted with tert-butyl 3-methyl-2-(4-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)phenyl)butylcarbamate (590 mg, 1.9 mmol) to afford the desired product (120 mg, 15%) as a yellow solid: ESI MS m/z 507 [C29H34N2O4S+H]+.


Example 541
(R)-tert-Butyl 2-(2-fluoro-4-(8-methoxy-6-methyl-4-oxo-4,5-dihydrothieno[2,3-c]quinolin-9-yl)phenyl)propylcarbamate



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Following General Procedure B, 9-bromo-8-methoxy-6-methylthieno[2,3-c]quinolin-4(5H)-one) (770 mg, 2.4 mmol) was reacted with (R)-tert-butyl 2-(2-fluoro-4-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)phenyl)propylcarbamate (770 mg, 2.0 mmol) to afford the desired product (500 mg, 49%) as a yellow solid: ESI MS m/z 497 [C27H29FN2O4S+H]+.


Example 542
(R)-tert-Butyl 2-(2-fluoro-4-(8-methoxy-6-methyl-4-oxo-4,5-dihydrothieno[2,3-c]quinolin-9-yl)phenyl)propyl(methyl)carbamate



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Following General Procedure B, 9-bromo-8-methoxy-6-methylthieno[2,3-c]quinolin-4(5H)-one) (180 mg, 0.57 mmol) was reacted with (R)-tert-butyl 2-(2-fluoro-4-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)phenyl)propyl(methyl)carbamate (150 mg, 0.38 mmol) to afford the desired product (190 mg, 36%) as a yellow solid: ESI MS m/z 511 [C28H31FN2O4S+H]+.


Example 543
(R)-tert-Butyl 2-(4-(8-methoxy-6-methyl-4-oxo-4,5-dihydrothieno[2,3-c]quinolin-9-yl)phenyl)butylcarbamate



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Following General Procedure B, 9-bromo-8-methoxy-6-methylthieno[2,3-c]quinolin-4(5H)-one) (900 mg, 2.9 mmol) was reacted with (R)-tert-butyl 2-(4-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)phenyl)butylcarbamate (900 mg, 2.7 mmol) to afford the desired product (190 mg, 15%) as a yellow solid: ESI MS m % z 493 [C28H32N2O4S+H]+.


Example 544
tert-Butyl 2-(2-fluoro-4-(8-methoxy-6-methyl-4-oxo-4,5-dihydrothieno[2,3-c]quinolin-9-yl)phenyl)propylcarbamate



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Following General Procedure B, 9-bromo-8-methoxy-6-methylthieno[2,3-c]quinolin-4(5H)-one) (900 mg, 2.8 mmol) was reacted with ter-butyl 2-(2-fluoro-4-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)phenyl)propylcarbamate (1.3 g, 3.3 mmol) to afford the desired product (200 mg, 27%) as a yellow solid: ESI MS m/z 497 [C27H29FN2O4S+H]+.


Example 545
tert-Butyl 2-(2-fluoro-4-(8-methoxy-6-methyl-4-oxo-4,5-dihydrothieno[2,3-c]quinolin-9-yl)phenyl)-3-methyl butylcarbamate



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Following General Procedure B, 9-bromo-8-methoxy-6-methylthieno[2,3-c]quinolin-4(5H)-one) (170 mg, 0.50 mmol) was reacted with tert-butyl 2-(2-fluoro-4-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)phenyl)-3-methylbutylcarbamate (200 mg, 0.50 mmol) to afford the desired product (65 mg, 25%) as a yellow solid: ESI MS m/z 525 [C29H33FN2O4S+H]+.


Example 546
tert-Butyl 2-(2-fluoro-4-(8-methoxy-6-methyl-4-oxo-4,5-dihydrothieno[2,3-c]quinolin-9-yl)phenyl)propyl(methyl)carbamate



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Following General Procedure B, 9-bromo-8-methoxy-6-methylthieno[2,3-c]quinolin-4(5H-1)-one) (380 mg, 1.16 mmol) was reacted with tert-butyl 2-(2-fluoro-4-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)phenyl)propyl(methyl)carbamate (400 mg, 1.1 mmol) to afford the desired product (190 mg, 36%) as a yellow solid: ESI MS m/z 511 [C28H31FN2O4S+H]+.


Example 547
tert-Butyl 2-(2-fluoro-4-(8-methoxy-6-methyl-4-oxo-4,5-dihydrothieno[2,3-c]quinolin-9-yl)phenyl-3-methylbutyl(methyl)carbamate



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Following General Procedure, 9-bromo-8-methoxy-6-methylthieno[2,3-c]quinolin-4(5H)-one) (265 mg, 0.81 mmol) was reacted with tert-butyl 2-(2-fluoro-44-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)phenyl)-3-methylbutyl(methyl)carbamate (300 mg, 0.89 mmol) to afford the desired product (80 mg, 18%) as a yellow solid: ESI MS m/z 539 [C30H35FN2O4S+H]+.


Example 548
(R)-tert-Butyl 2-(2-fluoro-4-(8-methoxy-6-methyl-4-oxo-4,5-dihydrothieno[2,3-c]quinolin-9-yl)phenyl)propylcarbamate



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Following General Procedure B, 9-bromo-8-methoxy-6-methylthieno[2,3-c]quinolin-4(5H)-one) (1.0 g, 3.3 mmol) was reacted with (R)-tert-butyl 2-(2-fluoro-4-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)phenyl)propylcarbamate (1.1 g, 3.0 mmol) to afford the desired product (510 mg, 34%) as a yellow solid: ESI MS m/z 497 [C27H19FN2O4S+H]+.


Example 549
tert-Butyl 2-(4-(8-methoxy-6-methyl-4-oxo-4,5-dihydrothieno[2,3-c]quinolin-9-yl)phenyl)-3-methylbutyl(methyl)carbamate



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Following General Procedure B, 9-bromo-8-methoxy-6-methylthieno[2,3-c]quinolin-4(5H)-one) (440 mg, 1.4 mmol) was reacted with tert-butyl methyl(3-methyl-2-(4-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)phenyl)butyl)carbamate (600 mg, 1.5 mmol) to afford the desired product (100 mg, 14%) as a yellow solid: ESI MS m/z 521 [C30H36N2O4S+H]+.


Example 550
(S)-tert-Butyl 2-(2-fluoro-44-(8-methoxy-6-methyl-4-oxo-4,5-dihydrothieno[2,3-c]quinolin-9-yl)phenyl)propylcarbamate



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Following General Procedure B, 9-bromo-8-methoxy-methylthieno[2,3-c]quinolin-4(5H)-one) (840 mg, 2.6 mmol) was reacted with (S)-tert-butyl 2-(2-fluoro-4-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)phenyl)propylcarbamate (900 mg, 2.4 mmol) to afford the desired


Example 551
(R)-tert-Butyl 2-(4-(8-methoxy-4-oxo-4,5-dihydrothieno[2,3-c]quinolin-9-yl)phenyl)propylcarbamate



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Following General Procedure B, 9-bromo-8-methoxy-thieno[2,3-c]quinolin-4(5H)-one (1.2 g, 4.0 mmol) was reacted with (R)-tert-butyl 2-(4-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)phenyl)propylcarbamate (2.2 g, 6.1 mmol) to afford the desired product (900 mg, 48%) as a yellow solid: ESI MS m/z 465 [C26H28N2O4S+H]+.


Example 1057
N-(1-Hydroxypropan-2-yl)-4-(8-methoxy-4-oxo-4,5-dihydrothieno[2,3-c]quinolin-9-yl)benzenesulfonamide



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Following General Procedure B, 9-bromo-8-methoxy-thieno[2,3-c]quinolin-4(5H)-one) (530 mg, 1.8 mmol) was reacted with N-(1-hydroxypropan-2-yl)-4-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)benzenesulfonamide (750 mg, 2.02 mmol) to afford the desired product (150 mg, 20%) as a yellow solid: ESI MS m/z 445 [C21H20N2O5S2+H]+.


Example 1238
3-(4-(8-Methoxy-6-methyl-4-oxo-4,5-dihydrothieno)[2,3-c]quinolin-9-yl)phenyl)propanenitrile



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Following General Procedure B, 9-bromo-8-methoxy-6-methylthieno[2,3-c]quinolin-4(5H)-one) (325 mg, 1.0 mmol) was reacted 3-(4-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)phenyl)propanenitrile (330 mg, 1.3 mmol) to afford the desired product (140 mg, 37%) as a yellow solid: ESI MS m/z 375 [C22H18N2O2S+H]+.


Example 552
tert-Butyl 2-cyclopentyl-2-(4-(8-methoxy-4-oxo-4,5-dihydrothieno[2,3-c]quinolin-9-yl)phenyl)ethylcarbamate



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Following General Procedure B, 9-bromo-8-methoxy-thieno[2,3-c]quinolin-4(5H)-one) (500 mg, 1.6 mmol) was reacted with tert-butyl 2-cyclopentyl-2-(4-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)phenyl)ethylcarbamate (1.3 g, 3.2 mmol) to afford the desired product (150 mg, 19%) as a yellow solid: ESI MS m/z 519 [C30H34N2O4S+H]+.


Example 553
tert-Butyl 3-(4-(8-methoxy-6-methyl-4-oxo-4,5-dihydrothieno[2,3-c]quinolin-9-yl)phenyl)piperidine-1-carboxylate



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Following General Procedure B, 9-bromo-8-methoxy-thieno[2,3-c]quinolin-4(5H)-one) (190 mg, 0.58 mmol) was reacted with tert-butyl 3-(4-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)phenyl)piperidine-1-carboxylate (180 mg, 0.46 mmol) to afford the desired product (79 mg, 34%) as a yellow solid: ESI MS m % z 505 [C29H32N2O4S+H]+.


Example 554
tert-Butyl 2-((4-(8-methoxy-6-methyl-4-oxo-4,5-dihydrothieno[2,3-c]quinolin-9-yl)phenyl)(methyl)amino ethylcarbamate



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Following General Procedure B, 9-bromo-8-methoxy-6-methylthieno[2,3-c]quinolin-4(5H)-one) (86 mg, 0.26 mmol) was reacted with tert-butyl 2-(methyl(4-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)phenyl)amino)ethylcarbamate (100 mg, 0.26 mmol) to afford the desired product (100 mg, 78%) as a yellow solid: ESI MS m/z 494 [C27H31N3O4S+H]+.


Example 1310
(S)-9-(4-(1-Aminopropan-2-yl)-3-fluorophenyl)-8-methoxy-6-methylthieno[1,3-c]quinolin-4(5H)-one Hydrochloride



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Following General Procedure D1, (S)-tert-butyl 2-(2-fluoro-4-(8-methoxy-6-methyl-4-oxo-4,5-dihydrothieno[2,3-c]quinolin-9-yl)phenyl)propylcarbamate (100 mg, 0.20 mmol) was reacted with HCl in ether (10 mL) to afford the desired product (80 mg, 98%) as an off-white solid: ESI MS m/z 397 [C22H21FN2O2S+H]+.


Example 1253
9-(4-(1-Amino-3-methylbutan-2-yl)phenyl)-8-methoxythieno[2,3-c]quinolin-4(5H)-one Hydrochloride



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Following General Procedure D1, tert-butyl 2-(4-(8-methoxy-4-oxo-4,5-dihydrothieno[2,3-c]quinolin-9-yl)phenyl)-3-methylbutylcarbamate (30 mg, 0.060 mmol) was reacted with HCl in ether (3 mL) to afford the desired product (22 mg, 97%) as an off-white solid; 1H NMR (500 MHz, DMSO-d) δ 7.93 (s, 3H), 7.62 (d, J=5.4 Hz, 1H), 7.53 (d, J=9.1 Hz, 1H), 7.41 (d, J=9.0 Hz, 2H), 7.38-7.33 (m, 1H), 7.24 (d, J=8.2 Hz, 2H), 5.72 (d, J=5.4 Hz, 1H), 3.70 (s, 3H), 3.38-3.26 (m, 2H), 2.87 (dt, J=12.9, 6.3 Hz, 1H), 2.01 (dq, J=13.3, 6.6 Hz, 1H), 0.97 (t, J=7.8 Hz, 3H), 0.82 (t, J=9.9 Hz, 3H); ESI MS m/z 393 [C23H24N2O2S+H]+. HPLC 98.4% (AUC), tR=11.65 min.


Example 555
9-(4-(1-Amino-3-methylbutan-2-yl)phenyl)-8-methoxy-6-methylthieno[2,3-c]quinolin-4(5H)-one Hydrochloride



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Following General Procedure D1, tert-butyl 2-(4-(8-methoxy-6-methyl-4-oxo-4,5-dihydrothieno[2,3-c]quinolin-9-yl)phenyl)-3-methylbutylcarbamate (50 mg, 0.060 mmol) was reacted with HCl in ether (3 mL) to afford the desired product (37 mg, 92%) as an off-white solid: ESI MS m/1407 [C24H26N2O2S+H]+.


Example 1317
(R)-9-(4-(1-Aminopropan-2-yl)-3-fluorophenyl)-8-methoxy-6-methylthieno[2,3-c]quinolin-4(5H)-one Hydrochloride



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Following General Procedure D1, (R)-tert-butyl 2-(2-fluoro-4-(8-methoxy-6-methyl-4-oxo-4,5-dihydrothieno[2,3-c]quinolin-9-yl)phenyl)propylcarbamate (150 mg, 0.30 mmol) was reacted with HCl in ether (15 mL) to afford the desired product (105 mg, 81%) as an off-white solid: 1H NMR (500 MHz, MeOD) δ 7.63 (dd, J=5.4, 2.4 Hz, 1H), 7.52 (dt, J=24.8, 7.8 Hz, 1H), 7.30 (s, 1H), 7.09 (m, 2H), 6.11 (dd, J=26.4, 5.4 Hz, 1H), 3.76 (s, 3H), 3.63-3.43 (m, 1H), 3.42-3.16 (m, 2H), 2.64 (s, 3H), 1.51 (d, J=7.0 Hz, 3H). ESI MS m/z 397 [C22H21FN2O2S+H]+; HPLC >99% (AUC), tR=11.57 min.


Example 1316
(R)-9-(3-Fluoro-4-(1-(methylamino)propan-2-yl)phenyl)-8-methoxy-6-methylthieno[2,3-c]quinolin-4(5H)-one Hydrochloride



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Following General Procedure D1, (R)-tert-butyl 2-(2-fluoro-4-(8-methoxy-6-methyl-4-oxo-4,5-dihydrothieno[2,3-c]quinolin-9-yl)phenyl)propyl(methyl)carbamate (50 mg, 0.10 mmol) was reacted with HCl in ether (5 mL) to afford the desired product (35 mg, 85%) as an yellow solid; 1H NMR (500 MHz, CD3OD) δ 7.63 (d, J=5.4 Hz, 1H), 7.53 (dt, J=28.7, 7.8 Hz, 1H), 7.29 (s, 1H), 7.17-7.04 (m, 2H), 6.10 (dd, J=31.6, 5.4 Hz, 1H), 3.75 (s, 3H), 3.68-3.24 (m, 3H), 2.78 (d, J=13.3 Hz, 3H), 2.64 (s, 3H), 1.52 (dd, J=7.0, 3.2 Hz, 3H); ESI MS m/z 411 [C23H23FN2O2S+H]+; HPLC 98.2% (AUC), tR=11.79 min.


Example 1344
(R)-9-(4-(1-Aminobutan-2-yl)phenyl)-8-methoxy-6-methylthieno[2,3-c]quinolin-4(5H)-one Hydrochloride



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Following General Procedure D1, (R)-tert-butyl 2-(4-(8-methoxy-6-methyl-4-oxo-4,5-dihydrothieno[2,3-c]quinolin-9-yl)phenyl)butylcarbamate (100 mg, 0.20 mmol) was reacted with HCl in ether (10 mL) to afford the desired product (75 mg, 94%) as an off-white solid: ESI MS m/z 393 [C23H24N2O2S+H]+.


Example 1273
9-(4-(1-Aminopropan-2-yl)-3-fluorophenyl)-8-methoxy-6-methylthieno[2,3-c]quinolin-4(5H)-one Hydrochloride



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Following General Procedure D1, tert-butyl 2-(2-fluoro-4-(8-methoxy-6-methyl-4-oxo-4,5-dihydrothieno[2,3-c]quinolin-9-yl)phenyl)propylcarbamate (200 mg, 0.40 mmol) was reacted with HCl in ether (20 mL) to afford the desired product (145 mg, 91%) as an off-white solid: 1H NMR (500 MHz, DMSO-d6) δ 10.80 (s, 1H), 8.06 (s, 3H), 7.74 (dd, J=14.6, 5.4 Hz, 1H), 7.52 (t, J=7.9 Hz, 1H), 7.30 (s, 1H), 7.16-7.02 (m, 2H), 5.87 (dd, J=43.2, 5.4 Hz, 1H), 3.70 (s, 3H), 3.51-3.40 (m, 1H), 3.26-3.07 (m, 2H), 2.59 (s, 3H), 1.39 (t, J=7.6 Hz, 3H); ESI MS m/z 397 [C22H21FN2O2S+H]+; HPLC 98.8% (AUC), tR=11.60 min.


Example 1283
9-(4-(1-Amino-3-methylbutan-2-yl)-3-fluorophenyl)-8-methoxy-6-methylthieno[2,3-c]quinolin-4(5H)-one Hydrochloride



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Following General Procedure D1, tert-butyl 2-(2-fluoro-4-(%-methoxy-6-methyl-4-oxo-4,5-dihydrothieno[2,3-c]quinolin-9-yl)phenyl)-3-methylbutylcarbamate (52 mg, 0.10 mmol) was reacted with HCl in ether (5 mL) to afford the desired product (25 mg, 59%) as an off-white solid; 1H NMR (500 MHz, DMSO-d6) δ 7.69 (dd, J=16.1, 5.4 Hz, 1H), 7.41 (dt, J=13.3, 8.0 Hz, 1H), 7.29 (d, J=3.4 Hz, 1H), 7.10-6.98 (m, 2H), 5.89-5.72 (m, 1H), 3.71 (t, J=6.8 Hz, 3H), 3.19-2.83 (m, 3H), 2.59 (s, 3H), 2.03 (dt, J=13.5, 6.7 Hz, 1H), 0.99 (t, J=10.0 Hz, 3H), 0.82 (dd, J=9.9, 6.8 Hz, 3H): ESI MS m/z 425 [C24H25FN2O2S+H]+; HPLC 93.4% (AUC), tR=11.20 min.


Example 556
8-Methoxy-6-methyl-9-(4-(3-methyl-1-(methylamino)butan-2-yl)phenyl)thieno[2,3-c]quinolin-4(5H)-one Hydrochloride



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Following General Procedure D1, tert-butyl 2-(4-(8-methoxy-6-methyl-4-oxo-4,5-dihydrothieno[2,3-c]quinolin-9-yl)phenyl)-3-methylbutyl(methyl)carbamate (100 mg, 0.2 mmol) was reacted with HCl in ether (8 mL) to afford the desired product (40 mg, 47%) as an off-white solid: ESI MS m/z 421 [C25H28N2O2S+H]+


Example 1286
9-(3-Fluoro-4-(1-(methylamino)propan-2-yl)phenyl)-8-methoxy-6-methylthieno[2,3-c]quinolin-4(5H)-one Hydrochloride



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Following General Procedure D1, tert-butyl 2-(2-fluoro-4-(8-methoxy-6-methyl-4-oxo-4,5-dihydrothieno[2,3-c]quinolin-9-yl)phenyl)propyl(methyl carbamate (100 mg, 0.20 mmol) was reacted with HCl in ether (5 mL) to afford the desired product (75 mg, 93%) as an off-white solid: 1H NMR (500 MHz, DMSO-d6) δ 10.80 (s, 1H), 7.75 (dd, J=11.7, 5.4 Hz, 1H), 7.52 (t, J=7.8 Hz, 1H), 7.30 (s, 1H), 7.17-7.04 (m, 2H), 5.87 (dd, J=35.8, 5.4 Hz, 1H), 3.71 (s, 3H), 3.55 (dd, J=14.0, 6.8 Hz, 1H), 3.28 (m, 2H), 2.63 (d, J=5.5 Hz, 3H), 2.59 (s, 3H), 1.39 (dt, J=17.4, 7.6 Hz, 3H); ESI MS m/z 411 [C23H23FN2O2S+H]+; HPLC 98.9% (AUC), tR=10.75 min.


Example 557
9-(3-Fluoro-4-(3-methyl-1-(methylamino)butan-2-yl)phenyl)-8-methoxy-6-methylthieno[2,3-c]quinolin-4(5H)-one Hydrochloride



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Following General Procedure D1, tert-butyl 2-(2-fluoro-4-(8-methoxy-6-methyl-4-oxo-4,5-dihydrothieno[2,3-c]quinolin-9-yl)phenyl)-3-methylbutyl(methyl)carbamate (100 mg, 0.18 mmol) was reacted with HCl in ether (6 mL) to afford the desired product (55 mg, 70%) as an off-white solid: ESI MS m/z 439 [C25H27FN2O2S+H]+


Example 1317
(R)-9-(4-(1-aminopropan-2-yl)-3-fluorophenyl)-8-methoxy-6-methylthieno[2,3-c]quinolin-4(5H)-one Hydrochloride



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Following General Procedure D1, (R)-tert-butyl 2-(2-fluoro-4-(8-methoxy-6-methyl-4-oxo-4,5-dihydrothieno[2,3-c]quinolin-9-yl)phenyl)propylcarbamate (510 mg, 1.1 mmol) was reacted with HCl in ether (25 mL) to afford the desired product (312 mg, 78%) as an off-white solid: ESI MS m/z 397 [C22H21FN2O2S+H]+


Example 1310
(S)-9-(4-(1-Aminopropan-2-yl)-3-fluorophenyl)-8-methoxy-6-methylthieno[2,3-c]quinolin-4(5H)-one Hydrochloride



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Following General Procedure D1, i(S)-tert-butyl 2-(2-fluoro-4-(8-methoxy-6-methyl-4-oxo-4,5-dihydrothieno[2,3-c]quinolin-9-yl)phenyl)propylcarbamate (520 mg, 1.1 mmol) was reacted with HCl (25 ml) to afford desire product (300 mg, 74%) as an off-white solid: 1H NMR (500 MHz, MeOD) δ 7.63 (d, J=5.4 Hz, 1H), 7.51 (dt, J=23.5, 7.8 Hz, 1H), 7.29 (s, 1H), 7.14-7.02 (m, 2H), 6.16-6.05 (m, 1H), 3.76 (s, 3H), 3.54 (ddd, J=46.9, 14.5, 7.3 Hz, 1H), 3.43-3.20 (m, 2H), 1.51 (d, J=7.0 Hz, 3H); ESI MS m/z 397 [C22H21FN2O2S+H]+; HPLC 98.9% (AUC), tR=10.75 min.


Example 1387
(S)-9-(4-(1-(dimethylamino)propan-2-yl)-3-fluorophenyl)-8-methoxy-6-methylthieno[2,3-c]quinolin-4(5H)-one Hydrochloride



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To a solution of (S)-9-(4-(1-aminopropan-2-yl)-3-fluorophenyl)-8-methoxy-6-methylthieno[2,3-c]quinolin-4(5H)-one hydrochloride (110 mg, 0.27 mmol)) in a 1:1 mixture of MeOH/THF (3 mL) was added paraformaldehyde (7.5 mg, 0.24 mmol) followed by NaCNBH3 (70 mg 1.2 mmol) and stirred at rt for 16 h. The reaction mixture was quenched by the addition of 2 N NaHCO3 (1 mL), eluted through an SCX ion-exchange column and converted to HCl salt using General Procedure D-2 (Scheme II) to obtain the desired product (67 mg, 60%) as a white solid: ESI MS m/z 425 [C24H25FN2O2S+H]+;


Example 558
(R)-9-(4-(1-Aminopropan-2-yl)phenyl)-8-methoxythieno[2,3-c]quinolin-4(5H)-one



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Following General Procedure C (R)-tert-butyl 2-(4-(8-methoxy-4-oxo-4,5-dihydrothieno[2,3-c]quinolin-9-yl)phenyl)propylcarbamate (2.5 g, 5.4 mmol) was reacted with TFA (10 mL) to afford the desired product (1.6 g, 81%) as an off-white solid: ESI MS m/z 365 [C21H20N2O2S+H]+


Example 1205
N-(1-Chloropropan-2-yl)-4-(8-methoxy-4-oxo-4,5-dihydrothieno[2,3-c]quinolin-9-yl)benzenesulfonamide



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To a mixture of N-(1-hydroxypropan-2-yl)-4-(8-methoxy-4-oxo-4,5-dihydrothieno[2,3-c]quinolin-9-yl)benzenesulfonamide (140 mg, 0.30 mmol) and triphenylphosphine (160 mg, 0.62 mmol) in DMF/CCl4 (1 mL/3 mL) was added NCS (41 mg, 0.31 mmol) and the reaction mixture was stirred at room temperature for 15 h. The reaction mixture was diluted with water (ca. 20 mL), and extracted with DCM (1×50 mL). The extract was washed with water (2×20 mL), brine (1×10 mL), dried over sodium sulfate, and evaporated under vacuum. The residue was purified by flash chromatography to afford the desired product (100 mg, 74%) as light yellow solid; ESI MS m/z 464 [C21H19ClN2O4S+H]+


Example 1239
9-(4-(2-Amino-1-cyclopentylethyl)phenyl)-8-methoxythieno[2,3-c]quinolin-4(5H)-one Hydrochloride



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Following General Procedure D, tert-butyl 2-cyclopentyl-2-(4-(8-methoxy-4-oxo-4,5-dihydrothieno[2,3-c]quinolin-9-yl)phenyl)ethylcarbamate (50 mg, 0.10 mmol) was reacted with HCl in ether (5 mL) to afford the desired product (29 mg, 69%) as an off-white solid: ESI MS m/z 419 [C25H26N2O2S+H]+; 1H NMR (500 MHz, DMSO-d6) δ 7.59 (d, J=5.4 Hz, 1H), 7.59 (d, J=5.4 Hz, 1H), 7.54 (d, J=9.0 Hz, 1H), 7.54 (d, J=9.0 Hz, 1H), 7.48 (d, J=7.9 Hz, 1H), 7.48 (d, J=7.9 Hz, 1H), 7.44-7.36 (m, 2H), 7.45-7.35 (m, 2H), 7.28-7.19 (m, 2H), 7.28-7.19 (m, 2H), 5.72 (d, J=5.4 Hz, 1H), 5.72 (d, J=5.4 Hz, 1H), 3.70 (s, 3H), 3.33-3.20 (m, 2H), 2.84 (td, J=9.2, 6.0 Hz, 1H), 2.20-2.03 (m, 1H), 1.98-1.84 (m, 1H), 1.76-1.35 (m, 5H), 1.28 (dq, J=18.0, 8.9 Hz, 1H), 1.18-1.02 (m, 1H). HPLC >99% (AUC), tR=12.45 min.


Example 1301
8-Methoxy-6-methyl-9-(4-(piperidin-3-yl)phenyl)thieno[2,3-c]quinolin-4(5H)-one Hydrochloride



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Following General Procedure D1, tert-butyl 3-(4-(8-methoxy-6-methyl-4-oxo-4,5-dihydrothieno[2,3-c]quinolin-9-yl)phenyl)piperidine-1-carboxylate (50 mg, 0.10 mmol) was reacted with HCl in ether (2.5 mL) to afford the desired product (31 mg, 77%) as an off-white solid: ESI MS m/z 405 [C24H24N2O2S+H]+


Example 1396
9-(4-((2-aminoethyl)(methyl)amino)phenyl)-8-methoxy-6-methylthieno[2,3-c]quinolin-4(5H)-one Hydrochloride



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Following General Procedure D1, tert-butyl 2-((4-(8-methoxy-6-methyl-4-oxo-4,5-dihydrothieno[2,3-c]quinolin-9-yl)phenyl)methyl)amino)ethylcarbamate (100 mg, 0.20 mmol) was reacted with HCl in ether (10 mL) to afford the desired product (65 mg, 83%) as an off-white solid: ESI MS m/z 394 [C22H23N3O2S+H]+


Example 559
tert-Butyl 1-(4-(8-methoxy-4-oxo-4,5-dihydrothieno[2,3-c]quinolin-9-yl)phenyl)ethylcarbamate



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Following General Procedure B, 9-bromo-8-methoxythieno[2,3-c]quinolin-4(5H)-one (600 mg, 1.9 mmol) was reacted with tert-butyl 1-(4-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)phenyl)ethylcarbamate (1.34 g, 3.87 mmol) to afford the desired product (340 mg, 39%) as a brown solid: ESI MS m/z 451 [C25H26N2O4S+H]+.


Example 560
(R)-tert-Butyl 1-(4-(8-methoxy-4-oxo-4,5-dihydrothieno[2,3-c]quinolin-9-yl)phenyl)ethyl(methyl)carbamate



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Following General Procedure B, 9-bromo-8-methoxythieno[2,3-c]quinolin-4(5H)-one (300 mg, 0.97 mmol) was reacted with (R)-tert-butyl methyl(1-(4-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)phenyl)ethyl)carbamate (520 mg, 1.45 mmol) to afford the desired product (120 mg, 27%) as a brown solid: ESI MS m/z 465 [C26H28N2O4S+H]+.


Example 561
tert-butyl 1-(4-(8-methoxy-4-oxo-4,5-dihydrothieno[2,3-c]quinolin-9-yl)phenyl)propan-2-ylcarbamate



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Following General Procedure B, 9-bromo-8-methoxythieno[2,3-c]quinolin-4(5H)-one (1.5 g, 4.4 mmol) was reacted with tert-butyl 1-(4-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)phenyl)propan-2-ylcarbamate (2.6 g, 7.3 mmol) to afford the desired product (1.1 g, 50%) as a brown solid: ESI MS m/z 465 [C26H28N2O4S+H]+.


Example 562
tert-butyl 2-(2-chloro-4-(8-methoxy-4-oxo-4,5-dihydrothieno[2,3-c]quinolin-9-yl)phenyl)propylcarbamate



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Following General Procedure B, 9-bromo-8-methoxythieno[2,3-c]quinolin-4(5H)-on (3.0 g, 9.7 mmol) was reacted with tert-butyl 2-(2-chloro-4-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)phenyl)propylcarbamate (5.7 g, 14 mmol) to afford the desired product (2.7 g, 56%) as a brown solid: ESI MS m/z 499 [C26H27ClN2O4S+H]+.


Example 563
2-(4-(8-Methoxy-4-oxo-4,5-dihydrothieno[2,3-c]quinolin-9-yl)phenyl)propanenitrile



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Following General Procedure B, 9-bromo-8-methoxythieno[2,3-c]quinolin-4(5H)-one (500 mg, 1.6 mmol) was reacted with 2-(4-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)phenyl)propanenitrile (600 g, 2.2 mmol) to afford the desired product (350 mg, 62%) as a brown solid: ESI MS m/z 361 [C21H16N2O2S+H]+.


Example 564
tert-Butyl 2-(4-(8-methoxy-4-oxo-4,5-dihydrothieno[2,3-c]quinolin-9-yl)phenyl)-2-methylpropylcarbamate



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Following General Procedure B, 9-bromo-8-methoxythieno[2,3-c]quinolin-4(5H)-one (2.0 g, 6.4 mmol) was reacted with tert-butyl 2-methyl-2-(4-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)phenyl)propylcarbamate (3.6 g, 9.7 mmol) to afford the desired product (864 mg, 28%) as a brown solid: ESI MS m/z 479 [C27H30N2O4S+H]+.


Example 565
(R)-tert-Butyl 1-(4-(8-methoxy-4-oxo-4,5-dihydrothieno[2,3-c]quinolin-9-yl)phenyl)ethylcarbamate



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Following General Procedure B, 9-bromo-8-methoxythieno[2,3-c]quinolin-4(5H)-one (3.0 g, 9.7 mmol) was reacted with (R)-tert-butyl 1-(4-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)phenyl)ethylcarbamate (5.0 g, 14 mmol) to afford the desired product (2.0 g, 47%) as a brown solid: ESI MS m/z 451 [C25H26N2O4S+H]+.


Example 566
tert-Butyl 2-ethyl-2-(4-(8-methoxy-4-oxo-4,5-dihydrothieno[2,3-c]quinolin-9-yl)phenyl)butylcarbamate



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Following General Procedure B, 9-bromo-8-methoxythieno[2,3-c]quinolin-4(5H)-one (120 mg, 0.39 mmol) was reacted with 2-ethyl-2-(4-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)phenyl)butan-1-amine (220 mg, 0.58 mmol) to afford the desired product (50 mg, 27%) as a brown solid: ESI MS m/z 507 [C29H34N2O4S+H]+.


Example 567
tert-Butyl 2-fluoro-4-(8-methoxy-4-oxo-4,5-dihydrothieno[2,3-c]quinolin-9-yl)phenethylcarbamate



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Following General Procedure B, 9-bromo-8-methoxythieno[2,3-c]quinolin-4(5H)-one (1.5 g, 4.8 mmol) was reacted with tert-butyl 2-fluoro-4-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)phenethylcarbamate (2.6 g, 7.3 mmol) to afford the desired product (1.5 g, 65%) as a brown solid: ESI MS m/z 469 [C25H25FN2O4S+H]+.


Example 568
(R)-tert-Butyl 2-(4-(8-methoxy-4-oxo-4,5-dihydrothieno[2,3-c]quinolin-9-yl)phenyl)propylcarbamate



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Following General Procedure B, 9-bromo-8-methoxythieno[2,3-c]quinolin-4(5H)-one (1.5 g, 4.4 mmol) was reacted with (R)-tert-butyl 2-(4-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)phenyl)propylcarbamate (2.0 g, 6.4 mmol) to afford the desired product (1.4 g, 48%) as a brown solid: ESI MS m/z 465 [C26H28N2O4S+H]+.


Example 569
tert-Butyl 2-(2-fluoro-4-(8-methoxy-4-oxo-4,5-dihydrothieno[2,3-c]quinolin-9-yl)phenyl)propylcarbamate



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Following General Procedure B, 9-bromo-8-methoxythieno[2,3-c]quinolin-4(5H)-one (1.2 g, 3.8 mmol) was reacted with tert-butyl 2-(2-fluoro-4-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)phenyl)propylcarbamate (2.2 g, 5.8 mmol) to afford the desired product (905 mg, 51%) as a brown solid: ESI MS m/z 483 [C26H27FN2O4S+H]+.


Example 570
(R)-tert-Butyl 2-(4-(8-methoxy-4-oxo-4,5-dihydrothieno[2,3-c]quinolin-9-yl)phenyl)propyl(methyl)carbamate



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Following General Procedure B, 9-bromo-8-methoxythieno[2,3-c]quinolin-4(5H)-one (700 mg, 2.3 mmol) was reacted with (R)-tert-butyl methyl(2-(4-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)phenyl)propyl)carbamate (1.3 g, 3.4 mmol) to afford the desired product (383 mg, 38%) as a yellow solid: ESI MS m/z 479 [C27H30N2O4S+H]+.


Example 571
tert-Butyl 4-(8-methoxy-4-oxo-4,5-dihydrothieno[2,3-c]quinolin-9-yl)phenethylcarbamate



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Following General Procedure B, 9-bromo-8-methoxythieno[2,3-c]quinolin-4(5-1H)-one (2.0 g, 6.4 mmol) was reacted with tert-butyl 4-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)phenethylcarbamate (3.4 g, 9.4 mmol) to afford the desired product (1.93 g, 65%) as a brown solid: ESI MS m/z 451 [(C25H26N2O4S+H]+.


Example 572
2-(4-(8-Methoxy-4-oxo-4,5-dihydrothieno[2,3-c]quinolin-9-yl)phenyl)propanenitrile



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Following General Procedure B, 9-bromo-8-methoxythieno[2,3-c]quinolin-4(5H)-one (1.5 g, 4.84 mmol) was reacted with 2-(4-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)phenyl)propanenitrile (1.87 g, 7.26 mmol) to afford the desired product (1.45 g, 82%) as a brown solid: ESI MS m/z 361 [C21H16N2O2S+H]+.


Example 573
(R)-tert-Butyl 2-(4-(8-methoxy-6-methyl-4-oxo-4,5-dihydrothieno[2,3-c]quinolin-9-yl)phenyl)propylcarbamate



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Following General Procedure B, 9-bromo-8-methoxy-6-methylthieno[2,3-c]quinolin-4(5H)-one (3.0 g, 9.26 mmol) was reacted with (R)-tert-butyl 2-(4-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)phenyl)propylcarbamate (5.2 g, 13.89 mmol) to afford the desired product (1.60 g, 35%) as a brown solid: ESI MS m/z 479 [C27H30N2O4S+H]+.


Example 574
tert-Butyl 2-(4-(8-methoxy-4-oxo-4,5-dihydrothieno[2,3-c]quinolin-9-yl)phenyl)propylcarbamate



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Following General Procedure B, 9-bromo-8-methoxythieno[2,3-c]quinolin-4(5H)-one (800 mg, 4.84 mmol) was reacted with tert-butyl 2-(4-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)phenyl)propylcarbamate (1.5 g, 4.16 mmol) to afford the desired product (550 mg, 46%) as a brown solid: ESI MS m/z 465 [C26H28N2O4S+H]+.


Example 575
tert-Butyl 2-(4-(8-methoxy-6-methyl-4-oxo-4,5-dihydrothieno[2,3-c]quinolin-9-yl)phenyl)-2-methylpropylcarbamate



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Following General Procedure B, 9-bromo-8-methoxy-6-methylthieno[2,3-c]quinolin-4(5H)-one (200 mg, 0.62 mmol) was reacted with tert-butyl 2-methyl-2-(4-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)phenyl)propylcarbamate (350 mg, 0.93 mmol) to afford the desired product (95 mg, 62%) as a brown solid: ESI MS m/z 493 [C28H32N2O4S+H]+.


Example 576
tert-Butyl 1-(4-(8-methoxy-6-methyl-4-oxo-4,5-dihydrothieno[2,3-c]quinolin-9-yl)phenyl)propan-2-ylcarbamate



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Following General Procedure B, 9-bromo-8-methoxy-6-methylthieno[2,3-c]quinolin-4(5H)-one (260 mg, 0.80 mmol) was reacted with tert-butyl 1-(4-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)phenyl)propan-2-ylcarbamate (430 g, 1.2 mmol) to afford the desired product (212 mg, 55%) as a yellow oil: ESI MS m/z 479 [C27H30N2O4S+H]+.


Example 577
tert-Butyl 1-(4-(6-chloro-%-methoxy-4-oxo-4,5-dihydrothieno[2,3-c]quinolin-9-yl)phenyl)ethylcarbamate



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Following General Procedure H, tert-butyl 1-(4-(8-methoxy-4-oxo-4,5-dihydrothieno[2,3-c]quinolin-9-yl)phenylethylcarbamate) (130 mg, 0.37 mmol) was reacted with NCS (64 mg, 0.48 mmol) to afford the desired product (58 mg, 32%) as a yellow solid. ESI MS m/z 485 [C25H25ClN2O4S+H]+.


Example 578
(S)-tert-Butyl 1-(4-(6-chloro-8-methoxy-4-oxo-4,5-dihydrothieno[2,3-c]quinolin-9-yl)phenyl)propyl(methyl)carbamate



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Following General Procedure H, ((S)-tert-butyl 1-(4-(8-methoxy-4-oxo-4,5-dihydrothieno[2,3-c]quinolin-9-yl)phenyl)propyl(methyl)carbamate) (200 mg, 0.41 mmol) was reacted with NCS (68 mg, 0.50 mmol) to afford the desired product (130 mg, 61%) as a yellow solid: ESI MS m/z 513 [C27H29ClN2O4S+H]+.


Example 579
(S)-tert-Butyl 2-(4-(6-chloro-8-methoxy-4-oxo-45-dihydrothieno[2,3-c]quinolin-9-yl)phenyl)propylcarbamate



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Following General Procedure H, (S)-tert-butyl 2-(4-(8-methoxy-4-oxo-4,5-dihydrothieno[2,3-c]quinolin-9-yl)phenyl)propylcarbamate (500 mg, 1.08 mmol) was reacted with NCS (175 mg, 1.29 mmol)) to afford the desired product (310 mg, 58%) as a yellow solid: ESI MS m/z 499 [C26H27ClN2O4S+H]+.


Example 580
tert-Butyl (1-(4-(6-chloro-8-methoxy-4-oxo-4,5-dihydrothieno[2,3-c]quinolin-9-yl)phenyl)cyclopropyl)methylcarbamate



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Following General Procedure H, tert-butyl (1-(4-(8-methoxy-4-oxo-4,5-dihydrothieno[2,3-c]quinolin-9-yl phenyl)cyclopropyl)methylcarbamate (300 mg, 0.629 mmol) was reacted with NCS (85 mg, 0.629 mmol) to afford the desired product (250 mg, 78%) as a yellow solid: ESI MS m/z 511 [C27H27ClN2O4S+H]+.


Example 581
tert-Butyl 2-chloro-44-(6-chloro-8-methoxy-4-oxo-4,5-dihydrothieno[2,3-c]quinolin-9-yl)phenethylcarbamate



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Following General Procedure H, tert-butyl 2-chloro-44-(8-methoxy-4-oxo-4,5-dihydrothieno[2,3-c]quinolin-9-yl)phenethylcarbamate (127 mg, 0.26 mmol) was reacted with NCS (43 mg, 0.312 mmol) to afford the desired product (70 mg, 52%) as a yellow solid: ESI MS m/z 519 [C25H25Cl2N2O4S+H]+.


Example 582
tert-Butyl 2-(4-(6-chloro-8-methoxy-4-oxo-4,5-dihydrothieno[2,3-c]quinolin-9-yl)phenyl)butylcarbamate



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Following General Procedure H, tert-butyl 2-(4-(8-methoxy-4-oxo-4,5-dihydrothieno[2,3-c]quinolin-9-yl)phenyl)butylcarbamate (100 mg, 0.21 mmol) in (DMF) was reacted with NCS (34 mg, 0.25 mmol) to afford the desired product (65 mg, 61%) as a yellow solid: ESI MS m/z 513 [C27H29ClN2O4S+H]+.


Example 583
tert-Butyl 4-(6-chloro-8-methoxy-4-oxo-4,5-dihydrothieno[2,3-c]quinolin-9-yl)phenethyl(methyl)carbamate



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Following General Procedure H, tert-butyl 4-(8-methoxy-4-oxo-4,5-dihydrothieno[2,3-c]quinolin-9-yl)phenethyl(methyl)carbamate (200 mg, 0.43 mmol) in (DMF) was reacted with NCS (70 mg, 0.50 mmol) to afford the desired product (120 mg, 55%) as a yellow solid: ESI MS m/z 500 [C26H27ClN2O4S+H]+.


Example 584
(R)-tert-Butyl 1-(4-(6-chloro-8-methoxy-4-oxo-4,5-dihydrothieno[2,3-c]quinolin-9-yl)phenyl)ethylcarbamate



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Following General Procedure H, (R)-tert-butyl 1-(4-(8-methoxy-4-oxo-4,5-dihydrothieno[2,3-c]quinolin-9-yl)phenyl)ethylcarbamate (300 mg, 0.67 mmol) was reacted with NCS (110 mg, 0.87 mmol) to afford the desired product (27 mg, 11%) as a yellow solid: ESI MS m/z 485 [C25H25ClN2O4S+H]+.


Example 585
tert-Butyl 4-(6-chloro-8-methoxy-4-oxo-4,5-dihydrothieno[2,3-c]quinolin-9-yl)-2-fluorophenethylcarbamate



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Following General Procedure H, tert-butyl 2-fluoro-4-(8-methoxy-4-oxo-4,5-dihydrothieno[2,3-c]quinolin-9-yl)phenethylcarbamate (300 mg, 0.64 mmol) was reacted with NCS (94 mg, 0.71 mmol) to afford the desired product (150 mg, 46%) as a yellow solid. ESI MS m/z 503 [C25H21ClFN2O4S+H]+.


Example 586
tert-Butyl 1-(4-(6-chloro-8-methoxy-4-oxo-4,5-dihydrothieno[2,3-c]quinolin-9-yl)phenyl)propan-2-ylcarbamate



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Following General Procedure H, tert-butyl 1-(4-(8-methoxy-4-oxo-4-oxo-4,5-dihydrothieno[2,3-c]quinolin-9-yl)phenyl)propan-2-ylcarbamate (220 mg, 0.47 mmol) was reacted with NCS (69 mg, 0.52 mmol) to afford the desired product (60 mg, 26%) as a brown solid. ESI MS m/z 499 [C26H27ClN2O4S+H]+.


Example 1041
9-(4-(1-Aminoethyl)phenyl)-6-chloro-8-hydroxythieno[2,3-c]quinolin-4(5H)-one Hydrochloride



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Following General Procedure F, tert-butyl 1-(4-(6-chloro-8-methoxy-4-oxo-4,5-dihydrothieno[2,3-c]quinolin-9-yl)phenyl)ethylcarbamate (50 mg, 0.10 mmol) was treated with BBr3 (1.0 M in CH2Cl2, 2 mL, 2 mmol) to afford the desired product (21 mg, 58%) as a light yellow solid (21 mg, 58%): 1H NMR (500 MHz, CD4OD) δ 7.65 (dt, J=5.2, 3.4 Hz, 2H), 7.59 (d, J=5.4 Hz, 1H), 7.41 (dt, J=4.0, 2.6 Hz, 2H), 7.30 (s, 1H), 6.07 (d, J=: 5.4 Hz, 1H), 4.62 (q, J=6.8 Hz, 1H), 1.76 (d, J=6.9 Hz, 3H); ESI MS m/z 371 [C19H15ClN1O2S+H]+; HPLC 97.8% (AUC), tR=9.72 min.


Example 1052
(R)-8-Hydroxy-9-(4-(1-(methylamino)ethyl)phenyl)thieno[2,3-c]quinolin-4(5)-one Hydrochloride



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Following General Procedure F, (R)-tert-butyl 1-(4-(8-methoxy-4-oxo-4,5-dihydrothieno[2,3-c]quinolin-9-yl)phenyl)ethyl(methyl)carbamate (120 mg, 0.25 mmol was treated with BBr3 (1.0 M in CH2Cl2, 3 mL, 3 mmol) to afford the desired product (50 mg, 56%) as a light yellow solid: 1H NMR (500 MHz, CD3OD) δ 7.64 (ddd, J=7.1, 5.6, 2.3 Hz, 2H), 7.57 (d, J=5.4 Hz, 1H), 7.49-7.39 (m, 3H), 7.18 (d, J=8.9 Hz, 1H), 6.04 (d, J=5.4 Hz, 1H), 4.48 (q, J=7.0 Hz, 1H), 2.72 (s, 3H), 1.80 (d, J=6.9 Hz, 3H); ESI MS m/z 351 [C20H18N2O2S+H]+; HPLC 97.6% (AUC), tR=7.82 min.


Example 1081
(R)-9-(4-(1-Aminoethyl)phenyl)-6-chloro-8-hydroxythieno[2,3-c]quinolin-4(5H)-one Hydrochloride



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Following General Procedure F, tert-butyl 1-(4-(6-chloro-8-methoxy-4-oxo-4,5-dihydrothieno[2,3-c]quinolin-9-yl)phenyl)ethylcarbamate (0.35 mg, 0.07 mmol) was treated with BBr3 (1.0 M in CH2Cl2, 2 mL, 2 mmol) to afford the desired product (23 mg, 84%) as a light yellow solid: 1H NMR (500 MHz, CD3OD) δ 7.67-7.61 (m, 2H), 7.59 (d, J=5.4 Hz, 1H), 7.44-7.39 (m, 2H), 7.30 (s, 1H), 6.07 (d, J=5.4 Hz, 1H), 4.62 (q, J=6.8 Hz, 1H), 1.76 (d, J=6.9 Hz, 3H); ESI MS m/z 371 [C19H15ClN2O2S+H]+; HPLC 97.2% (AUC), tR=9.58 min.


Example 1209
9-(4-(3-(Aminomethyl)pentan-3-yl)phenyl)-8-hydroxythieno[2,3-c]quinolin-4(5H)-one Hydrochloride



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Following General Procedure F, tert-butyl 2-ethyl-2-(4-(8-methoxy-4-oxo-4,5-dihydrothieno[2,3-c]quinolin-9-yl)phenyl)butyl)butylcarbamate (20 mg, 0.05 mmol) was treated with BBr3 (1.0 M in CH2Cl2, 3 mL, 3 mmol) to afford the desired product (7.0 mg, 36%) as a light yellow solid: 1H NMR (500 MHz, CD3OD) δ 7.63 (d, J=8.4 Hz, 2H), 7.54 (d, J=5.4 Hz, 1H), 7.45-7.37 (m, 3H), 7.19 (dd, J=8.9, 2.2 Hz, 1H), 6.08 (d, J=5.4 Hz, 1H), 3.29 (s, 2H), 1.97 (dt, J=14.6, 7.2 Hz, 4H), 0.93 (t, J=7.4 Hz, 6H). ESI MS m/z 393 [C23H24N2O2S+H]+; HPLC 99.6% (AUC), tR=9.47 min.


Example 1213
9-(4-(2-Aminoethyl)-3-fluorophenyl)-6-bromo-8-hydroxythieno[2,3-c]quinolin-4(5H)-one Hydrochloride



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Following General Procedure F, tert-butyl 4-(6-bromo-8-methoxy-4-oxo-4,5-dihydrothieno[2,3-c]quinolin-9-yl)-2-fluorophenethylcarbamate (100 mg, 0.18 mmol) was treated with BBr3 (1.0 M in CH2Cl2, 5 mL, 5 mmol) to afford the desired product as an off-white solid (24 mg, 30%): 1H NMR (500 MHz, CD3OD) δ 7.69 (d, J=5.4 Hz, 1H), 7.51 (t, J=7.7 Hz, 1H), 7.48 (s, 1H), 7.14 (d, J=9.0 Hz, 2H), 6.18 (d, J=5.4 Hz, 1H), 3.37-3.20 (m, 3H), 3.14-3.04 (m, 1H); ESI MS m/z 433 [C19H14BrFN2O2S+H]+; HPLC 98.6% (AUC), tR=9.12 min.


Example 1217
9-(4-(2-Aminoethyl)-3-fluorophenyl)-8-hydroxy-6-methylthieno[2,3-c]quinolin-4(5H)-one Hydrochloride



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Following General Procedure F, tert-butyl 2-fluoro-4-(8-methoxy-6-methyl-4-oxo-4,5-dihydrothieno[2,3-c]quinolin-9-yl)phenethylcarbamate (78 mg, 0.16 mmol) was treated with BBr3 (1.0 M in CH2Cl2, 3 mL, 3 mmol) to afford the desired product as a yellow solid (16 mg, 27%): 1H NMR (500 MHz, CD3OD) δ 7.62 (d, J=5.4 Hz, 1H), 7.49 (t, J=7.9 Hz, 1H), 7.14-7.05 (m, 3H), 6.21 (d, J=5.4 Hz, 1H), 3.36-3.21 (m, 2H), 3.13-3.04 (m, 1H), 2.57 (s, 3H); ESI MS m/z 369 [C20H17FN2O2S+H]+; HPLC 97.3% (AUC), tR=8.47 min.


Example 1166
(R)-9-(4(1-Aminopropan-2-yl)phenyl)-6-chloro-8-hydroxythieno[2,3-c]quinolin-4(5H)-one Hydrochloride



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Following General Procedure F, (R)-tert-butyl 2-(4-(6-chloro-8-methoxy-4-oxo-4,5-dihydrothieno[2,3-c]quinolin-9-yl)phenyl)propylcarbamate (100 mg, 0.20 mmol) was treated with BBr3 (1.0 M in CH2Cl2, 5 mL, 5 mmol) to afford the desired product as a white solid (23 mg, 30%): 1H NMR (500 MHz, CD3OD) δ 7.63 (d, J=5.4 Hz, 1H), 7.56 (dd, J=7.9, 1.9 Hz, 1H), 7.47 (dd, J=7.8, 1.9 Hz, 1H), 7.39-7.28 (m, 3H), 6.12 (d, J=5.4 Hz, 1H), 3.36-3.13 (m, 3H), 1.49 (d, J=6.5 Hz, 3H); ESI MS m/z 385 [C20H17ClN2O2S+H]+; HPLC 98.4% (AUC), tR=9.19 min.


Example 1174
9-(4-(1-Aminopropan-2-yl)-3-fluorophenyl)-8-hydroxythieno[2,3-c]quinolin-4(5H)-one Hydrochloride



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Following General Procedure F, tert-butyl 2-(2-fluoro-4-(8-methoxy-4-oxo-4,5-dihydrothieno[2,3-c]quinolin-9-yl)phenyl)propylcarbamate (120 mg, 0.25 mmol) was treated with BBr3 (1.0 M in CH2Cl2, 5 mL, 5 mmol) to afford the desired product as an off-white solid (35 mg, 37%). 1H NMR (500 MHz, CD3OD) δ 7.65 (dd, J=5.4, 3.4 Hz, 1H), 7.59 (s, 1H), 7.51 (s, 1H), 7.43 (dd, J=8.9, 2.3-1Hz, 1H), 7.24-7.09 (m, 2H), 6.22 (dd, J=9.4, 5.4 Hz, 1H), 3.62 (d, J=7.2 Hz, 1H), 3.49-3.25 (m, 2H), 1.52 (t, J=6.7 Hz, 3H); ESI MS m/z 369 [C20H17FN2O2S+H]+; HPLC 99.3% (AUC), tR=8.37 min.


Example 1187
(R)-8-Hydroxy-9-(4-(1-(methylamino)propan-2-yl)phenyl)thieno[2,3-c]quinolin-4(5H)-one Hydrochloride



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Following General Procedure F (R)-tert-butyl 2-(4-(8-methoxy-4-oxo-4,5-dihydrothieno[2,3-c]quinolin-9-yl)phenyl)propyl(methyl)carbamate (250 mg, 0.52 mmol) was treated with BBr3 (1.0 M in CH2Cl2, 4 mL, 4 mmol) to afford the desired product as an light yellow solid (39 mg, 42%). 1H NMR (500 MHz, CD3OD) δ 7.58 (dd, J=10.8, 3.6 Hz, 2H), 7.50-7.46 (m, 1H), 7.42 (d, J=8.9 Hz, 1H), 7.38 (dd, J=7.9, 1.8 Hz, 1H), 7.32 (dd, J=7.7, 1.7 Hz, 1H), 7.18 (d, J=8.9 Hz, 1H), 6.14 (d, J=5.4 Hz, 1H), 3.37-3.28 (m, 3H), 2.75 (s, 3H), 1.50 (d, J=6.7 Hz, 3H); ESI MS m/z 365 [C21H20N2O2S+H]+; HPLC 97.1% (AUC), tR=8.43 min.


Example 1190
9-(4-(1-Aminopropan-2-yl)-3-fluorophenyl)-8-hydroxy-6-methylthieno[2,3-c]quinolin-4(5H)-one Hydrochloride



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Following General Procedure F, tert-butyl 2-(2-fluoro-4-(8-methoxy-6-methyl-4-oxo-4,5-dihydrothieno[2,3-e]quinolin-9-yl)phenyl)propylcarbamate (120 mg, 0.25 mmol) was treated with BBr3 (1.0 M in CH2Cl2, 5 mL, 5 mmol) to afford the desired product as an off-white solid (39 mg, 42%). 1H NMR (500 MHz, CD3OD) δ 7.64 (dd, J=5.4, 4.6 Hz, 1H), 7.57 (t, J=7.8 Hz, 1H), 7.48 (t, J=7.8 Hz, 1H), 7.22-7.05 (m, 3H), 6.23 (dd, J=8.4, 5.4 Hz, 1H), 3.61 (dd, J=14.4, 7.2 Hz, 1H), 3.51-3.23 (m, 2H), 2.57 (s, 3H), 1.52 (t, J=7.0 Hz, 3H); ESI MS m/z 383 [C21H19FN2O2S+H]+; HPLC 96.1% (AUC), tR=8.85 min.


Example 1133
9-(4-(2-Aminoethyl)phenyl)-6-chloro-8-hydroxythieno[2,3-c]quinolin-4(5H)-one hydrochloride



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Following General Procedure F, tert-butyl 4-(6-chloro-8-methoxy-4-oxo-4,5-dihydrothieno[2,3-c]quinolin-9-yl)phenethylcarbamate (79 mg, 0.25 mmol) was treated with BBr3 (1.0 M in CH2Cl2, 9 mL, 9 mmol) to afford the desired product as a yellow solid (12 mg, 20%). 1H NMR (500 MHz, CD OD) δ 7.61 (d, J=5.4 Hz, 1H), 7.49 (d, J=8.1 Hz, 2H), 7.31 (d, J=7.0 Hz, 3H), 6.10 (d, J=5.4 Hz, 1H), 3.37-3.27 (m, 2H), 3.12 (t, J=7.6 Hz, 2H); ESI MS m/z 371 [C19H15ClN2O2S+H]+; HPLC 96.9% (AUC), tR=8.83 min.


Example 1142
9-(4-(2-Aminoethyl)phenyl)-6-bromo-8-hydroxythieno[2,3-c]quinolin-4(5H)-one Hydrochloride



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Following General Procedure F, tert-butyl 4-(6-chloro-8-methoxy-4-oxo-4,5-dihydrothieno[2,3-c]quinolin-9-yl)phenethylcarbamate (410 mg, 0.76 mmol) was treated with BBr3 (1.0 M in CH2Cl2, 10 mL, 10 mmol) to afford the desired product as an off-white solid (58 mg, 18%): 1H NMR (500 MHz, CD3OD) δ 7.62 (d, J=5.4 Hz, 1H), 7.53-7.45 (m, 3H), 7.31 (d, J=8.1 Hz, 2H), 6.10 (d, J=5.4 Hz, 1H), 3.31-3.28 (m, 2H), 3.11 (t, J=7.6 Hz, 2H); ESI MS m/z 415 [C19H15BrN2O2S+H]+; HPLC 94.9% (AUC), tR=9.02 min.


Example 1176
(R)-9-(4-(1-Aminopropan-2-yl)phenyl)-6-bromo-8-hydroxythieno[2,3-c]quinolin-4(5H)-one Hydrochloride



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Following General Procedure F, (R)-tert-butyl 2-(4-(8-methoxy-4-oxo-4,5-dihydrothieno[2,3-c]quinolin-9-yl)phenyl)propylcarbamate (60 mg, 0.11 mmol) was reacted with BBr3 (1.0 M in CH2Cl2, 6 mL, 6 mmol) to afford the desired product as an off-white solid (24 mg, 51%): 1H NMR (500 MHz, CD3OD) δ 7.64 (d, J=5.4 Hz, 1H), 7.56 (dd, J=7.9, 1.9 Hz, 1H), 7.50-7.45 (m, 2H), 7.37 (dd, J=7.9, 1.8 Hz, 1H), 7.32 (dd, J=7.7, 1.7 Hz, 1H), 6.12 (d, J=5.4 Hz, 1H), 3.36-3.18 (m, 3H), 1.49 (d, J=6.5 Hz, 3H): ESI MS m/z 429 [C20H17BrN2O2S+H]+; HPLC >99% (AUC), tR=9.30 min.


Example 1136
9-(4-(1-Aminopropan-2-yl)phenyl)-6-chloro-8-hydroxythieno[2,3-c]quinolin-4(5H)-one Hydrochloride



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Following General Procedure F, tert-butyl 2-(4-(6-chloro-8-methoxy-4-oxo-4,5-dihydrothieno[2,3-c]quinolin-9-yl)phenyl)propylcarbamate (40 mg, 0.08 mmol) was treated with BBr3 (1.0 M in CH2Cl2, 3 mL, 3 mmol) to afford the desired product as an yellow solid (13 mg, 40%): 1H NMR (500 MHz, CD3OD) δ 7.63 (d, J=5.4 Hz, 1H), 7.56 (dd, J=7.9, 1.8 Hz, 1H), 7.48 (dd, J=7.8, 1.8 Hz, 1H), 7.40-7.28 (m, 3H), 6.12 (d, J=5.4 Hz, 1H), 3.29-3.19 (m, 3H), 1.49 (d, J=6.3 Hz, 3H); ESI MS m/z 385 [C20H17ClN2O2S+H]+; HPLC 99% (AUC), tR=8.12 min.


Example 1132
(R)-6-Chloro-8-hydroxy-9-(4-(1-(methylamino)ethyl)phenyl)thieno[2,3-c]quinolin-4(5H)-one Hydrochloride



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Following General Procedure F, (R)-tert-butyl 1-(4-(6-chloro-8-methoxy-4-oxo-4,5-dihydrothieno[2,3-c]quinolin-9-yl)phenyl)ethyl(methyl)carbamate (43 mg, 0.09 mmol) was treated with BBr3 (1.0 M in CH2Cl2, 4 mL, 4 mmol) to afford the desired product as a white solid (15 mg, 45%): 1H NMR (500 MHz, CD3OD) δ 7.69-7.59 (m, 3H), 7.45 (ddd, J=7.0, 5.8, 2.1 Hz, 2H), 7.30 (s, 1H), 6.03 (d, J=5.4 Hz, 1H), 4.48 (q, J=6.9 Hz, 1H), 2.72 (s, 3H), 1.79 (d, J=6.9 Hz, 3H); ESI MS m/z 385 [C20H17ClN2O2S+H]+; HPLC 97.1% (AUC), tR=8.85 min.


Example 1219
9-(4-(2-Aminoethyl)-3-fluorophenyl)-6-chloro-8-hydroxythieno[2,3-c]quinolin-4(5H)-one Hydrochloride



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Following General Procedure F, tert-butyl 4-(6-chloro-8-methoxy-4-oxo-4,5-dihydrothieno[2,3-c]quinolin-9-yl)-2-fluorophenethylcarbamate (70 mg, 0.14 mmol) was treated with BBr3 (1.0 M in CH2Cl2, 6 mL, 6 mmol) to afford the desired product as a white solid (26 mg, 48%); 1H NMR (500 MHz, CD3OD) δ 7.67 (d, J=5.4 Hz, 1H), 7.51 (t, J=7.7 Hz, 1H), 7.30 (s, 1H), 7.17-7.11 (m, 2H), 6.18 (d, J=5.4 Hz, 1H), 3.35-3.20 (m, 2H), 3.14-3.04 (m, 1H); ESI MS m/z 389 [C19H14ClFN2O2S+H]+; HPLC >99% (AUC), tR=8.93 min.


Example 1228
9-(4-(1-Amino-2-methylpropan-2-yl)phenyl)-8-hydroxy-6-methylthieno[2,3-c]quinolin-4(5H)-one Hydrochloride



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Following General Procedure F, tert-butyl 2-(4-(8-methoxy-6-methyl-4-oxo-4,5-dihydrothieno[2,3-c]quinolin-9-yl)phenyl)-2-methylpropylcarbamate (40 mg, 0.08 mmol) was treated with BBr3 (1.0 M in CH2Cl2, 4 mL, 4 mmol) to afford the desired product as a brown solid (21 mg, 67%); 1H NMR (500 MHz, CD3OD) δ 7.64 (d, J=8.4 Hz, 2H), 7.58 (d, J=5.4 Hz, 1H), 7.36 (d, J=8.3 Hz, 2H), 7.09 (s, 1H), 6.18 (d, J=5.4 Hz, 1H), 3.28 (s, 2H), 2.58 (s, 3H), 1.58 (s, 6H): ESI MS m/z 379 [C22H22N2O2S+H]+; HPLC 96.5% (AUC), tR=9.04 min.


Example 1242
9-(4-(2-Aminopropyl)phenyl)-8-hydroxy-6-methylthieno[2,3-c]quinolin-4(5H)-one Hydrochloride



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Following General Procedure F, tert-butyl 1-(4-(8-methoxy-6-methyl-4-oxo-4,5-dihydrothieno[2,3-c]quinolin-9-yl)phenyl)propan-2-ylcarbamate (90 mg, 0.19 mmol) was treated with BBr3 (1.0 M in CH2Cl2, 8 mL, 8 mmol) to afford the desired product as a light brown solid (25 mg, 53%): 1H NMR (500 MHz, CD % OD) δ 7.57 (d, J=5.4 Hz, 1H), 7.45 (dd, J=20.6, 7.8 Hz, 2H), 7.32-7.26 (m, 2H), 7.09 (s, 1H), 6.12 (d, J=5.4 Hz, 1H), 3.65 (dd, J=13.7, 6.9 Hz, 1H), 3.14-2.99 (m, 2H), 2.57 (s, 3H), 1.41 (d, J=6.6 Hz, 3H); ESI MS m/z 365 [C21H20N2O2S+H]+; HPLC 98.6% (AUC), tR=8.68 min.


Example 1191
9-(4-(2-Aminoethyl)phenyl)-8-hydroxy-6-methylthieno[2,3-c]quinolin-4(5H)-one Hydrochloride



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Following General Procedure F, tert-butyl 4-(8-methoxy-6-methyl-4-oxo-4,5-dihydrothieno[2,3-c]quinolin-9-yl)phenethylcarbamate (30 mg, 0.06 mmol was treated with BBr3 (1.0 M in CH2Cl2, 4 mL, 4 mmol) to afford the desired product as a light yellow solid (20 mg, 90%): 1H NMR (500 MHz, CD3OD) δ 7.55 (d, J=5.4 Hz, 1H), 7.47 (d, J=8.1 Hz, 2H), 7.30 (d, J=8.1 Hz, 2H), 7.07 (d, J=0.8 Hz, 1H), 6.14 (d, J=5.4 Hz, 1H), 3.34-3.27 (m, 2H), 3.11 (t, J=7.5 Hz, 2H), 2.57 (s, 3H); ESI MS m/z 351 [C20H18N2O2S+H]+; HPLC 98.4% (AUC), tR=8.32 min.


Example 1364
8-Hydroxy-6-methyl-9-(4-(2-(methylamino)ethyl)phenyl)thieno[2,3-c]quinolin-4(5H)-one Hydrochloride



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Following General Procedure F, 8-methoxy-6-methyl-9-(4-(2-(methylamino)ethyl)phenyl)thieno[2,3-c]quinolin-4(5H)-one (32 mg, 0.06 mmol) was treated with BBr3 (1.0 M in CH2Cl2, 3 mL, 3 mmol) to afford the desired product as a light yellow solid (15 mg, 62%): 1H NMR (500 MHz, CD3OD) δ 7.55 (d, J=5.4 Hz, 1H), 7.47 (d, J=8.1 Hz, 2H), 7.34-7.27 (m, 2H), 7.07 (d, J=0.7 Hz, 1H), 6.12 (d, J=5.4 Hz, 1H), 3.39 (t, J=7.6 Hz, 2H), 3.18-3.10 (m, 2H), 2.79 (s, 3H), 2.57 (s, 3H); ESI MS m/z 365 [(C21H20N2O2S+H]+; HPLC >99% (AUC), tR=8.41 min.


Example 1307
(R)-8-Hydroxy-6-methyl-9-(4-(1-(methylamino)propan-2-yl)phenyl)thieno[2,3-c]quinolin-4(5H)-one Hydrobromide



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Following General Procedure F, (R)-tert-butyl 2-(4-(8-methoxy-6-methyl-4-oxo-4,5-dihydrothieno[2,3-c]quinolin-9-yl)phenyl)propyl(methyl)carbamate (2.08 g, 4.23 mmol) was treated with BBr3 (1.0 M in CH2Cl2, 40 mL, 40 mmol) to afford the desired product as a yellow solid (1.05 g, 65%); 1H NMR (500 MHz, CD3OD) δ 7.60-7.54 (m, 2H), 7.46 (dd, J=7.8, 1.9 Hz, 1H), 7.37 (dd, J=7.9, 1.8 Hz, 1H), 7.31 (dd, J=7.7, 1.7 Hz, 1H), 7.08 (d, J=0.8 Hz, 1H), 6.16 (d, J=5.4 Hz, 1H), 3.37-3.24 (m, 3H), 2.74 (s, 3H), 2.57 (s, 3H), 1.50 (d, J=6.8 Hz, 3H); ESI MS m/z 379 [C22H22N2O2S+H]+; HPLC >99% (AUC), tR=8.74 min.


Example 1169
(R)-9-(4-(1-Aminopropan-2-yl)phenyl)-8-hydroxy-6-methylthieno[2,3-c]quinolin-4(5H)-one Hydrobromide



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Following General Procedure F, (R)-tert-butyl 2-(4-(8-methoxy-6-methyl-4-oxo-4,5-dihydrothieno[2,3-c]quinolin-9-yl)phenyl)propyl(methyl)carbamate (2.20 g, 4.60 mmol) was treated with BBr3 (1.0 M in CH2Cl2, 50 mL, 50 mmol) to afford the desired product as a yellow solid (1.50 g, 73%): 1H NMR (500 MHz, CD3OD) δ 7.58 (d, J=5.4 Hz, 1H), 7.55 (dd, J=7.9, 1.8 Hz, 1H), 7.45 (dd, J=7.8, 1.9 Hz, 1H), 7.35 (dd, J=7.9, 1.7 Hz, 1H), 7.30 (dd, J=7.7, 1.6 Hz, 1H), 7.08 (d, J=0.8 Hz, 1H), 6.17 (d, J=5.4 Hz, 1H), 3.36-3.19 (m, 3H), 2.57 (d, J=0.6 Hz, 3H), 1.50 (d, J=6.4 Hz, 3H); ESI MS m/z 365 [C21H20N2O2S+H]+; HPLC 98.3% (AUC), tR=8.64 min.


Example 587
tert-Butyl 4-(6-bromo-8-methoxy-4-oxo-4,5-dihydrothieno[2,3-c]quinolin-9-yl)-2-fluorophenethylcarbamate



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Following General Procedure I, tert-butyl 2-fluoro-4-(8-methoxy-4-oxo-4,5-dihydrothieno[2,3-c]quinolin-9-yl)phenethylcarbamate (1.1 g, 2.3 mmol) was reacted with NBS (540 mg, 3.1 mmol) to afford the desired product (920 mg, 70%) as a brown solid. ESI MS m/z 547 [C25H24BrFN2O4S+H]+.


Example 588
tert-Butyl 2-(4-(6-bromo-8-methoxy-4-oxo-4,5-dihydrothieno[2,3-c]quinolin-9-yl)phenyl)-2-methylpropylcarbamate



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Following General Procedure I, tert-butyl 2-(4-(8-methoxy-4-oxo-4,5-dihydrothieno[2,3-c]quinolin-9-yl)phenyl)-2-methylpropylcarbamate (600 mg, 1.3 mmol) was reacted with NBS (330 mg, 1.9 mmol) to afford the desired product (350 mg, 51%) as a yellow solid: ESI MS m/z 557 [C27H29BrN2O4S+H]+.


Example 589
tert-Butyl 2-(4-(6-bromo-8-methoxy-4-oxo-4,5-dihydrothieno[2,3-c]quinolin-9-yl)-2-fluorophenyl)propylcarbamate



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Following General Procedure I, tert-butyl 2-(2-fluoro-4-(8-methoxy-4-oxo-4,5-dihydrothieno[2,3-c]quinolin-9-yl)phenyl)propylcarbamate (500 mg, 1.0 mmol) was reacted with NBS (220 mg, 1.2 mmol) to afford the desired product (280 mg, 48%) as a brown oil. ESI MS m/z 561 [C26H26BrFN2O4S+H]+.


Example 590
tert-Butyl 4-(6-bromo-8-methoxy-4-oxo-4,5-dihydrothieno[2,3-c]quinolin-9-yl)phenethylcarbamate



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Following General Procedure I, tert-butyl 4-(8-methoxy-4-oxo-4,5-dihydrothieno[2,3-c]quinolin-9-yl)phenethylcarbamate (600 mg, 1.3 mmol) was reacted with NBS (280 mg, 1.5 mmol) to afford the desired product (410 mg, 60%) as a reddish brown solid. ESI MS m/z 529 [C25H25BrN2O4S H]+.


Example 59
(R)-tert-Butyl 2-(4-(6-bromo-8-methoxy-4-oxo-4,5-dihydrothieno[2,3-c]quinolin-9-yl)phenyl)propylcarbamate



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Following General Procedure I, (R)-tert-butyl 2-(4-(8-methoxy-4-oxo-4,5-dihydrothieno[2,3-c]quinolin-9-yl)phenyl)propylcarbamate (220 mg, 0.39 mmol) was reacted with NBS (90 mg, 0.51 mmol) to afford the desired product (60 mg, 28%) as a reddish oil: ESI MS m/z 543 [C26H27BrN2O4S+H]+.


Example 592
tert-Butyl 2-fluoro-4-(8-methoxy-6-methyl-4-oxo-4,5-dihydrothieno[2,3-c]quinolin-9-yl)phenethylcarbamate



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Following General Procedure I, tert-butyl 4-(6-bromo-8-methoxy-4-oxo-4,5-dihydrothieno[2,3-c]quinolin-9-yl)-2-fluorophenethylcarbamate (300 mg, 0.55 mmol) was reacted with trimethylboroxine (207 mg, 1.65 mmol) and Pd(pph3)4 (63 mg, 0.05 mmol) to afford the desired product (155 mg, 58%) as a brown solid. ESI MS m/z 483 [C26H27FN2O4S+H]+.


Example 593
tert-Butyl 2-(2-fluoro-4-(8-methoxy-6-methyl-4-oxo-4,5-dihydrothieno[2,3-c]quinolin-9-yl)phenyl)propylcarbamate



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Following General Procedure I, tert-butyl 2-(4-(6-bromo-8-methoxy-4-oxo-4,5-dihydrothieno[2,3-c]quinolin-9-yl)-2-fluorophenyl)propylcarbamate (282 mg, 0.50 mmol) was reacted with trimethylboroxine (170 mg, 1.35 mmol) and Pd(pph3)4 (50 mg, 0.04 mmol) to afford the desired product (130 mg, 52%) as a yellow solid. ESI MS m/z 497 [C27H29FN2O4S+H]+.


Example 1216
9-(4-(2-Aminoethyl)-3-fluorophenyl)-8-methoxy-6-methylthieno[2,3-c]quinolin-4(5H)-one Hydrochloride



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Following General Procedure C, tert-butyl 2-fluoro-4-(8-methoxy-6-methyl-4-oxo-4,5-dihydrothieno[2,3-c]quinolin-9-yl)phenethylcarbamate (50 mg, 0.10 mmol) was reacted with TFA (2 mL) to afford the desired product (32 mg, 80%) as a yellow solid: 1H NMR (500 MHz, CD3OD) δ 7.62 (d, J=5.4 Hz, 1H), 7.48 (dd, J=9.7, 6.1 Hz, 1H), 7.29 (s, 1H), 7.08 (ddd, J=9.0, 6.2, 1.6 Hz, 2H), 6.12 (d, J=5.4 Hz, 1H), 3.75 (s, 3H), 3.34-3.27 (m, 1H), 3.27-3.06 (m, 3H), 2.64 (s, 3H); ESI MS m/z 383 [C21H19FN2O2S+H]+; HPLC 97.6% (AUC), tR=9.22 min.


Example 1161
(R)-9-(4-(1-Aminopropan-2-yl)phenyl)-8-methoxythieno[2,3-c]quinolin-4(5H)-one Hydrochloride



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Following General Procedure C, (R)-tert-butyl 2-(4-(8-methoxy-4-oxo-4,5-dihydrothieno[2,3-c]quinolin-9-yl)phenyl)propylcarbamate (200 mg, 0.55 mmol) was reacted with TFA (10 mL) to afford the desired product (51 mg, 26%) as a white solid: 1H NMR (500 MHz, CD3OD) δ 7.61-7.44 (m, 4H), 7.39 (d, J=9.1 Hz, 1H), 7.30 (ddd, J=13.2, 7.9, 1.7 Hz, 2H), 6.00 (d, J=5.4 Hz, 1H), 3.33-3.18 (m, 3H), 1.49 (d, J=6.6 Hz, 3H); ESI MS m/z 365 [C21H20N2O2S+H]+; HPLC 97.6% (AUC), tR=8.88 min


Example 1305
(R)-9-(4-(1-Aminopropan-2-yl)phenyl)-8-methoxy-6-methylthieno[2,3-c]quinolin-4(5H)-one Hydrochloride



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Following General Procedure C, (R)-tert-butyl 2-(4-(8-methoxy-6-methyl-4-oxo-4,5-dihydrothieno[2,3-c]quinolin-9-yl)phenyl)propylcarbamate (1.5 g, 3.1 mmol) was reacted with TFA (30 mL) to afford the desired product (520 mg, 47%) as a yellow solid: 1H NMR (500 MHz, CD3OD) δ 7.56 (d, J=5.4 Hz, 1H), 7.50 (dd, J=7.8, 1.8 Hz, 1H), 7.45 (dd, J=7.7, 1.9 Hz, 1H), 7.28 (ddd, J=9.4, 7.0, 1.7 Hz, 31-t), 6.01 (d, J=5.4 Hz, 1H), 3.75 (s, 3H), 3.36-3.18 (m, 3H), 2.64 (s, 3H), 1.48 (d, J=6.6 Hz, 3H); ESI MS m/z 379 [C22H12N2O2S+H]+; HPLC 99% (AUC), tR=8.81 min.


Example 1201
(R)-9-(4-(1-Aminopropan-2-yl)phenyl)-6-chloro-8-methoxythieno[2,3-c]quinolin-4(5H)-one Hydrochloride



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Following General Procedure C, (R)-tert-butyl 2-(4-(6-chloro-8-methoxy-4-oxo-4,5-dihydrothieno[2,3-c]quinolin-9-yl)phenyl)propylcarbamate (60 mg, 0.12 mmol) was reacted with TFA (4 mL) to afford the desired product (28 mg, 52%) as a yellow solid: 1H NMR (500 MHz, CD3OD) δ 7.61 (d, J=5.4 Hz, 1H), 7.54-7.50 (m, 2H), 7.48 (dd, J=7.8, 1.7 Hz, 1H), 7.32-7.25 (m, 2H), 5.97 (d, J=5.4 Hz, 1H), 3.76 (s, 1H), 3.29-3.17 (m, 3H), 1.48 (d, J=6.5 Hz, 2H); ESI MS m/z 399 [C21H19ClN2O2S+H]+; HPLC >99% (AUC), tR=9.65 min.


Example 1298
(R)-8-Methoxy-6-methyl-9-(4-(1-(methylamino)propan-2-yl)phenyl)thieno[2,3-c]quinolin-4(5H)-one Hydrochloride



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Following General Procedure C, (R)-tert-butyl 2-(4-(8-methoxy-6-methyl-4-oxo-4,5-dihydrothieno[2,3-c]quinolin-9-yl)phenyl)propyl(methyl)carbamate (600 mg, 1.2 mmol) was reacted with TFA (20 mL) to afford the desired product (330 mg, 69%) as a light yellow solid: 1H NMR (500 MHz, CD3OD) δ 7.56 (d, J=5.4 Hz, 1H), 7.52 (dd, J=7.9, 1.9 Hz, 1H), 7.47 (dd, J=7.7, 1.9 Hz, 1H), 7.28 (ddd, J=14.7, 7.9, 1.7 Hz, 3H), 6.00 (d, J=5.4 Hz, 1H), 3.36-3.26 (m, 3H), 2.76 (s, 3H), 2.64 (s, 3H), 1.48 (d, J=6.7 Hz, 3H); ESI MS m/z 393 [(C23H24N2O2S+H]+; HPLC 98.6% (AUC), tR=8.96 min.


Example 594
(R)-tert-Butyl 2-(4-(6-chloro-8-methoxy-4-oxo-4,5-dihydrothieno[2,3-c]quinolin-9-yl)phenyl)propylcarbamate



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Following General Procedure H, (R)-tert-butyl 2-(4-(8-methoxy-4-oxo-4,5-dihydrothieno[2,3-c]quinolin-9-yl)phenylpropylcarbamate (400 mg, 0.86 mmol) was reacted with NCS (138 mg, 1.03 mmol) to afford the desired product (210 mg, 49%) as a brown solid. ESI MS m/z 499 [C26H27ClN2O4S+H]+.


Example 595
tert-Butyl 4-(6-chloro-8-methoxy-4-oxo-4,5-dihydrothieno[2,3-c]quinolin-9-yl)phenethylcarbamate



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Following General Procedure 1H, tert-butyl 4-(8-methoxy-4-oxo-4,5-dihydrothieno[2,3-c]quinolin-9-yl)phenethylcarbamate (200 mg, 0.43 mmol) was reacted with NCS (68 mg, 0.52 mmol) to afford the desired product (79 mg, 38%) as a brown solid. ESI MS m/z 485 [C25H25ClN2O4S+H]+.


Example 596
tert-Butyl 2-(4-(6-chloro-8-methoxy-4-oxo-4,5-dihydrothieno[2,3-c]quinolin-9-yl)phenyl)propylcarbamate



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Following General Procedure H, tert-butyl 2-(4-(8-methoxy-4-oxo-4,5-dihydrothieno[2,3-c]quinolin-9-yl)phenyl)propylcarbamate (180 mg, 0.39 mmol) was reacted with NCS (57 mg, 0.42 mmol) to afford the desired product (110 mg, 56%) as a yellowish solid. ESI MS m/z 499 [C26H27ClN2O4S+H]+.


Example 597
(R)-tert-Butyl 1-(4-(6-chloro-8-methoxy-4-oxo-4,5-dihydrothieno[2,3-c]quinolin-9-yl)phenyl)ethyl(methyl)carbamate



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Following General Procedure H, (R)-tert-butyl 1-(4-(8-methoxy-4-oxo-4,5-dihydrothieno[2,3-c]quinolin-9-yl)phenyl)ethyl(methyl)carbamate (200 mg, 0.43 mmol) was reacted with NCS (69 mg, 0.52 mmol) to afford the desired product (43 mg, 20%) as a yellowish solid. ESI MS m/z 499 [C26H27ClN2O4S+H]+.


Example 598
tert-Butyl 4-(6-chloro-8-methoxy-4-oxo-4,5-dihydrothieno[2,3-c]quinolin-9-yl)-2-fluorophenethylcarbamate



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Following General Procedure H, tert-butyl 2-fluoro-4-(8-methoxy-4-oxo-4,5-dihydrothieno[2,3-c]quinolin-9-yl)phenethylcarbamate (300 mg, 0.64 mmol) was reacted with NCS (94 mg, 0.71 mmol) to afford the desired product (150 mg, 46%) as a yellow solid. ESI MS m/z 503 [C25H24ClFN2O4S+H]+.


Example 373
9-(4-(1-aminopropan-2-yl)phenyl)-8-methoxythieno[2,3-c]quinolin-4(5H)-one Hydrochloride



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To a solution of 2-(4-(8-methoxy-4-oxo-4,5-dihydrothieno[2,3-c]quinolin-9-yl)phenyl)propanenitrile (1.4 g, 4.0 mmol) in toluene (10 mL) at 0° C. was added BH3.THF (1.0 M in THF, 10 mL, 10 mmol) and the reaction was warmed to room temperature and heated at reflux for 4 h. The reaction was quenched by adding methanol (1 mL) at 0° C. The resulting mixture was concentrated and purified by preparatory HPLC (C18 silica, acetonitrile/water (with 0.05% TFA) gradient). The desired product was dissolved in aqueous HCl, concentrated and dried under high vacuum to afford the desired product (352 mg, 24%) as a brown solid: ESI MS m/z 365 [CH21H20N2O2S+H]+.


Example 1112
9-(4-(1-(Dimethylamino)propan-2-yl)phenyl)-8-hydroxythieno[2,3-c]quinolin-4(5H)-one Hydrochloride



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Following the procedure outlined for Example 1387, 9-(4-(1-aminopropan-2-yl)phenyl-8-hydroxythieno[2,3-c]quinolin-4(5H)-one hydrochloride (15 mg, 0.040 mmol) was reacted with paraformaldehyde (4.0 mg, 0.13 mmol) and after purification the resulting material was converted to the hydrochloride salt as outlined in General Procedure D-2 to afford the desired product (12 mg, 75%) as a light yellow solid: 1H NMR (500 MHz, CD3OD) δ 7.66-7.51 (m, 3H), 7.47-7.30 (m, 3H), 7.18 (d, J=8.9 Hz, 1H), 6.12 (d, J=5.4 Hz, 1H), 3.67-3.57 (m, 1H), 3.51-3.38 (m, 2H), 2.95 (d, J=16.0 Hz, 6H), 1.49 (d, J=6.5 Hz, 3H); ESI MS m/z 379 [C22H22N2O2S+H]+; HPLC >99% (AUC), tR=8.46 min.


Example 1126
(R)-6-Chloro-9-(4-(1-(dimethylamino)ethyl)phenyl)-8-hydroxythieno[2,3-c]quinolin-4(5H)-one Hydrochloride



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Following the procedure outlined for Example 1387, (R)-9-(4-(1-aminoethyl)phenyl-6-chloro-8-hydroxythieno[2,3-c]quinolin-4(5H)-one hydrochloride (120 mg, 0.32 mmol) was reacted with paraformaldehyde (29 mg, 0.97 mmol) and after purification the resulting material was converted to the hydrochloride salt as outlined in General Procedure D-2 to afford the desired product (21 mg, 16%) as a light yellow solid: 1H NMR (500 MHz, CD3OD) δ 7.71 (dd, J=10.5, 7.8 Hz, 2H), 7.64 (d, J=5.4 Hz, 1H), 7.47 (t, J=7.1 Hz, 2H), 7.31 (s, 1H), 6.01 (d, J=5.4 Hz, 1H), 4.66 (q, J=6.9 Hz, 1H), 2.97 (s, 3H), 2.86 (s, 3H), 1.86 (d, J=7.0 Hz, 3H). ESI MS m/z 399 [C21H19ClN2O2S+H]+; HPLC 97.5% (AUC), tR=9.96 min.


Example 1188
(R)-9-(4-(1-(dimethylamino)propan-2-yl)phenyl)-8-hydroxythieno[2,3-c]quinolin-4(5H)-one Hydrochloride



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Following the procedure outlined for Example 1387, (R)-8-methoxy-9-(4-(1-(methylamino)propan-2-yl)phenyl)thieno[2,3-c]quinolin-4(5H)-one hydrochloride (40 mg, 0.11 mmol) was reacted with paraformaldehyde (7 mg, 0.21 mmol) and after purification the resulting material was converted to the hydrochloride salt as outlined in General Procedure D-2 to afford the desired product (28 mg, 67%) as a white solid: 1H NMR (500 MHz, CD3OD) δ 7.65-7.52 (m, 3H), 7.44-7.32 (m, 3H), 7.18 (d, J=8.9 Hz, 1H), 6.12 (d, J=5.4 Hz, 1H), 3.62 (d, J=3.1 Hz, 1H), 3.46 (dd, J=13.2, 4.7 Hz, 2H), 2.97 (s, 3H), 2.94 (s, 3H), 1.49 (d, J=6.6 Hz, 3H); ESI MS m/z 379 [C22H22N2O2S+H]+; HPLC >99% (AUC), tR=8.57 min.


Example 1193
9-(4-(1-(Dimethylamino)propan-2-yl)-3-fluorophenyl)-8-hydroxy-6-methylthieno[2,3-c]quinolin-4(5H)-one Hydrochloride



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Following the procedure outlined for Example 1387, 9-(4-(1-Aminopropan-2-yl)-3-fluorophenyl)-8-hydroxy-6-methylthieno[2,3-c]quinolin-4(5H)-one Hydrochloride (30 mg, 0.08 mmol) was reacted with paraformaldehyde (9 mg, 0.31 mmol) and after purification the resulting material was converted to the Hydrochloride salt as outlined in General Procedure D-2 to afford the desired product (25 mg, 75(%) as a light yellow solid: 1H NMR (500 MHz, CD3OD) δ 7.67-7.51 (m, 2H), 7.26-7.10 (m, 2H), 7.08 (dd, J=1.6, 0.8 Hz, 1H), 6.20 (dd, J=8.1, 5.4 Hz, 1H), 3.88-3.40 (m, 3H), 3.0-2.96 (m, 6H), 2.57 (s, 3H), 1.57-1.46 (m, 3H); ESI MS m/z 411 [C23H23FN2O2S+H]+; HPLC >99% (AUC), tR=9.14 min.


Example 1347
(R)-6-chloro-9-(4-(1-(dimethylamino)propan-2-yl)phenyl)-8-hydroxythieno[2,3-c]quinolin-4(5H)-one Hydrochloride



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Following the procedure outlined for Example 1387, (R)-9-(4-(1-aminopropan-2-yl)phenyl)-6-chloro-8-hydroxythieno[2,3-c]quinolin-4(5H)-one hydrochloride (30 mg, 0.10 mmol) was reacted with paraformaldehyde (6 mg, 0.20 mmol) and after purification the resulting material was converted to the hydrochloride salt as outlined in General Procedure D-2 to afford the desired product (12 mg, 29%) as a yellow solid: 1H NMR (500 MHz, CD3OD) δ 7.66-7.57 (m, 2H), 7.55 (d, J=7.8 Hz, 1H), 7.40-7.27 (m, 3H), 6.07 (d, J=5.4 Hz, 1H), 3.62 (dd, J=12.2, 8.9 Hz, 1H), 3.46 (ddd, J=11.7, 9.3, 6.3 Hz, 2H), 2.98 (s, 3H), 2.94 (s, 3H), 1.48 (d, J=6.5 Hz, 3H); ESI MS m/z 413 [C22H21ClN2O2S+H]+; HPLC >99% (AUC), tR=9.46 min.


Example 1379
(R)-9-(4-(1-(ethyl(methyl)amino)propan-2-yl)phenyl)-8-hydroxy-6-methylthieno[2,3-c]quinolin-4(5H)-one Hydrochloride



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Following the procedure outlined for Example 1387, ((R)-8-hydroxy-6-methyl-9-(4-(1-(methylamino)propan-2-yl)phenyl)thieno[2,3-c]quinolin-4(5H)-one hydrochloride (15 mg, 0.04 mmol) was reacted with acetaldehyde (5 uL, 0.08 mmol) and after purification the resulting material was converted to the hydrochloride salt as outlined in General Procedure D-2 to afford the desired product (8 mg, 50%) as a yellow solid: 1H NMR (500 MHz, CD3OD) δ 7.66-7.49 (m, 3H), 7.42-7.27 (m, 2H), 7.08 (s, 1H), 6.13 (dd, J=19.9, 5.4 Hz, 1H), 3.70 (dd, J=12.8, 10.3 Hz, 1H), 3.58-3.14 (m, 4H), 2.91 (d, J=23.4 Hz, 3H), 2.57 (s, 3H), 1.49 (dd, J=6.8, 3.3 Hz, 3H), 1.36 (dt, J=12.8, 7.3 Hz, 3H); ESI MS m/z 407 [C24H11N2O2S+H]+; HPLC >99% (AUC), tR=9.16 min.


Example 1324
(R)-9-(4-(1-(Dimethylamino)propan-2-yl)phenyl)-8-hydroxy-6-methylthieno[2,3-c]quinolin-4(5H)-one Hydrochloride



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Following the procedure outlined for Example 1387, (R)-9-(4-(1-aminopropan-2-yl)phenyl)-8-hydroxy-6-methylthieno[2,3-c]quinolin-4(5H)-one hydrobromide (100 mg, 0.26 mmol) was reacted with paraformaldehyde (24 mg, 0.80 mmol) and after purification the resulting material was converted to the hydrochloride salt as outlined in General Procedure D-2 to afford the desired product (34 mg, 34%) as a white solid: 1H NMR (500 MHz, CD3OD) δ 7.61-7.55 (m, 1H), 7.53 (dd, J=7.8, 1.8 Hz, 1H), 7.36 (dd, J=7.9, 1.7 Hz, 1H), 7.31 (dd, J=7.7, 1.7 Hz, 1H), 7.08 (s, 1H), 6.12 (d, J=5.4 Hz, 1H), 3.61 (dd, J=12.3, 9.3 Hz, 1H), 3.45 (dt, J=9.1, 6.2 Hz, 2H), 2.97 (s, 1H), 2.94 (s, 1H), 2.57 (s, 1H), 1.48 (d, J=6.6 Hz, 1H); ESI MS m/z 393 [C23H24N2O2S+H]+; HPLC >99% (AUC), tR=8.90 min.


Example 1306
(R)-8-Hydroxy-6-methyl-9-(4-(1-(methylamino)propan-2-yl)phenyl)thieno[2,3-c]quinolin-4(5H)-one Hydrochloride



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Following General Procedure D-3, (R)-8-hydroxy-6-methyl-9-(4-(1-(methylamino)propan-2-yl)phenyl)thieno[2,3-c]quinolin-4(5H)-one hydrobromide (120 mg, 0.26 mmol) was dissolved in aqueous HCl (100 mmol) and stirred concentrated at room temperature for 2 h, concentrated and dried under high vacuum to afford the desired product as a hydrochloride salt. The desired product was dried under high vacuum to afford the desired product as a light yellow solid (27 mg, 28%): 1H NMR (500 M Hz, CD3OD) δ 7.61-7.53 (m, 2H), 7.46 (dd, J=7.8, 1.8 Hz, 1H), 7.36 (dd, J=7.9, 1.6 Hz, 1H), 7.31 (dd, J=7.7, 1.7 Hz, 1H), 7.08 (s, 1H), 6.16 (d, J=5.4 Hz, 1H), 3.41-3.24 (m, 3H), 2.74 (s, 3H), 2.57 (s, 3H), 1.50 (d, J=6.8 Hz, 3H); ESI MS m/z 379 [C22H22N2O2S+H]+; HPLC 98.7% (AUC), tR=8.82 min.


Example 408
N-tert-Butyl-4-(8-methoxy-4-oxo-4,5-dihydrothieno[2,3-c]quinolin-9-yl)benzenesulfonamide



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Following General Procedure B, 9-bromo-8-methoxythieno[2,3-c]quinolin-4(5H)-one (5.0 g, 16 mmol) was reacted with 4-(N-tert-butylsulfamoyl)phenylboronic acid (5.4 g, 21 mmol) to afford the desired product (4.3 g, 60%) as a yellow solid: ESI MS m/z [C22H22N2O4S2+H]+.


Example 409
9-(1H-Indazol-6-yl)-8-methoxythieno[2,3-c]quinolin-4(5H)-one



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Following General Procedure B, 9-bromo-8-methoxythieno[2,3-c]quinolin-4(5H)-one (100 mg, 0.32 mmol) was reacted with 6-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)-1H-indazole (120 mg, 0.48 mmol) to afford the desired product (35 mg, 31%) as brown solid: ESI MS m/z 348 [C18H11N3O2S+H]+.


Example 169
9-[4-(2-Aminoethyl)phenyl]-8-methoxythieno[2,3-c]quinolin-4(5H)-one



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Following General Procedure C, tert-butyl 4-(8-methoxy-4-oxo-4,5-dihydrothieno[2,3-c]quinolin-9-yl)phenethylcarbamate (310 mg, 0.69 mmol) was reacted with TFA (2 mL) to afford the desired product (220 mg, 90%) as an off-white solid: 1H NMR (500 MHz, DMSO-d) δ 7.91 (s, 1H), 7.91 (br s, 2H), 7.71 (d, J=5.4 Hz, 1H), 7.52 (d, J=9.1 Hz, 1H), 7.40 (m, 3H), 7.22 (d, J=8.1 Hz, 2H), 5.80 (d, J=5.4 Hz, 1H), 3.68 (s, 3H), 3.20-3.17 (m, 2H), 3.02-2.99 (m, 2H); ESI MS m/z 351 [C20H18N2O2S+H]+; HPLC 98.8% (AUC), tR=8.32 min.


Example 145
9-(4-{3-[2-(Diethylamino)ethylamino]propoxy}phenyl)-8-methoxythieno[2,3-c]quinolin-4(5H)-one



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Following General Procedure B, 9-bromo-8-methoxythieno[2,3-c]quinolin-4(5H)-one (100 mg, 0.33 mmol) was reacted with N′,N′-diethyl-N2-{3-[4-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)phenoxy]propyl}ethane-1,2-diamine (250 mg, 0.67 mmol) to afford the desired product (58 mg, 37%) as a brown solid: 1H NMR (500 MHz, CD3OD) δ 7.56 (d, J=5.4 Hz, 1H), 7.52 (d, J=9.1 Hz, 1H), 7.36 (d, J=9.1 Hz, 1H), 7.18 (d, J=8.6 Hz, 2H), 7.12 (d, J=8.6 Hz, 2H), 6.11 (d, J=5.4 Hz, 1H), 4.25 (t, J=5.7 Hz, 2H), 3.74 (s, 3H), 3.74-3.43 (m, 4H), 3.42 (t, J=7.4 Hz, 2H), 3.34-3.33 (m, 4H), 2.35-2.25 (m, 2H), 1.37 (t, J=7.3 Hz, 6H); ESI MS m/z 480 [C27H33N3O3S+H]+; HPLC 98.6%, tR=8.42 min.


Example 410
tert-Butyl 4-[4-(8-Methoxy-4-oxo-4,5-dihydrothieno[2,3-c]quinolin-9-yl)phenyl]piperazine-1-carboxylate



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Following General Procedure B, 9-bromo-8-methoxythieno[2,3-c]quinolin-4(5H)-one (80 mg, 0.26 mmol) was reacted with tert-butyl 4-[4-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)phenyl]piperazine-1-carboxylate (170 mg, 0.44 mmol) to afford the desired product (68 mg, 32%) as a yellow solid: ESI MS m/z 492 [C27H29N3O4S+H]+.


Example 411
8-Methoxy-9-[4-(piperazin-1-yl)phenyl]thieno[2,3-c]quinolin-4(5H)-one



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Following General Procedure C, tert-butyl 4-[4-(8-methoxy-4-oxo-4,5-dihydrothieno[2,3-c]quinolin-9-yl)phenyl]piperazine-1-carboxylate (160 mg, 0.33 mmol) was reacted with TFA (4 mL) to afford the desired product (23 mg, 22%) as a light yellow solid: 1H NMR (500 MHz, DMSO-d6) δ 11.84 (s, 1H), 8.72 (s, 2H), 7.76 (d, J=5.4 Hz, 1H), 7.49 (d, J=9.0 Hz, 1H), 7.37 (d, J=9.1 Hz, 1H), 7.20-7.03 (m, 4H), 5.95 (d, J=5.4 Hz, 1H), 3.68 (s, 3H), 3.52-3.41 (m, 4H), 3.31 (s, 4H).


Example 412
8-Methoxy-9-{4-[4-(methylsulfonyl)piperazin-1-yl]phenyl}thieno[2,3-c]quinolin-4(5H)-one



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To a solution of 8-methoxy-9-[4-(piperazin-1-yl)phenyl]thieno[2,3-c]quinolin-4(5H)-one (89 mg, 0.23 mmol) in methylene chloride (2 mL) was added N,N-diisopropylethylamine (0.42 mL, 0.68 mmol) and methanesulfonyl chloride (45 μL, 0.27 mmol) and the reaction mixture was stirred for 1 h. The reaction mixture was quenched with water and the layers were separated. The aqueous layer was extracted with ethyl acetate and the combined organic layers were dried over Na2SO4, filtered, concentrated and the residue was purified by preparatory HPLC (C18 silica, acetonitrile/water w/0.05% TFA gradient) to afford the desired product (72 mg, 68%) as a brown solid: ESI MS m/z 470 [C23H23N3O4S2+H]+.


Example 413
tert-Butyl 4-(8-Methoxy-2-methyl-4-oxo-4,5-dihydrothieno[2,3-c]quinolin-9-yl)benzylcarbamate



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Following General Procedure B A, 9-bromo-8-methoxy-2-methylthieno[2,3-c]quinolin-4(5H)-one (100 mg, 0.31 mmol) was reacted with 4-[(tert-butoxycarbonylamino)methyl]phenylboronic acid (120 mg, 0.40 mmol) to afford desired product (80 mg, 55%) as a brown solid: ESI MS m/z 451 [C25H26N2O4S+H]+.


Example 414
N-[4-(8-Methoxy-4-oxo-4,5-dihydrothieno[2,3-c]quinolin-9-yl)phenyl]methanesulfonamide



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Following Step 1 from General Procedure B, 9-bromo-8-methoxythieno[2,3-c]quinolin-4(5H)-one (50 mg, 0.10 mmol) was reacted with 4-(methylsulfonamido)phenylboronic acid (52 mg, 0.24 mmol) to afford the desired product (40 mg, 62%) as a brown solid: ESI MS m/z 400 [C19H16N2O4S2+H]+.


Example 415
tert-Butyl 1-[4-(8-Methoxy-4-oxo-4,5-dihydrothieno[2,3-c]quinolin-9-yl)phenyl]ethylcarbamate



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Following General Procedure B, 9-bromo-8-methoxythieno[2,3-c]quinolin-4(5H)-one (600 mg, 2.0 mmol) was reacted with tert-butyl 1-[4-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)phenyl]ethylcarbamate (340 mg, 39%) as a brown solid: ESI MS m/z 451 [C25H26N2O4S+H]+.


Example 416
8-Methoxy-9-{4-[1-(piperidin-1-yl)ethyl]phenyl}thieno[2,3-c]quinolin-4(5H)-one



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Following General Procedure B, 9-bromo-8-methoxythieno[2,3-c]quinolin-4(5H)-one (150 mg, 0.48 mmol) was reacted with 4-[1-(piperidin-1-yl)ethyl]phenylboronic acid (170 mg, 0.73 mmol) to afford the desired product (10 mg, 5%) as a yellow solid: 1H NMR (500 MHz, CD3OD) δ 7.74-7.66 (m, 2H), 7.62-7.53 (m, 2H), 7.49-7.34 (m, 3H), 5.94 (d, J=5.4 Hz, 1H), 4.61 (q, J=6.9 Hz, 1H), 3.86-3.78 (m, 1H), 3.76 (s, 1H), 3.47 (d, J=12.6 Hz, 1H), 3.10-2.98 (m, 1H), 2.96-2.82 (m, 1H), 2.11-1.91 (m, 2H), 1.89 (d, J=7.0 Hz, 2H), 1.85-1.70 (m, 1H).


Example 417
2-[2-Fluoro-4-(8-methoxy-4-oxo-4,5-dihydrothieno[2,3-c]quinolin-9-yl)phenyl]acetonitrile



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Following General Procedure B, 9-bromo-8-methoxythieno[2,3-c]quinolin-4(5H)-one (350 mg, 1.1 mmol) was reacted with 2-[2-fluoro-4-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)phenyl]acetonitrile (440 mg, 1.7 mmol) to afford the desired product (400 mg, >99%) as a brown solid: ESI MS m/z 365 [C20H13FN2O2S+H]+.


Example 265
9-[4-(2-Aminoethyl)-3-fluorophenyl]-8-methoxythieno[2,3-c]quinolin-4(5H)-one Hydrochloride



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To a solution of 2-[2-fluoro-4-(8-methoxy-4-oxo-4,5-dihydrothieno[2,3-c]quinolin-9-yl)phenyl]acetonitrile (49 mg, 0.14 mmol) in toluene (3 mL) was added borane (1.0 M in THF, 3.0 mL, 0.30 mmol) and the reaction was stirred at reflux for 3 h. The reaction mixture was cooled to room temperature, concentrated and the residue was purified by preparatory HPLC. The residue was dissolved in aqueous HCl, concentrated and dried under high vacuum to afford the hydrochloride salt (4.5 mg, 9%) as a brown solid: 1H NMR (500 MHz, CD3OD) δ 7.63 (d, J=5.4 Hz, 1H), 7.56 (d, J=9.0 Hz, 1H), 7.50 (t, J=7.8 Hz, 1H), 7.40 (d, J=9.1 Hz, 1H), 7.11-7.05 (m, 2H), 6.11 (d, J=5.4 Hz, 1H), 3.76 (s, 3H), 3.25-3.08 (m, 4H), 2.75 (br s, 3H); ESI MS m/z 369 [C20H17FN2O2S+H]+; HPLC 95.0% (AUC), tR=7.89 min.


Example 418
(S)-tert-Butyl 1-[4-(8-Methoxy-4-oxo-4,5-dihydrothieno[2,3-c]quinolin-9-yl)phenyl]ethylcarbamate



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Following General Procedure B, 9-bromo-8-methoxythieno[2,3-c]quinolin-4(5H)-one (280 mg, 0.89 mmol) was reacted with (S)-tert-butyl 1-[4-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)phenyl]ethylcarbamate (320 mg, 1.1 mmol) to afford the desired product (220 mg, 55%) as a white solid: ESI MS m/z 351 [C25H26N2O4S-Boc]+.


Example 232
(S)-9-[4-(1-Aminoethyl)phenyl]-8-methoxythieno[2,3-c]quinolin-4(5H)-one Hydrochloride



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Following General Procedure C, (S)-tert-butyl 1-[4-(8-methoxy-4-oxo-4,5-dihydrothieno[2,3-c]quinolin-9-yl)phenyl]ethylcarbamate (90 mg, 0.12 mmol) was reacted with TFA (3 mL) to afford the desired product (11 mg, 15%) as an off-white solid: 1H NMR (500 MHz, CD3OD) δ 7.65-7.62 (m, 2H), 7.56-7.54 (m, 2H), 7.40-7.38 (m, 3H), 6.04 (d, J=5.5 Hz, 1H), 4.62 (q, J=7.0 Hz, 1H), 7.73 (s, 3H), 1.77 (d, J=6.9 Hz, 3H); ESI MS m/z 351[C20H18N2O2S+H]+; HPLC 97.6% (AUC), tR=8.33 min.


Example 216
8-Methoxy-9-{4-[1-(pyrrolidin-1-yl)ethyl]phenyl}thieno[2,3-c]quinolin-4(5H)-one Hydrochloride



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Following General Procedure B, 9-bromo-8-methoxythieno[2,3-c]quinolin-4(5H)-one (120 mg, 0.39 mmol) was reacted with 4-[1-(pyrrolidin-1-yl)ethyl]phenylboronic acid (170 mg, 0.77 mmol) to afford the desired product (70 mg, 45%) as a white solid: 1H NMR (500 MHz, CD3OD) δ 7.69-7.67 (m, 2H), 7.60 (d, J=5.4 Hz, 1H), 7.56 (d, J=9.0 Hz, 1H), 7.44-7.40 (m, 3H), 5.96 (d, J=5.4 Hz, 1H), 4.54 (q, J=6.8 Hz, 1H), 3.89-3.84 (m, 1H), 3.76 (s, 3H), 3.38-3.16 (m, 3H), 2.29-2.00 (m, 4H), 1.87 (d, J=6.9 Hz, 3H); ESI MS m/z 405 [C24H24N2O2S+H]+; HPLC >99%, tR=8.98 min.


Example 419
8-Methoxy-9-{4-[1-(piperidin-1-yl)ethyl]phenyl}thieno[2,3-c]quinolin-4(5H)-one



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Following General Procedure B, 9-bromo-8-methoxythieno[2,3-c]quinolin-4(5H)-one (150 mg, 0.48 mmol) was reacted with 4-[1-(piperidin-1-yl)ethyl]phenylboronic acid (170 mg, 0.73 mmol) to afford the desired product (10 mg, 5%) as a yellow solid: 1H NMR (500 MHz, CD3OD) δ 7.74-7.66 (m, 2H), 7.62-7.53 (m, 2H), 7.49-7.34 (m, 3H), 5.94 (d, J=5.4 Hz, 1H), 4.61 (q, J=6.9 Hz, 1H), 3.86-3.78 (m, 1H), 3.76 (s, 1H), 3.47 (d, J=12.6 Hz, 1H), 3.10-2.98 (m, 1H), 2.96-2.82 (m, 1H), 2.11-1.91 (m, 2H), 1.89 (d, J=7.0 Hz, 2H), 1.85-1.70 (m, 1H).


Example 420
2-[2-Fluoro-4-(8-methoxy-4-oxo-4,5-dihydrothieno[2,3-c]quinolin-9-yl)phenyl]acetonitrile



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Following Step 1 from General Procedure B, 9-bromo-8-methoxythieno[2,3-c]quinolin-4(5H)-one (350 mg, 1.1 mmol) was reacted with 2-[2-fluoro-4-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)phenyl]acetonitrile (440 mg, 1.7 mmol) to afford the desired product (400 mg, >99%) as a brown solid: ESI MS m/z 365 [C20H13FN2O2S+H]+.


Example 421
9-[4-(3-Aminopropyl)phenyl]-8-methoxythieno[2,3-c]quinolin-4(5H)-one



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Following the procedure outlined for Example 265, 3-[4-(8-methoxy-4-oxo-4,5-dihydrothieno[2,3-c]quinolin-9-yl)phenyl]propanenitrile (250 mg, 0.69 mmol) was reacted with borane (1.0 M in THF, 10 mL, 10 mmol) to afford the desired product (150 mg, 60%) as a brown oil: ESI MS m/z 365 [C21H20N2O2S+H]+.


Example 274
(R)-9-[4-(1-Aminoethyl)phenyl]-8-methoxythieno[2,3-c]quinolin-4(5H)-one Hydrochloride



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Following General Procedure C, (R)-tert-butyl 1-[4-(8-methoxy-4-oxo-4,5-dihydrothieno[2,3-c]quinolin-9-yl)phenyl]ethylcarbamate (50 mg, 0.11 mmol) was reacted with TFA (3 mL) to afford the desired product (11 mg, 26%) as an off-white solid: 1H NMR (500 MHz, CD3OD) δ 7.63-7.62 (m, 2H), 7.56-7.55 (m, 2H), 7.40-7.37 (m, 3H), 6.04 (d, J=5.4 Hz, 1H), 4.62 (q, J=6.9 Hz, 1H), 3.79 (s, 3H), 2.77 (br s, 3H), 1.76 (d, J=6.9 Hz, 3H); ESI MS m/z 351 [C20H18N2O2S+H]+; HPLC 98.7% (AUC), tR=8.24 min.


Example 422
(R)-tert-Butyl 1-[4-(8-Methoxy-4-oxo-4,5-dihydrothieno[2,3-c]quinolin-9-yl)phenyl]ethylcarbamate



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Following Step 1 from General Procedure B, 9-bromo-8-methoxythieno[2,3-c]quinolin-4(5H)-one (480 mg, 1.5 mmol) was reacted with (R)-tert-butyl 1-[4-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)phenyl]ethylcarbamate (800 mg, 2.3 mmol) to afford the desired product (410 mg, 59%) as a brown solid: ESI MS m/z 451 [C25H26N2O4S+H]+.


Example 423
2-[4-(8-Methoxy-4-oxo-4,5-dihydrothieno[2,3-c]quinolin-9-yl)phenyl]-2-methylpropanenitrile



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Following General Procedure B, 9-bromo-8-methoxythieno[2,3-c]quinolin-4(5H)-one (380 mg, 1.2 mmol) was reacted with 2-methyl-2-[4-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)phenyl]propanenitrile (500 mg, 1.9 mmol) to afford the desired product (260 mg, 56%) as a brown solid: ESI MS m/z 375 [C22H18N2O2S+H]+.


Example 424
9-[4-(1-Amino-2-methylpropa-2-yl)phenyl]-8-methoxythieno[2,3-c]quinolin-4(5H)-one



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Following the procedure outlined for Example 265, 2-[4-(8-methoxy-4-oxo-4,5-dihydrothieno[2,3-c]quinolin-9-yl)phenyl]-2-methylpropanenitrile (250 mg, 0.67 mmol) was reacted with borane (1.0 M in THF, 10 mL, 10.0 mmol) to afford the desired product (100 mg, 40%) as a yellow solid: ESI MS m/z 379 [C22H22N2O2S+H]+.


Example 425
9-{3-Fluoro-4-[(3-hydroxypyrrolidin-1-yl)methyl]phenyl)}-8-methoxythieno[2,3-c]quinolin-4(5H)-one



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Following General Procedure B, 9-bromo-8-methoxythieno[2,3-c]quinolin-4(5H)-one (180 mg, 0.58 mmol) was reacted with 1-[2-fluoro-4-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)benzyl]pyrrolidin-3-ol (280 mg, 0.87 mmol) to afford the desired product (130 mg, 48%) as a brown solid: 1H NMR (500 MHz, CD3OD) δ 7.79-7.72 (m, 1H), 7.66 (d, J=5.4 Hz, 1H), 7.58 (d, J=9.1 Hz, 1H), 7.42 (d, J=9.1 Hz, 1H), 7.33-7.21 (m, 2H), 6.09 (td, J=5.3, 2.4 Hz, 1H), 4.75-4.53 (m, 3H), 3.91-3.66 (m, 4H), 3.66-3.34 (m, 3H), 2.55-2.44 (m, 1H), 2.28-2.15 (m, 1H), 2.14-2.04 (m, 1H).


Example 426
tert-Butyl 5-(8-Methoxy-4-oxo-4,5-dihydrothieno[2,3-c]quinolin-9-yl)-2,3-dihydro-1H-inden-2-ylcarbamate



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Following General Procedure B, 9-bromo-8-methoxythieno[2,3-c]quinolin-4(5H)-one (1.1 g, 3.6 mmol) was reacted with tert-butyl 5-bromo-2,3-dihydro-1H-inden-2-ylcarbamate (2.0 g, 5.6 mmol) to afford the desired product (250 mg, 15%) as a brown solid: ESI MS m/z 363 [C26H26N2O4S+H-100]+.


Example 427
1-[4-(8-Methoxy-4-oxo-4,5-dihydrothieno[2,3-c]quinolin-9-yl)phenyl]cyclopropanecarbonitrile



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Following General Procedure B, 1-(4-bromophenyl)cyclopropanecarbonitrile (1.5 g, 7.1 mmol) was reacted with bis(pinacolato)diboron (2.7 g, 10 mmol) to afford the crude boronic ester which was reacted with 9-bromo-8-methoxythieno[2,3-c]quinolin-4(5H)-one (1.3 g, 4.2 mmol) to afford the desired product (378 mg, 29%) as a white solid: ESI MS m/z 373 [C22H16N2O2S+H]+.


Example 428
tert-Butyl 7-(8-Methoxy-4-oxo-4,5-dihydrothieno[2,3-c]quinolin-9-yl)-3,4-dihydroisoquinoline-2(1H)-carboxylate



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Following General Procedure B, 9-bromo-8-methoxythieno[2,3-c]quinolin-4(5H)-one (1 g, 3.3 mmol) was reacted with tert-butyl 7-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)-3,4-dihydroisoquinoline-2(1H)-carboxylate (1.8 g, 5.0 mmol) to afford the desired product (720 mg, 48%) as a brown solid: ESI MS m/z 463 [C26H26N2O4S+H]+.


Example 429
8-Methoxy-9-(1,2,3,4-tetrahydroisoquinolin-7-yl)thieno[2,3-c]quinolin-4(5H)-one



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Following General Procedure C, tert-Butyl 7-(8-Methoxy-4-oxo-4,5-dihydrothieno[2,3-c]quinolin-9-yl)-3,4-dihydroisoquinoline-2(1H)-carboxylate (260 mg, 0.53 mmol) was reacted with TFA (5 mL) afford the desired product (180 mg, 20%) as a white solid: 1H NMR (500 MHz, CD3OD) δ 7.61-7.56 (m, 1H), 7.55 (dd, J=9.0, 3.2 Hz, 1H), 7.44 (d, J=7.8 Hz, 1H), 7.41-7.36 (m, 1H), 7.22 (d, J=7.8 Hz, 1H), 7.16 (s, 1H), 6.13 (d, J=5.4 Hz, 1H), 4.42 (s, 2H), 3.73 (s, 3H), 3.68-3.54 (m, 2H), 3.29-3.20 (m, 2H).


Example 430
tert-Butyl 1-[2-Fluoro-4-(8-methoxy-4-oxo-4,5-dihydrothieno[2,3-c]quinolin-9-yl)phenyl]ethylcarbamate



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Following General Procedure B, 9-bromo-8-methoxythieno[2,3-c]quinolin-4(5H)-one (800 mg, 2.6 mmoL) was reacted with tert-butyl 1-[2-fluoro-4-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)phenyl]ethylcarbamate (1.4 g, 3.9 mmol) to afford the desired product (480 mg, 40%) as a brown solid: ESI MS m/z 469 [C25H2FN2O4S+H]+.


Example 431
3-[4-(8-Methoxy-4-oxo-4,5-dihydrothieno[2,3-c]quinolin-9-yl)phenyl]propanenitrile



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Following General Procedure B, 9-bromo-8-methoxythieno[2,3-c]quinolin-4(5H)-one (400 mg, 1.3 mmol) was reacted with 3-[4-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)phenyl]propanenitrile (600 mg, 1.9 mmol) to afford the desired product (320 mg, 69%) as a brown solid: ESI MS m/z 361 [C21H16N2O2S+H]+.


Example 432
9-(4-Acetylphenyl-8-methoxythieno[2,3-c]quinolin-4(5H)-one



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Following General Procedure B, 9-bromo-8-methoxythieno[2,3-c]quinolin-4(5H)-one (1.0 g, 3.2 mmol) was reacted with 1-[4-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)phenyl]ethanone (1.2 g, 4.8 mmol) to afford the desired product (520 mg, 46%) as a brown solid: 1H NMR (500 MHz, CD3OD) δ 8.16 (d, J=8.1 Hz, 2H), 7.61-7.54 (m, 2H), 7.45-7.39 (m, 3H), 6.05 (d, J=5.4 Hz, 1H), 3.75 (s, 3H), 2.71 (s, 3H).


Example 433
9-{4-[1-(Cyclopentylamino)ethyl]phenyl}-8-methoxythieno[2,3-c]quinolin-4(5H)-one



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Following General Procedure E, N-[1-(4-bromophenyl)ethyl]cyclopentanamine (600 mg, 2.3 mmol) was reacted with bis(pinacolato)diboron (410 mg, 1.6 mmol) to afford the crude boronic ester which was reacted with 9-bromo-8-methoxythieno[2,3-c]quinolin-4(5H)-one (250 mg, 0.81 mmol) to afford the desired product (330 mg, 97%) as a brown solid: 1H NMR (300 MHz, CD3OD) δ 7.73-7.64 (m, 2H), 7.60-7.50 (m, 2H), 7.47-7.34 (m, 3H), 6.01 (d, J=5.4 Hz, 1H), 4.57 (q, J=6.8 Hz, 1H), 3.74 (s, 3H), 3.62-3.45 (m, 1H), 2.30-2.02 (m, 2H), 1.93-1.85 (m, 2H), 1.81 (d, J=6.7 Hz, 3H), 1.77-1.51 (m, 4H).


Example 434
tert-Butyl 1-[4-(8-Methoxy-4-oxo-4,5-dihydrothieno[2,3-c]quinolin-9-yl)phenyl]propylcarbamate



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Following General Procedure B, 9-bromo-8-methoxythieno[2,3-c]quinolin-4(5H)-one (1.1 g, 3.7 mmol) was reacted with tert-butyl 1-[4-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)phenyl]propylcarbamate (2.0 g, 5.5 mmol) to afford the desired product (1.2 g, 68%) as a white solid: ESI MS m/z 465 [C26H28N2O4S+H]+.


Example 337
9-[4-(1-Aminopropyl)phenyl]-8-methoxythieno[2,3-c]quinolin-4(5H)-one Hydrochloride



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Following General Procedure C, tert-butyl 1-[4-(8-methoxy-4-oxo-4,5-dihydrothieno[2,3-c]quinolin-9-yl)phenyl]propylcarbamate (30 mg, 0.064 mmol) was reacted with TFA (2 mL) to afford the desired product (17 mg, 72%) as a white solid: 1H NMR (500 MHz, CD3OD) δ 7.64-7.57 (m, 2H), 7.54 (d, J=2.0 Hz, 1H), 7.53 (d, J=1.6 Hz, 1H), 7.39-7.35 (m, 3H), 5.98 (d, J=5.4 Hz, 1H), 4.32 (q, J=5.1 Hz, 1H), 5.53 (s, 3H), 2.17-2.07 (m, 2H), 1.03 (t, J=7.4 Hz, 3H); ESI MS m/z 365 [C21H20N2O2S+H]+; HPLC >99% (AUC), tR=9.47 min.


Example 435
(S)-tert-Butyl 1-[4-(8-Methoxy-4-oxo-4,5-dihydrothieno[2,3-c]quinolin-9-yl)phenyl]ethylcarbamate



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Following General Procedure B, 9-bromo-8-methoxythieno[2,3-c]quinolin-4(5H)-one (760 mg, 2.4 mmol) was reacted with (S)-tert-butyl 1-[4-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)phenyl]ethylcarbamate (1.3 g, 3.7 mmol) to afford the desired product (730 mg, 66%) as a light yellow solid: ESI MS m/z 451 [C25H26N2O4S+H]+.


Example 436
9-{4-[1-(Dimethylamino)ethyl]-phenyl}-8-methoxythieno[2,3-c]quinolin-4(5H)-one



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Following General Procedure B, 9-bromo-8-methoxythieno[2,3-c]quinolin-4(5H)-one (1.5 g, 4.8 mmol) was reacted with 4-[1-(dimethylamino)ethyl]phenylboronic acid (1.5 g, 6.3 mmol) to afford the desired product (1.1 g, 58%) as a white solid: ESI MS m/z 379 [C22H22N2O2S+H]+.


Example 139
tert-Butyl {1-[4-(8-Methoxy-4-oxo-4,5-dihydrothieno[2,3-c]quinolin-9-yl)benzyl]piperidin-4-yl}methylcarbamate



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Following General Procedure B, 9-bromo-8-methoxythieno[2,3-c]quinolin-4(5H)-one (110 mg, 0.31 mmol) was reacted with 4-({4-[(tert-butoxycarbonylamino)methyl]piperidin-1-yl}methyl)phenylboronic acid (80 mg, 0.26 mol) to afford the desired product (25 mg, 20%) as a yellow glass: 1H NMR (500 MHz, CD3OD) δ 7.69-7.66 (m, 2H), 7.57-7.54 (m, 2H), 7.41-7.38 (m, 3H), 5.96-5.95 (m, 1H), 4.48-4.44 (m, 2H), 3.75 (s, 3H), 3.70-3.64 (m, 2H), 3.27-2.91 (m, 4H), 2.25-1.95 (m, 2H), 1.57 (s, 1H), 1.52-1.42 (m, 10H); ESI MS m/z 534 [C30H35N3O4S+H]+; HPLC 97.6% (AUC), tR=14.10 min.


Example 437
(E)-tert-Butyl 1-[3-(8-Methoxy-4-oxo-4,5-dihydrothieno[2,3-c]quinolin-9-yl)allyl]piperidin-4-ylcarbamate



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Following General Procedure B, 9-bromo-8-methoxythieno[2,3-c]quinolin-4(5H)-one (180 mg, 0.48 mmol) was reacted with (E)-tert-butyl 1-[3-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)allyl]piperidin-4-ylcarbamate (100 mg, 0.32 mmol) to afford the desired product (86 mg, 57%) as a brown solid: ESI MS m/z 470 [C25H31N3O4S+H]+.


Example 152
(E)-9-[3-(4-Aminopiperidin-1-yl)prop-1-enyl]-8-methoxythieno[2,3-c]quinolin-4(5H)-one



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Following General Procedure C, (E)-tert-butyl 1-[3-(8-methoxy-4-oxo-4,5-dihydrothieno[2,3-c]quinolin-9-yl)allyl]piperidin-4-ylcarbamate (40 mg, 0.085 mmol) was reacted with TFA (1 mL) to afford the desired product (15 mg, 86%) as a yellow solid: 1H NMR (500 MHz, CD3OD) δ 7.94 (d, J=5.3 Hz, 1H), 7.86 (d, J=5.3 Hz, 1H), 7.34 (d, J=9.1 Hz, 1H), 7.24 (d, J=9.1 Hz, 1H), 7.06 (d, J=16.0 Hz, 1H), 6.14-6.08 (m, 1H), 4.12 (d, J=7.1 Hz, 2H), 3.84 (br s, 2H), 3.55 (br s, 1H), 3.26 (br s, 3H), 2.38 (d, J=13.3 Hz, 2H), 2.12-2.07 (m, 2H), 1.35-1.31 (m, 1H), 0.96-0.90 (m, 1H); ESI MS m/z 370 [C20H23N3O2S+H]+; HPLC 95.6% (AUC), tR=6.78 min.


Example 164
9-{4-[(Dimethylamino)methyl]phenyl}-8-methoxythieno[2,3-c]quinolin-4(5H)-one



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Following the procedure outlined for Example 460, 9-[4-(aminomethyl)phenyl]-8-methoxythieno[2,3-c]quinolin-4(5H)-one (100 mg, 0.27 mmol) was reacted with formaldehyde (37% in water, 20 mg, 0.67 mmol) to afford the desired product (45 mg, 47%): 1H NMR (500 MHz, CD3OD) δ 7.67 (d, J=8.2 Hz, 2H), 7.58-7.54 (m, 2H), 7.42-7.38 (m, 3H), 5.96 (d, J=5.5 Hz, 1H), 4.47 (s, 2H), 3.75 (s, 3H), 2.98 (s, 6H); ESI MS m/z 365 [C21H20N2O2S+H]+; HPLC >99% (AUC), tR=8.50 min.


Example 438
9-{4-[(Diethylamino)methyl]phenyl}-8-methoxythieno[2,3-c]quinolin-4(5H)-one



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Following General Procedure E, N-(4-bromobenzyl)-N-ethylethanamine (200 mg, 0.83 mmol) was reacted with bis(pinacolato)diboron (230 mg, 0.91 mmol) to afford the crude boronic ester which was reacted with 9-bromo-8-methoxythieno[2,3-c]quinolin-4(5H)-one (260 mg, 0.83 mmol) to afford the desired product (58 mg, 25%) as a white solid: 1H NMR (500 MHz, CD3OD) δ 7.69 (d, J=8.2 Hz, 2H), 7.60-7.54 (m, 2H), 7.46-7.43 (m, 2H), 7.41 (d, J=9.1 Hz, 1H), 5.99 (d, J=5.4 Hz, 1H), 4.50 (s, 2H), 3.75 (s, 3H), 3.41-3.32 (m, 4H), 1.44 (t, J=7.3 Hz, 6H).


Example 188
8-Methoxy-9-{4-[(methylamino)methyl]phenyl}thieno[2,3-c]quinolin-4(5H)-one



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Following General Procedure E, 1-(4-bromophenyl)-N-methylmethanamine (200 mg, 1.0 mmol) was reacted to bis(pinacoato)diboron (280 mg, 1.1 mmol) to afford the crude boronic ester which was reacted with 9-bromo-8-methoxythieno[2,3-c]quinolin-4(5H)-one (310 mg, 1.0 mmol) to afford the desired product (145 mg, 42%) as a white solid: 1H NMR (500 MHz, CD3OD) δ 7.65 (d, J=8.1 Hz, 2H), 7.58-7.52 (m, 2H), 7.42-7.35 (m, 3H), 6.02 (d, J=5.4 Hz, 1H), 4.33 (s, 2H), 3.73 (s, 3H), 2.83 (s, 3H).


Example 439
tert-Butyl 4-(8-Methoxy-4-oxo-4,5-dihydrothieno[2,3-c]quinolin-9-yl)benzylcarbamate



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Following General Procedure B, 9-bromo-8-methoxythieno[2,3-c]quinolin-4(5H)-one (150 mg, 0.48 mmol) was reacted with 4-[(tert-butoxycarbonylamino)methyl]phenylboronic acid (180 mg, 0.73 mmol) to afford the desired product (180 mg, 83%) as a brown solid: ESI MS m/z 437 [C24H24N2O4S+H]+.


Example 440
9-{4-[(Isopropylamino)methyl]phenyl}-8-methoxythieno[2,3-c]quinolin-4(5H)-one



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Following General Procedure E, N-(4-bromobenzyl)propan-2-amine (200 mg, 0.88 mmol) was reacted with bis(pinacolato)diboron (240 mg, 0.96 mmol) to afford the crude boronic ester which was reacted with 9-bromo-8-methoxythieno[2,3-c]quinolin-4(5H)-one (270 mg, 0.88 mmol) to afford the desired product (190 mg, 57%) as a light brown solid: 1H NMR (500 MHz, CD3CD2OD) δ 7.68-7.63 (m, 2H), 7.56-7.49 (m, 2H), 7.41-7.34 (m, 3H), 6.04 (dd, J=5.4, 2.4 Hz, 1H), 4.33 (s, 2H), 3.72-3.67 (m, 3H), 3.56-3.50 (m, 1H), 1.45 (dd, J=6.6, 2.2 Hz, 6H).


Example 269
9-{4-[(Ethylamino)methyl]phenyl}-8-methoxythieno[2,3-c]quinolin-4(5H)-one Hydrochloride



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Following General Procedure E, N-(4-bromobenzyl)ethanamine (300 mg, 1.4 mmol) was reacted with bis(pinacolato)diboron (390 mg, 1.5 mmol) to afford the crude boronic ester which was reacted with 9-bromo-8-methoxythieno[2,3-c]quinolin-4(5H)-one (430 mg, 1.4 mmol) to afford the desired product (160 mg, 31%) as a brown solid: 1H NMR (500 MHz, CD3OD) δ 7.67 (d, J=8.1 Hz, 2H), 7.57-7.54 (m, 2H), 7.39-7.36 (m, 3H), 6.03 (d, J=5.5 Hz, 1H), 4.34 (s, 2H), 3.72 (s, 3H), 3.23 (q, J=7.3 Hz, 2H), 1.97 (s, 2H), 1.42 (t, J=7.3 Hz, 3H); ESI MS m/z 365 [C21H20N2O2S+H]+; HPLC >99% (AUC), tR=8.61 min.


Example 441
(E)-tert-Butyl 1-[3-(8-Methoxy-4-oxo-4,5-dihydrothieno[2,3-c]quinolin-9-yl)allyl]piperidin-3-ylcarbamate



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Following General Procedure B, 9-bromo-8-methoxythieno[2,3-c]quinolin-4(5H)-one (530 mg, 1.7 mmol) was reacted with (E)-tert-Butyl 1-[3-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)allyl]piperidin-3-ylcarbamate (320 mg, 0.88 mmol) to afford the desired product (190 mg, 47%) as a light brown solid: ESI MS m/z 456 [C24H29N3O4S+H]+.


Example 442
tert-Butyl 4-(6-Fluoro-8-methoxy-4-oxo-4,5-dihydrothieno[2,3-c]quinolin-9-yl)benzylcarbamate



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Following General Procedure B, 9-bromo-6-fluoro-8-methoxythieno[2,3-c]quinolin-4(5H)-one (150 mg, 0.50 mmol) was reacted with tert-butyl 4-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)benzylcarbamate (200 mg, 0.60 mmol) to afford the desired product (100 mg, 48%) as a brown solid: ESI MS m/z 455 [C24H23FN2O4S+H]+.


Example 257
9-[4-(Aminomethyl)phenyl]-6-fluoro-8-methoxythieno[2,3-c]quinolin-4(5H)-one Hydrochloride



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Following General Procedure D-1, tert-butyl 4-(6-fluoro-8-methoxy-4-oxo-4,5-dihydrothieno[2,3-c]quinolin-9-yl)benzylcarbamate (15 mg, 0.030 mmol) was reacted with HCl (2 N in diethyl ether, 1.5 mL) to afford the desired product (10 mg, 90%) as a white solid: 1H NMR (500 MHz, CD3OD) δ 7.63 (d, J=8.1 Hz, 2H), 7.58 (d, J=5.4 Hz, 1H), 7.36 (d, J=8.1 Hz, 2H), 7.32 (d, J=12.7 Hz, 1H), 6.04 (d, J=5.4 Hz, 1H), 4.27 (s, 2H), 3.72 (s, 3H); ESI MS m/z 355 [C19H15FN2O2S+H]+; HPLC 99% (AUC), tR=10.64 min.


Example 443
9-{4-[1-(Dimethylamino)ethyl]phenyl})-6,7-difluoro-8-methoxythieno[2,3-c]quinolin-4(5H)-one



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Following General Procedure B, 9-bromo-6,7-difluoro-8-methoxythieno[2,3-c]quinolin-4(5H)-one (150 mg, 0.40 mmol) was reacted with 4-[1-(dimethylamino)ethyl]phenylboronic acid (120 mg, 0.50 mmol) to afford the desired product (55 mg, 35%) as an off-white solid: ESI MS m/z 415 [C22H20F2N2O2S+H]+.


Example 444
9-{4-[2-(Dimethylamino)ethyl]phenyl}-8-methoxythieno[2,3-c]quinolin-4(5H)-one



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Following the procedure outlined for Example 460, 9-[4-(2-aminoethyl)phenyl]-8-methoxythieno[2,3-c]quinolin-4(5H)-one (100 mg, 0.30 mmol) was reacted with formaldehyde (100 mg, 1.0 mmol) to afford the desired product (85 mg, 84%) as a white solid: 1H NMR (500 MHz, CD3CN+D2O) δ 7.54-7.50 (m, 2H), 7.42 (d, J=7.8 Hz, 2H), 7.32 (d, J=9.1 Hz, 1H), 7.13 (d, 7.8 Hz, 2H), 5.83 (d, J=5.3 Hz, 1H), 3.69 (s, 3H), 3.43-3.40 (m, 2H), 3.16-3.13 (m, 2H), 2.92 (s, 6H).


Example 445
9-(4-Amino-3-methoxyphenyl)-8-methoxythieno[2,3-c]quinolin-4(5H)-one



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Following General Procedure B, 9-bromo-8-methoxythieno[2,3-c]quinolin-4(5H)-one (100 mg, 0.30 mmol) was reacted with 2-methoxy-4-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)aniline (150 mg, 0.50 mmol) to afford the desired product (64 mg, 60%) as a brown solid: 1H NMR (500 MHz, CD3OD) δ 7.61 (d, J=5.3 Hz, 1H), 7.58-7.53 (m, 2H), 7.41 (d, J=5.3 Hz, 1H), 7.16 (s, 1H), 7.01 (d, J=5.3 Hz, 1H), 6.09 (d, J=5.1 Hz, 1H), 3.93 (s, 3H), 3.77 (s, 3H).


Example 222
9-{4-[1-(Dimethylamino)ethyl]phenyl}-6-fluoro-8-methoxythieno[2,3-c]quinolin-4(5H)-one Hydrochloride



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Following General Procedure B, 9-bromo-6-fluoro-8-methoxythieno[2,3-c]quinolin-4(5H)-one (100 mg, 0.30 mmol) was reacted with 4-[1-(dimethylamino)ethyl]phenylboronic acid (100 mg, 0.45 mmol) to afford the desired product (49 mg, 41%) as a white solid: 1H NMR (500 MHz, DMSO-d6) δ 10.28 (s, 1H), 7.77 (d, J=5.4 Hz, 1H), 7.71 (q, J=8.0 Hz, 2H), 7.46 (d, J=12.8 Hz, 1H), 7.38 (d, J=8.2 Hz, 2H), 5.69 (d, J=5.4 Hz, 1H), 4.64 (t, J=6.0 Hz, 1H), 3.71 (s, 3H), 2.82 (d, J=4.2 Hz, 3H), 2.70 (d, J=4.4 Hz, 3H), 1.74 (d, J=6.8 Hz, 3H); ESI MS m/z 397 [C22H21FN2O2S+H]+; HPLC >99% (AUC), tR=9.85 min.


Example 446
tert-Butyl{(1-[2-Fluoro-4-(8-methoxy-4-oxo-4,5-dihydrothieno[2,3-c]quinolin-9-yl)benzyl]piperidin-4-yl}methylcarbamate



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Following General Procedure B, 9-bromo-8-methoxythieno[2,3-c]quinolin-4(5H)-one (100 mg, 0.30 mmol) was reacted with tert-butyl{1-[2-fluoro-4-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)benzyl]piperidin-4-yl}methylcarbamate (150 mg, 0.36 mmol) to afford the desired product (81 mg, 49% 0 was a yellow solid: ESI MS m/z 552 [C30H34FN3O4S+H]+.


Example 447
tert-Butyl[5-(8-Methoxy-4-oxo-4,5-dihydrothieno[2,3-c]quinolin-9-yl)thiophen-2-yl]methylcarbamate



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Following General Procedure B, 9-bromo-8-methoxythieno[2,3-c]quinolin-4(5H)-one (150 mg, 0.48 mmol) was reacted with 5-[(tert-butoxycarbonylamino)methyl]thiophen-2-ylboronic acid (130 mg, 0.53 mmol) to afford the desired product (30 mg, 18%) as a off-white solid: 1H NMR (500 MHz, CD3OD) δ 7.74 (d, J=5.4 Hz, 1H), 7.56 (d, J=9.1 Hz, 1H), 7.36 (d, J=9.1 Hz, 1H), 6.49 (d, J=3.1 Hz, 1H), 6.40 (br s, 1H), 6.01 (d, J=5.4 Hz, 1H), 4.27 (s, 2H), 3.82 (s, 3H), 1.39 (s, 9H).


Example 448
2-Fluoro-N-(2-hydroxyethyl)-4-(8-methoxy-4-oxo-4,5-dihydrothieno[2,3-c]quinolin-9-yl)benzenesulfonamide



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Following General Procedure E, 4-bromo-2-fluoro-N-(2-hydroxyethyl)benzenesulfonamide (3.30 mg, 1.1 mmol) was reacted with bis(pinacolato)diborane (300 mg, 1.2 mmol) to afford the crude boronic ester which was reacted with 9-bromo-8-methoxythieno[2,3-c]quinolin-4(5H)-one (310 mg, 1.0 mmol) to afford the desired product (68 mg, 13%) as an off-white solid: 1H NMR (300 MHz, DMSO-d6) δ 11.95 (s, 1H), 8.04 (t, J=5.8 Hz, 1H), 7.93 (t, J=7.8 Hz, 1H), 7.93 (d, J=5.4 Hz, 1H), 7.57 (d, J=9.1 Hz, 1H), 7.49-7.43 (m, 2H), 7.30 (dd, J=8.0, 1.5 Hz, 1H), 5.89 (d, J=5.4 Hz, 1H), 4.78 (t, J=5.6 Hz, 1H), 3.72 (s, 3H), 3.46 (q, J=6.2 Hz, 2H), 3.05 (m, 2H).


Example 449
4-(8-Methoxy-4-oxo-4,5-dihydrothieno[2,3-c]quinolin-9-yl)-N,N-dimethylbenzenesulfonamide



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Following General Procedure B, 9-bromo-8-methoxythieno[2,3-c]quinolin-4(5H)-one (100 mg, 0.32 mmol) was reacted with N,N-dimethyl-4-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)benzenesulfonamide (110 mg, 0.35 mmol) to afford the desired product (33 mg, crude) as a brown solid: ESI MS m/z 415 [C20H8N2O4S2+H]+.


Example 450
N-(2-Hydroxyethyl)-4-(8-methoxy-4-oxo-4,5-dihydrothieno[2,3-c]quinolin-9-yl)benzenesulfonamide



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Following General Procedure B, 9-bromo-8-methoxythieno[2,3-c]quinolin-4(5H)-one (500 mg, 1.5 mmol) was reacted with N-(2-hydroxyethyl)-4-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)benzenesulfonamide (450 mg, 1.5 mmol) to afford the desired product (130 mg, 20%) as an off-white solid: 1H NMR (300 MHz, DMSO-d6) δ 11.93 (s, 1H), 7.94 (d, J=8.4 Hz, 2H), 7.78-7.74 (m, 2H), 7.58-7.42 (m, 4H), 5.74 (d, J=5.4 Hz, 1H), 4.78 (t, J=5.6 Hz, 1H), 3.71 (s, 3H), 3.45 (q, J=6.1 Hz, 2H), 2.93 (q, J=6.2 Hz, 2H).


Example 333
N-(2-Fluoroethyl)-4-(8-methoxy-4-oxo-4,5-dihydrothieno[2,3-c]quinolin-9-yl)benzenesulfonamide



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To a solution of N-(2-hydroxyethyl)-4-(8-methoxy-4-oxo-4,5-dihydrothieno[2,3-c]quinolin-9-yl)benzenesulfonamide (120 mg, 0.28 mmol) in methylene chloride (10 mL) and THF (6 mL) under nitrogen at −78° C. was added DAST (89 mg, 0.56 mmol) and the reaction mixture was stirred at −78° C. for 2 h and warmed to room temperature and stirred for 16 h. The reaction mixture was concentrated and the residue was purified by column chromatography (silica gel, ethyl acetate/hexanes gradient). The resulting crude residue was triturated in methylene chloride and filtered to afford the desired product (90 mg, 75%) as a off-white solid: 1H NMR (500 MHz, DMSO-d6) δ 11.92 (s, 1H), 8.10 (t, J=5.9 Hz, 1H), 7.95 (d, J=8.4 Hz, 2H), 7.76 (d, J=5.4 Hz, 1H), 7.56 (d, J=9.1 Hz, 1H), 7.51 (d, J=8.4 Hz, 2H), 7.43 (d, J=9.2 Hz, 1H), 5.75 (d, J=5.4 Hz, 1H), 4.51 (t, J=4.9 Hz, 1H), 4.42 (t, J=4.9 Hz, 1H), 3.71 (s, 3H), 3.24 (q, J=5.2 Hz, 1H), 3.19 (q, J=5.2 Hz, 1H); ESI MS m/z 433 [C20H17FN2O4S2+H]+; HPLC 93.4% (AUC), tR=15.64 min.


Example 451
tert-Butyl 4-(8-Methoxy-4-oxo-4,5-dihydrothieno[2,3-c]quinolin-9-yl)benzylcarbamate



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Following General Procedure E, tert-butyl 4-bromobenzylcarbamate (2.9 g, 10 mmol) was reacted with bis(pinacolato)diborane (2.8 g, 11 mmol) to afford the crude boronic ester which was reacted with 9-bromo-8-methoxythieno[2,3-c]quinolin-4(5H)-one (2.8 g, 9.0 mmol) to afford the desired product (2.7 g, 68%) as a brown solid: ESI MS m/z 437 [C24H24N2O4S+H]+.


Example 452
tert-Butyl 4-(6-Bromo-8-methoxy-4-oxo-4,5-dihydrothieno[2,3-c]quinolin-9-yl)benzylcarbamate



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To a solution of tert-butyl 4-(8-methoxy-4-oxo-4,5-dihydrothieno[2,3-c]quinolin-9-yl)benzylcarbamate (29 mg, 0.055 mmol) in DMF (1 mL) was added N-bromosuccinimide (12 mg, 0.066 mmol) and the reaction was stirred at room temperature for 1 h and heated at 50° C. for 2 h. The reaction mixture was concentrated and the residue was purified by preparatory TLC (silica, methanol/methylene chloride gradient) to afford the desired product (10 mg, 35%): ESI MS m/z 516 [C24H23BrN2O4S+H]+.


Example 453
tert-Butyl 2-[4-(8-Methoxy-4-oxo-4,5-dihydrothieno[2,3-c]quinolin-9-yl)phenyl]propan-2-ylcarbamate



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Following General Procedure E, tert-butyl 2-(4-bromophenyl)propan-2-ylcarbamate (160 mg, 0.50 mmol) was reacted with bis(pinacolato)diboron (140 mg, 0.55 mmol) to afford the crude boronic ester which was reacted with 9-bromo-8-methoxythieno[2,3-c]quinolin-4(5H)-one (140 mg, 0.45 mmol) to afford the desired product (110 mg, 47%) as a brown solid: ESI MS m/z 465 [C26H28N2O4S+H]+.


Example 454
tert-Butyl 4-(6-Chloro-8-methoxy-4-oxo-4,5-dihydrothieno[2,3-c]quinolin-9-yl)benzylcarbamate



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A solution of tert-butyl 4-(8-methoxy-4-oxo-4,5-dihydrothieno[2,3-c]quinolin-9-yl)benzylcarbamate (45 mg, 0.10 mmol) and N-chlorosuccinimide (17 mg, 0.13 mmol) in DMF (1 mL) was heated at 50° C. for 3 h. The reaction mixture was concentrated under reduced pressure. The residue was purified by preparatory HPLC (water/acetonitrile w 0.05% TFA gradient) to afford the desired product (15 mg, 32%) as a brown solid: ESI MS m/z 471 [C24H23ClN2O4S+H]+.


Example 455
tert-Butyl 2-[4-(6-Chloro-8-methoxy-4-oxo-4,5-dihydrothieno[2,3-c]quinolin-9-yl)phenyl]propan-2-ylcarbamate



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A solution of tert-butyl 2-[4-(8-methoxy-4-oxo-4,5-dihydrothieno[2,3-c]quinolin-9-yl)phenyl]propan-2-ylcarbamate (130 mg, 0.27 mmol) and N-chlorosuccinimide (47 mg, 0.35 mmol) in DMF (3 mL) was heated at 70° C. for 2 h. The reaction mixture was cooled to room temperature, quenched with water and the aqueous layer was extracted with methylene chloride/methanol (9:1). The combined organic layers were dried over sodium sulfate, filtered, concentrated and the residue was purified by column chromatography (silica, methanol/methylene chloride gradient) to afford the desired product (42 mg, 31%) as a brown solid: ESI MS m/z 500 [C26H27ClN2O4S+H]+.


Example 456
N-[4-(8-Methoxy-4-oxo-4,5-dihydrothieno[2,3-c]quinolin-9-yl)-2-methylphenyl]methanesulfonamide



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Following General Procedure E, N-(4-bromo-2-methylphenyl)methanesulfonamide (130 mg, 0.50 mmol) was reacted with bis(pinacolato)diboron (140 mg, 0.55 mmol) to afford the crude boronic ester which was reacted with 9-bromo-8-methoxythieno[2,3-c]quinolin-4(5H)-one (140 mg, 0.45 mmol) to afford the desired product (51 mg, 27%) as a brown solid: ESI MS m/z 415 [C20H18N2O4S2+H]+.


Example 599
(R)-tert-butyl 2-(4-(8-methoxy-6-methyl-4-oxo-4,5-dihydrothieno[2,3-c]quinolin-9-yl)phenyl)propylcarbamate



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Following General Procedure E, (R)-tert-butyl 2-(4-bromophenyl)propylcarbamate (60 mg, 0.20 mmol) was reacted with 9-bromo-8-methoxy-6-methylthieno[2,3-c]quinolin-4(5H)-one (60 mg, 0.20 mmol) to afford the desired product (52 mg, 62%) as a brown solid: ESI MS m/z 479 [C27H30N2O4S]+


Example 600
tert-butyl 2-(4-(8-methoxy-6-methyl-4-oxo-4,5-dihydrothieno[2,3-c]quinolin-9-yl)phenyl)propan-2-ylcarbamate



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Following General Procedure E, tert-butyl 2-(4-bromophenyl)propan-2-ylcarbamate (0.44 g, 1.4 mmol) was reacted with 9-bromo-8-methoxy-6-methylthieno[2,3-c]quinolin-4(5H)-one (0.45 g, 1.4 mmol) to afford the desired product (0.53 g, 79%) as a brown solid: ESI MS m/z 479 [C27H30N2O4S+H]+.


Example 601
tert-butyl 4-(8-methoxy-4-oxo-4,5-dihydrothieno[2,3-c]quinolin-9-yl)benzylcarbamate



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Following General Procedure E, tert-butyl 4-bromobenzylcarbamate (0.78 g, 2.7 mmol) was reacted with 9-bromo-8-methoxythieno[2,3-c]quinolin-4(5H)-one (0.76 g, 2.5 mmol) to afford the desired product (0.66 g, 62%) as a brown solid: ESI MS m/z 437 [C24H24N2O4S+H]+.


Example 602
(R)-tert-Butyl 1-(4-(8-methoxy-6-methyl-4-oxo-4,5-dihydrothieno[2,3-c]quinolin-9-yl)phenyl)ethylcarbamate



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Following General Procedure E, (R1-tert-butyl 1-(4-bromophenyl)ethylcarbamate (60 mg, 0.20 mmol) was reacted with 9-bromo-8-methoxy-6-methylthieno[2,3-c]quinolin-4(5H)-one (60 mg, 0.20 mmol) to afford the desired product (52 mg, 62%) as a brown solid:


Example 603
(R)-tert-Butyl 1-(4-(8-methoxy-4-oxo-4,5-dihydrothieno[2,3-c]quinolin-9-yl)phenyl)ethylcarbamate



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Following General Procedure E, (R1-tert-butyl 1-(4-bromophenyl)ethylcarbamate (1.5 g, 5 mmol) was reacted with 9-bromo-8-methoxythieno[2,3-c]quinolin-4(5H)-one (1.4 g, 4.6 mmol) to afford the desired product (0.90 g, 43%) as a brown solid: ESI MS m/z 451 [C25H26N2O4S+H]+.


Example 604
(S)-tert-Butyl 1-(4-(8-methoxy-6-methyl-4-oxo-4,5-dihydrothieno[2,3-c]quinolin-9-yl)phenyl)ethylcarbamate



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Following General Procedure E, (S)-tert-butyl 1-(4-bromophenyl)ethylcarbamate (60 mg, 0.20 mmol) was reacted with 9-bromo-8-methoxy-6-methylthieno[2,3-c]quinolin-4(5H)-one (60 mg, 0.20 mmol) to afford the desired product (52 mg, 62%) as a brown solid: ESI MS m/z 465 [C26H28N2O4S+H]+.


Example 605
tert-Butyl 1-(4-(8-methoxy-4-oxo-4,5-dihydrothieno[2,3-c]quinolin-9-yl)phenyl)ethylcarbamate



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Following General Procedure E, tert-butyl 1-(4-bromophenyl)ethylcarbamate (3.0 g, 10 mmol) was reacted with 9-bromo-8-methoxythieno[2,3-c]quinolin-4(5H)-one (2.8 g, 9.0 mmol) to afford the desired product (2.0 g, 50%) as a brown solid: ESI MS m/z 451 [C25H26N2O4S+H]+.


Example 606
(R)-tert-Butyl 1-(4-(6-chloro-8-methoxy-4-oxo-4,5-dihydrothieno[2,3-c]quinolin-9-yl)phenyl)propylcarbamate



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Following General Procedure H, (R)-tert-butyl 1-(4-(8-methoxy-4-oxo-4,5-dihydrothieno[2,3-c]quinolin-9-yl)phenyl)propylcarbamate (0.67 g, 1.5 mmol) was reacted with N-chlorosuccinimide (0.29 g, 1.6 mmol) in DMF (10 mL) to afford the desired product (0.28 g, 35%) as a brown solid: ESI MS m/z 499 [C26H27ClN2O4S+H]+.


Example 607
tert-Butyl 1-(4-(6-bromo-8-methoxy-4-oxo-4,5-dihydrothieno[2,3-c]quinolin-9-yl)phenyl)ethylcarbamate



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Following General Procedure I, tert-butyl 1-(4-(8-methoxy-4-oxo-4,5-dihydrothieno[2,3-c]quinolin-9-yl)phenyl)ethylcarbamate (1.0 g, 2.2 mmol) was reacted with N-bromosuccinimide (0.45 g, 2.5 mmol) in DMF (10 mL) to afford the desired product (0.35 g, 29%) as a brown solid: ESI MS m/z 529 [C25H25BrN2O4S+H]+.


Example 608
tert-Butyl 4-(6-bromo-8-methoxy-4-oxo-4,5-dihydrothieno[2,3-c]quinolin-9-yl)benzylcarbamate



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Following General Procedure I, tert-butyl 4-(8-methoxy-4-oxo-4,5-dihydrothieno[2,3-c]quinolin-9-yl)benzylcarbamate (0.66 g, 1.5 mmol) was reacted with N-bromosuccinimide (0.30 g, 1.7 mmol) in DMF (10 mL) to afford the desired product (0.39 g, 51%) as a brown solid: ESI MS m/z 515 [C24H23BrN2O4S+H]+.


Example 609
tert-Butyl 4-(8-methoxy-6-methyl-4-oxo-4,5-dihydrothieno[2,3-c]quinolin-9-yl)benzylcarbamate



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Following General Procedure J, tert-butyl 4-(6-bromo-8-methoxy-4-oxo-4,5-dihydrothieno[2,3-c]quinolin-9-yl)benzylcarbamate (52 mg, 0.10 mmol) was reacted with trimethylboroxine (13 mg, 0.10 mmol) to afford the desired product (43 mg, 95%) as a grey solid: ESI MS m/z 451 [C25H26N2O4S+H]+.


Example 610
tert-Butyl 1-(4-(8-methoxy-6-methyl-4-oxo-4,5-dihydrothieno[2,3-c]quinolin-9-yl)phenyl)ethylcarbamate



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Following General Procedure J, tert-butyl 1-(4-(6-bromo-8-methoxy-4-oxo-4,5-dihydrothieno[2,3-c]quinolin-9-yl)phenyl)ethylcarbamate (32 mg, 0.060 mmol) was reacted with trimethylboroxine (8 mg, 0.060 mmol) to afford the desired product (20 mg, 61%) as a grey solid: ESI MS m/z 465 [C26H28N2O4S+H]+.


Example 1168
(R)-9-(4-(1-aminopropan-2-yl)phenyl)-8-hydroxy-6-methylthieno[2,3-c]quinolin-4(5H)-one



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Following General Procedure F, (R)-tert-butyl 2-(4-(8-methoxy-6-methyl-4-oxo-4,5-dihydrothieno[2,3-c]quinolin-9-yl)phenyl)propylcarbamate (43 mg, 0.095 mmol) was reacted with tribromoborane (1.0 M in methylene chloride, 1.0 mL, 1.0 mmol) to afford the desired product (18 mg, 51%) as a grey solid: 1H NMR (300 MHz, DMSO-d6) δ 10.75-10.65 (m, 1H), 9.14 (s, 1H), 8.09 (s, 3H), 7.68 (d, J=5.4 Hz, 1H), 7.43 (d, J=8.4 Hz, 2H), 7.21 (d, J=8.3 Hz, 2H), 7.05 (s, 1H), 5.86 (d, J=5.4 Hz, 1H), 3.27-2.95 (m, 3H), 1.38 (d, J=6.6 Hz, 3H); ESI MS m/z 365 [C21H20N2O2S+H]+; HPLC 98.6%, tR=8.42 min.


Example 1122
(R)-9-(4-(1-Aminoethyl)phenyl)-8-hydroxy-6-methylthieno[2,3-c]quinolin-4(5H)-one



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Following General Procedure F, (R)-tert-butyl 1-(4-(8-methoxy-6-methyl-4-oxo-4,5-dihydrothieno[2,3-c]quinolin-9-yl)phenyl)ethylcarbamate (43 mg, 0.095 mmol) was reacted with tribromoborane (1.0 M in methylene chloride, 1.0 mL, 1.0 mmol) to afford the desired product (18 mg, 51%) as a grey solid: 1H NMR (300 MHz, DMSO-d6) δ 10.72 (s, 1H), 8.52 (s, 3H), 7.65 (dd, J=13.3, 6.8 Hz, 3H), 7.30 (d, J=8.2 Hz, 2H), 7.06 (s, 1H), 5.87 (d, J=5.4 Hz, 1H), 4.64-4.45 (m, 1H), 2.50 (s, 3H), 1.63 (d, J=6.8 Hz, 3H); ESI MS m/z 480 [C27H33N3O3S+H]+; HPLC 98.6%, tR=8.42 min.


Example 1212
9-(4-(Aminomethyl)phenyl)-8-hydroxy-6-methylthieno[2,3-c]quinolin-4(5H)-one Hydrochloride



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Following General Procedure F, tert-butyl 4-(8-methoxy-6-methyl-4-oxo-4,5-dihydrothieno[2,3-c]quinolin-9-yl)benzylcarbamate (43 mg, 0.095 mmol) was reacted with tribromoborane (1.0 M in methylene chloride, 1.0 mL, 1.0 mmol) to afford the desired product (18 mg, 51%) as a grey solid: 1H NMR (500 MHz, CD3OD) δ 7.62 (d, J=8.1 Hz, 2H), 7.53 (d, J=5.4 Hz, 1H), 7.39 (d, J=8.0 Hz, 2H), 7.07 (s, 1H), 6.10 (d, J=5.4 Hz, 1H), 4.26 (s, 1H), 2.57 (s, 3H); ESI MS m/z 335 [C19H16N2O2S−H]; HPLC 96.7%, tR=7.99 min.


Example 1225
(S)-9-(4-(1-Aminoethyl)phenyl)-8-hydroxy-6-methylthieno[2,3-c]quinolin-4(5H)-one



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Following General Procedure F, (S)-9-(4-(1-aminoethyl)phenyl)-8-hydroxy-6-methylthieno[2,3-c]quinolin-4(5H)-one (52 mg, 0.11 mmol) was reacted with tribromoborane (1.0 M in methylene chloride, 1.0 mL, 1.0 mmol) to afford the desired product (20 mg, 46%) as an off-white solid: 1H NMR (500 MHz, CD3OD) δ 7.62 (d, J=7.4 Hz, 2H), 7.54 (d, J=5.4 Hz, 1H), 7.39 (d, J=7.4 Hz, 2H), 7.07 (s, 1H), 6.09 (d, J=5.4 Hz, 1H), 4.61 (q, J=6.9 Hz, 1H), 2.57 (s, 3H), 1.76 (d, J=6.9 Hz, 3H): ESI MS m/z 351 [C20H18N2O2S+H]+; HPLC >99%, tR=8.40 min.


Example 1032
9-(4-(1-Aminoethyl)phenyl)-6-bromo-8-hydroxythieno[2,3-c]quinolin-4(5H)-one hydrochloride



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Following General Procedure F, tert-butyl 1-(4-(6-bromo-8-methoxy-4-oxo-4,5-dihydrothieno[2,3-c]quinolin-9-yl)phenyl ethylcarbamate (17 mg, 0.032 mmol) was reacted with tribromoborane (1.0 M in methylene chloride, 1.0 mL, 1.0 mmol) to afford the desired product (8 mg, 55%) as a light yellow solid: 1H NMR (500 MHz, MeOD) δ 7.62 (d, J=7.4 Hz, 2H), 7.54 (d, J=5.4 Hz, 1H), 7.42-7.37 (m, 2H), 7.07 (d, J=0.7 Hz, 1H), 6.09 (d, J=5.4 Hz, 1H), 4.67-4.56 (m, 1H), 2.57 (s, 3H), 1.76 (d, J=6.9 Hz, 3H); ESI MS m/z 415 [C19H15BrN2O2S+H]+; HPLC 95.0%, tR=12.16 min.


Example 1066
9-(4-(1-Aminoethyl)phenyl)-8-hydroxy-6-methylthieno[2,3-c]quinolin-4(5H)-one



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Following General Procedure F, 9-(4-(1-aminoethyl)phenyl)-8-hydroxy-6-methylthieno[2,3-c]quinolin-4(5H)-one (20 mg, 0.043 mmol) was reacted with tribromoborane (1.0 M in methylene chloride, 1.0 mL, 1.0 mmol) to afford the desired product (10 mg, 60%) as a light grey solid: 1H NMR (500 MHz, MeOD) δ 7.62 (d, J=7.4 Hz, 2H), 7.54 (d, J=5.4 Hz, 1H), 7.42-7.37 (m, 2H), 7.07 (d, J=0.7 Hz, 1H), 6.09 (d, J=5.4 Hz, 1H), 4.67-4.56 (m, 1H), 2.57 (s, 3H), 1.76 (d, J=6.9 Hz, 3H); ESI MS m/z 351 [C20H18N2O2S+H]+; HPLC >99%, tR=8.40 min.


Example 1123
(R)-9-(4-(1-Aminoethyl)phenyl)-6-bromo-8-hydroxythieno[2,3-c]quinolin-4(5H)-one



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Following General Procedure F, (R)-tert-butyl 1-(4-(6-bromo-8-methoxy-4-oxo-4,5-dihydrothieno[2,3-c]quinolin-9-yl phenyl)ethylcarbamate (24 mg, 0.045 mmol) was reacted with tribromoborane (1.0 M in methylene chloride, 1.0 mL, 1.0 mmol) to afford the desired product (18 mg, 88%) as a light grey solid: 1H NMR (500 MHz, MeOD) δ 7.64 (dd, J=10.4, 3.5 Hz, 31H), 7.61 (d, J=5.4 Hz, 1H), 7.47 (s, 1H), 7.42 (d, J=7.5 Hz, 2H), 6.07 (d, J=5.4 Hz, 1H), 4.65-4.59 (m, 1H), 1.76 (d, J=6.9 Hz, 3H); ESI MS m/z 415 [C19H15BrN2O2S+H]+; HPLC 97.0%, tR=8.74 min.


Example 1159
(R)-9-(4-(1-Aminopropyl)phenyl)-6-chloro-8-hydroxythieno[2,3-c]quinolin-4(5H)-one hydrochloride



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Following General Procedure F, (R)-tert-butyl 1-(4-(6-chloro-8-methoxy-4-oxo-4,5-dihydrothieno[2,3-c]quinolin-9-yl)phenyl)propylcarbamate (30 mg, 0.063 mmol) was reacted with tribromoborane (1.0 M in methylene chloride, 1.0 mL, 1.0 mmol) to afford the desired product (22 mg, 87%) as a light yellow solid: 1H NMR (500 MHz, CD3OD) δ 7.63-7.56 (m, 2H), 7.53 (d, J=5.4 Hz, 1H), 7.40 (t, J=6.6 Hz, 3H), 7.08 (s, 1H), 6.04 (d, J=5.4 Hz, 1H), 4.31 (dd, J=9.2, 5.9 Hz, 1H), 2.57 (s, 3H), 2.21-2.01 (m, 2H), 1.03 (t, J=7.4 Hz, 3H); ESI MS m/z 383 [C20H17ClN2O2S−H]; HPLC 96.9%, tR=8.69 min.


Example 1157
(R)-9-(4-(1-Aminopropyl)phenyl)-8-hydroxy-6-methylthieno[2,3-c]quinolin-4(5H)-one hydrochloride



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Following General Procedure F, (R)-tert-butyl 1-(4-(8-methoxy-6-methyl-4-oxo-4,5-dihydrothieno[2,3-c]quinolin-9-yl)phenyl)propylcarbamate (30 mg, 0.063 mmol) was reacted with tribromoborane (1.0 M in methylene chloride, 1.0 mL, 1.0 mmol) to afford the desired product (22 mg, 87%) as a light grey solid: 1H NMR, (500 MHz, CD3OD) δ 7.63-7.56 (m, 2H), 7.53 (d, J=5.4 Hz, 1H), 7.40 (t, J=6.6 Hz, 3H), 7.08 (s, 1H), 6.04 (d, J=5.4 Hz, 1H), 4.31 (dd, J=9.2, 5.9 Hz, 1H), 2.57 (s, 3H), 2.21-2.01 (m, 2H), 1.03 (t, J=7.4 Hz, 3H); ESI MS m/z 365 [C21H20N2O2S+H]+; HPLC >99%, tR=8.69 min.


Example 1330
9-(4-(2-Aminopropan-2-yl)phenyl)-8-hydroxy-6-methylthieno[2,3-c]quinolin-4(5)-one



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Following General Procedure F, (S)-9-(4-(1-aminoethyl)phenyl-8-hydroxy-6-methylthieno[2,3-c]quinolin-4(5H)-one (52 mg, 0.11 mmol) was reacted with tribromoborane (1.0 M in methylene chloride, 1.0 mL, 1.0 mmol) to afford the desired product (20 mg, 46%) as an off-white solid: 1H NMR (500 MHz, CD % OD) δ 7.68 (d, J=8.4 Hz, 2H), 7.54 (d, J=5.4 Hz, 1H), 7.41 (d, J=8.4 Hz, 2H), 7.07 (s, 1H), 6.08 (d, J=5.4 Hz, 1H), 2.57 (s, 3H), 1.86 (s, 6H); ESI MS m/z 363 [C21H20N2O2S−H]; HPLC 98.7%, tR=8.51 min.


Example 611 982
9-bromo-8-methoxy-6-methyl-5-((2-(trimethylsilyl)ethoxy)methyl)thieno[2,3-c]quinolin-4(5H)-one



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To a suspension of 9-bromo-8-methoxy-6-methylthieno[2,3-c]quinolin-4(5H)-one (2.2 g, 6.8 mmol) in a mixture of DMF (15 mL) and THF (15 mL) at 0° C. was added sodium hydride (60%, 0.54 g, 13.6 mmol). The reaction mixture was stirred at 0° C. for 30 min before (2-(chloromethoxy)ethyl)trimethylsilane (3.4 g, 20 mmol) was added. The resulting mixture was stirred at rt overnight and then poured into ice-water (50 mL). The resulting precipitate was filtered and purified by column chromatography (silica, heptane/ethyl acetate) to afford the desired product (2.7 g, 87%) as a light yellow solid: ESI MS m/z 454 [C19H24BrNO3SSi+H]+.


Example 612
9-Bromo-8-methoxy-2,6-dimethyl-5-((2-(trimethylsilyl)ethoxy)methyl)thieno[2,3-c]quinolin-4(5H)-one



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To a stirred solution of diidopropylamine (85 μL, 0.6 mmol) in THF (2.5 mL) at −78° C. was added n-BuLi (2.5 M, 0.24 mL, 0.60 mmol) and the reaction mixture was stirred at 0° C. for 10 min then cooled to −78° C. A solution of 9-bromo-8-methoxy-6-methyl-5-((2-(trimethylsilyl)ethoxy)methyl)thieno[2,3-c]quinolin-4(5H)-one (0.23 g, 0.50 mmol) in THF (1 mL) was added dropwise and the reaction mixture was stirred at −78° C. for 30 min. Iodomethane (93 μL, 1.5 mmol) was added and the reaction mixture was stirred at −78° C. for 2 h and quenched by the addition of satd. aq. ammonium chloride and extracted with dichloromethane. The organics were dried over Na2SO4, filtered, concentrated in vacuo and the residue was purified by column chromatography (silica, heptane/ethyl acetate) to afford the desired product (0.13 g, 55%) as a white solid: ESI MS m/z 468 [C20H26BrNO3SSi+H]+.


Example 613
(R)-tert-Butyl 2-(4-(8-methoxy-2,6-dimethyl-4-oxo-5-((2-(trimethylsilyl)ethoxy)methyl)-4,5-dihydrothieno[2,3-c]quinolin-9-yl)phenyl)propylcarbamate



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Following General Procedure B, (R)-tert-butyl 2-(4-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)phenyl)propylcarbamate (0.12 g, 0.33 mmol) was reacted with 9-bromo-8-methoxy-2,6-dimethyl-5-((2-(trimethylsilyl)ethoxy)methyl)thieno[2,3-c]quinolin-4(5H)-one (0.12 g, 0.33 mmol) to afford the desired product (78 mg, 45%) as a solid: ESI MS m/z 623 [C34H46N2O5SSi+H]+.


Example 1341
(R)-9-(4-(1-Aminopropan-2-yl)phenyl)-8-methoxy-2,6-dimethylthieno[2,3-c]quinolin-4(5H)-one hydrochloride



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To a solution of (R)-tert-butyl 2-(4-(8-methoxy-2,6-dimethyl-4-oxo-5-((2-(trimethylsilyl)ethoxy)methyl)-4,5-dihydrothieno[2,3-c]quinolin-9-yl)phenyl)propylcarbamate (24 mg, 0.039 mmol) in CH2Cl2 (1 mL) at rt was added trifluoroacetic acid (1.0 mL) and the reaction was stirred at that temperature for 2 h. The mixture was concentrated and the residue was dissolved methanol (2 mL) and treated with NH4OH (2 mL). The resulting mixture was stirred at rt for 2 h and purified by preparatory HPLC (C18 silica, acetonitrile/water (with 0.05% TFA) gradient). The desired fractions were combined, concentrated and the residue was dissolved in aqueous HCl, concentrated and dried under high vacuum to afford the desired product (5 mg, 30%) as a hydrochloride salt: 1H NMR (500 MHz, CD3OD) δ 7.52 (dd, J=7.8, 1.5 Hz, 1H), 7.47 (dd, J=7.7, 1.5 Hz, 1H), 7.32 (s, 1H), 7.31-7.22 (m, 2H), 5.30 (d, J=2.7 Hz, 1.1H), 3.29-3.18 (m, 3H), 2.63 (s, 3H), 1.47 (d, J=6.1 Hz, 3H): ESI MS m/z 392 [C23H24N2O4S+H]+.


Example 1340
(R)-9-(4-(1-Aminopropan-2-yl)phenyl)-8-hydroxy-2,6-dimethylthieno[2,3-c]quinolin-4(5H)-one



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To a solution of (R)-tert-butyl 2-(4-(8-methoxy-2,6-dimethyl-4-oxo-5-((2-(trimethylsilyl)ethoxy)methyl)-4,5-dihydrothieno[2,3-c]quinolin-9-yl)phenyl)propylcarbamate (40 mg, 0.064 mmol) in CH2C2 (1 mL) at 0° C. was added BBr3 (1.0 M in methylene chloride, 1.0 mL, 1.0 mmol) and the reaction was stirred at that temperature for 1 h and quenched by pouring onto water or ice-water. The resulting mixture was concentrated and the residue was dissolved methanol (2 mL) and treated with NH4OH (2 mL). The resulting mixture was stirred at rt for 2 h and purified by preparatory HPLC (C18 silica, acetonitrile/water (with 0.05% TFA) gradient). The desired fractions were combined, concentrated and the residue was dissolved in aqueous HCl, concentrated and dried under high vacuum to afford the desired product as a hydrochloride salt: 1H NMR (500 MHz, CD OD) δ 7.55 (dd, J=7.9, 1.9 Hz, 1H), 7.45 (dd, J=7.7, 1.9 Hz, 1H), 7.34 (dd, J=7.9, 1.8 Hz, 1H), 7.28 (dd, J=7.7, 1.7 Hz, 1H), 7.06 (d, J=0.7 Hz, 1H), 5.70 (d, J=1.1 Hz, 1H), 3.29-3.13 (m, 3H), 2.55 (s, 3H), 2.30 (d, J=1.0 Hz, 3H), 1.50 (d, J=6.5 Hz, 3H); ESI MS m/z 378 [C22H22N2O2S+H]+.


Example 614
9-Bromo-2-chloro-8-methoxy-6-methyl-5-((2-(trimethylsilyl)ethoxy)methyl)thieno[2,3-c]quinolin-4(5H)-one



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To a stirred solution of diidopropylamine (85 μL, 0.6 mmol) in THF (2.5 mL) at −78° C. was added n-BuLi (2.5M, 0.24 mL, 0.6 mmol).The resulting mixture was stirred at 0° C. for 10 min and then cooled at −78° C. A solution of 9-bromo-8-methoxy-6-methyl-5-((2-(trimethylsilyl)ethoxy)methyl)thienio[2,3-c]quinolin-4(5H)-one (0.23 g, 0.50 mmol) in T-IF (1 mL) was added dropwise and the resulting mixture was stirred at −78° C. for 30 min. Hexachloroethane (0.24 g, 1.0 mmol) was added dropwise and the mixture was stirred at −78° C. for 2 h and allowed to warm to rt. The reaction was quenched by adding saturated ammonium chloride and extracted with dichloromethane (2×). The combined extracts were dried over Na2SO4, filtered and concentrated in vacuo. he residue was purified by column chromatography (heptane/ethyl acetate) to afford the desired product (0.13 g, 52%) as a white solid: ESI MS m/z 488 [C19H23BrClNO3SSi+H]+.


Example 615
(R)-tert-Butyl 2-(4-(2-chloro-8-methoxy-6-methyl-4-oxo-5-((2-(trimethylsilyl)ethoxy)methyl)-4,5-dihydrothieno[2,3-c]quinolin-9-yl)phenyl)propylcarbamate



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Following General Procedure E, (R)-tert-butyl 2-(4-bromophenyl)propylcarbamate (97 mg, 0.31 mmol) was reacted with 9-bromo-8-methoxy-2,6-dimethyl-5-((2-(trimethylsilyl)ethoxy)methyl)thieno[2,3-c]quinolin-4(5H)-one (0.10 g, 0.21 mmol) to afford the desired product (62 mg, 46%) as a solid: ESI MS m/z 643 [C33H43ClN2O5SSi+H]+.


Example 1354
(R)-9-(4-(1-Aminopropan-2-yl)phenyl)-2-chloro-8-methoxy-6-methylthieno[2,3-c]quinolin-4(5H)-one hydrochloride



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To a solution of (R)-tert-butyl 2-(4-(2-chloro-8-methoxy-6-methyl-4-oxo-5-((2-(trimethylsilyl)ethoxy)methyl)-4,5-dihydrothieno[2,3-c]quinolin-9-yl)phenyl)propylcarbamate (11 mg, 0.017 mmol) in CH2Cl2 (1 mL) at rt was added trifluoroacetic acid (1.0 mL) and the reaction was stirred at that temperature for 2 h. The mixture was concentrated and the residue was dissolved methanol (2 mL) and treated with NH4OH (2 mL). The resulting mixture was stirred at rt for 2 h and purified by preparatory HPLC (C18 silica, acetonitrile/water (with 0.05% TFA) gradient). The desired fractions were combined, concentrated and the residue was dissolved in aqueous HCl, concentrated and dried under high vacuum to afford the desired product (7 mg, 92%) as a hydrochloride salt: 1H NMR (500 MHz, CD3OD) δ 7.52 (dd, J=7.8, 1.5 Hz, 1H), 7.47 (dd, J=7.7, 1.5 Hz, 1H), 7.32 (s, 1H), 7.31-7.22 (m, 2H), 5.30 (d, J=2.7 Hz, 1H), 3.29-3.18 (m, 3H), 2.63 (s, 3H), 1.47 (d, J=6.1 Hz, 3H); ESI MS m/z 413 [C22H21ClN2O2S I H]+.


Example 1353
(R)-9-(4-(1-Aminopropan-2-yl)phenyl)-2-chloro-8-hydroxy-6-methylthieno[2,3-c]quinolin-4(5H)-one hydrochloride



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To a solution of (R)-tert-butyl 2-(4-(2-chloro-8-methoxy-6-methyl-4-oxo-5-((2-(trimethylsilyl)ethoxy)methyl)-4,5-dihydrothieno[2,3-c]quinolin-9-yl)phenyl)propylcarbamate (32 mg, 0.050 mmol) in CH2Cl2 at 0° C. was added BBr3 (1.0 M in methylene chloride, 1.0 mL, 1.0 mmol) and the reaction was stirred at that temperature for 1 h and quenched by pouring onto water or ice-water. The resulting mixture was concentrated and the residue was dissolved methanol (2 mL) and treated with NH4OH (2 mL). The resulting mixture was stirred at rt for 2 h and purified by preparatory HPLC (C18 silica, acetonitrile/water (with 0.05% TFA) gradient). The desired fractions were combined, concentrated and the residue was dissolved in aqueous HCl, concentrated and dried under high vacuum to afford the desired product as a hydrochloride salt: 1H NMR (500 MHz, MeOD) δ 7.57 (dd, J=7.9, 1.8 Hz, 1H), 7.48 (dd, J=7.8, 1.8 Hz, 1H), 7.35 (dd, J=7.9, 1.7 Hz, 1H), 7.29 (dd, J=7.8, 1.6 Hz, 1H), 7.10 (d, J=0.7 Hz, 1H), 5.75 (s, 1H), 3.28-3.19 (m, 3H), 2.55 (s, 3H), 1.50 (d, J=6.4 Hz, 3H). ESI MS m/z 399 [C21H19ClN2O2S+H]+.


Example 616
9-Bromo-2-fluoro-8-methoxy-6-methyl-5-((2-(trimethylsilyl)ethoxy)methyl)thieno[2,3-c]quinolin-4(5H)-one



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To a stirred solution of diidopropylamine (84 μL 0.6 mmol) in THF (2.5 mL) at −78° C. was added n-BuLi (2.5M, 0.24 mL, 0.6 mmol). The resulting mixture was stirred at 0° C. for 10 min and then cooled at −78° C. A solution of 9-bromo-8-methoxy-6-methyl-5-((2-(trimethylsilyl ethoxy)methyl)thieno[2,3-c]quinolin-4(5H)-one (0.23 g, 0.50 mmol) in THF (1 mL) was added dropwise and the resulting mixture was stirred at −78° C. for 30 min. A solution of N-fluorobenzenesulfonimide (0.32, 1.0 mmol) in THF (1 mL) was added and the mixture was stirred at −78° C. for 2 h. The reaction was quenched by adding saturated ammonium chloride and extracted with dichloromethane (2×). The combined extracts were dried over Na2SO4, filtered and concentrated in vacuo. The residue was purified by column chromatography (heptane/ethyl acetate) to afford the desired product (98 mg, 41%) as a white solid: ESI MS m/z 472 [C19H23BrFNO3SSi+H]+.


Example 617
(R)-tert-butyl 2-(4-(2-fluoro)-8-methoxy-6-methyl-4-oxo-5-((2-(trimethylsilyl)ethoxy)methyl)-4,5-dihydrothieno[2,3-c]quinolin-9-yl)phenyl)propylcarbamate



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Following General Procedure B, (R)-tert-butyl 2-(4-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)phenyl)propylcarbamate (0.11 g, 0.31 mmol) was reacted with 9-bromo-2-fluoro-8-methoxy-6-methyl-5-((2-(trimethylsilyl)ethoxy)methyl)thieno[2,3-c]quinolin-4(5H)-one (98 mg, 0.21 mmol) to afford the desired product (0.11 g, 85%) as a solid: ESI MS m/z 627 [C33H43FN2O2SSi+H]+.


Example 1375
(R)-9-(4-(1-Aminopropan-2-yl)phenyl)-2-fluoro-8-methoxy-6-methylthieno[2,3-c]quinolin-4(5H)-one



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To a solution (R)-tert-butyl 2-(4-(2-fluoro-8-methoxy-6-methyl-4-oxo-5-((2-(trimethylsilyl)ethoxy)methyl)-4,5-dihydrothieno[2,3-c]quinolin-9-yl)phenyl)propylcarbamate (17 mg, 0.027 mmol) in CH2C2 (1 mL) at rt was added trifluoroacetic acid (1.0 mL) and the reaction was stirred at that temperature for 2 h. The mixture was concentrated and the residue was dissolved methanol (2 mL) and treated with NH4OH (2 mL). The resulting mixture was stirred at rt for 2 h and purified by preparatory HPLC (C18 silica, acetonitrile/water (with 0.05% TFA) gradient). The desired fractions were combined, concentrated and the residue was dissolved in aqueous HCl, concentrated and dried under high vacuum to afford the desired product (5 mg, 43%) as a hydrochloride salt: 1H NMR (500 MHz, CD3OD) δ 7.52 (dd, J=7.8, 1.5 Hz, 1H), 7.47 (dd, J=7.7, 1.5 Hz, 1H), 7.32 (s, 1H), 7.31-7.22 (m, 2H), 5.30 (d, J=2.7 Hz, 1H), 3.29-3.18 (m, 3H), 2.63 (s, 3H), 1.47 (d, J=6.1 Hz, 3H): ESI MS m/z 397 [C22H21FN2O2S+H]+.


Example 1383
(R)-9-(4-(1-Aminopropan-2-yl)phenyl)-2-fluoro-8-hydroxy-6-methylthieno[2,3-c]quinolin-4(5H)-one



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To a solution of (R)-tert-butyl 2-(4-(2-fluoro-8-methoxy-6-methyl-4-oxo-5-((2-(trimethylsilyl)ethoxy)methyl)-4,5-dihydrothieno[2,3-c]quinolin-9-yl)phenyl)propylcarbamate (60 mg, 0.096 mmol) in CH2Cl2 (1 mL) at 0° C. was added BBr3 (1.0 M in methylene chloride, 1.0 mL, 1.0 mmol) and the reaction was stirred at that temperature for 1 h and quenched by pouring onto water or ice-water. The resulting mixture was concentrated and the residue was dissolved methanol (2 mL) and treated with NH4OH (2 mL). The resulting mixture was stirred at rt for 2 h and purified by preparatory HPLC (C18 silica, acetonitrile/water (with 0.05% TFA) gradient). The desired fractions were combined, concentrated and the residue was dissolved in aqueous HCl, concentrated and dried under high vacuum to afford the desired product as a hydrochloride salt: 1H NMR (500 MHz, CD3OD) δ 7.55 (dd, J=7.9, 1.7 Hz, 1H), 7.46 (dd, J=7.8, 1.8 Hz, 1H), 7.32 (dd, J=23.9, 7.9 Hz, 2H), 7.10 (s, 1H), 5.46 (d, J=2.9 Hz, 1H), 3.28-3.15 (m, 3H), 2.55 (s, 3H), 1.49 (d, J=6.3 Hz, 3H); ESI MS m/z 383 [C21H19FN2O2S+H]+.


Example 618
tert-butyl 1-(4-(8-hydroxy-4-oxo-4,5-dihydrothieno[2,3-c]quinolin-9-yl)phenyl)ethylcarbamate



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To a solution of tert-butyl 1-(4-(8-methoxy-4-oxo-4,5-dihydrothieno[2,3-c]quinolin-9-yl)phenyl)ethylcarbamate (0.96 g, 2.1 mmol) in dichloromethane (15 mL) at 0° C. was added BBr3 (1.0 M in methylene chloride, 15 mL, 15 mmol) and the reaction was stirred at that temperature for 1 h and quenched by pouring onto water or ice-water. The precipitate was filtered and suspended in DMF (8 mL). Di-tert-butyl dicarbonate (0.85 g, 3.9 mmol) and triethylamine (1.1 mL, 7.8 mmol) were added and the mixture was stirred at rt for 2 h. Water was added and the precipitate was filtered and purified by column chromatography to afford the desired product as a solid: ESI MS m/z 437 [C24H24N2O4S+H]+.


Example 619
tert-butyl 1-(4-(8-(isopropoxycarbonyloxy)-4-oxo-4,5-dihydrothieno[2,3-c]quinolin-9-yl)phenyl)ethylcarbamate



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To a solution of tert-butyl 1-(4-(8-hydroxy-4-oxo-4,5-dihydrothieno[2,3-c]quinolin-9-yl)phenyl)ethylcarbamate (44 mg, 0.10 mmol) in THF (2 mL) at 0° C. was added NaH (60%, 6 mg, 0.15 mmol) and the reaction was stirred at that temperature for 1 h. Isopropyl chloroformate (21 μL, 0.15 mmol) was added and the resulting mixture was stirred at rt for 3 h. Water was added and the mixture was extracted with dichloromethane (2×15 mL). The combined extracts were dried over Na2SO4, filtered and concentrated in vacuo. The residue was purified by column chromatography (heptane/ethyl acetate) to afford the desired product (26 mg, 50%) as a solid: ESI MS m/z 523 [C28H30N2O6S+H]+.


Example 1077
9-(4-(1-Aminoethyl)phenyl)-4-oxo-4,5-dihydrothieno[2,3-c]quinolin-8-yl isopropyl carbonate Hydrochloride



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Following General Procedure C, tert-butyl 1-(4-(8-(isopropoxycarbonyloxy)-4-oxo-4,5-dihydrothieno[2,3-c]quinolin-9-yl)phenyl)ethylcarbamate (20 mg, 0.038 mmol) was reacted with trifluoroacetic acid (3 mL) to afford the desired product (18 mg, quant.) as a light yellow solid: ESI MS m/z 423 [C23H22N2O4S+H]+.


Example 620

9-(4-(1-(tert-Butoxycarbonylamino)ethyl)phenyl)-4-oxo-4,5-dihydrothieno[2,3-c]quinolin-8-yl acetate




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Following Procedure Preparing tert-butyl 1-(4-(8-(isopropoxycarbonyloxy)-4-oxo-4,5-dihydrothieno[2,3-c]quinolin-9-yl)phenyl)ethylcarbamate, (44 mg, 0.10 mmol) was reacted with acetic anhydride (11 μL, 0.12 mmol) to afford the desired product (30 mg, 63%) as a solid: ESI MS m/z 479 [C26H26N2O5S+H]+.


Example 1099
9-(4-(1-Aminoethyl)phenyl)-4-oxo-4,5-dihydrothieno[2,3-c]quinolin-8-yl acetate Hydrochloride



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Example 621
2-(4-(8-methoxy-6-methyl-4-oxo-4,5-dihydrothieno[2,3-c]quinolin-9-yl)phenyl)propane-1-sulfonamide



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Following General Procedure E, 2-(4-bromophenyl)propane-1-sulfonamide (0.12 g, 0.43 mmol) was reacted with 9-bromo-8-methoxy-6-methylthieno[2,3-c]quinolin-4(5H)-one (0.14 g, 0.44 mmol) to afford the desired product (16 mg, 8%) as a brown solid: ESI MS m/z 443 [C22H22N2O4S2+H]+.


Example 1419
2-(4-(8-hydroxy-6-methyl-4-oxo-4,5-dihydrothieno[2,3-c]quinolin-9-yl)phenyl)propane-1-sulfonamide



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Following General Procedure F, 2-(4-(8-methoxy-6-methyl-4-oxo-4,5-dihydrothieno[2,3-c]quinolin-9-yl)phenyl)propane-1-sulfonamide (16 mg, 0.036 mmol) was reacted with tribromoborane (1.0 M in methylene chloride, 1.0 mL, 1.0 mmol) to afford the desired product (7.0 mg, 44%) as a light brown solid: 1H NMR (500 MHz, CD3OD) δ 7.68 (d, J=8.4 Hz, 2H), 7.54 (d, J=5.4 Hz, 1H), 7.41 (d, J=8.4 Hz, 2H), 7.07 (s, 1H), 6.08 (d, J=5.4 Hz, 1H), 2.57 (s, 3H), 1.86 (s, 6H); ESI MS m/z 429 [C21H20N2O4S2+H]+; HPLC 98.7%, tR=8.51 min.


Example 1057
N-(1-hydroxypropan-2-yl)-4-(8-methoxy-4-oxo-4,5-dihydrothieno[2,3-c]quinolin-9-yl)benzenesulfonamide



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Following General Procedure B, N-(1-hydroxypropan-2-yl)-4-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)benzenesulfonamide (570 mg, 1.7 mmol) was reacted with 9-bromo-8-methoxythieno[2,3-c]quinolin-4(5H)-one, (471 mg, 1.5 mmol) to afford the desired product (109 mg, 16%) as an off-white powder. ESI MS m/z 445 [C21H20N2O5S2+H]+;


Example 1062

N-(1-bromopropan-2-yl)-4-(8-hydroxy-4-oxo-4,5-dihydrothieno[2,3-c]quinolin-9-yl)benzenesulfonamide




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Following General Procedure F, N-(1-hydroxypropan-2-yl)-4-(8-methoxy-4-oxo-4,5-dihydrothieno[2,3-c]quinolin-9-yl)benzenesulfonamide (55 mg, 0.12 mmol) was reacted with tribromoborane (0.2 mL) to afford the desired product (48 mg, 79%) as an off-white solid: 1H NMR (500 MHz, CD3OD); ESI MS m/z 494 [C20H17BrN2O4S2+H]+; HPLC 99.0% (AUC), tR=11.39 min;


Example 1090
N-(2-Hydroxyethyl)-4-(8-methoxy-4-oxo-2,3,4,5-tetrahydro-1H-cyclopenta[c]quinolin-9-yl benzenesulfonamide



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Following General Procedure B, N-(2-hydroxyethyl)-4-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)benzenesulfonamide (268 mg, 0.82 mmol) was reacted with 9-bromo-8-methoxy-2,3-dihydro-1H-cyclopenta[c]quinolin-4(5H)-one, (268 mg, 0.68 mmol) to afford the desired product (68 mg, 16%) as an off-white solid: 1H NMR: (300 MHz, DMSO-d6) ESI MS m/z 415 [C21H22O3S+H]+; HPLC >99% (AUC), tR=11.73 min;


Example 1094
N-(2-Bromoethyl)-4-(8-hydroxy-4-oxo-2,3,4,5-tetrahydro-1H-cyclopenta[c]quinolin-9-yl)benzenesulfonamide



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Following General Procedure F, N-(2-hydroxyethyl-4-(8-methoxy-4-oxo-2,3,4,5-tetrahydro-1H-cyclopenta[c]quinolin-9-yl)benzenesulfonamide (55 mg, 0.13 mmol) was reacted with tribromoborane (0.2 mL) to afford the desired product (11 mg, 18%) as an off-white solid: 1H NMR (500 MHz, CD3OD) ESI MS m/z 464 [C20H19BrN2O4S+H]+; HPLC 94.9% (AUC), tR=14.88 min;


Example 622
2-(4-(8-Methoxy-4-oxo-2,3,4,5-tetrahydro-1H-cyclopenta[c]quinolin-9-yl)phenylsulfonamido)ethyl methanesulfonate



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To a stirred solution of N-(2-hydroxyethyl)-4-(8-methoxy-4-oxo-2,3,4,5-tetrahydro-1H-cyclopenta[c]quinolin-9-yl)benzenesulfonamide (230 mg, 0.555 mmol) and triethylamine (168 mg, 1.66 mmol) in anhydrous tetrahydrofuran (10 mL) was added methane sulfonyl chloride (88 mg, 0.666 mmol). The reaction mixture was stirred for 20 h at room temperature. After this time the reaction mixture was filtered to remove a white precipitate, which was washed with tetrahydrofuran (30 mL). The filtrate was concentrated under reduced pressure to an orange solid. The residue was purified by flash chromatography to afford the desired product as a brown solid (141 mg, 51%). ESI MS m/z 493 [C22H24N2O7S2+H]+


Example 1145
N-(2-chloroethyl)-4-(8-hydroxy-4-oxo-2,3,45-tetrahydro-1H-cyclopenta[c]quinolin-9-yl)benzenesulfonamide



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To a stirred solution of 2-(4-(8-methoxy-4-oxo-2,3,4,5-tetrahydro-1H-cyclopenta[c]quinolin-9-yl)phenylsulfonamido)ethyl methanesulfonate (141 mg, 0.286 mmol) in anhydrous dichloroethane (10 mL) was added aluminum chloride (190 mg, 1.43 mmol). The reaction mixture was stirred at reflux for 20 h. After this time the reaction was cooled to room temperature and concentrated under reduced pressure. The residue was treated with methanol (10 mL) and allowed to stand at room temperature for 1 h. Upon standing a precipitate formed and was subsequently filtered from the mother liquor. The precipitate was purified by preparatory HPLC (C18 silica, acetonitrile/water with 0.05% TFA gradient) to obtain the desired product (9 mg, 7.5%) as an off-white solid: 1H NMR (500 MHz, DMSO-d) ESI MS m/z 419 [C20H19N2O4S+H]+; HPLC 97.6% (AUC), tR=15.94 min.


Example 1154
(S)-6-chloro-8-hydroxy-9-(4-(1-(methylamino)propyl)phenyl)thieno[2,3-c]quinolin-4(5H)-one Hydrochloride



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Following General Procedure F, (S)-tert-butyl 1-(4-(6-chloro-%-methoxy-4-oxo-4,5-dihydrothieno[2,3-c]quinolin-9-yl)phenyl)propyl(methyl)carbamate (100 mg, 0.194 mmol was reacted with tribromoborane (1.0 M in methylene chloride 1.16 mL, 1.16 mmol) to afford the desired product (35 mg, 45%) as a white solid: 1H NMR (500 MHz, DMSO) δ 10.81 (d, J=10.5 Hz, 1H), 9.83 (s, 1H), 9.70-9.45 (m, 1H), 9.28 (s, 1H), 7.73 (d, J=5.4 Hz, 1H), 7.70-7.60 (m, 2H), 7.38 (dd, J=12.4, 4.7 Hz, 3H), 5.70 (d, J=5.4 Hz, 1H), 4.19 (dt, J=12.1, 6.0 Hz, 1H), 2.51 (s, 3H), 2.20 (ddd, J=14.4, 9.5, 5.9 Hz, 1H), 2.02-1.89 (m, 1H), 0.84 (t, J=7.4 Hz, 31); ESI MS m/z 399 [C22H22N2O2S+H]+; HPLC 96.9% (AUC), tR=9.36 min.


Example 1148
(S)-8-hydroxy-9-(4-(1-(methylamino)propyl)phenyl)thieno[2,3-c]quinolin-4(5H)-one Hydrochloride



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Following General Procedure F, (S)-tert-butyl 1-(4-(8-methoxy-4-oxo-4,5-dihydrothieno[2,3-c]quinolin-9-yl)phenyl)propyl(methyl)carbamate (135 mg, 0.282 mmol) was reacted with tribromoborane (1.0 M in methylene chloride, 1.69 mL, 1.69 mmol) to afford the desired product (48 mg, 47%) as a white solid: 1H NMR (500 MHz, MeOD) δ 7.62 (ddd, J=11.7, 8.0, 1.7 Hz, 2H), 7.56 (d, J=5.4 Hz, 1H), 7.51-7.40 (m, 3H), 7.19 (d, J=8.9 Hz, 1H), 5.97 (d, J=5.4 Hz, 1H), 4.22 (dd, J=10.7, 4.6 Hz, 1H), 2.70 (s, 3H), 2.34-2.02 (m, 2H), 1.04-0.96 (m, 3H); ESI MS m/z 365 [C21H20N2O2S+H]+; HPLC 95.9% (AUC), tR=8.38 min.


Example 1181
(S)-9-(4-(1-aminopropan-2-yl)phenyl)-6-chloro-8-hydroxythieno[2,3-c]quinolin-4(5H)-one Hydrochloride



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Following General Procedure F, (S)-tert-butyl 2-(4-(6-chloro-8-methoxy-4-oxo-4,5-dihydrothieno[2,3-c]quinolin-9-yl)phenyl)propylcarbamate (100 mg, 0.20 mmol) was reacted with tribromoborane (1.0 M in methylene chloride, 1.2 mL, 1.2 mmol) to afford the desired product (35 mg, 46%) as a white solid: 1H NMR (500 MHz, MeOD) δ 7.62 (d, J=5.4 Hz, 1H), 7.56 (dd, J=7.9, 1.9 Hz, 1H), 7.48 (dd, J=7.8, 1.9 Hz, 1H), 7.36 (dd, J=7.9, 1.7 Hz, 1H), 7.34-7.29 (m, 2H), 6.12 (d, J=5.4 Hz, 1H), 3.29-3.15 (m, 3H), 1.49 (d, J=6.5 Hz, 3H); ESI MS m/z 385 [C20H17ClN2O2S+H]+; HPLC >99% (AUC), tR=8.74 min.


Example 1163
(S)-9-(4-(1-Aminopropan-2-yl)phenyl)-8-hydroxythieno[2,3-c]quinolin-4(5H)-one Hydrochloride



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Following General Procedure F, (S)-tert-butyl 2-(4-(8-methoxy-4-oxo-4,5-dihydrothieno[2,3-c]quinolin-9-yl)phenyl)propylcarbamate (110 mg, 0.236 mmol) was reacted with tribromoborane (1.0 M in methylene chloride, 1.42 mL, 1.42 mmol) to afford the desired product (38 mg, 47%) as a white solid: 1H NMR (500 MHz, MeOD) δ 7.61-7.53 (m, 2H), 7.47 (dd, J=7.8, 1.9 Hz, 1H), 7.41 (dd, J=10.9, 6.1 Hz, 1H), 7.37 (dd, J=7.9, 1.7 Hz, 1H), 7.32 (dd, J=7.7, 1.7 Hz, 1H), 7.18 (d, J=8.9 Hz, 1H), 6.15 (d, J=5.4 Hz, 1H), 3.29-3.17 (m, 3H), 1.50 (d, J=6.4 Hz, 3H); ESI MS m/z 351 [C20H18N2O2S+H]+; HPLC >99% (AUC), tR=8.58 min.


Example 1116
9-(4-(1-(Aminomethyl)cyclopropyl)phenyl)-6-chloro-8-hydroxythieno[2,3-c]quinolin-4(5H)-one Hydrochloride



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Following General Procedure F, tert-butyl (1-(4-(6-chloro-8-methoxy-4-oxo-4,5-dihydrothieno[2,3-c]quinolin-9-yl)phenyl)cyclopropyl)methylcarbamate (50 mg, 0.09 mmol) was reacted with tribromoborane (1.0 M in methylene chloride, 0.58 mL, 0.58 mmol) to afford the desired product (19 mg, 48%) as a white solid: 1H NMR; (500 MHz, MeOD) δ 7.66-7.58 (m, 3H), 7.38-7.27 (m, 3H), 6.14 (d, J=5.4 Hz, 1H), 3.26 (s, 2H), 1.19 (t, J=5.5 Hz, 2H), 1.11 (t, J=5.5 Hz, 2H); ESI MS m/z 397 [C21H17ClN2O2S+H]+; HPLC 98.4% (AUC), tR=9.24 min.


Example 1401
9-(4-(1-(Aminomethyl)cyclopropyl)phenyl)-6-bromo-8-hydroxythieno[2,3-c]quinolin-4(5H)-one Hydrochloride



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Following General Procedure F, 9-(4-(1-(aminomethyl)cyclopropyl)phenyl)-6-bromo-8-methoxythieno[2,3-c]quinolin-4(5H)-one hydrochloride (100 mg, 0.22 mmol was reacted with tribromoborane (1.0 M in methylene chloride, 1.32 mL, 1.32 mmol) to afford the desired product (52 mg, 54%) as a white solid: 1H NMR (500 MHz, MeOD) δ 7.63 (t, J=6.8 Hz, 3H), 7.48 (s, 1H), 7.33 (d, J=8.2 Hz, 2H), 6.14 (d, J=5.4 Hz, 1H), 3.26 (s, 2H), 1.19 (t, J=5.6 Hz, 2H), 1.12 (t, J=5.5 Hz, 2H); ESI MS m/z 442 [C21H17BrN2O2S+H]+; HPLC >99% (AUC), tR=9.25 min.


Example 1254
9-(4-(1-(aminomethyl)cyclopropyl)phenyl)-8-hydroxy-6-methylthieno[2,3-c]quinolin-4(5H)-one Hydrochloride



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Following General Procedure F, tert-butyl(1-(4-(8-methoxy-6-methyl-4-oxo-4,5-dihydrothieno[2,3-c]quinolin-9-yl)phenyl)cyclopropyl)methylcarbamate (120 mg, 0.24 mmol) was reacted with tribromoborane (1.0 M in methylene chloride, 1.46 mL, 1.46 mmol) to afford the desired product (38 mg, 42%) as a white solid: 1H NMR (500 MHz, MeOD) δ 7.60 (ddd, J=12.3, 7.1, 3.6 Hz, 3H), 7.34-7.29 (m, 2H), 7.08 (d, J=0.6 Hz, 1H), 6.19 (d, J=5.4 Hz, 1H), 3.25 (s, 2H), 2.57 (s, 3H), 1.22-1.06 (m, 41-t); ESI MS m/z 377 [C23H22N2O2S+H]+; HPLC 98.6% (AUC), tR=8.97 min.


Example 1215
(S)-8-Hydroxy-6-methyl-9-(4-(1-(methylamino)propan-2-yl)phenyl)thieno[2,3-c]quinolin-4(5H)-one Hydrochloride



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Following General Procedure F, (S)-tert-butyl 2-(4-(8-methoxy-6-methyl-4-oxo-4,5-dihydrothieno[2,3-c]quinolin-9-yl)phenyl)propyl(methyl carbamate (50 mg, 0.10 mmol) was reacted with tribromoborane (1.0 M in methylene chloride, 0.61 mL, 0.61 mmol) to afford the desired product (12 mg, 32%) as a light yellow solid: 1H NMR (500 MHz, MeOD) δ 7.60-7.53 (m, 2H), 7.47 (dd, J=7.8, 1.8 Hz, 1H), 7.35 (dd, J=7.9, 1.7 Hz, 1H), 7.30 (dd, J=7.7, 1.7 Hz, 1H), 7.08 (s, 1H), 6.15 (d, J=5.4 Hz, 1H), 3.40-3.27 (m, 3H), 2.74 (s, 3H), 2.57 (s, 3H), 1.50 (d, J=6.6 Hz, 3H); ESI MS m/z 379 [C22H22N2O2S+H]+; HPLC >99% (AUC), tR=8.88 min.


Example 1232
(S)-9-(4-(1-aminopropan-2-yl)phenyl)-8-hydroxy-6-methylthieno[2,3-c]quinolin-4(5H)-one Hydrochloride



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Following General Procedure F, (S)-tert-butyl 2-(4-(8-methoxy-6-methyl-4-oxo-4,5-dihydrothieno[2,3-c]quinolin-9-yl)phenyl)propylcarbamate (100 mg, 0.209 mmol) was reacted with tribromoborane (1.0 M in methylene chloride, 1.25 mL, 1.25 mmol) to afford the desired product (38 mg, 52%) as a white solid: 1H NMR (500 MHz, MeOD) δ 7.60-7.52 (m, 2H), 7.45 (dd, J=7.8, 1.9 Hz, 1H), 7.35 (dd, J=7.9, 1.7 Hz, 1H), 7.29 (dd, J=7.7, 1.7 Hz, 1H), 7.08 (s, 1H), 6.16 (d, J=5.4 Hz, 1H), 3.29-3.17 (m, 3H), 2.57 (s, 3H), 1.50 (d, J=6.4 Hz, 3H); ESI MS m/z 365 [C21H20N2O2S+H]+; HPLC 98.0% (AUC), tR=8.63 min.


Example 1264
9-(4-(2-aminoethyl)-3-chlorophenyl)-8-hydroxy-6-methylthieno[2,3-c]quinolin-4(5H)-one Hydrochloride



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Following General Procedure F, tert-butyl 2-chloro-4-(8-methoxy-6-methyl-4-oxo-4,5-dihydrothieno[2,3-c]quinolin-9-yl)phenethylcarbamate (120 mg, 0.24 mmol) was reacted with tribromoborane (1.0 M in methylene chloride, 1.45 mL, 1.45 mmol) to afford the desired product (52 mg, 57%) as a white solid: 1H NMR (500 MHz, MeOD) δ 7.64 (d, J=5.4 Hz, 1H), 7.54 (d, J=7.8 Hz, 1H), 7.37 (d, J=1.4 Hz, 1H), 7.23 (dd, J=7.7, 1.4 Hz, 1H), 7.08 (s, 1H), 6.19 (d, J=5.4 Hz, 1H), 3.42-3.14 (m, 4H), 2.56 (s, 3H); ESI MS m/z 385 [C20H17ClN2O2S+H]+; HPLC 98.2% (AUC), tR=8.55 min.


Example 1268
9-(4-(2-aminoethyl)-3-chlorophenyl)-6-chloro-8-hydroxythieno[2,3-c]quinolin-4(5H)-one Hydrochloride



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Following General Procedure F, tert-butyl 2-chloro-4-(6-chloro-8-methoxy-4-oxo-4,5-dihydrothieno[2,3-c]quinolin-9-yl)phenethylcarbamate (80 mg, 0.154 mmol) was reacted with tribromoborane (1.0 M in methylene chloride, 0.92 mL, 0.92 mmol) to afford the desired product (37 mg, 59%) as a white solid: 1H NMR (500 MHz, MeOD) δ 7.68 (d, J=5.4 Hz, 1H), 7.56 (d, J=7.8 Hz, 1H), 7.42 (d, J=1.7 Hz, 1H), 7.30 (s, 1H), 7.27 (dd, J=7.8, 1.7 Hz, 1H), 6.17 (d, J=5.4 Hz, 1H), 3.39-3.25 (m, 4H); ESI MS m/z 405 [C19H14Cl2N2O2S+H]+; HPLC 98.1% (AUC), tR=9.17 min.


Example 1262
(R)-8-hydroxy-6-methyl-9-(4-(1-(methylamino)ethyl)phenyl)thieno[2,3-c]quinolin-4(5H)-one Hydrochloride



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Following General Procedure F, (R)-tert-butyl 1-(4-(8-methoxy-6-methyl-4-oxo-4,5-dihydrothieno[2,3-c]quinolin-9-yl)phenyl)ethyl(methyl)carbamate (150 mg, 0.313 mmol) was reacted with tribromoborane (1.0 M in methylene chloride, 1.9 mL, 1.9 mmol) to afford the desired product (85 mg, 74%) as a white solid: 1H NMR (500 MHz, MeOD) δ 7.63 (ddd, J=7.0, 5.5, 2.2 Hz, 2H), 7.57 (d, J=5.4-1Hz, 1H), 7.43 (ddd, J=7.4, 6.1, 2.1 Hz, 2H), 7.08 (s, 1H), 6.05 (d, J=5.4 Hz, 1H), 4.47 (q, J=6.9 Hz, 1H), 2.71 (s, 3H), 2.57 (s, 3H), 1.79 (d, J=6.9 Hz, 3H); ESI MS m/z 365 [C21H20N2O2S+H]+; HPLC >99% (AUC), tR=8.40 min.


Example 1135
(R)-6-bromo-8-hydroxy-9-(4-(1-(methylamino)ethyl)phenyl)thieno[2,3-c]quinolin-4(5H)-one Hydrochloride



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Following General Procedure F, (R)-tert-butyl 1-(4-(6-bromo-8-methoxy-4-oxo-4,5-dihydrothieno[2,3-c]quinolin-9-yl)phenyl)ethyl(methyl)carbamate (100 mg, 0.18 mmol) was reacted with tribromoborane (1.0 M in methylene chloride, 1.1 mL, 1.1 mmol) to afford the desired product (38 mg, 48%) as a white solid: 1H NMR (500 MHz, DMSO) δ 10.20 (s, 1H), 9.88 (s, 1H), 9.76-9.59 (m, 1H), 9.37-9.21 (m, 1H), 7.78 (d, J=5.4 Hz, 1H), 7.74-7.64 (m, 2H), 7.54 (s, 1H), 7.40-7.33 (m, 2H), 5.77 (d, J=5.4 Hz, 1H), 4.44 (dd, J=12.5, 6.4 Hz, 1H), 2.50 (s, 3H), 1.68 (d, J=6.8 Hz, 3H); ESI MS m/z 429 [C20H17BrN2O2S+H]+; HPLC >99% (AUC), tR=9.00 min.


Example 1271
9-(4-(1-Amino-2-methylpropan-2-yl)-3-fluorophenyl)-8-hydroxythieno[2,3-c]quinolin-4(5H)-one Hydrochloride



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Following General Procedure F, tert-butyl 2-(2-fluoro-4-(8-methoxy-4-oxo-4,5-dihydrothieno[2,3-c]quinolin-9-yl)phenyl)-2-methylpropylcarbamate (130 mg, 0.26 mmol) was reacted with tribromoborane (1.0 M in methylene chloride, 1.57 mL, 1.57 mmol) to afford the desired product (35 mg, 35%) as a white solid: 1H NMR (500 MHz, DMSO) δ 11.81 (s, 1H), 9.34 (s, 1H), 7.98 (s, 3H), 7.72 (d, J=5.4 Hz, 1H), 7.49 (t, J=8.5 Hz, 1H), 7.40 (d, J=8.9 Hz, 1H), 7.17 (t, J=9.0 Hz, 1H), 7.12 (ddd, J=10.7, 9.7, 1.7 Hz, 2H), 6.02 (d, J=5.4 Hz, 1H), 3.25 (s, 2H), 1.51 (d, J=9.1 Hz, 6H); ESI MS m/z 383 [C21H19FN2O2S+H]+; HPLC >99% (AUC), tR=8.77 min.


Example 1278
9-(4-(1-Amino-2-methylpropan-2-yl)-3-fluorophenyl)-8-hydroxy-6-methylthieno[2,3-c]quinolin-4(5H)-one Hydrochloride



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Following General Procedure F, tert-butyl 2-(2-fluoro-4-(8-methoxy-6-methyl-4-oxo-4,5-dihydrothieno[2,3-c]quinolin-9-yl)phenyl)-2-methylpropylcarbamate (50 mg, 0.10 mmol) was reacted with tribromoborane (1.0 M in methylene chloride, 0.58 mL, 0.58 mmol) to afford the desired product (22 mg, 58%) as a white solid: 1H NMR (500 MHz, MeOD) δ 7.64 (d, J=5.4 Hz, 1H), 7.57 (t, J=8.4 Hz, 1H), 7.15 (ddd, J=15.1, 10.7, 1.7 Hz, 2H), 7.08 (d, J=0.7 Hz, 1H), 6.26 (d, J=5.4 Hz, 1H), 3.31 (s, 2H), 2.57 (s, 3H), 1.62 (d, J=5.6 Hz, 6H); ESI MS m/z 397 [C22H21FN2O2S+H]+; HPLC >99% (AUC), tR=9.07 min.


Example 1291
9-(4-(1-Aminobutan-2-yl)phenyl)-8-hydroxy-6-methylthieno[2,3-c]quinolin-4(5H)-one Hydrochloride



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Following General Procedure F, tert-butyl 2-(4-(8-methoxy-6-methyl-4-oxo-4,5-dihydrothieno[2,3-c]quinolin-9-yl)phenyl)butylcarbamate (100 mg, 0.23 mmol) was reacted with tribromoborane (1.0 M in methylene chloride, 1.4 mL, 1.4 mmol)) to afford the desired product (42 mg, 55%) as a white solid: 1H NMR (500 MHz, MeOD) δ 7.57-7.50 (m, 2H), 7.40 (ddd, J=18.8, 7.8, 1.8 Hz, 2H), 7.31 (dd, J=7.7, 1.7 Hz, 1H), 7.09 (d, J=0.8 Hz, 1H), 6.13 (d, J=5.4 Hz, 1H), 3.25 (ddd, J=26.6, 13.1, 7.1 Hz, 2H), 2.93 (dq, J, J=15.3, 5.2 Hz, 1H), 2.57 (d, J=0.6 Hz, 3H), 1.97-1.74 (m, 2H), 0.99 (t, J=7.4 Hz, 3H); ESI MS m/z 379 [C22H22N2O2S+H]+; HPLC >99% (AUC), tR=9.21 min.


Example 1120
(S)-9-(4-(1-aminopropyl)phenyl)-8-hydroxythieno[2,3-c]quinolin-4(5H)-one Hydrochloride



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Following General Procedure F, (S)-tert-butyl 1-(4-(8-methoxy-4-oxo-4,5-dihydrothieno[2,3-c]quinolin-9-yl)phenyl)propylcarbamate (100 mg, 0.22 mmol) was reacted with tribromoborane (1.0 M in methylene chloride, 1.3 mL, 1.3 mmol) to afford the desired product (28 mg, 38%) as a white solid: 1H NMR (500 MHz, MeOD) δ 7.65-7.58 (m, 2H), 7.54 (d, J=5.4 Hz, 1H), 7.46-7.40 (m, 3H), 7.18 (d, J=8.9 Hz, 1H), 6.03 (d, J=5.4 Hz, 1H), 4.32 (dd, J=9.2, 5.9 Hz, 1H), 2.21-2.03 (m, 2H), 1.04 (t, J=7.4 Hz, 3H); ESI MS m/z 351 [C20H18N2O2S+H]+; HPLC >99% (AUC), tR=8.24 min.


Example 1290
9-(4-(1-(Aminomethyl)cyclobutyl)phenyl)-8-hydroxy-6-methylthieno[2,3-c]quinolin-4(5H)-one Hydrochloride



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Following General Procedure F, tert-butyl (1-(4-(8-methoxy-6-methyl-4-oxo-4,5-dihydrothieno[2,3-c]quinolin-9-yl)phenyl)cyclobutyl)methylcarbamate (130 mg, 0.32 mmol was reacted with tribromoborane (1.0 M in methylene chloride, 1.9 mL, 1.9 mmol to afford the desired product (82 mg, 65%) as a white solid: 1H NMR (500 MHz, MeOD) δ 7.63 (d, J=5.4 Hz, 1H), 7.46-7.41 (m, 2H), 7.38-7.32 (m, 2H), 7.09 (d, J=0.7 Hz, 1H), 6.26 (d, J=5.4 Hz, 1H), 3.36-3.33 (m, 2H), 2.65 (dd, J=21.2, 9.3 Hz, 2H), 2.58 (s, 3H), 2.45-2.37 (m, 2H), 2.27 (ddd, J=17.7, 11.5, 8.6 Hz, 1H), 2.12-2.01 (m, 1H); ESI MS m/z 391 [C23H22N2O2S+H]+; HPLC >99% (AUC), tR=9.37 min.


Example 1300
9-(4-(1-(Aminomethyl)cyclobutyl)phenyl)-8-hydroxythieno[2,3-c]quinolin-4(5H)-one Hydrochloride



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Following General Procedure F, tert-butyl (1-(4-(8-methoxy-4-oxo-4,5-dihydrothieno[2,3-c]quinolin-9-yl)phenyl)cyclobutyl)methylcarbamate (100 mg, 0.20 mmol) was reacted with tribromoborane (1.0 M in methylene chloride, 1.23 mL, 1.23 mmol) to afford the desired product (52 mg, 68%) as a white solid: 1H NMR (500 MHz, MeOD) δ 7.64 (d, J=5.4 Hz, 1H), 7.44 (ddd, J=17.8, 10.5, 3.8 Hz, 3H), 7.39-7.35 (m, 2H), 7.19 (d, J=8.9 Hz, 1H), 6.25 (d, J=5.4 Hz, 1H), 3.44 (s, 2H), 2.65 (dd, J=21.3, 9.4 Hz, 2H), 2.46-2.36 (m, 2H), 2.33-2.20 (m, 1H), 2.14-2.00 (m, 1H); ESI MS m/z 377 [C22H20N2O2S+H]+; HPLC >99% (AUC), tR=9.00 min.


Example 1309
9-(4-(1-Aminobutan-2-yl)phenyl)-8-hydroxythieno[2,3-c]quinolin-4(5H)-one Hydrochloride



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Following General Procedure F, tert-butyl 2-(4-(8-methoxy-4-oxo-4,5 dihydrothieno[2,3-c]quinolin-9-yl)phenyl)butylcarbamate (100 mg, 0.21 mmol) was reacted with tribromoborane (1.0 M in methylene chloride, 1.25 mL, 1.25 mmol) to afford the desired product (45 mg, 60%) as a white solid: 1H NMR (500 MHz, MeOD) δ 7.58-7.50 (m, 2H), 7.46-7.36 (m, 3H), 7.32 (dt, J=12.4, 6.2 Hz, 1H), 7.19 (d, J=8.9 Hz, 1H), 6.11 (d, J=5.4 Hz, 1H), 3.40-3.19 (m, 2H), 2.95 (dq, J=15.3, 5.2 Hz, 1H), 1.98-1.85 (m, 1H), 1.86-1.71 (m, 1H), 1.06-0.91 (m, 3H); ESI MS m/z 365 [C21H20N2O2S+H]+; HPLC >99% (AUC), tR=8.15 min.


Example 1312
9-(4-(1-Aminobutan-2-yl)phenyl)-6-chloro-8-hydroxythieno[2,3-c]quinolin-4(5H)-one Hydrochloride



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Following General Procedure F, tert-butyl 2-(4-(6-chloro-8-methoxy-4-oxo-4,5-dihydrothieno[2,3-c]quinolin-9-yl)phenyl)butylcarbamate (65 mg, 0.13 mmol) was reacted with tribromoborane (1.0 M in methylene chloride, 0.76 mL, 0.76 mmol) to afford the desired product (28 mg, 56%) as a white solid: 1H NMR (500 MHz, MeOD) δ 7.60 (d, J=5.4 Hz, 1H), 7.54 (dd, J=7.9, 1.8 Hz, 1H), 7.44 (dd, J=7.7, 1.8 Hz, 1H), 7.39 (dd, J=7.9, 1.8 Hz, 1H), 7.35-7.30 (m, 2H), 6.08 (d, J=5.4 Hz, 1H), 3.38-3.22 (m, 2H), 2.98-2.89 (m, 1H), 1.97-1.85 (m, 1H), 1.85-1.72 (m, 1H), 0.98 (t, J=7.4 Hz, 3H); ESI MS m/z 399 [C21H19ClN2O2S+H]+; HPLC >99%, (AUC), tR=10.29 min.


Example 385
9-(4-(1-(Ethylamino)ethyl)phenyl)-8-hydroxythieno[2,3-c]quinolin-4(5H)-one Hydrochloride



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Following General Procedure F, tert-butyl ethyl(1-(4-(8-methoxy-4-oxo-4,5-dihydrothieno[2,3-c]quinolin-9-yl)phenyl)ethyl)carbamate (150 mg, 0.31 mmol) was reacted with tribromoborane (1.0 M in methylene chloride, 1.9 mL, 1.9 mmol) to afford the desired product (37 mg, 33%) as a white glass: 1H NMR (500 MHz, MeOD); δ 7.65 (dd, J=13.2, 4.9 Hz, 2H), 7.57 (d, J=5.4 Hz, 1H), 7.48-7.39 (m, 3H), 7.18 (d, J=8.9 Hz, 1H), 6.04 (d, J=5.4 Hz, 1H), 4.53 (q, J=6.8 Hz, 1H), 3.20-3.08 (m, 1H), 3.08-2.96 (m, 1H), 1.79 (d, J=6.9 Hz, 3H), 1.36 (t, J=7.3 Hz, 3H). ESI MS m/z 365 [+H]+; HPLC >99% (AUC), tR=12.05 min.


Example 1165
6-chloro-8-hydroxy-9-(4-(2-(methylamino)ethyl)phenyl)thieno[2,3-c]quinolin-4(5H)-one Hydrochloride



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Following General Procedure F, tert-butyl 4-(6-chloro-8-methoxy-4-oxo-4,5-dihydrothieno[2,3-c]quinolin-9-yl)phenethyl(methyl)carbamate (60 mg, 0.12 mmol) was reacted with tribromoborane (1.0 M in methylene chloride, 0.72 mL, 0.72 mmol) to afford the desired product (22 mg, 50%) as a white solid: 1H NMR (500 MHz, DMSO-d6) δ 10.77 (s, 1H), 9.72 (s, 1H), 8.72 (s, 1H), 7.76 (d, J=5.4 Hz, 1H), 7.42 (d, J=8.1 Hz, 2H), 7.31 (s, 1H), 7.24 (d, J=8.1 Hz, 2H), 5.85 (d, J=5.4 Hz, 1H), 3.30-3.23 (m, 2H), 3.09-3.02 (m, 2H), 2.65 (s, 3H); ESI MS m/z 385 [C20H17ClN2O2S+H]+; HPLC >99% (AUC), tR=9.03 min.


Example 1197
(S)-8-hydroxy-9-(4-(1-(methylamino)propan-2-yl)phenyl)thieno[2,3-c]quinolin-4(5H)-one Hydrochloride



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Following General Procedure F, (S)-tert-butyl 2-(4-(8-methoxy-4-oxo-4,5-dihydrothieno[2,3-c]quinolin-9-yl)phenyl)propyl(methyl)carbamate (100 mg, 0.21 mmol) was reacted with tribromoborane (1.0 M in methylene chloride, 1.25 mL, 1.25 mmol) to afford the desired product (31 mg, 41%) as a white solid: 1H NMR (500 MHz, MeOD) δ 7.61-7.53 (m, 2H), 7.48 (dd, J=7.8, 1.9 Hz, 1H), 7.44-7.37 (m, 2H), 7.33 (dd, J=7.7, 1.7 Hz, 1H), 7.18 (d, J=8.9 Hz, 1H), 6.14 (d, J=5.4 Hz, 1H), 3.41-3.25 (m, 3H), 2.75 (s, 3H), 1.50 (d, J=6.8 Hz, 3H); ESI MS m/z 365 [C21H20N2O2S+H]+; HPLC >99% (AUC), tR=8.36 min.


Example 1224
9-(4-(2-aminoethyl)-2-bromo-5-hydroxyphenyl)-8-hydroxythieno[2,3-c]quinolin-4(5H)-one Hydrochloride



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Following General Procedure F, (tert-butyl 5-bromo-2-hydroxy-4-(8-methoxy-4-oxo-4,5-dihydrothieno[2,3-c]quinolin-9-yl)phenethylcarbamate (50 mg, 0.90 mmol) was reacted with tribromoborane (1.0 M in methylene chloride, 0.54 mL, 0.54 mmol) to afford the desired product (18 mg, 48%) as a white solid: 1H NMR (500 MHz, MeOD) δ 7.68 (d, J=5.5 Hz, 1H), 7.58 (s, 1H), 7.44 (d, J=9.0 Hz, 1H), 7.18 (d, J=9.0 Hz, 1H), 6.82 (s, 1H), 6.33 (d, J=5.5 Hz, 1H), 3.25 (m, 2H), 2.95 (m, 2H); ESI MS m/z 432 [C19H15BrN2O3S+H]+; HPLC 96.9% (AUC), tR=8.10 min.


Example 1082
(S)-8-hydroxy-9-(4-(1-(methylamino)ethyl)phenyl)thieno[2,3-c]quinolin-4(5H)-one Hydrochloride



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Following General Procedure F, (S)-tert-butyl 1-(4-(8-methoxy-4-oxo-4,5-dihydrothieno[2,3-c]quinolin-9-yl)phenyl)ethyl(methyl)carbamate (100 mg, 0.22 mmol) was reacted with tribromoborane (1.0 M in methylene chloride, 1.30 mL, 13.0 mmol) to afford the desired product (50 mg, 66%) as a white solid: 1H NMR (500 MHz, MeOD) δ 7.68-7.61 (m, 2H), 7.57 (d, J=5.4 Hz, 1H), 7.49-7.39 (m, 3H), 7.18 (d, J=8.9 Hz, 1H), 6.04 (d, J=5.4 Hz, 1H), 4.48 (q, J=6.8 Hz, 1H), 2.72 (s, 3H), 1.80 (d, J=6.9 Hz, 3H); ESI MS m/z 351 [C20H18N2O2S+H]+; HPLC 96.9% (AUC), tR=7.68 min.


Example 1088
9-(4-(1-aminopropyl)phenyl)-6-chloro-8-hydroxythieno[2,3-c]quinolin-4(5H)-one Hydrochloride



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Following General Procedure F, tert-butyl 1-(4-(6-chloro-8-methoxy-4-oxo-4,5-dihydrothieno[2,3-c]quinolin-9-yl)phenyl)propylcarbamate (40 mg, 0.08 mmol) was reacted with tribromoborane (1.0 M in methylene chloride, 0.48 mL, 0.48 mmol) to afford the desired product (12 mg, 40%) as a white solid: 1H NMR (500 MHz, MeOD) δ 7.65-7.56 (m, 3H), 7.46-7.39 (m, 2H), 7.30 (s, 1H), 6.02 (d, J=5.4 Hz, 1H), 4.32 (dd, J=9.1, 6.0 Hz, 1H), 2.21-2.02 (m, 2H), 1.03 (t, J=7.4 Hz, 3H); ESI MS m/z 385 [C20H17N2O2S+H]+; HPLC 95.9% (AUC), tR=9.15 min.


Example 1087
(S)-6-chloro-8-hydroxy-9-(4-(1-(methylamino)ethyl)phenyl)thieno[2,3-c]quinolin-4(5H)-one Hydrochloride



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Following General Procedure F, (S)-tert-butyl 1-(4-(6-chloro-8-methoxy-4-oxo-4,5-dihydrothieno[2,3-c]quinolin-9-yl)phenyl)ethyl(methyl)carbamate (40 mg, 0.08 mmol) was reacted with tribromoborane (1.0 M in methylene chloride, 0.48 mL, 0.48 mmol) to afford the desired product (18 mg, 60%) as a white solid: 1H NMR (500 MHz, MeOD) δ 7.72-7.60 (m, 3H), 7.49-7.39 (m, 2H), 7.30 (s, 1H), 6.03 (d, J=5.4 Hz, 1H), 4.49 (q, J=6.9 Hz, 1H), 2.73 (d, J=4.3 Hz, 3H), 1.80 (d, J=6.9 Hz, 3H); ESI MS m/z 385 [C20H17ClN2O2S+H]+; HPLC >99% (AUC), tR=13.60 min.


Example 1209
9-(4-(3-(aminomethyl)pentan-3-yl)phenyl)-8-hydroxythieno[2,3-c]quinolin-4(5H)-one Hydrochloride



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Following General Procedure F, tert-butyl 2-ethyl-2-(4-(8-methoxy-4-oxo-4,5-dihydrothieno[2,3-c]quinolin-9-yl)phenyl)butylcarbamate (200 mg, 0.40 mmol) was reacted with tribromoborane (1.0 M in methylene chloride, 2.37 mL, 2.37 mmol) to afford the desired product (120 mg, 78%) as a white solid: 1H NMR (500 MHz, MeOD) δ 7.62 (d, J=8.4 Hz, 2H), 7.54 (d, J=5.4 Hz, 1H), 7.41 (dd, J=15.2, 8.6 Hz, 3H), 7.19 (d, J=8.9 Hz, 1H), 6.08 (d, J=5.4 Hz, 1H), 3.34 (s, 2H), 2.05-1.88 (m, 4H), 0.93 (t, J=7.4 Hz, 6H); ESI MS m/z 393 [C21H24N2O2S+H]+; HPLC >99% (AUC), tR=9.38 min.


Example 1271
9-(4-(1-amino-2-methylpropan-2-yl)-3-fluorophenyl)-8-hydroxythieno[2,3-c]quinolin-4(5H)-one Hydrochloride



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Following General Procedure F, tert-butyl 2-(2-fluoro-4-(8-methoxy-4-oxo-4,5-dihydrothieno[2,3-c]quinolin-9-yl)phenyl)-2-methylpropylcarbamate (80 mg, 0.16 mmol) was reacted with tribromoborane (1.0 M in methylene chloride, 1.0 mL, 1.0 mmol) to afford the desired product (35 mg, 56%) as a yellow glass: 1H NMR (500 MHz, MeOD) δ 7.67 (d, J=5.4 Hz, 1H), 7.59 (t, J=8.4 Hz, 1H), 7.44 (d, J=8.9 Hz, 1H), 7.20 (d, J=8.9 Hz, 3H), 6.25 (d, J=5.4 Hz, 1H), 3.54 (d, J=13.0 Hz, 2H), 3.28 (s, 1H), 1.63 (d, J=4.6 Hz, 6H); ESI MS m/z 383 [C21H19FN2O2S+H]+; HPLC >99% (AUC), tR=8.89 min.


Example 623
tert-butyl (1-(4-(6-bromo-8-methoxy-4-oxo-4,5-dihydrothieno[2,3-c]quinolin-9-yl)phenyl)cyclopropyl)methylcarbamate



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Following General Procedure I, tert-butyl (1-(4-(8-methoxy-4-oxo-4,5-dihydrothieno[2,3-c]quinolin-9-yl)phenyl)cyclopropyl)methylcarbamate (750 mg, 1.57 mmol) was reacted with NBS (280 mg, 1.57 mmol)) to afford the desired product (473 mg, 54%) as a yellow solid: ESI MS m/z 555 [C27H27BrN2O4S+H]+.


Example 624
(S)-tert-butyl 2-(4-(6-bromo-8-methoxy-4-oxo-4,5-dihydrothieno[2,3-c]quinolin-9-yl)phenyl)propyl(methyl)carbamate



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Following General Procedure I, (S)-tert-butyl 2-(4-(8-methoxy-4-oxo-4,5-dihydrothieno[2,3-c]quinolin-9-yl)phenyl)propyl(methyl)carbamate (1.0 g, 2.0 mmol was reacted with NBS (446 mg, 2.5 mmol) to afford the desired product (500 mg, 43%) as a yellow solid: ESI MS m/z 557 [C27H29BrN2O4S+H]+.


Example 625
(R)-tert-butyl 1-(4-(6-bromo-8-methoxy-4-oxo-4,5-dihydrothieno[2,3-c]quinolin-9-yl)phenyl)ethyl(methyl)carbamate



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Following General Procedure I, (R)-tert-butyl 1-(4-(8-methoxy-4-oxo-4,5-dihydrothieno[2,3-c]quinolin-9-yl)phenyl)ethyl(methyl)carbamate (400 mg, 0.86 mmol) was reacted with NBS (184 mg, 1.03 mmol) to afford the desired product (285 mg, 61%) as a yellow solid: ESI MS m/z 543 [C26H30BrN2O4S+H]+.


Example 1263
9-(4-(2-aminoethyl)-3-chlorophenyl)-8-methoxy-6-methylthieno[2,3-c]quinolin-4(5H)-one Hydrochloride



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Following General Procedure C, tert-butyl 2-chloro-4-(8-methoxy-6-methyl-4-oxo-4,5-dihydrothieno[2,3-c]quinolin-9-yl)phenethylcarbamate (50 mg, 0.10 mmol) was reacted with TFA (3.0 mL) to afford the desired product as a light yellow solid (27 mg, 68%): 1H NMR (500 MHz, MeOD) δ 7.62 (t, J=5.8-1Hz, 1H), 7.53 (d, J=7.8 Hz, 1H), 7.35 (d, J=1.6 Hz, 1H), 7.29 (s, 1H), 7.21 (dd, J=7.7, 1.7 Hz, 1H), 6.11 (d, J=5.4 Hz, 1H), 3.75 (d, J=7.4 Hz, 3H), 3.38-3.16 (m, 4H), 2.64 (s, 3H); ESI MS m/z 399 [C21H19ClN2O2S+H]+; HPLC 98.8% (AUC), tR=9.50 min.


Example 1265
(R)-8-methoxy-6-methyl-9-(4-(1-(methylamino)ethyl)phenyl)thieno[2,3-c]quinolin-4(5H)-one Hydrochloride



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Following General Procedure C, (R)-tert-butyl 1-(4-(8-methoxy-6-methyl-4-oxo-4,5-dihydrothieno[2,3-c]quinolin-9-yl)phenyl)ethyl(methyl)carbamate (50 mg, 0.10 mmol) was reacted with TFA (3.0 mL) to afford the desired product as a yellow solid 25 mg, 63%): 1H NMR (500 MHz, MeOD) δ 7.64 (d, J=8.4 Hz, 2H), 7.57 (d, J=5.4 Hz, 1H), 7.38 (d, J=8.6 Hz, 2H), 7.29 (s, 1H), 5.99 (d, J=5.4 Hz, 1H), 4.48 (q, J=6.8 Hz, 1H), 3.73 (s, 3H), 2.72 (s, 3H), 2.64 (s, 3H), 1.80 (d, J=6.9 Hz, 3H). ESI MS m/z 379 [C22H21N2O2S+H]+; HPLC 98.0% (AUC), tR=9.51 min.


Example 1277
9-(4-(1-aminobutan-2-yl)phenyl)-8-methoxy-6-methylthieno[2,3-c]quinolin-4(5H)-one Hydrochloride



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Following General Procedure C, tert-butyl 2-(4-(8-methoxy-6-methyl-4-oxo-4,5-dihydrothieno[2,3-c]quinolin-9-yl)phenyl)butylcarbamate (40 mg, 0.08 mmol) was reacted with TFA (3.0 mL) to afford the desired product as a white solid 14 mg, 44%): 1H NMR (500 MHz, MeOD) δ 7.54-7.47 (m, 2H), 7.42 (dd, J: 7.7, 1.8 Hz, 1H), 7.35-7.25 (m, 3H), 5.96 (d, J=5.4 Hz, 1H), 3.75 (s, 3H), 3.37-3.26 (m, 2H), 3.02-2.89 (m, 1H), 2.64 (s, 3H), 1.97-1.85 (m, 1H), 1.81-1.67 (m, 1H), 0.96 (t, J=7.3 Hz, 3H); ESI MS m/z 39.3 [C23H24N2O2S+H]+; HPLC >99% (AUC), LR=9.74 min.


Example 1064
(S)-8-methoxy-9-(4-(1-(methylamino)ethyl)phenyl)thieno[2,3-c]quinolin-4(5H)-one Hydrochloride



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Following General Procedure C, (S)-tert-butyl 1-(4-(8-methoxy-4-oxo-4,5-dihydrothieno[2,3-c]quinolin-9-yl)phenyl)ethyl(methyl)carbamate (30 mg, 0.06 mmol) was reacted with TFA (1.5 mL) to afford the desired product (15 mg, 65%) as a white solid: 1H NMR (500 MHz, MeOD); δ 7.64 (d, J=8.5 Hz, 2H), 7.61-7.52 (m, 2H), 7.45-7.36 (m, 3H), 5.98 (d, J=5.4 Hz, 1H), 4.48 (q, J=6.8 Hz, 1H), 3.74 (s, 3H), 2.73 (s, 3H), 1.79 (t, J=8.0 Hz, 3H). ESI MS m/z 365 [C21H20N2O2S+H]+; HPLC >99% (AUC), tR=13.69 min.


Example 1121
(S)-9-(4-(1-aminopropyl)phenyl)-8-methoxythieno[2,3-c]quinolin-4(5H)-one Hydrochloride



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Following General Procedure C, (S)-tert-butyl 1-(4-(8-methoxy-4-oxo-4,5-dihydrothieno[2,3-c]quinolin-9-yl)phenyl)propylcarbamate (40 mg, 0.09 mmol) was reacted with TFA (2.0 mL) to afford the desired product (15 mg, 49%) as a light yellow glass: 1H NMR (500 MHz, MeOD)) δ 7.60 (tt, J=7.1, 3.6 Hz, 2H), 7.57-7.51 (m, 2H), 7.42-7.36 (m, 3H), 6.00 (d, J=5.4 Hz, 1H), 4.32 (dd, J=9.2, 6.0 Hz, 1H), 3.73 (s, 3H), 2.11 (qdd, J=13.6, 8.3, 6.7 Hz, 3H), 1.08-0.98 (m, 3H); ESI MS m/z 365 [C21H20N2O2S+H]+; HPLC >99% (AUC), tR=8.74 min.


Example 1391
9-(4-(1-(aminomethyl)cyclopropyl)phenyl)-6-bromo-8-methoxythieno[2,3-c]quinolin-4(5H)-one Hydrochloride



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Following General Procedure C, tert-butyl (1-(4-(6-bromo-8-methoxy-4-oxo-4,5-dihydrothieno[2,3-c]quinolin-9-yl)phenyl)cyclopropyl)methylcarbamate (50 mg, 0.09 mmol) was reacted with TFA (5.0 mL) to afford the desired product (19 mg, 47%) as a white solid: 1H NMR (500 MHz, MeOD) δ 7.71-7.65 (m, 1H), 7.65-7.57 (m, 3H), 7.32-7.27 (m, 2H), 5.99 (t, J=6.4 Hz, 1H), 3.75 (s, 3H), 3.29 (s, 2H), 1.21-1.10 (m, 4H); ESI MS m/z 456 [C22H19BrN2O2S+H]+; HPLC >99% (AUC), tR=10.83 min.


Example 1251
9-(4-(1-(aminomethyl)cyclopropyl)phenyl)-8-methoxy-6-methylthieno[2,3-c]quinolin-4(5H)-one Hydrochloride



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Following General Procedure C, tert-butyl (1-(4-(8-methoxy-6-methyl-4-oxo-4,5-dihydrothieno[2,3-c]quinolin-9-yl)phenyl)cyclopropyl)methylcarbamate (70 mg, 0.14 mmol) was reacted with TFA (4.0 mL) to afford the desired product (32 mg, 56%) as a white solid: 1H NMR (500 MHz, MeOD) δ 7.63-7.51 (m, 3H), 7.32-7.23 (m, 3H), 6.02 (d, J=5.4 Hz, 1H), 3.74 (s, 3H), 3.28 (s, 2H), 2.64 (s, 3H), 1.21-1.08 (m, 4H); ESI MS m/z 391 [C23H22N2O2S+H]+; HPLC 95.7% (AUC), tR=9.15 min.


Example 1297
9-(4-(1-(aminomethyl)cyclobutyl)phenyl)-8-methoxy-6-methylthieno[2,3-c]quinolin-4(5H)-one Hydrochloride



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Following General Procedure C, tert-butyl(1-(4-(8-methoxy-6-methyl-4-oxo-4,5-dihydrothieno[2,3-c]quinolin-9-yl)phenyl)cyclobutyl)methylcarbamate (200 mg, 0.42 mmol) was reacted with TFA (5.0 mL) to afford the desired product (150 mg, 89%) as a white solid: 1H NMR (500 MHz, MeOD) δ 7.61 (d, J=5.4 Hz, 1H), 7.47-7.41 (m, 2H), 7.35-7.30 (m, 3H), 6.07 (d, J=5.4 Hz, 1H), 3.76 (s, 3H), 3.46 (s, 2H), 2.65 (s, 3H), 2.64-2.57 (m, 2H), 2.47-2.37 (m, 2H), 2.32-2.15 (m, 1H), 2.12-1.97 (m, 1H); ESI MS m/z 405 [C24H24N2O2S+H]+; HPLC >99% (AUC), tR=12.27 min.


Example 1321
9-(4-(1-(aminomethyl)cyclobutyl)phenyl)-6-chloro-8-methoxythieno[2,3-c]quinolin-4(5H)-one Hydrochloride



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Following General Procedure C, tert-butyl(1-(4-(6-chloro-8-methoxy-4-oxo-4,5-dihydrothieno[2,3-c]quinolin-9-yl)phenyl)cyclobutyl)methylcarbamate (25 mg, 0.05 mmol) was reacted with TFA (2.5 mL) to afford the desired product (16 mg, 80%) as a white solid: 1H NMR (500 MHz, MeOD) δ 7.66 (s, 1H), 7.55 (s, 1H), 7.47 (s, 2H), 7.34 (s, 2H), 6.04 (s, 1H), 3.77 (s, 3H), 3.47 (s, 2H), 2.68-2.54 (m, 2H), 2.47-2.35 (m, 2H), 2.31-2.20 (m, 1H), 2.12-2.02 (m, 1H); ESI MS m/z 426 [C23H21ClN2O2S+H]+; HPLC >99% (AUC), tR=9.87 min.


Example 1154
(S)-6-chloro-8-hydroxy-9-(4-(1-(methylamino)propyl)phenyl)thieno[2,3-c]quinolin-4(5H)-one Hydrochloride



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Following General Procedure F, (S)-tert-butyl 1-(4-(6-chloro-8-methoxy-4-oxo-4,5-dihydrothieno[2,3-c]quinolin-9-yl)phenyl)propyl(methyl)carbamate (100 mg, 0.194 mmol was reacted with tribromoborane (1.0 M in methylene chloride 1.2 mL, 1.16 mmol) to afford the desired product (35 mg, 45%) as a white solid: 1H NMR (500 MHz, DMSO) δ 10.81 (d, J=10.5 Hz, 1H), 9.83 (s, 1H), 9.70-9.45 (m, 1H), 9.28 (s, 1H), 7.73 (d, J=5.4 Hz, 1H), 7.70-7.60 (m, 2H), 7.38 (dd, J=12.4, 4.7 Hz, 3H), 5.70 (d, J=5.4 Hz, 1H), 4.19 (dt, J=12.1, 6.0 Hz, 1H), 2.51 (s, 3H), 2.20 (ddd, J=14.4, Z


Example 626
(S)-tert-butyl 2-(4-(8-methoxy-6-methyl-4-oxo-4,5-dihydrothieno[2,3-c]quinolin-9-yl)phenyl)propyl(methyl)carbamate



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Following General Procedure J, (S)-tert-butyl 2-(4-(6-bromo-8-methoxy-4-oxo-4,5-dihydrothieno[2,3-c]quinolin-9-yl)phenyl)propyl (methyl)carbamate (150 mg, 0.269 mmol) was reacted with trimethyl boroxine (102 mg, 0.8 mmol) to afford the desired product (95 mg, 75%) as a brown solid: ESI MS m/z 493 [C28H32BrN2O4S+H]+.


Example 1372
9-(4-(1-((dimethylamino)methyl)cyclobutyl)phenyl)-8-hydroxy-6-methylthieno[2,3-c]quinolin-4(5H)-one Hydrochloride



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Following the procedure outlined for Example 460, 9-(4-(1-(aminomethyl)cyclobutyl)phenyl)-8-hydroxy-6-methylthieno[2,3-c]quinolin-4(5H)-one hydrochloride (110 mg, 0.28 mmol)) was reacted with formaldehyde (37% in water, 22 mg, 0.70 mmol) to afford the desired product as a white solid (28 mg, 25%): 1H NMR (500 MHz, MeOD) δ 7.65 (t, J=7.4 Hz, 3H), 7.43 (d, J=8.1 Hz, 2H), 7.12 (s, 1H), 6.24 (d, J=5.3 Hz, 1H), 3.80 (s, 2H), 2.86 (s, 6H), 2.77-2.67 (m, 2H), 2.60 (s, 3H), 2.52 (dt, J=11.9, 8.8 Hz, 2H), 2.30-2.17 (m, 1H), 2.17-2.05 (m, 1H); ESI MS m/z 419 [C25H26N2O2S+H]+; HPLC >99% (AUC), tR=9.51 min.


Example 1172
(S)-9-(4-(1-(dimethylamino)propan-2-yl)phenyl)-8-hydroxythieno[2,3-c]quinolin-4(5H)-one Hydrochloride



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Following the procedure outlined for Example 460, (S)-9-(4-(1-aminopropan-2-yl)phenyl)-8-hydroxythieno[2,3-c]quinolin-4(5H)-one hydrochloride (20 mg, 0.06 mmol)) was reacted with formaldehyde (37% in water, 5.0 mg, 0.15 mmol) to afford the desired product as a white solid (15 mg, 70%): 1H NMR (500 MHz, MeOD) δ 7.64-7.51 (m, 3H), 7.45-7.37 (m, 2H), 7.34 (dd, J=7.7, 1.7 Hz, 1H), 7.19 (t, J=7.7 Hz, 1H), 6.12 (d, J=5.4 Hz, 1H), 3.62 (td, J=11.5, 2.6 Hz, 1H), 3.50-3.40 (m, 2H), 2.97 (s, 3H), 2.94 (s, 3H), 1.48 (d, J=6.6 Hz, 3H); ESI MS m/z 379 [C22H22N2O2S+H]+; HPLC >99% (AUC), tR=8.63 min.


Example 1128
(S)-9-(4-(1-(dimethylamino)propyl)phenyl)-8-hydroxythieno[2,3-c]quinolin-4(5H)-one Hydrochloride



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Following the procedure outlined for Example 460, (S)-9-(4-(1-aminopropyl)phenyl)-8-hydroxythieno[2,3-c]quinolin-4(5H)-one hydrochloride (25 mg, 0.07 mmol)) was reacted with formaldehyde (37% in water, 5.5 mg, 0.18 mmol) to afford the desired product as a white solid (12 mg, 45%): 1H NMR (500 MHz, MeOD) δ 7.66 (ddd, J=19.7, 7.7, 1.6 Hz, 2H), 7.55 (d, J=5.4 Hz, 1H), 7.52-7.45 (m, 2H), 7.43 (d, J=8.9 Hz, 1H), 7.20 (d, J=8.9 Hz, 1H), 5.95 (d, J=5.4 Hz, 1H), 4.38 (dd, J=11.3, 4.4 Hz, 1H), 2.99 (d, J=2.1 Hz, 3H), 2.85 (d, J=3.2 Hz, 3H), 2.40-2.18 (m, 2H), 1.03-0.93 (m, 3H); ESI MS m/z 379 [C22H22N2O2S+H]+; HPLC 98.4% (AUC), tR=8.14 min.


Example 1127
(S)-9-(4-(1-(ethylamino)propyl)phenyl)-8-hydroxythieno[2,3-c]quinolin-4(5H)-one Hydrochloride



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Following the procedure outlined for Example 460, (S)-9-(4-(1-aminopropyl)phenyl)-8-hydroxythieno[2,3-c]quinolin-4(5H)-one hydrochloride (30 mg, 0.09 mmol)) was reacted with formaldehyde (37% in water, 9.5 mg, 0.21 mmol) to afford the desired product as a white solid (15 mg, 46%): 1H NMR (500 MHz, MeOD) δ 7.68-7.57 (m, 2H), 7.54 (d, J=5.4 Hz, 1H), 7.45 (ddd, J=17.0, 10.1, 5.3 Hz, 3H), 7.19 (d, J=8.9 Hz, 1H), 5.97 (d. J=15.4 Hz, 1H), 4.26 (dd, J=11.1, 4.3 Hz, 1H), 3.11 (tt, J=14.6, 7.3 Hz, 1H), 3.05-2.95 (m, 1H), 2.25 (ddd, J=13.0, 7.4, 4.4 Hz, 1H), 2.09 (ddd, J=13.1, 11.2, 7.4 Hz, 1H), 1.35 (t, J=7.3 Hz, 3H); ESI MS m/z 379 [C22H22N2O2S+H]+; HPLC 98.4% (AUC), tR=8.51 min.


Example 1095
9-(4-(2-aminopropyl)phenyl)-8-hydroxythieno[2,3-c]quinolin-4(5H)-one Hydrochloride



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Following General Procedure F, tert-butyl 1-(4-(8-methoxy-4-oxo-4,5-dihydrothieno[2,3-c]quinolin-9-yl)phenyl)propan-2-ylcarbamate (650 mg, 1.40 mmol) was reacted with BBr3 (1.0 M in CH2Cl2, 10 mL, 10 mmol) to afford the desired product (152 mg, 31%) as a light yellow solid: 1H NMR (500 MHz, CD3OD) δ 7.56 (d, J=5.4 Hz, 1H), 7.49 (d, J=7.9 Hz, 1H), 7.43 (dd, J=13.3, 8.3 Hz, 2H), 7.34 (d, J=7.9 Hz, 2H), 7.18 (d, J=8.9 Hz, 1H), 6.11 (d, J=5.4 Hz, 1H), 3.71-3.60 (m, 1H), 3.05 (dd, J=7.2, 2.2 Hz, 2H), 1.40 (d, J=6.6 Hz, 3H): ESI MS m/z 351 [C20H18N2O2S+H]+; HPLC 98.6% (AUC), tR=8.08 min.


Example 1106
9-(4-(2-aminopropyl)phenyl)-6-chloro-8-hydroxythieno[2,3-c]quinolin-4(5H)-one Hydrochloride



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Following General Procedure F, a tert-butyl 1-(4-(6-chloro-8-methoxy-4-oxo-4,5-dihydrothieno[2,3-c]quinolin-9-yl)phenyl)propan-2-ylcarbamate (55 mg, 0.11 mmol) was reacted with BBr3 (1.0 M in CH2Cl2, 2 mL, 2 mmol) to afford the desired product (28 mg, 66%) as a white solid: 1H NMR (500 MHz, CD3OD) δ 7.61 (d, J=5.4 Hz, 1H), 7.47 (dd, J=22.8, 7.8 Hz, 2H), 7.36-7.29 (m, 3H), 6.08 (d, J=5.4 Hz, 1H), 3.65 (dd, J=13.7, 6.9 Hz, 1H), 3.05 (ddd, J=34.9, 13.6, 7.3 Hz, 2H), 1.39 (d, J=6.6 Hz, 3H): ESI MS m/z 385 [C20H17ClN2O2S+H]+; HPLC >99% (AUC), tR=8.77 min.


Example 379
9-(4-(1-((dimethylamino)methyl)cyclopropyl)phenyl)-8-hydroxythieno[2,3-c]quinolin-4(5H)-one Hydrochloride



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Following the procedure outlined for Example 1387, 9-(4-(1-(aminomethyl)cyclopropyl)phenyl)-8-hydroxythieno[2,3-c]quinolin-4(5H)-one hydrochloride (10 mg, 0.03 mmol) was reacted with paraformaldehyde (8 mg, 0.11 mmol) and after purification the resulting material was converted to the hydrochloride salt as outlined in General Procedure D-2 to afford the desired product (7.0 mg, 87%) as a light yellow solid: 1H NMR (500 MHz, CD3OD) δ 7.70 (d, J=7.9 Hz, 2H), 7.58 (d, J=5.4 Hz, 1H), 7.39 (dd, J=25.8, 8.4 Hz, 3H), 7.18 (d, J=8.9 Hz, 1H), 6.12 (d, J=5.4 Hz, 1H), 2.94 (s, 6H), 1.34-1.25 (m, 2H), 1.23-1.14 (m, 2H); ESI MS m/z 391 [C23H22N2O2S+H]+; HPLC 96.7% (AUC), tR=8.72 min.


Example 373
9-(4-(1-aminopropan-2-yl)phenyl)-8-methoxythieno[2,3-c]quinolin-4(5H)-one Hydrochloride



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To a solution of 2-(4-(8-methoxy-4-oxo-4,5-dihydrothieno[2,3-c]quinolin-9-yl)phenyl)propanenitrile (50 mg, 0.14 mmol) in toluene (13 mL) at 0° C. was added BH3.THF (1.0 M, 13 mL, 13 mmol) and the reaction was warmed to room temperature and heated at reflux for 4 h. The reaction was quenched by pouring onto water or ice-water and the resulting mixture was concentrated and purified by preparatory HPLC (C18 silica, acetonitrile/water (with 0.05% TFA) gradient). The desired product was dissolved in aqueous HCl, concentrated and dried under high vacuum to afford the desired product as a light yellow solid (5.4 mg, 10%): 1H NMR (500 MHz, CD3OD) δ 7.60-7.49 (m, 3H), 7.47 (dd, J=7.7, 1.7 Hz, 1H), 7.39 (d, J=9.1 Hz, 1H), 7.34-7.25 (m, 2H), 6.00 (d, J=5.4 Hz, 1H), 3.75 (s, 3H), 3.30-3.18 (m, 3H), 1.49 (d, J=6.5 Hz, 3H): ESI MS m/z 365 [C21H20N2O2S+H]+; HPLC 99% (AUC), tR=8.76 min.


Example 1218
9-(4-(2-aminoethyl)-3-fluorophenyl)-6-chloro-8-methoxythieno[2,3-c]quinolin-4(5H)-one Hydrochloride



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Following General Procedure F, tert-butyl 2-fluor-4-(8-methoxy-4-oxo-4,5-dihydrothieno[2,3-c]quinolin-9-yl)phenethylcarbamate (70 mg, 0.14 mmol) was treated with BBr3 (1.0 M in CH2Cl2, 5 mL, 5 mmol) to afford the desired product as a white solid (17 mg, 30%): 1H NMR (500 MHz, CD3OD) δ 7.66 (d, J=5.4 Hz, 1H), 7.54 (s, 1H), 7.50 (t, J=7.9 Hz, 1H), 7.10 (d, J=7.9 Hz, 2H), 6.09 (d, J=5.4 Hz, 1H), 3.76 (s, 3H), 3.25-3.06 (m, 4H); ESI MS m/z 403 [C20H16ClFN2O2S+H]+; HPLC 97.9% (AUC), tR=9.63 min.


Example 1247
9-(4-(1-amino-2-methylpropan-2-yl)phenyl)-6-bromo-8-hydroxythieno[2,3-c]quinolin-4(5H)-one Hydrochloride



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Following General Procedure F, tert-butyl 2-(4-(6-bromo-8-methoxy-4-oxo-4,5-dihydrothieno[2,3-c]quinolin-9-yl)phenyl)-2-methylpropylcarbamate (110 mg, 0.20 mmol) was treated with BBr3 (1.0 M in CH2Cl2, 10 mL, 10 mmol) to afford the desired product as a brown solid (39 mg, 45%): ESI MS m/z 443 [C21H19BrN2O2S+H]+; HPLC 96.3% (AUC), tR=9.56 min.


Example 1245
6-bromo-9-(3-fluoro-4-(2-(methylamino)ethyl)phenyl)-8-hydroxythieno[2,3-c]quinolin-4(5H)-one Hydrochloride



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Following General Procedure F, tert-butyl 4-(6-bromo-8-methoxy-4-oxo-4,5-dihydrothieno[2,3-c]quinolin-9-yl)-2-fluorophenethyl(methyl)carbamate (90 mg, 0.16 mmol) in CH2Cl2 at 0° C. was added BBr3 (1.0 M in CH2Cl2, 6 mL, 6 mmol) and the reaction was warmed to room temperature for 4 h. The reaction was quenched by pouring onto water or ice-water and the resulting mixture was concentrated and purified by preparatory HPLC (C18 silica, acetonitrile/water (with 0.05% TFA) gradient). The desired product was dissolved in aqueous HCl, concentrated and dried under high vacuum to afford the desired product as a white solid (15 mg, 21%): ESI MS m/z 447 [C20H16BrFN2O2S+H]+; HPLC >99% (AUC), tR=9.26 min.


Example 1258
9-(3-fluoro-4-(2-(methylamino)ethyl)phenyl)-8-hydroxy-6-methylthieno[2,3-c]quinolin-4(5H)-one Hydrochloride



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Following General Procedure F, tert-butyl 2-fluoro-4-(8-methoxy-6-methyl-4-oxo-4,5-dihydrothieno[2,3-c]quinolin-9-yl)phenethyl(methyl)carbamate (60 mg, 0.12 mmol) in CH2Cl2 at 0° C. was added BBr3 (1.0 M in CH2Cl2, 6 mL, 6 mmol) and the reaction was warmed to room temperature for 4 h. The reaction was quenched by pouring onto water or ice-water and the resulting mixture was concentrated and purified by preparatory HPLC (C18 silica, acetonitrile/water (with 0.05% TFA) gradient). The desired product was dissolved in aqueous HCl, concentrated and dried under high vacuum to afford the desired product as a off-white solid (31 mg, 67%): 1H NMR (500 MHz, (CD3OD) 7.63 (d, J=5.4 Hz, 1H), 7.51 (t, J=7.9 Hz, 1H), 7.15-7.06 (m, 3H), 6.20 (d, J=5.4 Hz, 1H), 3.42-3.35 (m, 2H), 3.30-3.10 (m, 2H), 2.80 (s, 3H), 2.57 (s, 3H); ESI MS m/z 383 [C21H11FN2O2S+H]+, HPLC >99% (AUC), tR=8.65 min.


Example 1260
9-(4-(1-amino-2-methylpropan-2-yl)phenyl)-6-chloro-8-hydroxythieno[2,3-c]quinolin-4(5H)-one Hydrochloride



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Following General Procedure F, tert-butyl 2-(4-(8-methoxy-4-oxo-4,5-dihydrothieno[2,3-c]quinolin-9-yl)phenyl)-2-methylpropylcarbamate (70 mg, 0.14 mmol) in CH2C2 at 0° C. was added BBr3 (1.0 M in CH2Cl2, 5 mL, 5 mmol) and the reaction was warmed to room temperature for 4 h. The reaction was quenched by pouring onto water or ice-water and the resulting mixture was concentrated and purified by preparatory HPLC (C18 silica, acetonitrile/water (with 0.05% TFA) gradient). The desired product was dissolved in aqueous HCl, concentrated and dried under high vacuum to afford the desired product as a brown solid (12 mg, 38%): 1H NMR (500 MHz, CD3OD) δ 7.66 (d, J=8.4 Hz, 2H), 7.63 (d, J=5.4 Hz, 1H), 7.36 (d, J=8.4 Hz, 2H), 7.32 (s, 1H), 6.13 (d, J=5.4 Hz, 1H), 3.29 (s, 2H), 1.58 (s, 6H); ESI MS m/z 399 [C21H19ClN2O2S+H]+; HPLC 98.8% (AUC), tR=9.26 min.


Example 1280
9-(4-(1-aminopropan-2-yl)-3-chlorophenyl)-8-hydroxythieno[2,3-c]quinolin-4(5H)-one Hydrochloride



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Following General Procedure F, tert-butyl 2-(2-chloro-4-(8-methoxy-4-oxo-4,5-dihydrothieno[2,3-c]quinolin-9-yl)phenyl)propylcarbamate (120 mg, 0.24 mmol) in CH2Cl2 at 0° C. was added BBr3 (1.0 M in CH2Cl2. 15 mL, 15 mmol) and the reaction was warmed to room temperature for 4 h. The reaction was quenched by pouring onto water or ice-water and the resulting mixture was concentrated and purified by preparatory HPLC (C18 silica, acetonitrile/water (with 0.05% TFA) gradient). The desired product was dissolved in aqueous HCl, concentrated and dried under high vacuum to afford the desired product as a brown solid (40 mg, 43%): 1H NMR (500 MHz, CD3OD) δ 7.65 (ddd, J=9.9, 9.3, 6.1 Hz, 2H), 7.46-7.36 (m, 2H), 7.33-7.27 (m, 1H), 7.18 (t, J=9.0 Hz, 1H), 6.10 (dd, J=28.8, 5.4 Hz, 1H), 3.86-3.66 (m, 1H), 3.29-3.12 (m, 2H), 1.44-1.28 (m, 3H); ESI MS m/z 385 [C20H17ClN2O2S+H]+; HPLC >99% (AUC), tR=9.07 min.


Example 1111
9-(4-(1-aminopropan-2-yl)phenyl)-8-hydroxythieno[2,3-c]quinolin-4(5H)-one Hydrochloride



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Following General Procedure F, 9-(4-(1-aminopropan-2-yl)phenyl)-8-methoxythieno[2,3-c]quinolin-4(5H)-one (120 mg, 0.33 mmol) in CH2Cl2 at 0° C. was added BBr3 (1.0 M in CH2Cl2, 5 mL, 5 mmol) and the reaction was warmed to room temperature for 4 h. The reaction was quenched by pouring onto water or ice-water and the resulting mixture was concentrated and purified by preparatory HPLC (C18 silica, acetonitrile/water (with 0.05% TFA) gradient). The desired product was dissolved in aqueous HCl, concentrated and dried under high vacuum to afford the desired product as a light yellow solid (48 mg, 42%): 1H NMR (500 MHz, CD3OD) δ 7.57 (dd, J=12.7, 6.7 Hz, 2H), 7.47 (d, J=6.9 Hz, 1H), 7.42 (d, J=8.9 Hz, 1H), 7.37 (d, J=7.9 Hz, 1H), 7.32 (d, J=7.7 Hz, 1H), 7.18 (d, J=8.9 Hz, 1H), 6.15 (d, J=5.4 Hz, 1H), 3.28-3.17 (m, 3H), 1.50 (d, J=6.1 Hz, 3H); ESI MS m/z 351 [C20H18N2O2S+H]+; HPLC >99% (AUC), tR=8.25 min.


Example 1151
(R)-9-(4-(1-(dimethylamino)propyl)phenyl)-8-hydroxythieno[2,3-c]quinolin-4(5H)-one Hydrochloride



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Following the procedure outlined for Example 1387, (R)-9-(4-(1-aminopropyl)phenyl)-8-methoxythieno[2,3-c]quinolin-4(5H)-one hydrochloride (20 mg, 0.06 mmol) was reacted with paraformaldehyde (10 mg, 0.17 mmol) and after purification the resulting material was converted to the hydrochloride salt as outlined in General Procedure D-2 to afford the desired product (5 mg, 24%) as a light yellow solid: 1H NMR (500 MHz, CD3OD) δ 7.71 (dd, J=10.5, 7.8 Hz, 2H), 7.64 (d, J=5.4 Hz, 1H), 7.47 (t, J=7.1 Hz, 2H), 7.31 (d, J=8.9 Hz, 2H), 6.01 (d, J=5.4 Hz, 1H), 4.66 (q, J=6.9 Hz, 1H), 2.97 (s, 3H), 2.86 (s, 3H), 2.20-2.00 (m, 2H), 1.86 (d, J=7.0 Hz, 3H); ESI MS m/z 379 [C12H22N2O2S+H]+; HPLC 95.6% (AUC), tR=8.92 min.


Example 1162
2-(4-(8-hydroxy-4-oxo-4,5-dihydrothieno[2,3-c]quinolin-9-yl)phenyl)butanenitrile



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Following General Procedure F, 2-(4-(8-methoxy-4-oxo-4,5-dihydrothieno[2,3-c]quinolin-9-yl phenyl)butanenitrile (80 mg, 0.21 mmol) in CH2Cl2 at 0° C. was added BBr3 (1.0 M in CH2Cl2, 3 mL, 3 mmol) and the reaction was warmed to room temperature for 4 h. The reaction was quenched by pouring onto water or ice-water and the resulting mixture was concentrated and purified by preparatory HPLC (C18 silica, acetonitrile/water (with 0.05% TFA) gradient). The desired product was dissolved in aqueous HCl, concentrated and dried under high vacuum to afford the desired product as a light yellow solid (4.3 mg, 6%): 1H NMR (500 MHz, CD3OD) δ 7.56 (dd, J=10.8, 4.6 Hz, 3H), 7.43-7.31 (m, 3H), 7.17 (d, J=8.9 Hz, 1H), 6.00 (d, J=5.4 Hz, 1H), 4.15 (t, J=7.2 Hz, 1H), 2.07 (p, J=7.3 Hz, 2H), 1.16 (t, J=7.4 Hz, 3H): ESI MS m/z 361 [C21H16N2O2S+H]+; HPLC 98.5% (AUC), tR=12.2 min.


Example 1174
9-(4-(1-aminopropan-2-yl)-3-fluorophenyl)-8-hydroxythieno[2,3-c]quinolin-4(5H)-one Hydrochloride



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Following General Procedure C tert-butyl 2-(2-fluoro-4-(8-methoxy-4-oxo-4,5-dihydrothieno[2,3-c]quinolin-9-yl)phenyl)propylcarbamate (120 mg, 0.25 mmol) was reacted with TFA (10 mL) to afford the desired product (35 mg, 37%) as a off-white solid: 1H NMR (500 MHz, CD3OD) δ 7.64 (dd, J=5.4, 3.1 Hz, 1H), 7.54 (ddd, J=25.0, 11.7, 5.2 Hz, 2H), 7.40 (dd, J=9.1, 1.1 Hz, 1H), 7.18-7.06 (m, 2H), 6.10 (dd, J=27.5, 5.4 Hz, 1H), 3.77 (s, 3H), 3.64-3.43 (m, 1H), 3.42-3.22 (m, 2H), 1.51 (d, J=7.0 Hz, 3H): ESI MS m/z 383 [C21H19FN2O2S+H]+; HPLC 96.5% (AUC), tR=−9.07 min.


Example 1189
(R)-8-methoxy-9-(4-(1-(methylamino)propan-2-yl)phenyl)thieno[2,3-c]quinolin-4(5H)-one Hydrochloride



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Following General Procedure C (R)-tert-butyl 2-(4-(8-methoxy-4-oxo-4,5-dihydrothieno[2,3-c]quinolin-9-yl)phenyl)propyl(methyl)carbamate (120 mg, 0.25 mmol) was reacted with TFA (8 mL) to afford the desired product (56 mg, 59%) as a white solid: 1H NMR (500 MHz, CD3OD) δ 7.60-7.51 (m, 3H), 7.48 (dd, J=7.8, 1.9 Hz, 1H), 7.39 (d, J=9.1 Hz, 1H), 7.31 (ddd, J=15.8, 7.8, 1.8 Hz, 2H), 5.99 (d, J=5.4 Hz, 1H), 3.75 (s, 3H), 3.46-3.36 (m, 1H), 3.37-3.24 (m, 2H), 2.76 (s, 3H), 1.49 (d, J=6.7 Hz, 3H); ESI MS m/z 379 [C22H22N2O2S+H]+; HPLC >99% (AUC), tR=8.96 min.


Example 1131
(R)-9-(4-(1-aminopropyl)phenyl)-8-hydroxythieno[2,3-c]quinolin-4(5H)-one Hydrochloride



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Following General Procedure F, (R)-tert-butyl 1-(4-(8-methoxy-4-oxo-4,5-dihydrothieno[2,3-c]quinolin-9-yl)phenyl)propylcarbamate (70 mg, 0.15 mmol) in CH2Cl2 at 0° C. was added BBr3 (1.0 M in C(H2Cl2, 3 mL, 3 mmol) and the reaction was warmed to room temperature for 4 h. The reaction was quenched by pouring onto water or ice-water and the resulting mixture was concentrated and purified by preparatory HPLC (C18 silica, acetonitrile/water (with 0.05% TFA) gradient). The desired product was dissolved in aqueous HCl, concentrated and dried under high vacuum to afford the desired product as a light yellow solid (35 mg, 67%): 1H NMR (500 MHz, CD3OD) δ 7.61 (s, 2H), 7.55 (d, J=5.4 Hz, 1H), 7.45-7.40 (m, 3H), 7.18 (d, J=8.9 Hz, 1H), 6.03 (d, J=5.4 Hz, 1H), 4.32 (dd, J=9.2, 5.9 Hz, 1H), 2.23-2.01 (m, 2H), 1.04 (t, J=7.4 Hz, 3H); ESI MS m/z 351 [C20H18N2O2S+H]+; HPLC >99% (AUC), tR=8.06 min.


Example 1150
(R)-9-(4-(1-aminopropyl)phenyl)-6-bromo-8-hydroxythieno[2,3-c]quinolin-4(5H)-one Hydrochloride



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Following General Procedure F, (R-tert-butyl 1-(4-(6-bromo-8-methoxy-4-oxo-4,5-dihydrothieno[2,3-c]quinolin-9-yl)phenyl)propylcarbamate (50 mg, 0.09 mmol) in CH2Cl2 at 0° C. was added BBr3 (1.0 M in CH2Cl2, 5 mL, 5 mmol) and the reaction was warmed to room temperature for 4 h. The reaction was quenched by pouring onto water or ice-water and the resulting mixture was concentrated and purified by preparatory HPLC (C18 silica, acetonitrile/water (with 0.05% TFA) gradient). The desired product was dissolved in aqueous HCl, concentrated and dried under high vacuum to afford the desired product as a light yellow solid (36 mg, 92%): 1H NMR (500 MHz, CD3OD) δ 7.65-7.57 (m, 3H), 7.50-7.46 (m, 1H), 7.45-7.39 (m, 2H), 6.02 (d, J=5.4 Hz, 1H), 4.32 (dd, J=9.2, 6.0 Hz, 1H), 2.20-2.00 (m, 2H), 1.03 (t, J=7.4 Hz, 3H); ESI MS m/z 429 [C20H17BrN2O2S+H]+; HPLC >99% (AUC), tR=9.17 min.


Example 254
N-[4-(8-Hydroxy-4-oxo-4,5-dihydrothieno[2,3-c]quinolin-9-yl)-2-methylphenyl]methanesulfonamide



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Following General Procedure F, N-[4-(8-methoxy-4-oxo-4,5-dihydrothieno[2,3-c]quinolin-9-yl)-2-methylphenyl]methanesulfonamide (47 mg, 0.11 mmol) was reacted with tribromoborane (1.0 M in methylene chloride, 3.0 mL, 3.0 mmol) to afford the desired product (17 mg, 39%) as an off-white solid: 1H NMR (500 MHz, CD3OD) δ 7.58 (d, J=5.4 Hz, 1H), 7.55 (d, J=8.1 Hz, 1H), 7.39 (d, J=8.9 Hz, 1H), 7.21 (s, 1H), 7.17-7.14 (m, 2H), 6.10 (d, J=5.4 Hz, 1H), 3.40 (s, 3H), 2.43 (s, 3H); ESI MS m/z 401 [C19H6N2O4S2+H]+; HPLC 96.4% (AUC), tR=10.23 min.


Example 334
9-[4-(2-Aminopropan-2-yl)phenyl]-6-chloro-8-hydroxythieno[2,3-c]quinolin-4(5H)-one Hydrochloride



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Following General Procedure F, tert-butyl 2-[4-(6-chloro-8-methoxy-4-oxo-4,5-dihydrothieno[2,3-c]quinolin-9-yl)phenyl]propan-2-ylcarbamate (10 mg, 0.020 mmol) was reacted with tribromoborane (1.0 M in methylene chloride, 1.0 mL, 1.0 mmol) to afford the desired product (9.7 mg, 97%) as an off-white solid: 1H NMR (500 MHz, CD3OD) δ 7.71 (d, J=8.4 Hz, 2H), 7.60 (d, J=5.4 Hz, 1H), 7.42 (d, J=8.4 Hz, 2H), 7.30 (s, 1H), 6.06 (d, J=5.4 Hz, 1H), 1.86 (s, 6H); ESI MS m/z 385 [C20H17ClN2O2S+H]+; HPLC >99% (AUC), tR=10.89 min


Example 329
9-[4-(Aminomethyl)phenyl]-6-chloro-8-hydroxythieno[2,3-c]quinolin-4(5H)-one Hydrochloride



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Following General Procedure F, tert-butyl 4-(6-chloro-8-methoxy-4-oxo-4,5-dihydrothieno[2,3-c]quinolin-9-yl)benzylcarbamate (15 mg, 0.032 mmol) was reacted with tribromoborane (1.0 M in methylene chloride, 1 mL, 1 mmol) to afford the desired product (10 mg, 80%) as a brown solid: 1H NMR (500 MHz, CD3OD) δ 7.64 (d, J=8.2 Hz, 2H), 7.59 (d, J=5.4 Hz, 1H), 7.43-7.38 (m, 2H), 7.30 (s, 1H), 6.08 (d, J=5.4 Hz, 1H), 4.27 (s, 2H); ESI MS m/z 357 [C18H13ClN2O2S+H]+; ESI MS m/z 357 [C18H13ClN2O2S+H]+; HPLC 98.4% (AUC), tR=8.62 min.


Example 457
tert-Butyl 4-(8-Hydroxy-4-oxo-4,5-dihydrothieno[2,3-c]quinolin-9-yl)benzylcarbamate



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Following the procedure from Example 463, 9-[4-(aminomethyl)phenyl]-8-hydroxythieno[2,3-c]quinolin-4(5H)-one (320 mg, 1.0 mmol) was reacted with di-tert-butyl dicarbonate (260 mg, 1.2 mmol) to afford the desired product (150 mg, 36%): ESI MS m/z 323 [C23H22N2O4S+H]+.


Example 319
9-[4-(2-Aminopropan-2-yl)phenyl]-8-hydroxythieno[2,3-c]quinolin-4(5H)-one Hydrochloride



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Following General Procedure F, tert-butyl 2-[4-(8-methoxy-4-oxo-4,5-dihydrothieno[2,3-c]quinolin-9-yl)phenyl]propan-2-ylcarbamate (29 mg, 0.063 mmol) was reacted with tribromoborane (1.0 M, 1.0 mL, 0.10 mmol) to afford the desired product (12 mg, 52%) as a white solid: 1H NMR (500 MHz, CD3OD) δ 7.70 (d, J=8.4 Hz, 2H), 7.55 (d, J=5.4 Hz, 1H), 7.46-7.37 (m, J=8.6, 7.7 Hz, 3H), 7.17 (d, J=8.9 Hz, 1H), 6.07 (d, J=5.4 Hz, 1H), 1.86 (s, 6H); ESI MS m/z 351[C20H18N2O2S+H]+; HPLC 98.3% (AUC), tR=10.48 min.


Example 270
9-[4-(Aminomethyl)phenyl]-6-bromo-8-hydroxythieno[2,3-c]quinolin-4(5H)-one Hydrochloride



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Following General Procedure F, tert-butyl 4-(6-bromo-8-methoxy-4-oxo-4,5-dihydrothieno[2,3-c]quinolin-9-yl)benzylcarbamate (10 mg, 0.019 mmol) was reacted with tribromoborane (1.0 M in methylene chloride, 1.0 mL, 1.0 mmol) to afford the desired product (3.9 mg, 47%) as a white solid: 1H NMR (500 MHz, CD3OD) δ 7.64 (d, J=8.1 Hz, 2H), 7.60 (d, J=5.4 Hz, 1H), 7.47 (s, 1H), 7.42-7.40 (m, 2H), 6.08 (d, J=5.5 Hz, 1H), 4.27 (s, 2H); ESI MS m/z 403 [(C18H13BrN2O2S+2)+H]+; HPLC 97.1% (AUC), tR=7.90 min.


Example 210
N-(2-Bromoethyl)-4-(8-hydroxy-4-oxo-4,5-dihydrothieno[2,3-c]quinolin-9-yl)benzenesulfonamide



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Following General Procedure F, N-(2-hydroxyethyl)-4-(8-methoxy-4-oxo-4,5-dihydrothieno[2,3-c]quinolin-9-yl)benzenesulfonamide (1.7 g, 3.9 mmol) was reacted with tribromoborane (3.7 mL, 24 mmol) to afford the desired product (1.7 g, 91%) as an off-white solid: 1H NMR (500 MHz, DMSO-d6) δ 11.84 (s, 1H), 9.43 (s, 1H), 8.16 (t, J=5.9 Hz, 1H), 7.94 (d, J=8.3 Hz, 2H), 7.75 (d, J=5.4 Hz, 1H), 7.52 (d, J=8.3 Hz, 2H), 7.41 (d, J=8.9 Hz, 1H), 7.19 (d, J=8.9 Hz, 1H), 5.83 (d, J=5.4 Hz, 1H), 3.51 (t, J=6.4 Hz, 2H), 3.28 (q, J=6.2 Hz, 2H); ESI MS m/z 478 [C19H15BrN2O4S2+H]+; HPLC 98.5% (AUC), tR=15.23 min.


Example 458
2-{4-[8-Hydroxy-4-oxo-4,5-dihydrothieno[2,3-c]quinolin-9-yl]phenylsulfonamido}ethyl methanesulfonate



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To a solution of N-(2-hydroxyethyl)-4-(8-methoxy-4-oxo-4,5-dihydrothieno[2,3-c]quinolin-9-yl)benzenesulfonamide (390 mg, 0.90 mmol) and triethylamine (450 mg, 4.5 mmol) in anhydrous THF (20 mL) was added methane sulfonyl chloride (0.21 mL, 2.7 mmol) and the reaction mixture was stirred for 20 h at room temperature. The resulting precipitate was filtered and the filter cake was washed with THF (50 mL). The filtrate was concentrated and the residue was purified by flash chromatography (silica, ethyl acetate/hexanes gradient) to afford the desired product as a brown solid (250 mg, 55%). 1H NMR (300 MHz, DMSO-d6) δ 11.93 (s, 1H), 8.14 (t, J=11.7 Hz, 1H), 7.95 (d, J=8.4 Hz, 2H), 7.79 (d, J=5.4 Hz, 1H), 7.56 (d, J=9.0 Hz, 1H), 7.53 (d, J=8.4 Hz, 2H), 7.43 (d, J=9.0 Hz, 1H), 5.74 (d, J=5.4 Hz, 1H), 4.24 (t, J=10.5 Hz, 2H), 3.71 (s, 3H), 3.20 (q, J=11.7 Hz, 2H) ESI MS m/z 509 [C21H20N2O7S3+H]+


Example 332
N-(2-Chloroethyl)-4-(8-hydroxy-4-oxo-4,5-dihydrothieno[2,3-c]quinolin-9-yl)benzenesulfonamide



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To a solution of 2-(4-(8-methoxy-4-oxo-4,5-dihydrothieno[2,3-c]quinolin-9-yl)phenylsulfonamido)ethyl methanesulfonate (250 mg, 0.49 mmol) in anhydrous dichloroethane was added aluminum chloride (330 mg, 2.5 mmol) and the reaction mixture was heated at reflux for 20 h. The reaction was cooled to room temperature, concentrated and quenched with methanol (10 mL). The resulting mixture was allowed to stand at room temperature for 1 h and the resulting precipitate was filtered and dried to afford the desired product (88 mg, 41%) as an off-white solid: 1H NMR (500 MHz, DMSO-d) δ 11.83 (s, 1H), 9.42 (s, 1H), 8.13 (t, J=7.2 Hz, 1H), 7.94 (d, J=5.1 Hz, 2H), 7.74 (d, J=3.3 Hz, 1H), 7.51 (d, J=5.1 Hz, 2H), 7.41 (d, J=5.4 Hz, 1H), 7.18 (d, J=5.4 Hz, 1H), 5.82 (d, J=3.3 Hz, 1H), 3.65 (t, J=3.9 Hz, 2H), 3.22 (q, J=3.6 Hz, 2H); ESI MS m/z 435 [C19H15ClN2O4S2+H]+; HPLC 97.2% (AUC), tR=14.98 min,


Example 304
4-(8-Hydroxy-4-oxo-4,5-dihydrothieno[2,3-c]quinolin-9-yl)-N,N-dimethylbenzenesulfonamide



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Following General Procedure F, the crude material from Example 74, 4-(8-methoxy-4-oxo-4,5-dihydrothieno[2,3-c]quinolin-9-yl)-N,N-dimethylbenzenesulfonamide (33 mg, 0.080 mmol), was reacted with tribromoborane (0.2 mL) to afford the desired product (9 mg, 7% over 2 steps) as a brown solid: 1H NMR (500 MHz, DMSO-d6) δ 11.85 (s, 1H), 9.44 (s, 1H), 7.88 (dd, J=6.8, 1.6 Hz, 2H), 7.79 (d, J=5.4 Hz, 1H), 7.57 (dd, J=6.6, 1.7 Hz, 2H), 7.42 (d, J=8.9 Hz, 1H), 7.20 (d, J=8.9 Hz, 1H), 5.69 (d, J=5.4 Hz, 1H), 2.71 (s, 6H); ESI MS m/z 401 [C19H6N2O4S2+H]+; HPLC 94.5% (AUC), tR=14.84 min.


Example 297
N-(2-Bromoethyl)-2-fluoro-4-(8-hydroxy-4-oxo-4,5-dihydrothieno[2,3-c]quinolin-9-yl)benzenesulfonamide



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Following General Procedure F, 2-fluoro-N-(2-hydroxyethyl)-4-(8-methoxy-4-oxo-4,5-dihydrothieno[2,3-c]quinolin-9-yl)benzenesulfonamide (52 mg, 0.12 mmol) was reacted with tribromoborane (0.80 mL, 0.23 mmol) to afford the desired product (47 mg, 81%) as a white solid: 1H NMR (500 MHz, DMSO-d6) δ 11.86 (s, 1H), 9.52 (s, 1H), 8.45 (t, J=5.7 Hz, 1H), 7.92 (t, J=7.8 Hz, 1H), 7.80 (d, J=5.5 Hz, 1H), 7.46 (d, J=10.9 Hz, 1H), 7.42 (d, J=8.9 Hz, 1H), 7.30 (dd, J=8.0, 1.4 Hz, 1H), 7.19 (d, J=9.0 Hz, 1H), 6.00 (d, J=5.4 Hz, 1H), 3.53 (t, J=6.3 Hz, 2H), 3.42 (q, J=6.0 Hz, 2H); ESI MS m/z 499 [C19H14BrFN2O4S2+H]+; HPLC 98.3% (AUC), tR=15.61 min.


Example 266
9-[5-(Aminomethyl)thiophen-2-yl]-8-hydroxythieno[2,3-c]quinolin-4(5H)-one



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Following General Procedure F, tert-butyl[5-(8-methoxy-4-oxo-4,5-dihydrothieno[2,3-c]quinolin-9-yl)thiophen-2-yl]methylcarbamate (30 mg, 0.067 mmol) was reacted with tribromoborane (0.50 mL) to afford the desired product (25 mg, 91%) as a off-white solid: 1H NMR (500 MHz, CD3OD) δ 7.67 (d, J=5.4 Hz, 1H), 7.43 (d, J=9.0 Hz, 1H), 7.16-7.14 (m, 2H), 6.86 (d, J=3.5 Hz, 1H), 6.35 (d, J=5.4 Hz, 1H), 4.12 (s, 2H); ESI MS m/z 329 [C16H12N2O2S2+H]+; HPLC 95.6% (AUC), tR=9.59 min.


Example 235
9-{4-[(4-(Aminomethyl)piperidin-1-yl)methyl]-3-fluorophenyl-8-hydroxythieno[2,3-c]quinolin-4(5H)-one



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Following General Procedure F, tert-Butyl {1-[2-Fluoro-4-(8-methoxy-4-oxo-4,5-dihydrothieno[2,3-c]quinolin-9-yl)benzyl]piperidin-4-yl}methylcarbamate (10 mg, 0.020 mmol) was reacted with tribromoborane (1.0 M in methylene chloride, 0.20 mL, 0.20 mmol) to afford the desired product (6.0 mg, 65%) as a light yellow solid: 1H NMR (500 MHz, CD3CN+D2O) δ 7.73 (t, J=7.8 Hz, 1H), 7.63 (d, J=5.4 Hz, 1H), 7.46 (d, J=8.9 Hz, 1H), 7.24 (d, J=8.9 Hz, 1H), 7.21-7.18 (m, 2H), 6.07 (d, J=5.4 Hz, 1H), 4.45 (q, 14.0 Hz, 2H), 3.15-3.11 (m, 2H), 2.94-2.90 (m, 2H), 2.51 (s, 2H), 2.09-2.06 (m, 3H), 2.00-1.96 (m, 4H); ESI MS m/z 438 [C24H24FN3O2S+H]+; HPLC 94.6% (AUC), tR=7.26 min.


Example 225
9-{4-[2-(Dimethylamino)ethyl]phenyl}-6-fluoro-8-hydroxythieno[2,3-c]quinolin-4(5H)-one



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Following General Procedure F, 9-{4-[1-(dimethylamino)ethyl]phenyl}-6-fluoro-8-methoxythieno[2,3-c]quinolin-4(5H)-one (6.0 mg, 0.015 mmol) was reacted with tribromoborane (1.0 M in methylene chloride, 0.10 mL, 0.075 mmol) to afford the desired product (5.2 mg, 90%) as an off-white solid: 1H NMR (500 MHz, CD3OD) δ 7.72 (t, J=9.4 Hz, 2H), 7.63 (d, J=5.4 Hz, 1H), 7.46 (t, J=7.6 Hz, 2H), 7.04 (d, J=12.0 Hz, 1H), 6.02 (d, J=5.4 Hz, 1H), 4.68 (q, J=4.3 Hz, 1H), 2.98 (s, 3H), 2.87 (s, 3H), 1.87 (d, J=7.0 Hz, 3H); ESI MS m/z 383 [C21H19FN2O2S+H]+; HPLC 96.0% (AUC), tR=9.97 min.


Example 217
9-(4-Amino-3-hydroxyphenyl)-8-hydroxythieno[2,3-c]quinolin-4(5H)-one Hydrochloride



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Following General Procedure F, 9-(4-Amino-3-methoxyphenyl)-8-methoxythieno[2,3-c]quinolin-4(5H)-one (20 mg, 0.060 mmol) was reacted with tribromoborane (1.0 M in methylene chloride, 0.20 mL, 0.18 mmol) to afford the desired product (16 mg, 84%) as an off-white solid: 1H NMR (500 MHz, CD3OD) δ 7.62 (d, J=5.4 Hz, 1H), 7.48 (d, J=8.0 Hz, 1H), 7.42 (d, J=8.9 Hz, 1H), 7.18 (d, J=8.9 Hz, 1H), 6.97 (d, J=1.7 Hz, 1H), 6.91 (dd, J=8.0, 1.7 Hz, 1H), 6.21 (d, J=5.4 Hz, 1H); ESI MS m/z 325 [C17H12N2O3S+H]+; HPLC 94.3% (AUC), tR=8.17 min.


Example 93
9-{4-[2-(Dimethylamino)ethyl]phenyl}-8-hydroxythieno[2,3-c]quinolin-4(5H)-one



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Following General Procedure F, 9-{4-[2-(dimethylamino)ethyl]phenyl}-8-methoxythieno[2,3-c]quinolin-4(5H)-one (25 mg, 0.060 mmol) was reacted with tribromoborane (1.0 M in methylene chloride, 0.20 mL, 0.18 mmol) to afford the desired product (20 mg, 89%) as a yellow solid: 1H NMR (500 MHz, CD3CN+D2O) δ 7.55 (d, J=5.4 Hz, 1H), 7.43-7.41 (m, 3H), 7.22-7.18 (m, 3H), 5.99 (d, J=5.4 Hz, 1H), 3.00 (s, 4H), 2.56 (s, 6H); ESI MS m/z 365 [C21H20N2O2S+H]+; HPLC 98.3% (AUC), tR=9.24 min.


Example 341
9-{4-[1-(Dimethylamino)ethyl]phenyl}-6,7-difluoro-8-hydroxythieno[2,3-c]quinolin-4(5Hone Hydrochloride



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Following General Procedure F, 9-{4-[1-(dimethylamino)ethyl]phenyl})-6,7-difluoro-8-methoxythieno[2,3-c]quinolin-4(5H)-one (20 mg, 0.050 mmol) was reacted with tribromoborane (1.0 M in methylene chloride, 0.50 mL, 0.50 mmol) to afford the desired product (15 mg, 72%) as an off-white solid: 1H NMR (500 MHz, CD3CN+D2O) δ 7.68-7.67 (m, 2H), 7.61-7.59 (m, 1H), 7.43-7.41 (m, 2H), 5.86-5.84 (m, 1H), 4.58-4.54 (m, 1H), 2.86 (s, 3H), 2.76 (s, 3H), 1.79-1.77 (m, 3H); ESI MS m/z 401[C21H18F2N2O2S+H]+; HPLC 97.8% (AUC), tR=9.35 min.


Example 256
9-[4-(Aminomethyl)phenyl]-6-fluoro-8-hydroxythieno[2,3-c]quinolin-4(5H)-one Hydrochloride



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Following General Procedure F, tert-butyl


4-(6-fluoro-8-methoxy-4-oxo-4,5-dihydrothieno[2,3-c]quinolin-9-yl)benzylcarbamate (30 mg, 0.075 mmol) was reacted with tribromoborane (1.0 M in methylene chloride, 0.75 mL, 0.75 mmol) to afford the desired product (22 mg, 88%) as an off-white solid: 1H NMR (500 MHz, CD3OD) δ 7.64 (d, J=8.0 Hz, 2H), 7.58 (d, J=5.4 Hz, 1H), 7.39 (d, J=8.0 Hz, 2H), 7.02 (d, J=12.0 Hz, 1H), 6.07 (d, J=5.4 Hz, 1H), 4.28 (s, 2H); ESI MS m/z 341 [C18H13FN2O2S+H]+; HPLC >99% (AUC), tR=8.34 min.


Example 335
(S)-9-{4-[1-(Dimethylamino)ethyl]phenyl}-8-hydroxythieno[2,3-c]quinolin-4(5H)-one Hydrochloride



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Following the procedure outlined for Example 460, (S)-9-[4-(1-aminoethyl)phenyl]-8-hydroxythieno[2,3-c]quinolin-4(5H)-one (100 mg, 0.30 mmol) was reacted with formaldehyde (37% in water, 27 mg, 0.89 mmol) and after purification the resulting material was converted to the hydrochloride salt as outlined in General Procedure D-2 to afford the desired product (43 mg, 40%) as a white solid: 1H NMR (500 MHz, CD3OD) δ 7.69 (q, J=7.8 Hz, 2H), 7.58 (d, J=5.4 Hz, 1H), 7.48-7.42 (m, 3H), 7.18 (d, J=8.9 Hz, 1H), 6.01 (d, J=5.4 Hz, 1H), 4.65 (q, J=6.6 Hz, 1H), 2.97 (s, 3H), 2.87 (s, 3H), 1.86 (d, J=7.0 Hz, 3H); ESI MS m/z 365 [C21H20N2O2S+H]+; HPLC >99% (AUC), tR=9.30 min.


Example 459
(E)-9-[3-(3-Aminopiperidin-1-yl)prop-1-enyl]-8-hydroxythieno[2,3-c]quinolin-4(5H)-one



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Following General Procedure F, (E)-tert-Butyl 1-[3-(8-Methoxy-4-oxo-4,5-dihydrothieno[2,3-c]quinolin-9-yl)allyl]piperidin-3-ylcarbamate (320 mg, 0.88 mmol) was reacted with tribromoborane (1.0 M in methylene chloride, 4.0 mL, 4.0 mmol) to afford the desired product (100 mg, 41%) as a yellow solid: 1H NMR (500 MHz, CD3OD) δ 8.00 (dd, J=19.3, 5.4 Hz, 2H), 7.32 (d, J=8.9 Hz, 1H), 7.24 (d, J=16.0 Hz, 1H), 7.12 (d, J=8.9 Hz, 1H), 6.39-6.25 (m, 1H), 4.25 (d, J=6.8 Hz, 1H), 3.94 (d, J=11.4 Hz, 1H), 3.83 (d, J=11.9 Hz, 1H), 3.76-3.65 (m, 1H), 3.28-3.10 (m, 2H), 2.24 (dd, J=35.1, 13.6 Hz, 2H), 2.06-1.98 (m, 1H), 1.81-1.68 (m, 1H).


Example 460
(E)-9-{3-[3-(Dimethylamino)piperidin-1-yl]prop-1-enyl)}-8-hydroxythieno[2,3-c]quinolin-4(5H)-one



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A solution of (E)-9-[3-(3-aminopiperidin-1-yl)prop-1-enyl]-8-hydroxythieno[2,3-c]quinolin-4(5H)-one (60 mg, 0.15 mmol) and formaldehyde (37% in water, 13 mg, 0.44 mmol) in methanol (1 mL) was stirred at room temperature for 30 min followed by the addition of sodium cyanoborohydride (28 mg, 0.44 mmol). The reaction mixture was stirred at room temperature overnight, concentrated and partitioned between water and ethyl acetate. The layers were separated and the aqueous layer was extracted with methylene chloride. The combined organic layers were washed with brine, dried over sodium sulfate, filtered, and concentrated. The residue was purified by preparatory HPLC (C18 silica, water/acetonitrile w/0.05% TFA gradient) to afford the desired product (30 mg, 53%) as a yellow solid: 1H NMR (500 MHz, CD3OD) δ 7.97 (dd, J=19.4, 5.3 Hz, 2H), 7.30 (d, J=8.9 Hz, 1H), 7.23 (d, J=15.9 Hz, 1H), 7.07 (d, J=8.9 Hz, 1H), 6.33-6.22 (m, 1H), 4.32-4.18 (m, 3H), 3.90-3.77 (m, 2H), 3.47 (t, J=11.6 Hz, 1H), 3.18 (t, J=11.3 Hz, 1H), 3.01 (s, 6H), 2.40-2.23 (m, 2H), 2.10-1.84 (m, 2H).


Example 298
9-{3-[3-(Dimethylamino)piperidin-1-yl]propyl}-8-hydroxythieno[2,3-c]quinolin-4(5H-one Hydrochloride



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To a solution of (E)-9-{3-[3-(dimethylamino)piperidin-1-yl]prop-1-enyl}-8-hydroxythieno[2,3-c]quinolin-4(5H)-one (20 mg, 0.052 mmol) in methanol (10 mL) under nitrogen was added Pd on carbon (10 wt %, 12 mg) and the reaction mixture was placed in a Parr shaker for 18 h under an atmosphere of hydrogen (40 psi). The reaction mixture was filtered over diatomaceous earth and the filtrate was concentrated. The residue was purified by preparatory HPLC (C18 Silica, water/acetonitrile w/0.05% TFA gradient) and the resulting material was converted to the hydrochloride salt as outlined in General Procedure D-2 to afford the desired product (5.6 mg, 40%) as a white solid: 1H NMR (500 MHz, CD3OD) δ 8.08 (d, J=5.4 Hz, 1H), 8.03 (d, J=5.4 Hz, 1H), 7.27 (d, J=8.8 Hz, 1H), 7.11 (d, J=8.8 Hz, 1H), 3.94-3.87 (m, 1H), 3.72-3.61 (m, 2H), 3.45-3.35 (m, 4H), 2.99-2.94 (m, 1H), 2.94 (s, 6H), 2.26-2.14 (m, 4H), 1.90-1.72 (m, 2H), 1.24 (s, 2H), 1.20 (s, 1H); ESI MS m/z 386 [C21H27N3O2S+H]+; HPLC >99% (AUC), tR=6.71 min.


Example 267
9-{4-[(Ethylamino)methyl]phenyl}-8-hydroxythieno[2,3-c]quinolin-4(5H)-one Hydrochloride



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Following General Procedure F, 9-{4-[(ethylamino)methyl]phenyl}-8-methoxythieno[2,3-c]quinolin-4(5H)-one (70 mg, 0.19 mmol) was reacted with tribromoborane (1.0 M in methylene chloride, 1.2 mL, 1.2 mmol) to afford the desired product (42 mg, 63%) as a yellow solid: 1H NMR (500 MHz, CD3OD) δ 7.66 (d, J=8.2 Hz, 2H), 7.55 (d, J=5.4 Hz, 1H), 7.43-7.41 (m, 3H), 7.17 (d, J=8.9 Hz, 1H), 6.08 (d, J=5.4 Hz, 1H), 4.34 (s, 2H), 3.22 (q, J=7.3 Hz, 2H), 1.41 (t, J=7.3 Hz, 3H); ESI MS m/z 351 [C20H18N2O2S+H]+; HPLC >99% (AUC), tR=8.01 min.


Example 229
8-Hydroxy-9-{4-[(isopropylamino)methyl]phenyl}thieno[2,3-c]quinolin-4(5H)-one Hydrochloride



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Following General Procedure F, 9-{4-[(isopropylamino)methyl]phenyl}-8-methoxythieno[2,3-c]quinolin-4(5H)-one was reacted with tribromoborane (1.0 M in methylene chloride, 1.6 mL, 1.6 mmol) to afford the desired product (48 mg, 50%) as a light brown glass: 1H NMR (500 MHz, CD3OD) δ 7.70 (d, J=7.6 Hz, 2H), 7.58 (d, J=9.7 Hz, 1H), 7.44-7.41 (m, 3H), 7.18 (d, J=8.9 Hz, 1H), 6.12 (d, J=5.1 Hz, 1H), 4.37 (s, 2H), 3.59-3.55 (m, 1H), 1.48 (d, J=6.5 Hz, 6H); ESI MS m/z 365 [C21H20N2O2S+H]+; HPLC >97.8% (AUC), tR=7.93 min.


Example 212
N-[4-(8-Hydroxy-4-oxo-4,5-dihydrothieno[2,3-c]quinolin-9-yl)benzyl]methanesulfonamide



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A solution of 9-[4-(aminomethyl)phenyl]-8-hydroxythieno[2,3-c]quinolin-4(5H)-one (50 mg, 0.16 mmol) and methanesulfonyl chloride (43 mg, 0.37 mmol) in methylene chloride (5 mL) was stirred at room temperature for 10 min. N,N-diisopropylethylamine (48 mg, 0.37 mmol) was added and the reaction mixture was stirred for 1.5 h, concentrated under reduced pressure and the residue was purified by preparatory HPLC (C18 silica, water/acetonitrile w/0.05% TFA gradient) to afford the desired product (28 mg, 45%) as a white solid: 1H NMR (500 MHz, DMSO-d6) δ 11.77 (s, 1H), 9.22 (s, 1H), 7.70-7.67 (m, 2H), 7.49 (d, J=8.0 Hz, 2H), 7.36 (d, J=8.9 Hz, 1H), 7.23 (d, J=8.0 Hz, 2H), 7.15 (d, J=8.9 Hz, 1H), 5.89 (d, J=5.4 Hz, 1H), 4.29 (d, J=6.4 Hz, 2H), 2.94 (s, 3H); ESI MS m/z 401 [C19H16N2O4S+H]+; HPLC >99% (AUC), tR=12.12 min.


Example 187
8-Hydroxy-9-{4-[(methylamino)methyl]phenyl}thieno[2,3-c]quinolin-4(5H)-one



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Following General Procedure F, 8-methoxy-9-{4-[(methylamino)methyl]phenyl}thieno[2,3-c]quinolin-4(5H)-one (100 mg, 0.29 mmol) was reacted with tribromoborane (1.0 M in methylene chloride, 1.7 mL, 1.7 mmol) to afford the desired product (28 mg, 30%) as a white solid: 1H NMR (500 MHz, CD3OD) δ 7.65 (d, J=8.1 Hz, 2H), 7.55 (d, J=5.4 Hz, 1H), 7.44-7.41 (m, 3H), 7.17 (d, J=8.9 Hz, 1H), 6.05 (d, J=5.4 Hz, 1H), 4.33 (s, 2H), 2.83 (s, 3H); ESI MS m/z 337 [C19H16N2O2S+H]+; HPLC >99% (AUC), tR=10.02 min.


Example 184
9-{4-[(Diethylamino)methyl]phenyl}-8-hydroxythieno[2,3-c]quinolin-4(5H)-one



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Following General Procedure F, 9-{4-[(diethylamino)methyl]phenyl}-8-methoxythieno[2,3-c]quinolin-4(5H)-one (30 mg, 0.076 mmol) was reacted with tribromoborane (1.0 M in methylene chloride, 0.46 mL, 0.46 mmol) to afford the desired product (12 mg, 42%) as a white solid: 1H NMR (500 MHz, CD3OD) δ 7.69 (d, J=8.1 Hz, 2H), 7.56 (d, J=5.4 Hz, 1H), 7.48-7.42 (m, 3H), 7.18 (d, J=8.9 Hz, 1H), 6.03 (d, J=5.4 Hz, 1H), 4.50 (s, 2H), 3.36-3.31 (m, 4H), 1.43 (t, J=7.3 Hz, 6H); ESI MS m/z 379 [C22H22N2O2S+H]+; HPLC 97.2% (AUC), tR=8.27 min.


Example 165
9-{4-[(Dimethylamino)methyl]phenyl}hydroxythieno[2,3-c]quinolin-4(5H)-one



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Following General Procedure F, 9-{4-[(dimethylamino)methyl]phenyl}-8-methoxythieno[2,3-c]quinolin-4(5H)-one (30 mg, 0.082 mmol) was reacted with tribromoborane (1.0 M in methylene chloride, 0.49 mL, 0.49 mmol) to afford the desired product (11 mg, 40%) as a white solid: 1H NMR (500 MHz, CD3OD) δ 7.54-7.50 (m, 3H), 7.39 (d, J=8.9 Hz, 1H), 7.29 (d, J=8.0 Hz, 2H), 7.18 (d, J=8.9 Hz, 1H), 5.99 (d, J=5.5 Hz, 1H), 3.64 (s, 2H), 2.36 (s, 6H); ESI MS m/z 351 [C20H18N2O2S+H]+; HPLC 98.5% (AUC), tR=7.71 min.


Example 191
9-{4-[1-(Dimethylamino)ethyl]phenyl}-8-hydroxythieno[2,3-c]quinolin-4(5H)-one



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Following the procedure outlined for Example 460, 9-[4-(1-Aminoethyl)phenyl]-8-hydroxythieno[2,3-c]quinolin-4(5H)-one (40 mg, 0.12 mmol) was reacted with formaldehyde (37% in water, 14 mg, 0.50 mmol) and after purification the resulting material was converted to the hydrochloride salt as outlined in General Procedure D-2 to afford the desired product (20 mg, 42%) as a white solid: 1H NMR (500 MHz, CD3OD) δ 7.71-7.67 (m, 2H), 7.58 (d, J=4.4 Hz, 1H), 7.48-7.41 (m, 3H), 7.18 (d, J=8.9 Hz, 1H), 6.01 (d, J=5.4 Hz, 1H), 4.65 (q, J=7.0 Hz, 1H), 2.97 (s, 3H), 2.87 (s, 3H), 1.86 (d, J=7.0 Hz, 3H); ESI MS m/z 365 [C21H20N2O2S+H]+; HPLC >99% (AUC), tR=7.86 min.


Example 192
9-(4-(1-(dimethylamino)ethyl)phenyl)-8-hydroxythieno[2,3-c]quinolin-4(5H)-one Hydrochloride



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Following General Procedure F, 9-{4-[1-(dimethylamino)ethyl]phenyl}-8-methoxythieno[2,3-c]quinolin-4(5H)-one (3.2 g, 7.1 mmol) was reacted with tribromoborane (1.0 M in methylene chloride, 43 mL, 43 mmol) and the resulting material was converted to the hydrochloride salt as outlined in General Procedure D-2 to afford the desired product (1.3 g, 92%) as a white solid: 1H NMR (500 MHz, CD3OD) δ 7.71-7.67 (m, 2H), 7.58 (d, J=4.4 Hz, 1H), 7.48-7.41 (m, 3H), 7.18 (d, J=8.9 Hz, 1H), 6.01 (d, J=5.4 Hz, 1H), 4.65 (q, J=7.0 Hz, 1H), 2.97 (s, 3H), 2.87 (s, 3H), 1.86 (d, J=7.0 Hz, 3H); ESI MS m/z 365 [C21H20N2O2S+H]+; HPLC >99% (AUC), tR=7.86 min.


Example 72
9-[4-(Aminomethyl)phenyl]-8-hydroxythieno[2,3-c]quinolin-4(5H)-one



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Following General Procedure F, tert-Butyl 4-(8-Methoxy-4-oxo-4,5-dihydrothieno[2,3-c]quinolin-9-yl)benzylcarbamate (70 mg, 0.16 mmol) was reacted with tribromoborane (1.0 M in methylene chloride, 0.96 mL, 0.96 mmol) to afford the desired product (37 mg, 60%) as a white solid: 1H NMR (500 MHz, DMSO-d6) δ 11.80 (s, 1H), 9.28 (s, 1H), 8.25 (br s, 2H), 7.68 (d, J=5.4 Hz, 1H), 7.60 (d, J=8.0 Hz, 2H), 7.39 (d, J=8.9 Hz, 1H), 7.33 (d, J=8.1 Hz, 2H), 7.17 (d, J=8.8 Hz, 1H), 5.92 (d, J=5.4 Hz, 1H), 4.18 (m, 2H); ESI MS m/z 323 [C18H14N2O2S+H]+; HPLC 98.3% (AUC), tR=10.74 min.


Example 73
9-[4-(Aminomethyl)phenyl]-8-hydroxythieno[2,3-c]quinolin-4(5H)-one Hydrochloride



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Following General Procedure F, tert-butyl 4-(8-methoxy-4-oxo-4,5-dihydrothieno[2,3-c]quinolin-9-yl)benzylcarbamate (260 mg, 0.60 mmol) was reacted with tribromoborane (1.0 M in methylene chloride, 3.6 mL, 3.6 mmol) and the resulting material was converted to the hydrochloride salt as outlined in General Procedure D-2 to afford the desired product (120 mg, 50%) as a off-white solid: 1H NMR (500 MHz, DMSO-d6) δ 11.80 (s, 1H), 9.28 (s, 1H), 8.25 (br s, 2H), 7.68 (d, J=5.4 Hz, 1H), 7.60 (d, J=8.0 Hz, 2H), 7.39 (d, J=8.9 Hz, 1H), 7.33 (d, J=8.1 Hz, 2H), 7.17 (d, J=8.8 Hz, 1H), 5.92 (d, J=5.4 Hz, 1H), 4.18 (m, 2H); ESI MS m/z 323 [C18H14N2O2S+H]+; HPLC 98.3% (AUC), tR=10.74 min.


Example 233
(S)-9-[4-(1-Aminoethyl)phenyl]-8-hydroxythieno[2,3-c]quinolin-4(5H-one Hydrochloride



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Following General Procedure F, (S)-9-[4-(1-aminoethyl)phenyl]-8-methoxythieno[2,3-c]quinolin-4(5H)-one (100 mg, 0.22 mmol) was reacted with tribromoborane (3.0 mL) to afford the desired product (16 mg, 22%) as a yellow solid: 1H NMR (500 MHz, CD3OD) δ 7.63-7.61 (m, 2H), 7.56-7.55 (m, 1H), 7.43-7.41 (m, 3H), 7.17 (d, J=8.9 Hz, 1H), 6.08 (d, J=5.4 Hz, 1H), 4.61 (q, J=4.7 Hz, 1H), 1.76 (d, J=6.9 Hz, 3H); ESI MS m/z 337 [C19H16N2O2S+H]+; HPLC 98.6% (AUC), tR=7.62 min.


Example 347
(S)—N-{1-[4-(8-Hydroxy-4-oxo-4,5-dihydrothieno[2,3-c]quinolin-9-yl)phenyl]ethyl}methanesulfonamide



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Following the procedure outlined for Example 301, (S)-9-[4-(1-aminoethyl)phenyl]-8-hydroxythieno[2,3-c]quinolin-4(5H)-one (100 mg, 0.30 mmol) was reacted with methanesulfonyl chloride (100 mg, 0.89 mmol) to afford the desired product (70 mg, 56%) as a light brown solid: 1H NMR (500 MHz, CD3OD) δ 5.89-7.55 (m, 2H), 7.52 (d, J=5.4 Hz, 1H), 7.38 (d J=8.9 Hz, 1H), 7.30-7.28 (m, 2H), 7.15 (d, J=8.9 Hz, 1H), 6.00 (d, J=5.4 Hz, 1H), 4.71 (q, J=7.1 Hz, 1H), 2.82 (s, 3H), 1.61 (d, J=7.0 Hz, 3H); ESI MS m/z 415 [C20H18N2O4S2+H]+; HPLC >99% (AUC), tR=12.43 min.


Example 339
9-{4-[1-(Dimethylamino)propyl]phenyl}-8-hydroxythieno[2,3-c]quinolin-4(5H)-one Hydrochloride



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Following the procedure outlined for Example 460, 9-[4-(1-aminopropyl)phenyl]-8-hydroxythieno[2,3-c]quinolin-4(5H)-one (100 mg, 0.29 mmol) was reacted with formaldehyde (26 mg, 0.86 mmol) and the resulting material was converted to the hydrochloride salt as outlined in General Procedure D-2 to afford the desired product (62 mg, 58%) as a white solid: 1H NMR (500 MHz, CD3OD) δ 7.69-7.64 (m, 2H), 7.56 (d, J=5.4 Hz, 1H), 7.51-7.47 (m, 2H), 7.43 (d, J=8.9 Hz, 1H), 7.19 (d, J=8.0 Hz, 1H), 5.95 (d, J=5.4 Hz, 1H), 4.38 (dd, J=11.3, 4.3 Hz, 1H), 2.99 (s, 3H), 2.85 (s, 3H), 2.32-2.25 (m, 2H), 0.98 (t, J=7.3 Hz, 3H); ESI MS m/z 379 [C22H22N2O2S+H]+; HPLC 97.2% (AUC), tR=9.45 min.


Example 338
9-{4-[1-(Diethylamino)propyl]phenyl}-8-hydroxythieno[2,3-c]quinolin-4(5H)-one Hydrochloride



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Following the procedure outlined for Example 460, (9-[4-(1-aminopropyl)phenyl]-8-hydroxythieno[2,3-c]quinolin-4(5H)-one (100 mg, 0.29 mmol) was reacted with formaldehyde (38 mg, 0.86 mmol) and the resulting material was converted to the hydrochloride salt as outlined in General Procedure D-2 to afford the desired product (52 mg, 45%) as a light brown solid: 1H NMR (500 MHz, CD3OD) δ 7.71 (dd, J=7.7, 1.8 Hz, 1H), 7.66 (dd, J=7.9 Hz, 1.9 Hz, 1H), 7.54 (d, J=5.5 Hz, 1H), 7.49-7.45 (m, 2H), 7.42 (d, J=5.5 Hz, 1H), 7.19 (d, J=4.2 Hz, 1H), 5.95 (d, J=5.4 Hz, 1H), 4.48 (dd, J=11.7, 3.8 Hz, 1H), 3.47-3.40 (m, 3H), 3.12-3.08 (m, 1H), 2.35-2.21 (m, 2H), 1.45 (t, J=7.3 Hz, 3H), 1.35 (t, J=7.3 Hz, 3H), 0.95 (t, J=7.3 Hz, 3H); ESI MS m/z 407 [C24H26N2O2S+H]+; HPLC 96.3% (AUC), tR=10.74 min.


Example 336
9-[4-(1-Aminopropyl)phenyl]-8-hydroxythieno[2,3-c]quinolin-4(5H)-one Hydrochloride



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Following General Procedure F, tert-butyl


1-[4-(8-methoxy-4-oxo-4,5-dihydrothieno[2,3-c]quinolin-9-yl)phenyl]propylcarbamate (70 mg, 0.15 mmol) was reacted with tribromoborane (1.0 M in methylene chloride, 0.90 mL, 0.90 mmol) to afford the desired product (35 mg, 52%) as a light yellow solid: 1H NMR (500 MHz, CD3OD) δ 7.63-7.58 (m, 2H), 7.53 (d, J=5.4 Hz, 1H), 7.42-7.39 (m, 3H), 7.17 (d, J=8.9 Hz, 1H), 6.02 (d, J=5.4 Hz, 1H), 4.32 (q, J=5.9 Hz, 1H), 2.17-2.08 (m, 2H), 1.03 (t, J=7.4 Hz, 3H); ESI MS m/z 351 [C20H18N2O2S+H]+; HPLC >99% (AUC), tR=9.39 min.


Example 314
9-{4-[1-(Cyclopentylamino)ethyl]phenyl}-8-hydroxythieno[2,3-c]quinolin-4(5H)-one Hydrochloride



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Following General Procedure F, 9-{4-[1-(cyclopentylamino)ethyl]phenyl}-8-methoxythieno[2,3-c]quinolin-4(5H)-one (200 mg, 0.48 mmol) was reacted with tribromoborane (15 mL) to afford the desired product (25 mg, 13%) as a brown solid: 1H NMR (300 MHz, CD3OD) δ 7.71-7.64 (m, 2H), 7.56 (d, J=5.4 Hz, 1H), 7.48-7.41 (m, 3H), 7.18 (d, J=8.9 Hz, 1H), 6.06 (d, J=5.4 Hz, 1H), 4.57 (q, J=6.8 Hz, 1H), 3.59-3.49 (m, 1H), 2.26-2.08 (m, 2H), 1.87-1.62 (m, 9H); ESI MS m/z 405 [C24H24N2O2S+H]+; HPLC >99% (AUC), tR=8.84 min.


Example 313
8-Hydroxy-9-[4-(1-hydroxyethyl)phenyl]thieno[2,3-c]quinolin-4(5H)-one



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A solution of 9-(4-acetylphenyl)-8-hydroxythieno[2,3-c]quinolin-4(5H)-one (200 mg, 0.59 mmol) in ethanol (4 mL) was cooled to 0° C. and sodium borohydride (45 mg, 1.2 mmol) was added. The reaction mixture was stirred at room temperature for 18 h however starting material was present. The reaction was cooled to 0° C. and lithium aluminum hydride (1.0 M in THF, 1.2 mL, 1.2 mmol) was added and the reaction mixture was stirred at room temperature for 2 h. The reaction was cooled to 0° C., quenched with methanol and concentrated. The residue was purified by preparatory HPLC (C18 silica, water/acetonitrile w/0.05% TFA gradient) to afford the desired product (2.6 mg, 1%) as a light brown solid: 1H NMR (300 MHz, CD3OD) δ 7.59-7.52 (m, 3H), 7.39 (d, J=8.9 Hz, 1H), 7.29-7.25 (m, 2H), 7.16 (d, J=8.9 Hz, 1H), 6.03 (d, J=5.4 Hz, 1H), 4.97 (q, J=6.4 Hz, 1H), 1.56 (d, J=6.5 Hz, 3H); ESI MS m/z 338 [C19H15NO3S+H]+; HPLC 98.6% (AUC), tR=9.78 min.


Example 308
9-{4-[1-(Dimethylamino)-2-methylpropan-2-yl]phenyl}-8-hydroxythieno[2,3-c]quinolin-4(5H)-one Hydrochloride



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Following the procedure outlined for Example 460, 9-[4-(1-amino-2-methylpropan-2-yl)phenyl]-8-hydroxythieno[2,3-c]quinolin-4(5H)-one (30 mg, 0.082 mmol) was reacted with formaldehyde (7.4 mL, 0.25 mmol) and the resulting material was converted to the hydrochloride salt as outlined in General Procedure D-2 to afford the desired product (7 mg, 22%) as a light yellow solid: 1H NMR (500 MHz, CD3OD) δ 7.71 (d, J=8.3 Hz, 2H), 7.56 (d, J=5.4 Hz, 1H), 7.40 (q, J=6.6 Hz, 3H), 7.17 (d, J=8.9 Hz, 1H), 6.07 (d, J=5.4 Hz, 1H), 3.68 (s, 2H), 2.81 (s, 6H), 1.62 (s, 6H); ESI MS m/z 393 [C23H24N2O2S+H]+; HPLC 97.5% (AUC), tR=8.46 min.


Example 301
(R)—N-{1-[4-(8-Hydroxy-4-oxo-4,5-dihydrothieno[2,3-c]quinolin-9-yl)phenyl]ethyl}methanesulfonamide



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A solution of (R)-9-[4-(1-aminoethyl)phenyl]-8-hydroxythieno[2,3-c]quinolin-4(5H)-one (28 mg, 0.83 mmol) and methanesulfonyl chloride (82 μL, 1.0 mmol) in 1:1 methylene chloride/THF (6 mL) and DMF (1.5 mL) was stirred at room temperature for 10 min followed by the addition of N,N-diisopropylethylamine (170 μL, 1.0 mmol). The reaction mixture was stirred for 1.5 h, concentrated and purified by preparatory HPLC (C18 silica, water/acetonitrile w/0.05% TFA gradient) to afford the desired product (8.9 mg, 2%) as a light brown solid: 1H NMR (500 MHz, CD3OD) δ 7.59-7.55 (m, 2H), 7.53 (d, J=5.5 Hz, 1H), 7.39 (d, J=8.9 Hz, 1H), 7.31-7.30 (m, 2H), 7.16 (d, J=8.9 Hz, 1H), 6.02 (d, J=5.4 Hz, 1H), 4.71 (q, J=4.6 Hz, 1H), 2.82 (s, 3H), 1.62 (d, J=7.0 Hz, 3H); ESI MS m/z 415 [C20H18N2O4S2+H]+; HPLC 96.4% (AUC), tR=10.14 min.


Example 296
9-(4-Acetylphenyl)-8-hydroxythieno[2,3-c]quinolin-4(5H)-one



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Following General Procedure F, 9-(4-acetylphenyl)-8-methoxythieno[2,3-c]quinolin-4(5H)-one (450 mg, 1.3 mmol) was reacted with tribromoborane (15 mL) to afford the desired product (320 mg, 74%) as a light brown solid: 1H NMR (500 MHz, DMSO-d6) δ 11.82 (s, 1H), 9.38 (s, 1H), 8.10 (d, J=8.3 Hz, 2H), 7.74 (d, J=5.4 Hz, 1H), 7.44-7.39 (m, 3H), 7.18 (d, J=8.9 Hz, 1H), 5.90 (d, J=5.4 Hz, 1H), 2.68 (s, 3H); ESI MS m/z 336 [C19H13NO3S+H]+; HPLC 98.3% (AUC), tR=10.59 min.


Example 290
3-[4-(8-Hydroxy-4-oxo-4,5-dihydrothieno[2,3-c]quinolin-9-yl)phenyl]propanenitrile



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Following General Procedure F, 3-[4-(8-methoxy-4-oxo-4,5-dihydrothieno[2,3-c]quinolin-9-yl)phenyl]propanenitrile (45 mg, 0.13 mmol) was reacted with tribromoborane (3 mL) to afford the desired product (5.6 mg, 13%) as a white solid: 1H NMR (500 MHz, CD3OD) δ 7.53 (d, J=5.4 Hz, 1H), 7.48 (d, J=7.9 Hz, 2H), 7.39 (d, J=8.9 Hz, 1H), 7.28 (d, J=7.9 Hz, 2H), 7.16 (d, J=8.9 Hz, 1H), 5.96 (d, J=5.4 Hz, 1H), 3.10 (t, J=3.8 Hz, 2H), 2.89 (t, J=7.1 Hz, 2H); ESI MS m/z 347 [C20H14N2O2S+H]+; HPLC >99% (AUC), tR=10.99 min.


Example 356
9-{4-[1-(Diethylamino)ethyl]-3-fluorophenyl}-8-hydroxythieno[2,3-c]quinolin-4(5H)-one Hydrochloride



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A solution of 9-(4-(1-aminoethyl)-3-fluorophenyl)-8-hydroxythieno[2,3-c]quinolin-4(5H)-one (40 mg, 0.11 mmol) and acetaldehyde (25 mg, 0.45 mmol) in methanol (2 mL) was stirred at room temperature for 30 min followed by the addition of sodium cyanoborohydride (28 mg, 0.452 mmol) and the reaction mixture was stirred at room temperature for 18 h. The reaction mixture was concentrated, partitioned between water and ethyl acetate and the layers were separated. The aqueous layer was extracted with methylene chloride and the combined organic layers were washed with brine, dried over anhydrous sodium sulfate, filtered, and concentrated. The residue was purified by preparatory HPLC (C18 silica, water/acetonitrile w/0.05% TFA gradient) and the resulting material was converted to the hydrochloride salt as outlined in General Procedure D-2 to afford the desired product (30 mg, 65%) as a yellow solid: 1H NMR (500 MHz, CD3OD) δ 7.84-7.82 (m, 1H), 7.67-7.65 (m, 1H), 7.44 (dd, J=9.1, 1.5 Hz, 1H), 7.34-7.28 (m, 2H), 7.19 (dd, J=8.9, 2.5 Hz, 1H), 6.14 (t, J=5.1 Hz, 1H), 5.16-5.06 (m, 1H), 3.46-3.35 (m, 3H), 3.30-3.15 (m, 1H), 2.79 (s, 1H), 1.88 (t, J=6.2 Hz, 3H), 1.48-1.37 (m, 6H); ESI MS m/z 411 [C23H23FN2O2S+H]+; HPLC >99% (AUC), tR=8.57 min.


Example 359
9-[4-(1-Aminoethyl)-3-fluorophenyl]-8-hydroxythieno[2,3-c]quinolin-4(5H)-one Hydrochloride



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Following General Procedure F, tert-butyl 1-[2-fluoro-4-(8-methoxy-4-oxo-4,5-dihydrothieno[2,3-c]quinolin-9-yl)phenyl]ethylcarbamate (400 mg, 0.856 mmol) was reacted with tribromoborane (4 mL) to afford the desired product (99 mg, 33%) as a white solid: 1H NMR (300 MHz, CD3OD) δ 7.70-7.60 (m, 2H), 7.43 (d, J=8.9 Hz, 1H), 7.27-7.15 (m, 3H), 6.18 (q, J=3.0 Hz, 1H), 1.78 (t, J=6.5 Hz, 3H); ESI MS m/z 355 [C19H15FN2O2S+H]+; HPLC >99% (AUC), tR=7.84 min.


Example 353
8-Hydroxy-9-(1,2,3,4-tetrahydroisoquinolin-7-yl)thieno[2,3-c]quinolin-4(5H)-one Hydrochloride



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Following General Procedure F, 8-methoxy-9-(1,2,3,4-tetrahydroisoquinolin-7-yl)thieno[2,3-c]quinolin-4(5H)-one (40 mL, 0.11 mmol) was reacted with tribromoborane (2 mL) to afford the desired product (26 mg, 68%) as an off-white solid: 1H NMR (500 MHz, CD3OD) δ 7.56 (d, J=5.5 Hz, 1H), 7.45 (d, J=8.0 Hz, 1H), 7.40 (d, J=8.9 Hz, 1H), 7.27-7.25 (m, 1H), 7.19 (br s, 1H), 7.16 (d, J=8.9 Hz, 1H), 6.17 (d, J=5.4 Hz, 1H), 4.12 (s, 2H), 3.67-3.57 (m, 2H), 3.29-3.22 (m, 2H); ESI MS m/z 349 [C20H16N2O2S+H]+; HPLC >99% (AUC), tR=7.82 min.


Example 349
9-{4-[1-(Dimethylamino)ethyl]-3-fluorophenyl}-8-hydroxythieno[2,3-c]quinolin-4(5H)-one Hydrochloride



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Following the procedure outlined for Example 460, 9-[4-(1-aminoethyl)-3-fluorophenyl]-8-hydroxythieno[2,3-c]quinolin-4(5H)-one (40 mg, 0.11 mmol) was reacted with formaldehyde (14 mg, 0.45 mmol) to afford the desired product (23 mg, 53%) as a yellow solid: 1H NMR (500 MHz, CD3OD) δ 7.81-7.73 (m, 1H), 7.66 (q, J=4.3 Hz, 1H), 7.44 (dd, J=8.9, 2.3 Hz, 1H), 7.34-7.29 (m, 2H), 7.20-7.18 (m, 1H), 6.14 (t, J=6.0 Hz, 1H), 5.03-4.92 (m, 1H), 3.03-2.86 (m, 6H), 2.78 (br s, 1H), 1.88 (dd, J=7.0, 2.4 Hz, 3H); ESI MS m/z 383 [C21H19FN2O2S+H]+; HPLC >99% (AUC), tR=8.04 min.


Example 361
1-[4-(8-Hydroxy-4-oxo-4,5-dihydrothieno[2,3-c]quinolin-9-yl)phenyl]cyclopropanecarbonitrile



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Following General Procedure F, 1-[4-(8-methoxy-4-oxo-4,5-dihydrothieno[2,3-c]quinolin-9-yl)phenyl]cyclopropanecarbonitrile (340 mg, 0.91 mmol) was reacted with tribromoborane (1.3 mL) to afford the desired product (90 mg, 28%) as a light brown solid: ESI MS m/z 359 [C21H14N2O2S+H]+.


Example 348
9-{4-[1-(Aminomethyl)cyclopropyl]phenyl}-8-hydroxythieno[2,3-c]quinolin-4(5H)-one Hydrochloride



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Following the procedure outlined for Example 265, 1-[4-(8-hydroxy-4-oxo-4,5-dihydrothieno[2,3-c]quinolin-9-yl)phenyl]cyclopropanecarbonitrile (80 mg, 0.11 mmol) was reacted with borane (3 mL) and the resulting material was converted to the hydrochloride salt as outlined in General Procedure D-2 to afford the desired product (20 mg, 28%) as a brown solid: 1H NMR (500 MHz, CD3OD) δ 7.62 (d, J=8.1 Hz, 2H), 7.58 (d, J=5.4 Hz, 1H), 7.41 (d, J=8.9 Hz, 1H), 7.34 (d, J=8.0 Hz, 2H), 7.18 (d, J=8.9 Hz, 1H), 6.17 (d, J=5.4 Hz, 1H), 3.25 (s, 2H), 1.21-1.12 (m, 4H); ESI MS m/z 363 [C21H18N2O2S+H]+; HPLC 97.3% (AUC), tR=8.38 min.


Example 345
9-(2-Amino-2,3-dihydro-1H-inden-5-yl)-8-hydroxythieno[2,3-c]quinolin-4(5H)-one Hydrochloride



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Following General Procedure F, tert-butyl 5-(8-methoxy-4-oxo-4,5-dihydrothieno[2,3-c]quinolin-9-yl)-2,3-dihydro-1H-inden-2-ylcarbamate (210 mg, 0.59 mmol) was reacted tribromoborane (10 mL) to afford the desired product (55 mg, 27%) as a yellow solid:


Major Isomer: 1H NMR (500 MHz, CD3OD) δ 7.56 (d, J=2.4 Hz, 1H), 7.49 (d, J=7.7 Hz, 1H), 7.39 (d, J=1.3 Hz, 1H), 7.26 (s, 1H), 7.19-7.15 (m, 2H), 6.14 (d, J=5.4 Hz, 1H), 4.24-4.20 (m, 1H), 3.62-3.49 (m, 2H), 3.22-3.07 (m, 2H); ESI MS m/z 349 [C20H16N2O2S+H]+; HPLC 60.4% (AUC), tR=7.89 min;


Minor Isomer: 1H NMR (500 MHz, CD3OD) δ 7.55 (d, J=2.4 Hz, 1H), 7.46 (d, J=7.7 Hz, 1H), 7.41 (d, J=1.3 Hz, 1H), 7.24 (s, 1H), 7.19-7.15 (m, 2H), 6.26 (d, J=5.4 Hz, 1H), 4.24-4.20 (m, 1H), 3.62-3.49 (m, 2H), 3.22-3.07 (m, 2H); ESI MS m/z 349 [C20H6N2O2S+H]+; HPLC 39.5% (AUC), tR=7.65 min.


Example 327
9-{4-[2-(Dimethylamino)ethyl]-3-fluorophenyl}-8-hydroxythieno[2,3-c]quinolin-4(5H)-one Hydrochloride



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Following General Procedure F, 9-[4-(2-aminoethyl)-3-fluorophenyl]-8-hydroxythieno[2,3-c]quinolin-4(5H)-one (25 mg, 0.063 mmol) was reacted with tribromoborane (3 mL) to afford the desired product (3.5 mg, 13%) as a brown solid: 1H NMR (500 MHz, CD3OD) δ 7.62 (d, J=5.4 Hz, 1H), 7.55 (t, J=7.9 Hz, 1H), 7.42 (d, J=8.9 Hz, 1H), 7.18-7.11 (m, 3H), 6.15 (d, J=5.4 Hz, 1H), 3.52 (t, J=8.2 Hz, 2H), 3.26-3.19 (m, 1H), 3.04 (s, 6H); ESI MS m/z 383 [C21H19FN2O2S+H]+; HPLC 96.2% (AUC), tR=8.06 min.


Example 278
9-{3-Fluoro-4-[(3-hydroxypyrrolidin-1-yl)methyl]phenyl}-8-hydroxythieno[2,3-c]quinolin-4(5H)-one Hydrochloride



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Following General Procedure F, 9-{3-fluoro-4-[(3-hydroxypyrrolidin-1-yl)methyl]phenyl}-8-methoxythieno[2,3-c]quinolin-4(5H)-one (90 mg, 0.21 mmol) was reacted with tribromoborane (2 mL) to afford the desired product (32 mg, 34%) as a light yellow solid: 1H NMR (500 MHz, CD3OD) δ 7.78-7.75 (m, 1H), 7.65 (d, J=5.3 Hz, 1H), 7.44 (d, J=8.9 Hz, 1H), 7.30-7.27 (m, 2H), 7.19 (d, J=8.9 Hz, 1H), 6.15-6.13 (m, 1H), 4.76-4.57 (m, 3H), 3.86-3.72 (m, 1H), 3.62-3.53 (m, 1H), 3.49-3.40 (m, 1H), 2.78 (br s, 1H), 2.54-2.46 (m, 1H), 2.22-2.20 (m, 1H), 2.15-2.05 (m, 1H); ESI MS m/z 411 [C22H19FN2O3S+H]+; HPLC >99% (AUC), tR=7.58 min.


Example 277
9-[4-(1-Amino-2-methylpropan-2-yl)phenyl]-8-hydroxythieno[2,3-c]quinolin-4(5H)-one Hydrochloride



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Following General Procedure F, 9-[4-(1-amino-2-methylpropan-2-yl)phenyl]-8-methoxythieno[2,3-c]quinolin-4(5H)-one (100 mg, 0.27 mmol) was reacted with tribromoborane (3 mL) to afford the desired product (25 mg, 22%) as an off-white solid: 1H NMR (500 MHz, CD3OD) δ 7.66 (d, J=8.4 Hz, 2H), 7.59 (d, J=5.4 Hz, 1H), 7.42 (d, J=8.9 Hz, 1H), 7.37 (d, J=8.3 Hz, 2H), 7.19 (d, J=8.9 Hz, 1H), 6.16 (d, J=5.4 Hz, 1H), 3.28 (s, 2H), 1.59 (s, 6H); ESI MS m/z 365 [C21H20N2O2S+H]+; HPLC 96.9% (AUC), tR=9.47 min.


Example 276
9-[4-(2-Aminoethyl)-3-fluorophenyl]-8-hydroxythieno[2,3-c]quinolin-4(5Hone Hydrochloride



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Following General Procedure F, 9-[4-(2-aminoethyl)-3-fluorophenyl]-8-methoxythieno[2,3-c]quinolin-4(5H)-one (260 mg, 0.71 mmol) was reacted with tribromoborane (6 mL) to afford the desired product (12 mg, 12%) as a light yellow solid: 1H NMR (500 MHz, CD3OD) δ 7.63 (d, J=5.4 Hz, 1H), 7.52-7.49 (m, 1H), 7.42 (d, J=8.9 Hz, 1H), 7.17 (d, J=8.9 Hz, 1H), 7.15-7.12 (m, 2H), 6.20 (d, J=5.4 Hz, 1H), 3.30-3.23 (m, 2H), 3.12-3.06 (m, 2H), 2.79 (br s, 3H); ESI MS m/z 355 [C19H15FN2O2S+H]+; HPLC 94.9% (AUC), tR=7.80 min.


Example 275
(R)-9-[4-(1-Aminoethyl)phenyl]-8-hydroxythieno[2,3-c]quinolin-4(5H)-one Hydrochloride



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Following General Procedure F, (R)-tert-butyl 1-[4-(8-methoxy-4-oxo-4,5-dihydrothieno[2,3-c]quinolin-9-yl)phenyl]ethylcarbamate (350 mg, 0.78 mmol) was reacted with tribromoborane (15 mL) to afford the desired product (120 mg, 42%) as an off-white solid: 1H NMR (500 MHz, CD3OD) δ 7.65-7.62 (m, 2H), 7.55 (d, J=5.4 Hz, 1H), 7.42-7.41 (m, 3H), 7.17 (d, J=8.9 Hz, 1H), 6.08 (d, J=5.4 Hz, 1H), 4.61 (q, J=4.5 Hz, 1H), 2.78 (br s, 3H), 1.76 (d, J=6.9 Hz, 3H); ESI MS m/z 337[C19H16N2O2S+H]+; HPLC >99% (AUC), tR=7.49 min.


Example 273
9-[4-(3-Aminopropyl)phenyl]-8-hydroxythieno[2,3-c]quinolin-4(5H)-one Hydrochloride



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Following General Procedure F, 9-[4-(3-aminopropyl)phenyl]-8-methoxythieno[2,3-c]quinolin-4(5H)-one (140 mg, 0.39 mmol) was reacted with tribromoborane (6 mL) to afford the desired product (18 mg, 12%) as a light yellow solid: 1H NMR (500 MHz, CD3OD) δ 7.53 (d, J=5.5 Hz, 1H), 7.43 (d, J=8.0 Hz, 2H), 7.39 (d, J=8.9 Hz, 1H), 7.26 (d, J=8.1 Hz, 2H), 7.16 (d, J=8.9 Hz, 1H), 6.02 (d, J=5.5 Hz, 1H), 3.04 (t, J=7.7 Hz, 2H), 2.88 (t, J=7.7 Hz, 2H), 2.11-2.08 (m, 2H); ESI MS m/z 351 [C20H18N2O2S+H]+; HPLC 96.2%, tR=8.91 min.


Example 65
4-(8-Hydroxy-4-oxo-4,5-dihydrothieno[2,3-c]quinolin-9-yl)benzenesulfonamide



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Following General Procedure F, N-tert-butyl-4-(8-methoxy-4-oxo-4,5-dihydrothieno[2,3-c]quinolin-9-yl)benzenesulfonamide (4.3 g, 9.9 mmol) was reacted with tribromoborane (1.0 M in methylene chloride, 48 mL, 48 mmol) to afford the desired product (3.4 g, 94%) as a light red solid: 1H NMR (300 MHz, DMSO-d6) δ 11.83 (s, 1H), 9.12 (s, 1H), 7.96-7.95 (m, 2H), 7.76 (d, J=5.4 Hz, 1H), 7.48-7.47 (m, 4H), 7.41 (d, J=8.9 Hz, 1H), 7.18 (d, J=8.9 Hz, 1H), 5.91 (d, J=5.4 Hz, 1H); ESI MS m/z 373 [C17H12N2O4S2+H]+; HPLC 98.1% (AUC), tR=10.29 min.


Example 61
8-Hydroxy-9-(1H-indazol-6-yl)thieno[2,3-c]quinolin-4(5H)-one



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Following General Procedure F, 9-(1H-indazol-6-yl)-8-methoxythieno[2,3-c]quinolin-4(5H)-one (35 mg, 0.10 mmol) was reacted with tribromoborane (1.5 mL, 0.15 mmol) to afford the desired product (3.6 mg, 11%) as a light brown solid: 1H NMR (500 MHz, CD3OD) δ 8.17 (s, 1H), 7.75-7.73 (m, 2H), 7.48 (d, J=5.5 Hz, 1H), 7.42 (d, J=8.9 Hz, 1H), 7.34 (d, J=9.2 Hz, 1H), 7.19 (d, J=8.9 Hz, 1H), 5.91 (d, J=5.5 Hz, 1H); ESI MS m/z 334 [C18H11N3O2S+H]+; HPLC 96.3% (AUC), tR=9.20 min.


Example 193
N-{1-[4-(8-Hydroxy-4-oxo-4,5-dihydrothieno[2,3-c]quinolin-9-yl)phenyl]ethyl}methanesulfonamide



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A solution of 9-[4-(1-aminoethyl)phenyl]-8-hydroxythieno[2,3-c]quinolin-4(5H)-one (30 mg, 0.089 mmol) and methanesulfonyl chloride (9.0 μL, 0.11 mmol) in 2:1 methylene chloride/THF (3 mL) was stirred at room temperature for 10 min followed by the addition of N,N-diisopropylethylamine (19 μL, 0.11 mmol). The reaction mixture was stirred for 1.5 h, concentrated and purified by preparatory HPLC (C18 silica, water/acetonitrile w/0.05% TFA gradient) to afford the desired product (7.2 mg, 20%) as an amorphous brown solid: 1H NMR (500 MHz, CD3OD) δ 7.57-7.56 (m, 2H), 7.53 (d, J=5.4 Hz, 1H), 7.39 (d, J=8.9 Hz, 1H), 7.32-7.30 (m, 2H), 7.16 (d, J=8.9 Hz, 1H), 6.02 (d, J=5.4 Hz, 1H), 4.71 (q, J=4.6 Hz, 1H), 2.82 (s, 3H), 1.62 (d, J=7.0 Hz, 3H); ESI MS m/z 415 [C20H18N2O4S2+H]+; HPLC >99%, tR=10.18 min.


Example 175
9-[4-(2-Aminoethyl)phenyl]-8-hydroxythieno[2,3-c]quinolin-4(5H)-one



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Following General Procedure F, 9-[4-(2-aminoethyl)phenyl]-8-methoxythieno[2,3-c]quinolin-4(5H)-one (800 mg, 1.8 mmol) was reacted with tribromoborane (10 mL) to afford the desired product (520 mg, 88%) as an off-white solid: 1H NMR (500 MHz, DMSO-d6) δ 11.78 (s, 1H), 9.20 (s, 1H), 7.88 (br s, 2H), 7.69 (d, J=5.4 Hz, 1H), 7.41-7.36 (m, 3H), 7.22 (d, J=8.1 Hz, 2H), 7.15 (d, J=8.9 Hz, 1H), 5.88 (d, J=5.4 Hz, 1H), 3.21-3.14 (m, 2H), 3.01-2.98 (m, 2H); ESI MS m/z 337 [C19H16N2O2S+H]+; HPLC >99% (AUC), tR=7.72 min.


Example 176
9-[4-(2-Aminoethyl)phenyl]-8-hydroxythieno[2,3-c]quinolin-4(5H)-one Hydrochloride



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Following General Procedure F, 9-[4-(2-aminoethyl)phenyl]-8-methoxythieno[2,3-c]quinolin-4(5H)-one (800 mg, 1.8 mmol) was reacted with tribromoborane (10 mL) and the resulting material was converted to the hydrochloride salt as outlined in General Procedure D-2 to afford the desired product (520 mg, 88%) as an off-white solid: 1H NMR (500 MHz, DMSO-d6) δ 11.78 (s, 1H), 9.20 (s, 1H), 7.88 (br s, 2H), 7.69 (d, J=5.4 Hz, 1H), 7.41-7.36 (m, 3H), 7.22 (d, J=8.1 Hz, 2H), 7.15 (d, J=8.9 Hz, 1H), 5.88 (d, J=5.4 Hz, 1H), 3.21-3.14 (m, 2H), 3.01-2.98 (m, 2H); ESI MS m/z 337 [C19H16N2O2S+H]+; HPLC >99% (AUC), tR=7.72 min.


Example 112
8-Hydroxy-9-{4-[4-(methylsulfonyl)piperazin-1-yl]phenyl}thieno[2,3-c]quinolin-4(5H)-one



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Following General Procedure F, 8-methoxy-9-{4-[4-(methylsulfonyl)piperazin-1-yl]phenyl}thieno[2,3-c]quinolin-4(5H)-one (32 mg, 0.068 mmol) was reacted with tribromoborane (1.0 mL) to afford the desired product (5.2 mg, 17%) as an off-white solid: 1H NMR (500 MHz, CD3OD) δ 7.58 (d, J=5.4 Hz, 1H), 7.37 (d, J=8.9 Hz, 1H), 7.20 (s, 4H), 7.15 (d, J=8.9 Hz, 1H), 6.16 (d, J=5.4 Hz, 1H), 3.44-3.43 (m, 8H), 2.92 (s, 3H); ESI MS m/z 456[C22H21N3O4S2+H]+; HPLC >99%, tR=10.47 min.


Example 95
9-[4-(Aminomethyl)phenyl]-8-hydroxy-2-methylthieno[2,3-c]quinolin-4(5H)-one



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Following General Procedure F, tert-butyl 4-(8-methoxy-2-methyl-4-oxo-4,5-dihydrothieno[2,3-c]quinolin-9-yl)benzylcarbamate (80 mg, 0.17 mmol) was reacted with tribromoborane (2.0 mL) to afford the desired product (20 mg, 37%) as an off-white solid: 1H NMR (500 MHz, CD3OD) δ 7.63 (d, J=8.9 Hz, 2H), 7.40-7.37 (m, 3H), 7.15 (d, J=8.1 Hz, 1H), 5.76 (s, 1H), 4.28 (s, 2H), 2.33 (s, 3H); ESI MS m/z 337 [C19H16N2O2S+H]+; HPLC >99%, tR=5.91 min.


Example 84
8-Hydroxy-9-(1,2,3,6-tetrahydropyridin-4-yl)thieno[2,3-c]quinolin-4(5H)-one



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Following General Procedure B, 9-bromo-8-(tert-butyldimethylsilyloxy)thieno[2,3-c]quinolin-4(5H)-one (80 mg, 0.20 mmol) was reacted with tert-butyl 4-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)cyclohex-3-enylcarbamate (90 mg, 0.29 mmol) to afford the desired product (140 mg, 23%) as an off-white solid: 1H NMR (500 MHz, CD3OD) δ 8.01-7.98 (m, 2H), 7.35 (d, J=8.9 Hz, 1H), 7.12 (d, J=8.9 Hz, 1H), 5.80 (s, 1H), 4.01-3.91 (m, 2H), 3.63-3.60 (m, 2H), 2.88-2.84 (m, 1H), 2.57-2.53 (m, 1H); ESI MS m/z 299 [C16H14N2O2S+H]+; HPLC >99% (AUC), tR=6.70 min.


Example 77
N-[4-(8-Hydroxy-4-oxo-4,5-dihydrothieno[2,3-c]quinolin-9-yl)phenyl]methanesulfonamide



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Following General Procedure F, N-[4-(8-methoxy-4-oxo-4,5-dihydrothieno[2,3-c]quinolin-9-yl)phenyl]methanesulfonamide (40 mg, 0.10 mmol) was reacted with tribromoborane (3.0 mL) to afford the desired product (3.8 mg, 10%) as an off-white solid: 1H NMR (500 MHz, CD3OD) δ 7.61 (d, J=5.4 Hz, 1H), 7.44-7.43 (m, 2H), 7.39 (d, J=5.4 Hz, 1H), 7.29-7.27 (m, 2H), 7.16 (d, J=8.4 Hz, 1H), 6.12 (d, J=5.0 Hz, 1H), 3.09 (s, 3); ESI MS m/z 387 [C18H14N2O4S2+H]+; HPLC >99%, tR=9.69 min.


Example 196
9-{4-[1-(Diethylamino)ethyl]phenyl}-8-hydroxythieno[2,3-c]quinolin-4(5H)-one Hydrochloride



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Following the procedure outlined for Example 460, 9-[4-(1-aminoethyl)phenyl]-8-hydroxythieno[2,3-c]quinolin-4(5H)-one (30 mg, 0.081 mmol) was reacted with formaldehyde (37% in water, 15 mg, 0.26 mmol) and the resulting material was converted to the hydrochloride salt as outlined in General Procedure D-2 to afford the desired product (7.2 mg, 21%) as a light brown solid: 1H NMR (500 MHz, CD3OD) δ 7.73 (q, J=6.9 Hz, 2H), 7.58 (d, J=5.4 Hz, 1H), 7.48-7.45 (m, 2H), 7.43 (d, J=8.9 Hz, 1H), 7.19 (d, J=8.9 Hz, 1H), 6.02 (d, J=5.4 Hz, 1H), 4.78 (q, J=4.7 Hz, 1H), 3.51-3.34 (m, 3H), 3.19-3.12 (m, 1H), 1.86 (d, J=6.9 Hz, 3H), 1.43 (t, J=7.3 Hz, 3H), 1.37 (t, J=7.3 Hz, 3H); ESI MS m/z 393 [C23H24N2O2S+H]+; HPLC >99% (AUC), tR=8.29 min.


Example 195
9-[4-(1-Aminoethyl)phenyl]-8-hydroxythieno[2,3-c]quinolin-4(5H)-one Hydrochloride



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Following General Procedure F, tert-butyl 1-[4-(8-methoxy-4-oxo-4,5-dihydrothieno[2,3-c]quinolin-9-yl)phenyl]ethylcarbamate (320 mg, 0.71 mmol) was reacted with tribromoborane (10 mL) to afford the desired product (160 mg, 59%) as a light brown solid: 1H NMR (500 MHz, CD3OD) δ 7.64-7.63 (m, 2H), 7.55 (d, J=5.4 Hz, 1H), 7.43-7.40 (m, 3H), 7.17 (d, J=8.9 Hz, 1H), 6.08 (d, J=5.4 Hz, 1H), 4.61 (q, J=6.9 Hz, 1H), 1.76 (d, J=6.9 Hz, 3H); ESI MS m/z 337 [C19H16N2O2S+H]+; HPLC 98.1% (AUC), tR=7.63 min.


Example 194
8-Hydroxy-9-{4-[1-(pyrrolidin-1-yl)ethyl]phenyl}thieno[2,3-c]quinolin-4(5H)-one Hydrochloride



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Following General Procedure F, 8-methoxy-9-{4-[1-(pyrrolidin-1-yl)ethyl]phenyl}thieno[2,3-c]quinolin-4(5H)-one (70 mg, 0.17 mmol) was reacted with tribromoborane (2.0 mL) to afford the desired product (43 mg, 58%) as an off-white solid: 1H NMR (500 MHz, CD3OD) δ 7.70-7.66 (m, 2H), 7.59 (d, J=5.4 Hz, 1H), 7.48-7.44 (m, 2H), 7.42 (d, J=8.9 Hz, 1H), 7.18 (d, J=8.9 Hz, 1H), 6.01 (d, J=5.4 Hz, 1H), 4.53 (q, J=6.8 Hz, 1H), 3.45 (br s, 1H), 3.20-3.10 (m, 1H), 2.20-2.00 (m, 4H), 1.87 (d, J=6.9 Hz, 3H); ESI MS m/z 391 [C23H22N2O2S+H]+; HPLC >99%, tR=8.21 min.


Example 272
(R)-9-{4-[1-(Dimethylamino)ethyl]phenyl}-8-hydroxythieno[2,3-c]quinolin-4(5H)-one Hydrochloride



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Following the procedure outlined for Example 460, (R)-9-[4-(1-aminoethyl)phenyl]-8-hydroxythieno[2,3-c]quinolin-4(5H)-one (50 mg, 0.15 mmol) was reacted with formaldehyde (14 mL, 0.45 mmol) and the resulting material was converted to the hydrochloride salt as outlined in General Procedure D-2 to afford the desired product (12 mg, 20%) as an off-white solid: 1H NMR (500 MHz, CD3OD) δ 7.71 (q, J=2.6 Hz, 2H), 7.59 (d, J=5.4 Hz, 1H), 7.48 (t, J=7.5 Hz, 2H), 7.43 (d, J=8.9 Hz, 1H), 7.19 (d, J=8.9 Hz, 1H), 6.02 (d, J=5.4 Hz, 1H), 4.66 (q, J=7.1 Hz, 1H), 2.97 (s, 3H), 2.87 (s, 3H), 1.86 (d, J=7.0 Hz, 3H); ESI MS m/z 365 [C21H20N2O2S+H]+; HPLC 97.1% (AUC), tR=8.57 min.


Example 262
8-Hydroxy-9-{4-[1-(piperidin-1-yl)ethyl]phenyl}thieno[2,3-c]quinolin-4(5H)-one Hydrochloride



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Following General Procedure F, 8-methoxy-9-{4-[1-(piperidin-1-yl)ethyl]phenyl}thieno[2,3-c]quinolin-4(5H)-one (40 mg, 0.096 mmol) was reacted with tribromoborane (1.0 mL) to afford the desired product (4.9 mg, 13%) as a yellow solid: 1H NMR (500 MHz, CD3OD) δ 7.73 (d, J=8.4 Hz, 1H), 7.68 (d, J=7.8 Hz, 1H), 7.58 (d, J=5.5 Hz, 1H), 7.48-7.42 (m, 3H), 7.19 (d, J=8.9 Hz, 1H), 6.01 (d, J=5.4 Hz, 1H), 4.60 (q, J=4.5 Hz, 1H), 3.79 (d, J=12.0 Hz, 1H), 3.50 (d, J=11.7 Hz, 1H), 3.02 (t, J=11.3 Hz, 1H), 2.89 (t, J=6.0 Hz, 1H), 2.09-1.72 (m, 8H), 1.55-1.45 (m, 1H); ESI MS m/z 405 [C24H24N2O2S+H]+; HPLC 95.0% (AUC), tR=7.83 min.


Example 261
2-[2-Fluoro-4-(8-hydroxy-4-oxo-4,5-dihydrothieno[2,3-c]quinolin-9-yl)phenyl]acetonitrile



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Following General Procedure F, 2-[2-fluoro-4-(8-hydroxy-4-oxo-4,5-dihydrothieno[2,3-c]quinolin-9-yl)phenyl]acetonitrile (42 mg, 1.2 mmol) was reacted with tribromoborane (12 mL, 12 mmol) to afford the desired product (22 mg, 55%) as a light brown solid: 1H NMR (500 MHz, CD3OD) δ 7.65 (m, 2H), 7.42 (d, J=8.9 Hz, 1H), 7.19-7.14 (m, 3H), 6.16 (d, J=5.5 Hz, 1H), 4.07 (s, 2H); ESI MS m/z 351 [C19H11FN2O2S+H]+; HPLC 97.1% (AUC), tR=13.67 min.


Example 81
2-[4-(8-Hydroxy-4-oxo-4,5-dihydrothieno[2,3-c]quinolin-9-yl)phenyl]acetonitrile



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Following General Procedure B, 9-bromo-8-(tert-butyldimethylsilyloxy)thieno[2,3-c]quinolin-4(5H)-one (50 mg, 0.12 mmol) was reacted with 4-(cyanomethyl)phenylboronic acid (26 mg, 0.18 mmol) to afford the TBS protected intermediate which was treated with aqueous lithium hydroxide to afford the desired product (20 mg, 50%) as an off-white solid: 1H NMR (500 MHz, DMSO-d6) δ 9.28 (s, 1H), 7.73 (d, J=5.4 Hz, 1H), 7.50 (d, J=8.1 Hz, 2H), 7.38 (d, J=8.9 Hz, 1H), 7.29 (d, J=8.1 Hz, 2H), 7.18 (m, 1H), 5.90 (d, J=5.4 Hz, 1H), 4.19 (s, 2H); ESI MS m/z 333 [C19H12N2O2S+H]+; HPLC 96.2% (AUC), tR=12.07 min.


Example 346
9-{4-[1-(Dimethylamino)ethyl]phenyl}thieno[2,3-c]quinolin-4(5H)-one



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To a solution of 9-{4-[1-(dimethylamino)ethyl]phenyl}-8-hydroxythieno[2,3-c]quinolin-4(5H)-one (350 mg, 1.0 mmol) in anhydrous THF (20 mL) at 0° C. was added sodium hydride (60 wt %, 160 mg, 5.0 mmol) and the reaction mixture was heated to 60° C. for 1 h. The reaction mixture was cooled to 0° C. and trifluoro-N-phenyl-N-[(trifluoromethyl)sulfonyl]methanesulfonamide (450 mg, 1.1 mmol) was added and the reaction mixture was warmed to room temperature and stirred for 1 h. The reaction mixture was quenched with satd. aq. ammonium chloride and the layers were separated. The aqueous layer was extracted with 3:1 chloroform/isopropanol and the combined organic layers were dried over anhydrous sodium sulfate, filtered, and concentrated to afford the crude triflate (400 mg) as a brown solid. The crude triflate was dissolved in anhydrous DMF (30 mL) was degassed for 10 min followed by the addition of triethylamine (1.7 mL, 12 mmol), 1,1′-bis(diphenylphosphino)ferrocene dichloropalladium(II) (70 mg, 0.080 mmol), and formic acid (0.3 mL, 8.00 mmol). The reaction mixture was heated at 100° C. for 24 h, cooled, concentrated, and the residue was purified by preparatory HPLC (C18 silica, water/acetonitrile w/0.05% TFA gradient) to afford the desired product (60 mg, 21% for two steps) as a white solid: 1H NMR (500 MHz, CDCl3) δ 12.00 (s, 1H), 7.61 (d, J=8.0 Hz, 1H), 7.51 (t, J=7.7 Hz, 1H), 7.45-7.42 (m, 3H), 7.35-7.34 (m, 2H), 7.16 (d, J=7.2 Hz, 1H), 6.30 (d, J=5.4 Hz, 1H), 3.45 (d, J=6.3 Hz, 1H), 2.32 (s, 6H), 1.50 (d, J=6.6 Hz, 3H); ESI MS m/z 349 [C21H20N2OS+H]+; HPLC 98.5% (AUC), tR=10.86 min.


Example 461
9-{4-[(tert-Butoxycarbonylamino)methyl]phenyl}-4-oxo-4,5-dihydrothieno[2,3-c]quinolin-8-yl Trifluoromethanesulfonate



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To a solution of tert-butyl 4-(8-hydroxy-4-oxo-4,5-dihydrothieno[2,3-c]quinolin-9-yl)benzylcarbamate (150 mg, 0.36 mmol) in THF (3 mL) at 0° C. was added sodium hydride (60 wt %, 18 mg, 0.44 mmol) and the reaction mixture was stirred at 0° C. for 1 h. N-Phenyl-bis(trifluoromethanesulfonimide) (160 mg, 0.44 mmol) was added and the reaction mixture was warmed to room temperature and stirred for 18 h. The reaction mixture was quenched with water and the aqueous layer was extracted with methylene chloride. The combined organic layers were dried over anhydrous sodium sulfate, filtered, concentrated and the residue was purified by column chromatography (silica, methanol/methylene chloride gradient) to afford the desired product (200 mg, 98%): ESI MS m/z 555 [C24H21F3N2O6S2+H]+.


Example 462
tert-Butyl 4-(8-Cyano-4-oxo-4,5-dihydrothieno[2,3-c]quinolin-9-yl)benzylcarbamate



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A solution of 9-{4-[(tert-butoxycarbonylamino)methyl]phenyl}-4-oxo-4,5-dihydrothieno[2,3-c]quinolin-8-yl trifluoromethanesulfonate (176 mg, 0.320 mmol), zinc chloride (75 mg, 0.640 mmol), 1,1′-bis(diphenylphosphino)ferrocene (18 mg, 0.032 mmol), and tris(dibenzylideneacetone)dipalladium(0) (15 mg, 0.016 mmol) in anhydrous DMF (4 mL) was heated at 130° C. for 3 h. The reaction mixture was cooled, quenched with water and the resulting precipitate was filtered and purified by column chromatography (silica, methanol/methylene chloride gradient) to afford the desired product (120 mg, 87%) as a brown solid: ESI MS m/z 432 [C24H21N3O3S+H]+.


Example 326
9-[4-(Aminomethyl)phenyl]-4-oxo-4,5-dihydrothieno[2,3-c]quinoline-8-carbonitrile Hydrochloride



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Following General Procedure D-3, tert-butyl 4-(8-cyano-4-oxo-4,5-dihydrothieno[2,3-c]quinolin-9-yl)benzylcarbamate (10 mg, 0.023 mmol) was reacted with 4 N HCl (3 mL) to afford the desired product (7.4 mg, 74%) as a dark brown solid: 1H NMR (500 MHz, CD3OD) δ 7.89 (d, J=8.6 Hz, 1H), 7.74 (t, J=9.5 Hz, 2H), 7.65 (dd, J=14.4, 7.0 Hz, 2H), 7.55-7.53 (m, 2H), 6.08 (d, J=5.4 Hz, 1H), 4.32 (s, 2H); ESI MS m/z 330 [C19H13N3OS−H]; HPLC 98.3% (AUC), tR=9.36 min.


Example 627
(S)-4-benzyl-3-(2-(4-bromo-2-fluorophenyl)acetyl)oxazolidin-2-one



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To a solution of (2-(4-bromo-2-fluorophenyl)acetic acid) (3 g, 13 mmol) and triethylamine (2.5 mL, 14 mmol) in toluene (50 mL) at 0° C. was added trimethylacetyl chloride (6.1 mL, 65 mmol) dropwise. After 10 mins the reaction mixture was cooled to −78° C. In a separate flask, to a solution of (S-(+)-4-benzyl-2-oxazolidinone (2.5 g, 14 mmol) in tetrahydrofuran (50 mL) at −78° C. was added LiHMDS (1 M in hexane, 17 mL, 17 mmol)) until yellowish color persisted. After 10 mins the resulting solution was transferred through a cannula into the suspension of mixed anhydride prepared as described above. The reaction mixture was allowed to reach rt over the period of 4 h, then diluted with saturated aqueous sodium bisulfate (ca. 20 mL), and extracted with ethyl acetate (ca. 100 mL). The extract was washed with brine (2×50 mL), dried over sodium sulfate, and evaporated under vacuum. Flash chromatography of the residue followed by trituration (hexanes) afforded the desired product (2.1 g, 42%) as white solid. ESI MS m/z 393 [C18H15BrFNO3+H]+


Example 628
(R)-4-benzyl-3-(2-(4-bromo-2-fluorophenyl)acetyl)oxazolidin-2-one



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Following the procedure outlined for Example 627. (2-(4-bromo-2-fluorophenyl)acetic acid) (10.8 g, 30.7 mmol) reacted with (S)-(+)-4-benzyl-2-oxazolidinone (5.44 g, 30.7 mmol) to obtain the desired product (4.5 g, 36%) as white solid. ESI MS nm/393 [C18H15BrFNO3+H]+


Example 629
(S)-4-benzyl-3-((S)-2-(4-bromo-2-fluorophenyl)propanoyl)oxazolidin-2-one



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To a solution of (S)-4-benzyl-3-(2-(4-bromo-2-fluorophenyl)acetyl)oxazolidin-2-one (3.6 g, 9.2 mmol) in THF (40 mL) was added a solution of methyl iodide (1 M solution in toluene, 9.6 mL, 9.6 mmol). The mixture was cooled to −78° C. and a solution of sodium bis(trimethylsilyl)amide (1 M in THF, 9.6 mL, 9.6 mmol) was added dropwise. The resultant dark red mixture was stirred for 15 min at ca. −78° C. and allowed to warm up to room temperature. After 3.5 h the reaction mixture was diluted with saturated aqueous sodium bisulfate (ca. 20 mL), and extracted with ethyl acetate (1×50 mL). The extract was washed with brine (2×50 mL), dried over sodium sulfate, and evaporated under vacuum. Flash chromatography of the residue afforded the desired product (1.7 g, 45%) as light yellow solid: ESI MS m/z 407 [C19H17BrFNO3+H]+


Example 630
(R)-4-benzyl-3-((R)-2-(4-bromo-2-fluorophenyl)propanoyl)oxazolidin-2-one



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Following the procedure outlined for Example 628, (R)-4-benzyl-3-(2-(4-bromo-2-fluorophenyl)acetyl)oxazolidin-2-one (4.6 g, 12 mmol) was reacted with methyl iodide (1M solution in toluene, 12.3 mL, 12.3 mmol) to obtain the desired product (3.0 g, 60%) as light yellow solid: ESI MS m/z 407 [C19H17BrFNO3+H]+


Example 631
(S)-2-(4-bromo-2-fluorophenyl)propan-1-ol



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To a solution of ((S)-4-benzyl-3-((S)-2-(4-bromo-2-fluorophenyl)propanoyl)oxazolidin-2-one) (1.7 g, 4.2 mmol) in THF (12 mL) was added a solution of sodium borohydride (700 mg, 21 mmol) in water (2 mL). The reaction mixture was stirred for 3 h at room temperature. The excess hydride was quenched by slow addition of aqueous hydrochloric acid (1 N, ca. 2.9 mL). The mixture was further diluted with water (10 mL) and extracted with ethyl acetate (1×30 mL). The combined organics were washed with brine (2×10 mL), dried over sodium sulfate, and evaporated under vacuum. The residue was purified by flash chromatography of the residue afforded the desired product (0.8 g, 82%) as light yellow oil: ESI MS m/z 234 [C9H10BrFO+H]+


Example 632
(R)-2-(4-bromo-2-fluorophenyl)propan-1-ol



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Following the procedure outlined for Example 630, (R)-4-benzyl-3-((R)-2-(4-bromo-2-fluorophenyl)propanoyl)oxazolidin-2-one (3 g, 7.4 mmol) was reacted with sodium borohydride (1.2 g, 37 mmol) to obtain the desired product (1.5 g, 87%) as light yellow oil; ESI MS m/z 234 [C11H10BrFO+H]+


Example 633
(S)-2-(2-(4-bromo-2-fluorophenyl)propyl)isoindoline-1,3-dione



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To a solution of (S)-2-(4-bromo-2-fluorophenyl)propan-1-ol (800 mg, 3.43 mmol), phthalimide (554 mg, 3.77 mmol), and triphenylphosphine (1.34 g, 5.14 mmol) in THF (2 mL) was added DIAD (1 mL, 5.14 mmol) dropwise. The reaction mixture was stirred at room temperature for 18 h and evaporated under vacuum. Flash chromatography of the residue afforded the desired product (1 g, 81%) as a white solid ESI MS m/z 363 [C17H13BrFNO2+H]+


Example 634
(R)-2-(2-(4-bromo-2-fluorophenyl)propyl)isoindoline-1,3-dione



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Following the procedure described for Example 633, (R)-2-(4-bromo-2-fluorophenyl)propan-1-ol (1.5 mg, 6.4 mmol) was reacted with phthalimide (1.0 mg, 7.008 mmol) to obtain the desired product (1.6 g, 69%) as a white solid: ESI MS m/z 363 [C17H13BrFNO2+H]+


Example 635
(S)-tert-butyl 2-(2-fluoro-4-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)phenyl)propylcarbamate



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To a solution of(S)-2-(2-(4-bromo-2-fluorophenyl)propyl)isoindoline-1,3-dione) (1.0 g, 2.8 mmol) in toluene (10 mL) was added hydrazine (1.3 mL, 41.5 mmol) dropwise. The reaction mixture was heated at 80-90° C. for 1 h and cooled to room temperature. The supernatant was decanted, and the residual solid was washed with toluene. The combined solution was evaporated under vacuum, dissolved in DCM (10 mL) and cooled to 0° C. Next, Boc2O (870 mg, 4 mmol) and Et3N (0.5 mL, 4 mmol) were added and the reaction mixture stirred for 30 min at room temperature. The reaction mixture diluted with DCM (20 mL) and washed with 1N HCl (1×10 mL), water (1×20 mL) followed by brine (1×10 mL), dried over sodium sulfate, and evaporated under vacuum to afford the desire product (860 mg, 99%) which was taken to next step without further purification. ESI MS m/n 333 [C14H19BrFNO2+H]+


The next step carried out following the procedure G (Scheme II): (S)-tert-butyl 2-(4-bromo-2-fluorophenyl)propylcarbamate (860 mg, 2.66) was reacted with KOAc (833 mg, 8.5 mmol), Pd(dppf)Cl2 (200 mg, 0.26 mmol) and bis(pinacolato)diboron (863 mg, 3.4 mmol) to afford (S)-tert-butyl 2-(2-fluoro-4-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)phenyl)propylcarbamate as a colourless paste (900 mg, 89%): ESI MS m/z 380 [C20H31BFNO4+H]+


Example 636
(R)-tert-butyl 2-(2-fluoro-4-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)phenyl)propylcarbamate



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Followed the procedure outlined for Example 635 (R)-2-(2-(4-bromo-2-fluorophenyl)propyl)isoindoline-1,3-dione) (1.6 g, 4.42 mmol) was reacted with hydrazine (2.1 g, 66 mmol), Boc2O (2.0 g, 8.8 mmol) followed by bis(pinacolato)diboron (1.0 g, 4.0 mmol) to obtain the desired product (1.1 g, 80%) as a colourless paste: ESI MS m/z 380 [C20H31BFNO4+H]+


Example 637
(R)-tert-butyl 2-(2-fluoro-4-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)phenyl)propyl(methyl)carbamate



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Following the procedure described for Example 647, (R)-tert-butyl 2-(2-fluoro-4-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)phenyl)propylcarbamate (400 mg, 1 mmol) was reacted with methyl iodide (1 M solution in toluene, 2 mL, 2 mmol) and NaHMDS (1 M solution, 2 mL, 2 mmol) to afford the desired product (330 mg, 82%) as viscous mass. ESI MS m/z 394 [C21H38BFNO4+H]+


Example 638
tert-butyl 3-methyl-2-(4-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)phenyl)butylcarbamate



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Following the procedure described for Example 647, 2-(4-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)phenyl)acetonitrile (5.6 g, 23 mmol) was reacted with iso propyl iodide (4 g, 24 mmol) NaHMDS (1 M solution, 24 m L, 24 mmol) to afford the desired product (2.1 g, 23%) as viscous mass. ESI MS not 390 [C22H36BNO4+H]+.


Example 639
tert-butyl 2-(2-fluoro-4-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)phenyl)-3-methylbutylcarbamate



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Following the procedure described for Example 647, 2-(2-fluoro-4-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)phenyl)acetonitrile (1.7 g, 6.5 mmol) was reacted with iso propyl iodide (1.1 g, 6.8 mmol) NaHMDS (1 M solution, 7.1 mL, 7.1 mmol) to afford the desired product (0.65 g, 24%) as viscous mass. ESI MS m/z 408 [C22H36FBNO4+H]+


Example 640
tert-butyl 2-cyclopentyl-2-(4-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)phenyl)ethylcarbamate



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Following the procedure described for Example 647, 2-(4-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)phenyl)acetonitrile (1.7 g, 7.16 mmol) was reacted with cyclopentyl iodide (1 M solution in toluene, 7.16 mL, 7.16 mmol) and NaHMDS (M solution, 7.16 mL, 7.16 mmol) to afford the desired product (1.6 g, 53%) as viscous mass. ESI MS m/z 415 [C24H38BNO4+H]+.


Example 641
tert-butyl methyl(3-methyl-2-(4-(4-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)phenyl)butyl)carbamate



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Example 642

Following the procedure described for Example 647, tert-butyl 3-methyl-2-(4-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)phenyl)butylcarbamate (400 mg, 1 mmol) was reacted with methyl iodide (1M solution in toluene, 2 mL, 2 mmol) and NaHMDS (1 M solution, 2 mL, 2 mmol) to afford the desired product (350 mg, 84%) as viscous mass. ESI MS m/z 403 [C23H38BNO4+H]+.


Example 643
tert-butyl 2-(2-fluoro-4-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)phenyl)-3-methylbutyl(methyl)carbamate



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Following the procedure described for Example 647, tert-butyl 2-(2-fluoro-4-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)phenyl)-3-methylbutylcarbamate (650 mg, 1.6 mmol) was reacted with methyl iodide (1M solution in toluene, 3.2 mL, 3.2 mmol) and NaHMDS (1 M solution, 4.8 mL, 4.8 mmol) to afford the desired product (650 mg, 94%) as viscous mass. ESI MS m/z 421 [C23H38FBNO4+H]+


Example 644
tert-butyl 3-(4-bromophenyl)piperidine-1-carboxylate



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To a solution of 3-(4-bromophenyl)pyridine (0.4 g, 1.68 mmol) and HCl (1.0 N solution in water, 1.7 mL, 1.7 mmol) in MeOH (20 mL) was added PtO2 (0.5 g) and stirred for 24 h at room temperature under H2 atmosphere (50 psi) in a Parr hydrogenation apparatus. The mixture was filtered through Celite, and the filtrate was evaporated under reduced pressure. The resulting white solid was dissolved in EtOAc (50 mL) and washed with 1 N NaOH (10 mL). The aqueous phase was extracted with EtOAc (3×50 mL), and the combined organic phase was dried (Na2SO4). Evaporation of the solvent gave a white solid which was redissolved in DCM and added Boc2O followed by Et3N at 0° C. After stirring the reaction mixture for 1 h at room temperature diluted with DCM and washed sequentially with 1 N HCl, water and brine, dried over sodium sulfate, and evaporated under vacuum. Flash chromatography of the residue afforded the desired product as viscous mass (350 mg, 61%) ESI MS m/z 341 [C16H22BrNO2+H]+.


Example 645
tert-butyl 3-(4-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)phenyl)piperidine-1-carboxylate



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General Procedure G, tert-butyl 3-(4-bromophenyl)piperidine-1-carboxylate (350 mg, 1) was reacted with bis(pinacolato)diboron (275, 1.2 mmol) to to afford the desired product (190 mg, 48%) as a viscous mass: ESI MS m/z 388 [C22H34BNO4+H]+.


Example 646
3-(4-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)phenyl)propanenitrile



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General Procedure G, tert-butyl 3-(4-bromophenyl)piperidine-1-carboxylate (350 mg, l) was reacted with bis(pinacolato)diboron (275, 1.2 mmol) to to afford the desired product (190 mg, 48%) as a viscous mass: ESI MS m/z 388 [C22H34BNO4+H]+.


Example 647
N-methyl(R)-tert-butyl methyl(1-(4-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)phenyl)ethyl)carbamate



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To a solution of (R)-tert-butyl 1-(4-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)phenyl)ethylcarbamate (1.0 g, 2.88 mmol) in anhydrous THF (20 mL) was cooled to 0° C. and sodium hydride (60 wt %, 330 mg, 8.64 mmol) added portion wise. The mixture was stirred for min and then heated at 60° C. for 1 h. The flask was then cooled down to room temperature and methyl iodide (277 mL, 4.32 mmol) was added. The mixture was heated again at 60° C. for 12 h. LCMS showed completion of reaction. The reaction mixture was quenched with water and diluted with ethyl acetate (200 mL). The layers were separated and the organic layer was dried over anhydrous sodium sulfate, filtered, concentrated and the residue purified by column chromatography (silica, 0-30% ethyl acetate/heptane) to afford the desired product (520 mg, 43%) as a white solid: ESI MS m/z 306 [C20H32BNO4+H]+.


Example 648
(R)-tert-butyl methyl(2-(4-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)phenyl)propyl)carbamate



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A solution of (R)-tert-butyl 2-(4-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)phenyl)propylcarbamate (9.0 g, 24.93 mmol) in anhydrous THF (120 mL) was cooled to 0° C. and NaHMDS (30 mL, 29.9 mmol) was added. The mixture was stirred for 1 h, methyl iodide (1.9 mL, 29.9) in THF (40 mL) added and stirred for 14 h. The reaction mixture was quenched with water (20 mL) and diluted with ethyl acetate (250 mL). The layers were separated and the organic layer was dried over anhydrous sodium sulfate, filtered, concentrated and the residue purified by column chromatography (silica, 0-30% ethyl acetate/heptane) to afford the desired product (6.2 g, 66%) as light yellow oil: ESI MS m/z 376 [C21H13NO4+H]+.


Example 649
2-(4-bromophenyl)propanenitrile



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To a solution of 2-(4-bromophenyl)acetonitrile (5.0 g, 25.5 mmol) in anhydrous THF (70 mL) was cooled to 0° C. and sodium hydride (60 wt %, 1.5 g, 38.3 mmol) added portion wise. The mixture was stirred at room temperature for 1 h. After which methyl iodide (1.$ mL, 28.1 mmol) was added and the mixture stirred for 14 h. The reaction mixture was carefully quenched with water at 0° C. and diluted with ethyl acetate (200 mL). The layers were separated and the organic layer was dried over anhydrous sodium sulfate, filtered, concentrated and the residue purified by column chromatography (silica, 0-30% ethyl acetate/heptane) to afford the desired product (3.8 g, 72%) as a yellow oil: ESI MS m/z 210 [C9H8BrN+H]+.


Example 650
2-(2-chlorophenyl)propanenitrile



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Following the procedure outlined for Example 649, 2-(2-chlorophenyl)acetonitrile (15 g, 98.9 mmol) was reacted with NaHMDS (118 mL, 118 mmol), and methyl iodie (7.0 mL, 108 mmol) to afford the desired product (14 g, 87%) as a brown oil: ESI MS m/z 166 [C9H8ClN+H]+.


Example 651
2-(2-chlorophenyl)propan-1-amine



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To a solution of 2-(2-chlorophenyl)propanenitrile (14 g, 84.8 mmol) in toluene at 0° C. was added BH3.THF (127, 255 mmol) and the reaction was warmed to room temperature and heated at reflux for 4 h. The reaction mixture was cooled; quenched with water, concentrated and the residue was purified by column chromatography (silica, ethyl acetate/hexanes gradient) to obtain the desired product (13.9 g, 97%) as a reddish oil: ESI MS m/z 170 [C9H12ClN+H]+.


Example 652
N-(2-(4-bromo-2-chlorophenyl)propyl)-2,2,2-trifluoroacetamide



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A solution of trifluoro acetic anhydride (12.8 mL, 90.1 mmol) in anhydrous methylene chloride (82 mL) was cooled to 0° C. and 2-(2-chlorophenyl)propan-1-amine (14 g, 82.8 mmol) in anhydrous methylene chloride (30 mL) was added dropwise. The mixture was stirred at room temperature for 1.5 h. The flask was again cooled to 0° C. and methane sulfonic acid (13 mL) followed by 1,3-Dibromo-5,5-Dimethylhydantoin (11.8 g, 41.4 mmol) was added in one portion. The mixture was stirred for 14 h and quenched with water (30 mL) and diluted with methylene chloride (150 mL). The layers were separated and the organic layer was dried over anhydrous sodium sulfate, filtered, concentrated and the residue purified by column chromatography (silica, 0-30% ethyl acetate/heptane) to afford the desired product (14 g, 50%) as a yellowish oil: ESI MS m/z 344 [C11H10BrClF3NO+H]+.


Example 653
tert-butyl 2-(2-chloro-4-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)phenyl)propylcarbamate



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A mixture of N-(2-(4-bromo-2-chlorophenyl)propyl)-2,2,2-trifluoroacetamide (14 g, 40.6 mmol), methanol (200 mL) and sodium hydroxide (2M, 200 mL, 81.2 mmol) was stirred at room temperature for 14 h. LCMS showed completion of the reaction. The solvent was removed, extraction with methylene chloride (200 mL) and concentrated to give an oil. The residue was dissolved in methylene chloride (100 mL) and cooled to 0° C. Triethylamine (8.3 mL, 61.0 mmol) and di-tert-butyl dicarbonate (13.3 g, 61.0 mmol) and the reaction mixture stirred at room temperature for 18 h. The reaction mixture concentrated and the residue was purified by column chromatography (silica, ethyl acetate/hexanes gradient) to obtain the desired product (13.8 g, 90%) as white solid: ESI MS m/z 293 [C14H11BrClNO2−56]+.


Example 654
tert-butyl 2-(2-chloro-4-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)phenyl)propylcarbamate



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Following General Procedure G, tert-butyl 2-(4-bromo-2-chlorophenyl)propylcarbamate (12.0 g, 34.5 mmol) was reacted with bis(pinacolata)diboron (13.2 g, 51.7 mmol) to afford the desired product (8.0 g, 58%) as a amorphous reddish oil: ESI MS m/z 396 [C20H31BClNO4+H]+.


Example 655
2-(4-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)phenyl)propanenitrile



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Following General Procedure G, 2-(4-bromophenyl)propanenitrile (3.5 g, 18.2 mmol) was reacted with bis(pinacolata)diboron (4.6 g, 27.1 mmol) to afford the desired product (2.5 g, 53%) as a brown solid: ESI MS m/z 258 [C15H20BNO2+H]+.


Example 656
2-ethyl-2-(4-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)phenyl)butanenitrile



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To a solution of 2-(4-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)phenyl)acetonitrile (2.0 g, 8.23 mmol) in DMF (40 mL) was cooled to 0° C. and sodium hydride (60 wt %, 1.2 g, 32.9 mmol) added portion wise. The mixture was stirred for 10 min and ethyl iodide (0.74 mL, 9.05 mmol) in THF (10 mL) was added. The mixture was stirred at room temperature for 12 h. The reaction mixture was quenched with water and diluted with ethyl acetate. The layers were separated and the organic layer was dried over anhydrous sodium sulfate, filtered, concentrated and the residue purified by column chromatography (silica, 0-30% ethyl acetate/heptane) to afford the desired product (950 mg, 38%) as a brown solid: ESI MS m/z 300 [C18H26BNO2+H]+.


Example 657
2-(4-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)phenyl)propanenitrile



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Following General Procedure G, 2-(4-bromophenyl)propanenitrile (5.0 g, 22.3 mmol) was reacted with bis(pinacolata)diboron (8.7 g, 33.5 mmol) to afford the desired product (5.8 g, 95%) as a white solid: ESI MS m/z 272 [C16H22BNO2+H]+.


Example 658
(R)—N-(2-(4-bromophenyl)propyl)-2,2,2-trifluoroacetamide



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A solution of trifluoro acetic anhydride (11.4 mL, 81.4 mmol) in anhydrous methylene chloride (73 mL) was cooled to 0° C. and (R)-2-phenylpropan-1-amine (10 g, 73.9 mmol) in anhydrous methylene chloride (20 mL) was added dropwise. The mixture was stirred at room temperature for 1.5 h. The flask was again cooled to 0° C. and methane sulfonic acid (12 mL) followed by 1,3-Dibromo-5,5-Dimethylhydantoin (11 g, 36.9 mmol) was added in one portion. The mixture was stirred for 14 h and quenched with water (30 mL) and diluted with methylene chloride (100 mL). The layers were separated and the organic layer was dried over anhydrous sodium sulfate, filtered, concentrated and the residue purified by column chromatography (silica, 0-30% ethyl acetate/heptane) to afford the desired product (21 g, 91%) as a yellow solid: ESI MS m/z 310 [C11H11BrF3NO+H]+.


Example 659
(R)-tert-buty 12-(4-bromophenyl)propylcarbamate



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A mixture of (R)—N-(2-(4-bromophenyl)propyl)-2,2,2-trifluoroacetamide (21 g, 68.3 mmol), methanol (40 mL) and sodium hydroxide (2M, 68 mL, 136 mmol) was stirred at room temperature for 14 h. LCMS showed completion of the reaction. The solvent was removed, extraction with methylene chloride (250 mL) and concentrated to give an oil. The residue was dissolved in methylene chloride (100 mL) and cooled to 0° C. Triethylamine (14 mL, 102 mmol) and di-tert-butyl dicarbonate (22 g, 102 mmol) and the reaction mixture stirred at room temperature for 18 h. The reaction mixture concentrated and the residue was purified by column chromatography (silica, ethyl acetate/hexanes gradient) to obtain the desired product (19 g, 91%) as yellow oil: ESI MS m/z 257 [C14H20BrNO2−56]+.


Example 660
(R)-tert-butyl 2-(4-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)phenyl)propylcarbamate



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Following General Procedure G, (R)-tert-butyl 2-(4-bromophenyl)propylcarbamate (19 g, 60.5 mmol) was reacted with bis(pinacolata)diboron (24 g, 94.4 mmol) to afford the desired product (22 g, 99%) as a light yellow solid: ESI MS m/z 362 [C20H32BNO4+H]+.


Example 661
(R)—N-(1-(4-bromophenyl)propyl)-2,2,2-trifluoroacetamide



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A solution of trifluoro acetic anhydride (5.7 mL, 40.7 mmol) in anhydrous methylene chloride (40 mL) was cooled to 0° C. and (R)-1-phenylpropan-1-amine (5 g, 36.9 mmol) in anhydrous methylene chloride (10 mL) was added dropwise. The mixture was stirred at room temperature for 1.5 h. The flask was again cooled to 0° C. and methane sulfonic acid (6.3 mL) followed by 1,3-dibromo-5,5-dimethylhydantoin (5.3 g, 18.5 mmol) was added in one portion. The mixture was stirred for 14 h and quenched with water (30 mL) and diluted with methylene chloride (50 mL). The layers were separated and the organic layer was dried over anhydrous sodium sulfate, filtered, concentrated and the residue purified by column chromatography (silica, 0-30% ethyl acetate/heptane) to afford the desired product (8.1 g, 73%) as a white solid: ESI MS m/z 310 [C11H11BrF3NO+H]+.


Example 662
(R)-tert-butyl 1-(4-bromophenyl)propylcarbamate



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A mixture of (R)—N-(1-(4-bromophenyl)propyl)-2,2,2-trifluoroacetamide (8.1 g, 68.3 mmol), methanol (20 mL) and sodium hydroxide (2M, 15 mL, 30.6 mmol) was stirred at room temperature for 14 h. LCMS showed completion of the reaction. The solvent was removed, extraction with methylene chloride (150 mL) and concentrated to give an oil. The residue was dissolved in methylene chloride (100 mL) and cooled to 0° C. Triethylamine (2.2 mL, 15.3 mmol) and di-tert-butyl dicarbonate (3.3 g, 15.3 mmol) and the reaction mixture stirred at room temperature for 18 h. The reaction mixture concentrated and the residue was purified by column chromatography (silica, ethyl acetate/hexanes gradient) to obtain the desired product (5.8 g, 70%) as off-white solid: ESI MS m/z 257 [C14H20BrNO2−56]+.


Example 663
(R)-tert-butyl 1-(4-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)phenyl)propylcarbamate



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Following General Procedure G, (R)-tert-butyl 1-(4-bromophenyl)propylcarbamate (5.8 g, 18.4 mmol) was reacted with bis(pinacolata)diboron (7.03 g, 27.7 mmol) to afford the desired product (6.18 g, 92%) as yellow oil: ESI MS m/z 362 [C20H32BNO4+H]+.


Example 664
tert-butyl 1-(4-bromophenyl)propan-2-ylcarbamate



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To a solution of 1-(4-bromophenyl)propan-2-one (5.0 g, 23.4 mmol) in ethanol (115 mL) was added ammonia in methanol (9 N, 20.2 mL, 140 mmol) followed by Titanium isoperoxide (13.3 mL, 46.9 mmol). The mixture was heated at 50° C. overnight. The flask was cooled to 0° C. and NaBH4 (142 mg, 3.76 mmol) was added in portions. After stirring for 1 h, NH4OH (2 N, 4.0 mL) was added and the mixture stirred for 1 h. The white solid was filtered off and the filtrate extracted with methylene chloride. Solvent was removed and oil obtained was dissolved in methylene chloride (100 mL) and cooled to 0° C. Triethylamine (4.8 mL, 35.2 mmol) and di-tert-butyl dicarbonate (10.2 g, 46.9 mmol) and the reaction mixture stirred at room temperature for 18 h. The reaction mixture concentrated and the residue was purified by column chromatography (silica, ethyl acetate/hexanes gradient) to obtain the desired product (4.2 g, 57%) as white solid: ESI MS m/z 257 [C14H20BrNO2−56]+.


Example 665
tert-butyl 1-(4-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)phenyl)propan-2-ylcarbamate



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Following General Procedure G, tert-butyl 1-(4-bromophenyl)propan-2-ylcarbamate (8.8 g, 28.03 mmol) was reacted with bis(pinacolata)diboron (10.7 g, 42.0 mmol) to afford the desired product (10.5 g, 99%) as a brown oil: ESI MS m/z 362 [C20H32BNO4+H]+.


Example 666
tert-butyl 2-ethyl-2-(4-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)phenyl)butylcarbamate



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To a solution of cyano compound (500 mg, 1.67 mmol) in toluene (10 mL) at 0° C. was added BH3.THF (1.0 M in THF, 16 mL, 10 mmol) and the reaction was warmed to room temperature and heated at reflux for 4 h. The reaction mixture was cooled; quenched with water, concentrated. The residue was dissolved in methylene chloride (30 mL) and cooled to 0° C. Triethylamine (0.36 mL, 2.51 mmol) and di-tert-butyl dicarbonate (547 mg, 2.51 mmol) and the reaction mixture stirred at room temperature for 18 h. The reaction mixture concentrated and the residue was purified by column chromatography (silica, ethyl acetate/hexanes gradient) to obtain the desired product (480 mg, 71%) as a brown solid: ESI MS m/z 404 [C23H38BNO4+H]+.


Example 667
tert-butyl 2-methyl-2-(4-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)phenyl)propylcarbamate



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Following the procedure outlined for Example 666, 2-(4-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)phenyl)propanenitrile (5.8 g, 21.4 mmol) was reacted with BH3.THF (1.0 M in THF, 64 mL, 64 mmol) and di-tert-butyl dicarbonate (7.0 g, 32.1 mmol) to give the desired product (6.9 g, 86%) as a white solid: ESI MS m/z 310 [C21H34BNO4−56]+.


Example 668
1-(4-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)phenyl)cyclobutanecarbonitrile



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To a solution of 2-(4-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)phenyl)acetonitrile (7.0 g, 29 mmol) in THF at 0° C. was added NaHMDS (1.0 M, 120 mL, 120 mmol). After stirring for 20 min 1,3-diiodopropane (26 g, 86 mmol) was added and the reaction mixture was stirred at room temperature for 2 h. The reaction mixture was cooled to 0° C., quenched with MeOH (5.0 mL) and the residue was purified by column chromatography (silica, ethyl acetate/hexanes gradient) to afford the desired product (4.0 g, 47%) as a yellow oil: ESI MS m/z 286 [C17H22BNO2+H]+.


Example 669
(1-(4-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)phenyl)cyclobutyl)methanamine



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Following the procedure outlined for Example 666, 1-(4-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)phenyl)cyclobutane carbonitrile (4.0 g, 14 mmol) was reacted with BH3.THF (1.0 M in THF, 60 mL, 60 mmol) to afford the desired product (3.7 g, 91%) as a yellow oil: ESI MS m/z 288 [C11H2BNO2+H]+.


Example 670
tert-butyl (1-(4-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)phenyl)cyclobutyl)methylcarbamate



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Following the procedure outlined for Example 463, (1-(4-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)phenyl)cyclobutyl)methanamine (3.7 g, 13 mmol)) was reacted with di-tert-butyl dicarbonate (3.4 g, 16 mmol) to afford the desired product (3.5 g, 71%) as a yellow oil: ESI MS m/z 388 [C22H34BNO4+H]+.


Example 671
4-bromo-2-chloro-1-(2-nitrovinyl)benzene



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To a solution of 4-bromo-2-chlorobenzaldehyde (7.5 g, 34 mmol) in nitromethane was added methylamine hydrochloride (1.3 g, 22 mmol), NaOAc (1.8 g, 22 mmol). The mixture was vigorously stirred for 18 h at room temperature. The reaction mixture was diluted with water (60 mL) and extracted with CH2Cl2 (3×100 mL), organic phases dried (Na2SO4), evaporated to afford the desired product (8.5 g, 95%) as a light yellow oil: ESI MS m/z 262 [C8H5BrClNO2+H]+.


Example 672
2-(4-bromo-2-chlorophenyl)ethanamine



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To a stirred suspension of LiBH4 (2.0 M, 73 mL, 145 mmol) in THF (60 mL) at room temperature was added chlorotrimethylsilane (32 g, 290 mmol), dropwise over 10 min. After stirring at room temperature for 20 min, nitrogen gas was bubbled through the mixture for 5 min to remove the remaining trimethylsilane that had formed. A solution of 4-bromo-2-chloro-1-(2-nitrovinyl)benzene (9.5 g, 36.2 mmol) in THF (60 mL) was added dropwise over 10 min with stirring at room temperature. The resulting mixture was heated at reflux for 1 h. The reaction mixture was cooled in an ice bath and carefully quenched with MeOH (100 mL). The solvent was evaporated and the residue was partitioned between 20% KOH (120 mL) and CH2Cl2 (60 mL). The organic layer was dried, concentrated, purified by column chromatography (silica, ethyl acetate/hexanes gradient) to obtain the desired product (8.5 g, 95%) as a light yellow oil: ESI MS m/z 234 [C8H9BrClN+H]+.


Example 673
tert-butyl 4-bromo-2-chlorophenethyl carbamate



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Following the procedure outlined for Example 463, 2-(4-bromo-2-chlorophenyl)ethanamine (7.5 g, 32 mmol) was reacted with di-tert-butyl dicarbonate (8.3 g, 38 mmol) to afford the desired product (9.7 g, 90%) as a white solid: ESI MS m/z 334 [C13H17BrCLNO2+H]+.


Example 674
tert-butyl 2-chloro-4-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)phenethylcarbamate



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Following General Procedure G, tert-butyl 4-bromo-2-chlorophenethylcarbamate (9.6 g, 30 mmol) was reacted with bis(pinacolato)diboron (11 g, 45 mmol to afford the desired product (8.2 g, 73%) as a colorless oil: ESI MS m/z 382 [C19H29BCLNO2+H]+.


Example 675
2-(4-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)phenyl)butanenitrile



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Following the procedure outlined for Example 649, 2-(4-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)phenyl)acetonitrile (5.2 g, 21 mmol)) was reacted with ethyl bromide (2.6 g, 24 mmol) to afford the desired product (3.4 g, 59%) as colorless oil: ESI MS m/z 272 [C16H22BNO2+H]+.


Example 676
2-(4-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)phenyl)butan-1-amine



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Following the procedure outlined for Example 666, 2-(4-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)phenyl)butanenitrile (3.4 g, 12.5 mmol) was reacted with BH3.THF (1.0 M in THF, 64 mL, 64 mmol) to afford the desired product (3.2 g, 93%) as light yellow oil: ESI MS m/z 276 [C16H26BNO2+H]+.


Example 677
(1-(4-bromophenyl)cyclopropyl)methanamine



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Following the procedure outlined for Example 666, 1-(4-bromophenyl)cyclopropane carbonitrile (2.0 g, 9.0 mmol) was reacted with BH3.THF (1.0 M in THF, 50 mL, 50 mmol) to afford the desired product (1.9 g, 94%) as a yellow oil: ESI MS m/z 226 [C10H12BrN+H]+.


Example 678
tert-butyl 2-(4-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)phenyl)butylcarbamate



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Following the procedure outlined for Example 463, 2-(4-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)phenyl)butan-1-amine (2.9 g, 10.5 mmol) was reacted with di-tert-butyl dicarbonate (2.8 g, 12.6 mmol) to afford the desired product (2.4 g, 62%) as a light yellow oil: ESI MS m/z 376 [C12H34BNO4+H]+.


Example 679
tert-butyl (1-(4-bromophenyl)cyclopropyl)methylcarbamate



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Following the procedure outlined for Example 463, (1-(4-bromophenyl)cyclopropyl)methanamine (2.2 g, 9.5 mmol) was reacted with di-tert-butyl dicarbonate (2.5 g, 12 mmol) to afford the desired product (1.5 g, 52%) as a yellow oil: ESI MS m/z 326 [C15H20BrNO2+H]+.


Example 680
tert-butyl (1-(4-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)phenyl)cyclopropyl)methylcarbamate



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Following General Procedure G, tert-butyl (1-(4-bromophenyl)cyclopropyl)methyl carbamate (1.3 g, 4.0 mmol) was reacted with bis(pinacolato)diboron (1.55 g, 6.1 mmol) to afford the desired product (1.8 g, 60%) as a colorless oil: ESI MS m/z 374 [C21H32BNO4+H]+.


Example 463
tert-Butyl 4-Bromophenethylcarbamate



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To a solution of 2-(4-bromophenyl)ethanamine (3.0 g, 15 mmol) in methylene chloride (75 mL) at 0° C. was added triethylamine (2.5 mL, 18 mmol) and di-tert-butyl dicarbonate (3.9 g, 18 mmol) and the reaction mixture was stirred at room temperature for 18 h. The reaction mixture was concentrated and the residue was triturated with acetonitrile and filtered to afford the desired product (3.5 g, 75%) as a yellow solid: ESI MS m/z 301 [C13H18BrNO2+H]+.


Example 464
tert-Butyl 4-(4,4,5,5-Tetramethyl-1,3,2-dioxaborolan-2-yl)phenethylcarbamate



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Following General Procedure G, tert-butyl 4-bromophenethylcarbamate (1.3 g, 4.3 mmol) was reacted with bis(pinacolato)diboron (1.3 g, 5.1 mmol) to afford the desired product (1.1 g, 70%) as a light brown solid: ESI MS m/z 348 [C19H30BNO4+H]+.


Example 465
tert-Butyl 4-(8-Methoxy-4-oxo-45-dihydrothieno[2,3-c]quinolin-9-yl)phenethylcarbamate



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Following General Procedure B, 9-bromo-8-methoxythieno[2,3-c]quinolin-4(5H)-one (780 mg, 2.5 mmol) was reacted with tert-butyl 4-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)phenethylcarbamate (1.5 g, 4.3 mmol) to afford the desired product (1.0 g, 90%) as a brown solid: ESI MS m/z 451 [C25H26N2O4S+H]+.


Example 466
2-[4-(3-Bromopropoxy)phenyl]-4,4,5,5-tetramethyl-1,3,2-dioxaborolane



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To a solution of 4-(3-bromopropoxy)phenylboronic acid (1.0 g, 3.9 mmol) in diethyl ether (40 mL) was added pinacol (1.4 g, 12 mmol) and the reaction mixture was stirred for 18 h and concentrated to afford the desired product (1.5 g, crude) as a light brown oil which carried onto the next step without further purification: ESI MS m/z 247 [C15H22BBrO3−94]+.


Example 467
N1,N1-Diethyl-N2-{3-[4-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)phenoxy]propyl}ethane-1,2-diamine



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A solution of 2-[4-(3-bromopropoxy)phenyl]-4,4,5,5-tetramethyl-1,3,2-dioxaborolane (500 mL, 2.02 mmol), N1,N1-diethylethane-1,2-diamine (0.87 mL, 6.1 mmol), and potassium carbonate (550 mg, 4.0 mmol) in acetonitrile (15 mL) was heated to 50° C. for 3 h. The reaction mixture was cooled, filtered and the filtrate was concentrated to afford the desired product (400 mg, 53%) as a yellow oil: ESI MS m/z 377 [C21H37BN2O3+H]+.


Example 468
tert-Butyl 1-(4-Bromophenyl)ethylcarbamate



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Following the procedure outlined for Example 463, 1-(4-bromophenyl)ethanamine (3.0 g, 15 mmol) was reacted with di-tert-butyl dicarbonate (3.9 g, 18 mmol) to afford the desired product (4.2 g, 93%) as a white solid: ESI MS m/z 301 [C13H18BrNO2+H]+.


Example 469
tert-Butyl 1-[4-(4,4,5,5-Tetramethyl-1,3,2-dioxaborolan-2-yl)phenyl]ethylcarbamate



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Following General Procedure G, tert-butyl 1-(4-bromophenyl)ethylcarbamate (2.2 g, 7.3 mmol) was reacted with bis(pinacolata)diboron (3.9 g, 11 mmol) to afford the desired product (1.3 g, 53%) as an off-white solid: ESI MS m/z 247 [C19H30BNO4+H]+.


Example 470
(S)-tert-Butyl 1-(4-Bromophenyl)ethylcarbamate



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Following the procedure outlined for Example 463, (S)-1-(4-bromophenyl)ethanamine (500 mg, 2.5 mmol) was reacted with di-tert-butyl dicarbonate (650 mg, 3.0 mmol) to afford the desired product (640 mg, 82%) as a white solid: ESI MS m/z 247 [C13H18BrNO2+H]+.


Example 471
(S)-tert-Butyl 1-[4-(4,4,5,5-Tetramethyl-1,3,2-dioxaborolan-2-yl)phenyl]ethylcarbamate



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Following General Procedure G, (S)-tert-butyl 1-(4-bromophenyl)ethylcarbamate (630 mg, 2.1 mmol) was reacted with bis(pinacolato)diboron (1.1 g, 3.1 mmol) to afford the desired product (320 mg, 44%) as a brown solid: ESI MS m/z 347 [C19H30BNO4-Boc]+.


Example 472
2-[2-Fluoro-4-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)phenyl]acetonitrile



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Following General Procedure G, 2-(4-bromo-2-fluorophenyl)acetonitrile (4.0 g, 19 mmol) was reacted with bis(pinacolato)diboron (7.1 g, 28 mmol) to afford the desired product (2.5 g, 57%) as a brown solid: ESI MS m/z 232 [C14H17BFNO2+H]+.


Example 473
(R)-tert-Butyl 1-(4-Bromophenyl)ethylcarbamate



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Following the procedure outlined for Example 463, (R)-1-(4-bromophenyl)ethanamine (1.0 g, 5.0 mmol) was reacted with di-tert-butyl dicarbonate (1.3 g, 5.9 mmol) to afford the desired product (1.2 g, 86%) as an off-white solid: ESI MS m/z 301 [C13H18BrNO2+H]+.


Example 474
(R)-tert-Butyl 1-[4-(4,4,5,5-Tetramethyl-1,3,2-dioxaborolan-2-yl)phenyl]ethylcarbamate



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Following General Procedure G, (R)-tert-butyl 1-(4-bromophenyl)ethylcarbamate (1.2 g, 4.0 mmol) was reacted with bis(pinacolato)diboron (1.5 g, 6.0 mmol) to afford the desired product (1.0 g, 77%) as a colorless oil: ESI MS m/z 292 [C19H30BNO4−55]+.


Example 475
2-Methyl-2-[4-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)phenyl]propanenitrile



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Following General Procedure G, 2-(4-bromophenyl)-2-methylpropanenitrile (1.0 g, 4.5 mmol) was reacted with bis(pinacolato)diboron (1.7 g, 6.7 mmol) to afford the desired product (980 mg, 81%) as an off-white solid: ESI MS m/z 272 [C16H22BNO2+H]+.


Example 476
1-[2-Fluoro-4-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)benzyl]pyrrolidin-3-ol



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A solution of 2-[4-(bromomethyl)-3-fluorophenyl]-4,4,5,5-tetramethyl-1,3,2-dioxaborolane (300 mg, 0.95 mmol), pyrrolidin-3-ol (99 mg, 1.1 mmol), and potassium carbonate (160 mg, 1.1 mmol) in acetonitrile (5 mL) was heated to 50° C. for 3 h. The reaction mixture was cooled, filtered and the filtrate was concentrated to afford the desired product (280 mg, 92%) as a red oil: ESI MS m/z 322 [C17H25BFNO3+H]+.


Example 477
tert-Butyl 5-Bromo-2,3-dihydro-1H-inden-2-ylcarbamate



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Following the procedure outlined for Example 463, 5-bromo-2,3-dihydro-1H-inden-2-amine (2.5 g, 8.5 mmol) was reacted with di-tert-butyl dicarbonate (2.8 g, 13 mmol) to afford the desired product (2.5 g, 96%) as a white solid: ESI MS m/z 313 [C14H18BrNO2+H]+.


Example 478
tert-Butyl 5-(4,4,5,5-Tetramethyl-1,3,2-dioxaborolan-2-yl)-2,3-dihydro-1H-inden-2-ylcarbamate



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Following General Procedure G, tert-butyl 5-bromo-2,3-dihydro-1H-inden-2-ylcarbamate (2.5 g, 8.0 mmol) was reacted with bis(pinacolato)diboron (3.0 g, 12 mmol) to afford the desired product (2.1 g, 72%) as a colorless oil: ESI MS m/z 360 [C20H30BNO4+H]+.


Example 479
tert-Butyl 7-(4,4,5,5-Tetramethyl-1,3,2-dioxaborolan-2-1y)-3,4-dihydroisoquinoline-2(1H)-carboxylate



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Following General Procedure G, tert-butyl 7-bromo-3,4-dihydroisoquinoline-2(1H)-carboxylate (1.3 g, 4.4 mmol) was reacted with bis(pinacolato)diboron (1.7 g, 6.6 mmol) to afford the desired product (1.1 g, 72%) as a colorless oil: ESI MS m/z 360 [C20H30BNO4+H]+.


Example 480
1-(4-Bromo-2-fluorophenyl)ethanamine



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To a solution of 1-(4-bromo-2-fluorophenyl)ethanone (2.0 g, 9.2 mmol) in methanol (50 mL) was added ammonia (7 N in methanol, 8.0 mL, 55 mmol) and titanium(IV) isopropoxide (5.4 mL, 18 mmol). The reaction mixture was stirred at room temperature for 18 h, cooled to 0° C. and sodium borohydride (520 mg, 14 mmol) was added. The reaction mixture was warmed to room temperature, stirred for 20 min, quenched with 2 M ammonium hydroxide and filtered. The reaction mixture was extracted with methylene chloride and the combined organic layers were dried over sodium sulfate, filtered, and concentrated to afford the desired product (1.2 g, 63%) as an oil: ESI MS m/z 219 [C8H9BrFN+H]+.


Example 481
tert-Butyl 1-(4-Bromo-2-fluorophenyl)ethylcarbamate



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Following the procedure outlined for Example 463, 1-(4-bromo-2-fluorophenyl)ethanamine (1.2 g, 5.6 mmol) was reacted with di-tert-butyl dicarbonate (1.4 g, 6.7 mmol) to afford the desired product (1.3 g, 73%) as a white solid: ESI MS m/z 219 [C13H17BrFNO2+H−100]+.


Example 482
tert-Butyl 1-[2-Fluoro-4-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)phenyl]ethylcarbamate



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Following General Procedure G, tert-butyl 1-(4-bromo-2-fluorophenyl)ethylcarbamate (1.3 g, 4.4 mmol) was reacted with bis(pinacolato)diboron (1.7 g, 6.6 mmol) to afford the desired product (1.5 g, 93%) as a white solid: ESI MS m/z 266 [C19H29BFNO4+H−100].


Example 483
3-[4-(4,4,5,5-Tetramethyl-1,3,2-dioxaborolan-2-yl)phenyl]propanenitrile



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Following General Procedure G, 3-(4-bromophenyl)propanenitrile (1.0 g, 4.8 mmol) was reacted with bis(pinacolato)diboron (1.8 g, 7.1 mmol) to afford the desired product (1.1 g, 97%) as a light brown solid: ESI MS m/z 258 [C15H20BNO2+H]+.


Example 484
N-(1-[4-Bromophenyl)ethyl]cyclopentanamine



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To a solution of 1-(4-bromophenyl)ethanone (500 mg, 2.5 mmol) in ethanol (16 mL) was added cyclopentanamine (320 mg, 3.8 mmol) and the reaction mixture was heated at 50° C. for 18 h. The reaction mixture was cooled to 0° C. and sodium borohydride (140 mg, 3.8 mmol) was added and the reaction mixture was warmed to room temperature and stirred for 30 min. The reaction mixture was quenched with 2 M aqueous ammonium hydroxide and extracted with methylene chloride. The combined organic layers were dried over sodium sulfate, filtered and concentrated to afford the desired product (600 mg, 90%) as a red oil: ESI MS m/z 269 [C13H18BrN+H]+.


Example 485
tert-Butyl 1-[4-(4,4,5,5-Tetramethyl-1,3,2-dioxaborolan-2-yl)phenyl]propylcarbamate



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Following General Procedure G, tert-butyl 1-(4-bromophenyl)propylcarbamate (2.0 g, 6.4 mmol) was reacted with bis(pinacolato)diboron (2.4 g, 9.6 mmol) to afford the desired product (2.1 g, 93%) as a yellow solid: ESI MS m/z 305 [C20H32BNO4−56]+.


Example 486
(S)-tert-Butyl 1-(4-Bromophenyl)ethylcarbamate



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Following the procedure outlined for Example 463, (S)-1-(4-bromophenyl)ethanamine (1.0 g, 5.0 mmol) was reacted with di-tert-butyl dicarbonate (1.3 g, 6.0 mmol) to afford the desired product (1.3 g, 88%) as a white solid: ESI MS m/z 300 [C13H18BrNO2+H]+.


Example 487
(S)-tert-Butyl 1-[4-(4,4,5,5-Tetramethyl-1,3,2-dioxaborolan-2-yl)phenyl]ethylcarbamate



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Following General Procedure G, (S)-tert-butyl 1-(4-bromophenyl)ethylcarbamate (1.3 g, 4.4 mmol) was reacted with bis(pinacolato)diboron (1.7 g, 6.6 mmol) to afford the desired product (1.4 g, 96%) as a brown solid: ESI MS m/z 348 [C19H30BNO4+H]+.


Example 488
N-(4-Bromobenzyl)propan-2-amine



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A solution of 1-bromo-4-(bromomethyl)benzene (2.0 g, 8.0 mmol), isopropylamine (950 mg, 16 mmol) and potassium carbonate (2.2 g, 16 mmol) in acetonitrile (40 mL) was stirred at room temperature for 18 h. The reaction mixture was quenched with water and extracted with ethyl acetate. The combined organic layers were washed with brine, dried over anhydrous sodium sulfate, filtered, and concentrated. The residue was purified by column chromatography (silica, 0-100% methylene chloride/methanol) to afford the desired product (1.4 g, 78%) as a brown solid: ESI MS m/z 228 [C10H14BrN+H]+.


Example 489
4-({4-[(tert-Butoxycarbonylamino)methyl]piperidin-1-yl)}methyl)phenylboronic acid



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Following the procedure outlined for Example 488, 4-formylphenylboronic acid (100 mg, 0.47 mmol) was reacted with tert-butyl piperidin-4-ylmethylcarbamate (70 mg, 0.47 mmol) to afford the desired product (120 mg, 77%) as a brown solid: ESI MS m/z 349 [C18H29BN2O4+H]+.


Example 490
(E)-tert-Butyl 1-[3-(4,4,5,5-Tetramethyl-1,3,2-dioxaborolan-2-yl)allyl]piperidin-4-ylcarbamate



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Following the procedure outlined for Example 488, (Z)-2-(3-chloroprop-1-enyl)-4,4,5,5-tetramethyl-1,3,2-dioxaborolane (210 mg, 1.1 mmol) was reacted with tert-butyl piperidin-4-ylcarbamate (640 mg, 3.2 mmol) to afford the desired product (100 mg, 30%) as a brown solid: ESI MS m/z 367 [C14H27BN2O2+H]+.


Example 491
1-(4-Bromophenyl)-N-methylmethanamine



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Following the procedure outlined for Example 488, 1-bromo-4-(bromomethyl)benzene (1.0 g, 4.0 mmol) was reacted with methanamine (620 mg, 20 mmol) to afford the desired product (750 mg, 93%) as a brown solid: ESI MS m/z 201 [C8H10BrN+H]+.


Example 492
N-(4-Bromobenzyl)ethanamine



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Following the procedure outlined for Example 488, 1-bromo-4-(bromomethyl)benzene (2.0 g, 8.0 mmol) was reacted with ethanamine (720 mg, 16 mmol) to afford the desired product (1.3 g, 75%) as a brown solid: ESI MS m/z 215 [C9H12BrN+H]+.


Example 493
(E)-2-(3-Chloroprop-1-enyl)-4,4,5,5-tetramethyl-1,3,2-dioxaborolane



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A solution of (E)-3-chloroprop-1-enylboronic acid (5 g, 41 mmol), pinacol (4.9 g, 41 mmol), and magnesium sulfate (15 g, 120 mmol) in methylene chloride (100 mL) was stirred at room temperature for 18 h. The reaction mixture was filtered through silica gel and the filter cake was washed with methylene chloride. The filtrate was concentrated to afford the desired product (4.8 g, 60%) as a colorless oil: ESI MS m/z 203 [C9H16BClO2+H]+.


Example 494
(E)-tert-Butyl 1-[3-(4,4,5,5-Tetramethyl-1,3,2-dioxaborolan-2-yl)allyl]piperidin-3-ylcarbamate



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Following the procedure outlined for Example 488, (E)-2-(3-chloroprop-1-enyl)-4,4,5,5-tetramethyl-1,3,2-dioxaborolane (500 mg, 2.5 mmol) was reacted with tert-butyl piperidin-3-ylcarbamate (740 mg, 3.7 mmol) to afford the desired product (320 mg, 24%) as a yellow oil: ESI MS m/z 367 [C19H35BN2O4+H]+.


Example 495
4-Bromo-2-fluoro-N-(2-hydroxyethyl)benzenesulfonamide



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To a solution of 2-aminoethanol (0.24 mL, 4.0 mmol), and triethylamine (1.5 mL, 11 mmol) in anhydrous THF (15 mL) was added 4-bromo-2-fluorobenzene-1-sulfonyl chloride (1.0 g, 3.7 mmol) portion wise and the reaction mixture stirred at room temperature for 16 h. The reaction was filtered, the filtrate was concentrated and the residue was purified by column chromatography (silica, ethyl acetate/hexanes gradient) to afford the desired product (850 mg, 77%): ESI MS m/z 298 [C8H9BrFNO3S+H]+.


Example 496
4-Bromo-N-(2-hydroxyethyl)benzenesulfonamide



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To a solution of 2-aminoethanol (2.3 mL, 39 mmol), and triethylamine (16 mL, 120 mmol) in anhydrous THF (100 mL) was added 4-bromobenzene-1-sulfonyl chloride (10 g, 39 mmol) portion wise and the reaction mixture stirred at room temperature for 16 h. The reaction was filtered, the filtrate was concentrated and the residue was purified by column chromatography (silica, ethyl acetate/hexanes gradient) to afford the desired product (5.5 g, 50%): 1H NMR (500 MHz, CDCl3) δ 7.74 (td, J=9.0, 2.1 Hz, 2H), 7.67 (td, J=9.0, 2.1 Hz, 2H), 5.08 (s, 1H), 3.72 (t, J=5.1 Hz, 2H), 3.12 (t, J=4.8 Hz, 2H), 1.83 (s, 1H).


Example 497
N-(2-Hydroxyethyl)-4-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)benzenesulfonamide



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Following General Procedure G, 4-bromo-N-(2-hydroxyethyl)benzenesulfonamide (5.0 g, 18 mmol) was reacted with bis(pinacolato)diboron (4.9 g, 20 mmol) to afford the desired product (4.2 g, 40%) as a yellow solid: 1H NMR (300 MHz, CDCl3) δ 7.95 (d, J=8.3 Hz, 2H), 7.85 (d, J=8.3 Hz, 2H), 5.14 (t, J=6.1 Hz, 1H), 3.68 (t, J=5.0 Hz, 2H), 3.09 (q, J=5.4 Hz, 2H), 1.36 (s, 12H).


Example 498
(S)-tert-Butyl 1-(3-Bromo-4-nitrophenyl)pyrrolidin-3-ylcarbamate



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A solution of 2-bromo-4-fluoro-1-nitrobenzene (1.5 g, 6.8 mmol), (S)-tert-butyl pyrrolidin-3-ylcarbamate (1.9 g, 10 mmol), and sodium bicarbonate (1.7 g, 20 mmol) in DMSO (40 mL) was heated at 80° C. for 1 h. The reaction mixture was cooled to room temperature, poured into excess water and the resulting precipitate was filtered. The solids were washed with aqueous ammonium chloride, brine and water to afford the desired product (2.5 g, 96%) as a yellow solid: 387 [C15H20BrN3O4+H]+.


Example 499
(S)-tert-Butyl 1-(4-Amino-3-bromophenyl)pyrrolidin-3-ylcarbamate



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A solution of (S)-tert-butyl 1-(3-bromo-4-nitrophenyl)pyrrolidin-3-ylcarbamate (2.5 g, 6.5 mmol), ammonium chloride (380 mg, 7.1 mmol), and iron (1.8 g, 32 mmol) in ethanol (20 mL) and water (10 mL) was heated to reflux for 1 h. The reaction mixture was cooled to room temperature and filtered through diatomaceous earth. The filtrate was concentrated to afford the desired product (2.3 g, >99%) as a blue solid: ESI MS m/z 357 [C15H22BrN3O2+H]+.


Example 500
Methyl 5-Bromothiophene-2-carboxylate



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A solution of 5-bromothiophene-2-carboxylic acid (5.0 g, 24 mmol), methyl iodide (5.1 g, 30 mmol), and potassium carbonate (6.7 g, 48 mmol) in DMF (50 mL) was stirred at room temperature for 64 h. The reaction was quenched with water and the aqueous layer was extracted multiple times with ethyl acetate. The combined organic layers were washed with aqueous lithium chloride and brine, dried over anhydrous sodium sulfate, filtered, and concentrated. The residue was purified by column chromatography (silica, ethyl acetate/hexanes gradient) to afford the desired product (4.2 g, 79%): 1H NMR (500 MHz, CDCl3) δ 7.54 (d, J=4.0 Hz, 1H), 7.07 (d, J=4.0 Hz, 1H), 3.87 (s, 3H).


Example 501
Methyl 5-(4-Methoxyphenyl)thiophene-2-carboxylate



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Following General Procedure B, 4-methoxyphenylboronic acid (2.7 g, 18 mmol) was reacted with methyl 5-bromothiophene-2-carboxylate (2.0 g, 9.0 mmol) to afford the desired product (1.4 g, 61%): 1H NMR (300 MHz, CDCl3) δ 7.71 (d, J=3.9 Hz, 1H), 7.53 (td, J=9.7, 2.5 Hz, 2H), 7.14 (d, J=3.9 Hz, 1H), 6.89 (td, J=9.7, 2.5 Hz, 2H), 3.87 (s, 3H), 3.80 (s, 3H).


Example 502
5-(4-Methoxyphenyl)thiophene-2-carboxylic Acid



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A solution of methyl 5-(4-methoxyphenyl)thiophene-2-carboxylate (1.4 g, 5.6 mmol), and 1 M sodium hydroxide (55 mL) in methanol (55 mL) was heated at 80° C. for 18 h. The reaction mixture was cooled to room temperature and diluted with ethyl acetate. The organic layer was washed with 1 N hydrochloric acid and aqueous sodium chloride, dried over anhydrous sodium sulfate, filtered, and concentrated to afford the desired product (1.2 g, 93%) as an off-white solid: ESI MS m/z 325 [C12H10O3S+H]+.


Example 503
5-(4-Methoxyphenyl)thiophene-2-carbonyl chloride



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To a solution of 5-(4-methoxyphenyl)thiophene-2-carboxylic acid (0.60 g, 2.5 mmol) in toluene (4 mL) was added thionylchloride (560 mL, 7.7 mmol) and the reaction mixture was heated at 100° C. for 18 h. The reaction mixture was cooled to room temperature and concentrated to afford the desire product (642 mg, crude): ESI MS m/z 253 [C12H9ClO2S+H]+.


Example 504
(S)-tert-Butyl 1-{3-Bromo-4-[5-(4-methoxyphenyl)thiophene-2-carboxamido]phenyl}pyrrolidin-3-ylcarbamate



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Following Step 1 from General Procedure A, 5-(4-methoxyphenyl)thiophene-2-carbonyl chloride (640 mg, 2.5 mmol) was reacted with (S)-tert-butyl 1-(4-amino-3-bromophenyl)pyrrolidin-3-ylcarbamate (800 mg, 2.2 mmol) to afford the desired product (500 mg, 39%) as a light yellow solid: ESI MS m/z 573 [C27H30BrN3O4S+H]+.


Example 505
(S)-tert-Butyl 1-{3-Bromo-4-[5-(4-methoxyphenyl)-N-{[2-(trimethylsilyl)ethoxy]methyl}thiophene-2-carboxamido]phenyl}pyrrolidin-3-ylcarbamate



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A solution of (S)-tert-butyl 1-{3-bromo-4-[5-(4-methoxyphenyl)thiophene-2-carboxamido]phenyl}pyrrolidin-3-ylcarbamate (400 mg, 0.69 mmol) in THF (20 mL) was cooled to 0° C. and sodium hydride (60 wt %, 140 mg, 3.5 mmol) was added. The reaction was warmed to room temperature followed by the addition of 2-(trimethylsilyl)ethoxymethyl chloride (370 mL, 2.1 mmol) and the reaction mixture was stirred at room temperature for 18 h. The reaction mixture was quenched with water and diluted with ethyl acetate. The layers were separated and the organic layer was dried over anhydrous sodium sulfate, filtered, concentrated and the residue was purified by column chromatography (silica, 0-30% ethyl acetate/heptane) to afford the desired product (400 mg, 87%): ESI MS m/z 703 [C33H44BrN3O5SSi+H]+.


Example 506
(S)-8-(3-Aminopyrrolidin-1-yl)-2-(4-methoxyphenyl)-5-{[2-(trimethylsilyl)ethoxy]methyl}thieno[2,3-c]quinolin-4(5H)-one



embedded image


Following Step 3 from General Procedure A, (S)-tert-butyl 1-{3-bromo-4-[5-(4-methoxyphenyl)-N-{[2-(trimethylsilyl)ethoxy]methyl}thiophene-2-carboxamido]phenyl}pyrrolidin-3-ylcarbamate (210 mg, 0.29 mmol) was reacted with bis(tri-tert-butylphosphine)palladium (15 mg, 0.029 mmol) to afford the desired product (25 mg, 14%): ESI MS m/z 622 [C28H35N3O3SSi+H]+.


Example 51
(S)-8-(3-Aminopyrrolidin-1-yl)-2-(4-hydroxyphenyl)thieno[2,3-c]quinolin-4(5H)-one Hydrochloride



embedded image


Following General Procedure F, (S)-8-(3-aminopyrrolidin-1-yl)-2-(4-methoxyphenyl)-5-{[2-(trimethylsilyl)ethoxy]methyl}thieno[2,3-c]quinolin-4(5H)-one (25 mg, 0.040 mmol) was reacted with tribromoborane (38 mL, 0.40 mmol) to afford the desired product (6.4 mg, 43%) as a yellow-green solid: 1H NMR (500 MHz, CD3OD) δ 8.06 (s, 1H), 7.71 (d, J=8.6 Hz, 2H), 7.36 (d, J=9.0 Hz, 1H), 7.26 (s, 1H), 6.99 (d, J=8.4 Hz, 1H), 6.90 (d, J=8.5 Hz, 2H), 4.09 (s, 1H), 3.74-3.69 (m, 2H), 3.59-3.57 (m, 1H), 3.48-3.39 (m, 1H), 2.57-2.52 (m, 1H), 2.25-2.23 (m, 1H); ESI MS m/z 378 [C21H19N3O2S+H]+; HPLC 97.1% (AUC), tR=10.89 min.


Compounds of the invention of this application that the specific procedure for producing the compound was not particularly described in the Examples above were also synthesized by the similar or analogous methods by referring to the above-mentioned general procedures for producing the present compounds, Examples and such.


Examples 507
Kinase Assay

PBK activity was determined in the presence or absence of compounds using fluorescein isothiocyanate-labeled (FITC-labeled) histone H3 peptide as a substrate. The extent of FITC-labeled histone H3 peptide phosphorylation was measured by immobilized metal ion affinity-based fluorescence polarization (IMAP) technology (Sportsman J R, et al., Assay Drug Dev. Technol. 2: 205-14, 2004) using IMAP FP Progressive Binding System (Molecular Devices Corporation). Test compounds were dissolved in DMSO at 12.5 mM and then serially diluted as the DMSO concentration in the assays to be 1%. The serially diluted compounds, 0.8 ng/micro-L PBK (Carna Biosciences) and 100 nM FITC-labeled histone H3 peptide were reacted in a reaction buffer (20 mM HEPES, 0.01% Tween-20, 0.3 mM MgCl2, 2 mM dithiothreitol, 50 micro-M ATP, pH 7.4) at room temperature for 1 hour. The reaction was stopped by the addition of three fold assay volume of progressive binding solution. Following 0.5 hour incubation at room temperature, fluorescence polarization was measured by Wallac EnVision 2103 multilabel reader (PerkinElmer). IC50 values were calculated by nonlinear four parameter fit using SigmaPlot, version 10.0 (Systat Software, Inc.).


IC50 values of the typical compounds of the present invention are shown in following table 2:











TABLE 2







IC50 (microM)


ID.
Compound
(kinase assay)

















51
(S)-8-(3-Aminopyrrolidin-1-yl)-2-(4-hydroxyphenyl)thieno[2,3-c]quinolin-4
0.078



(5H)-one Dihydrochloride



61
8-Hydroxy-9-(1H-indazol-6-yl)thieno[2,3-c]quinolin-4(5H)-one
0.0035


65
4-(8-Hydroxy-4-oxo-4,5-dihydrothieno[2,3-c]quinolin-9-yl)benzene-
0.0018



sulfonamide



72
9-[4-(Aminomethyl)phenyl]-8-hydroxythieno[2,3-c]quinolin-4(5H)-one
0.00063


73
9-[4-(Aminomethyl)phenyl]-8-hydroxythieno[2,3-c]quinolin-4(5H)-one
0.00038



Hydrochloride



77
N-[4-(8-Hydroxy-4-oxo-4,5-dihydrothieno[2,3-c]quinolin-9-yl)phenyl]
0.0026



methanesulfonamide



81
2-[4-(8-Hydroxy-4-oxo-4,5-dihydrothieno[2,3-c]quinolin-9-yl)phenyl]
0.012



acetonitrile



84
8-Hydroxy-9-(1,2,3,6-tetrahydropyridin-4-yl)thieno[2,3-c]quinolin-4(5H)-one
0.00078


93
9-{4-4[2-(Dimethylamino)ethyl[phenyl}-8-hydroxythieno[2,3-c]quinolin-4
0.0054



(5H)-one



95
9-[4-(Aminomethyl)phenyl]-8-hydroxy-2-methylthieno][2,3-c]quinolin-4(5H)-
0.0044



one



112
8-Hydroxy-9-{4-[4-(methylsulfonyl)piperazin-1-yl]phenyl}thieno[2,3-c]
0.012



quinolin-4(5H)-one



139
tert-Butyl
0.0094



{1-[4-(8-Methoxy-4-oxo-4,5-dihydrothieno[2,3-c]quinolin-9-yl)benzyl]




piperidin-4-yl}methylcarbamate



145
9-(4-{3-[2-Diethylamino)ethylamino]propoxy}phenyl)-8-methoxythieno
0.047



[2,3-c]quinolin-4(5H)-one



152
(E)-9-[3-(4-Aminopiperidin-1-yl)prop-1-enyl]-8-methoxythieno[2,3-c]
0.031



quinolin-4(5H)-one



164
9-{4-[(Dimethylamino)methyl]phenyl}-8-methoxythieno[2,3-c]quinolin-4(5H)-
0.011



one



165
9-{4-[(Dimethylamino)methyl]phenyl}-8-hydroxythieno[2,3-c]quinolin-4(5H)-
0.0069



one



169
9-[4-(2-Aminoethyl)phenyl]-8-methoxythieno[2,3-c]quinolin-4(5H)-one
0.022


175
9-[4-(2-Aminoethyl)phenyl]-8-hydroxythieno[2,3-c]quinolin-4(5H)-one
0.0012


176
9-[4-(2-Aminoethyl)phenyl]-8-hydroxythieno[2,3-c]quinolin-4(5H)-one
0.0011



Hydrochloride



184
9-{4-[(Diethylamino)methyl]phenyl}-8-hydroxythieno[2,3-c]quinolin-4(5H)-
0.0077



one



187
8-Hydroxy-9-{4-[(methylamino)methyl]phenyl}thieno[2,3-c]quinolin-4(5H)-
0.0009



one



188
8-Methoxy-9-{4-[(methylamino)methyl]phenyl}thieno[2,3-c]quinolin-4(5H)-
0.0078



one



192
9-(4-(1-(dimethylamino)ethyl)phenyl)-8-hydroxythieno[2,3-c]quinolin-4(5H)-
0.0016



one Hydrochloride



191
9-{4-[1-(Dimethylamino)ethyl]phenyl}-8-hydroxythieno[2,3-c]quinolin-4(5H)-
0.0019



one



193
N-{1-[4-(8-Hydroxy-4-oxo-4,5-dihydrothieno[2,3-c]quinolin-9-yl)phenyl]ethyl}
0.0037



methanesulfonamide



194
8-Hydroxy-9-{4-[1-(pyrrolidin-1-yl)ethyl]phenyl}thieno[2,3-c]quinolin-4(5H)-
0.0028



one Hydrochloride



195
9-[4-(1-Aminoethyl)phenyl]-8-hydroxythieno[2,3-c]quinolin-4(5H)-one Hydro-
0.00073



chloride



196
9-{4-(1-(dimethylamino)ethyl]phenyl}-8-hydroxythieno[2,3-c]quinolin-4(5H)-
0.0045



one Hydrochloride



210
N-(2-Bromoethyl)-4-(8-hydroxy-4-oxo-4,5-dihydrothieno[2,3-c]quinolin-9-yl)
0.0113



benzenesulfonamide



212
N-[4-(8-Hydroxy-4-oxo-4,5-dihydrothieno[2,3-c]quinolin-9-yl)benzyl]
0.0055



methanesulfonamide



216
8-Methoxy-9-{4-[1-(pyrrolidin-1-yl)ethyl]phenyl}thieno[2,3-c]quinolin-4(5H)-
0.021



one Hydrochloride



217
9-(4-Amino-3-hydroxyphenyl)-8-hydroxythieno[2,3-c]quinolin-4(5H)-one
0.0023



Hydrochloride



222
9-{4-[1-(Dimethylamino)ethyl]phenyl}-6-fluoro-8-methoxythieno[2,3-c]
0.082



quinolin-4(5H)-one Hydrochloride



225
9-{4-[2-(Dimethylamino)ethyl]phenyl}-6-fluoro-8-hydroxythieno[2,3-c]
0.023



quinolin-4(5H)-one



229
8-Hydroxy-9-{4-[(isopropylamino)methyl]phenyl}thieno[2,3-c]quinolin-4(5H)-
0.0042



one Hydrochloride



232
(S)-9-[4-(1-Aminoethyl)phenyl]-8-methoxythieno[2,3-c]quinolin-4(5H)-one
0.0074



Hydrochloride



233
(S)-9-[4-(1-Aminoethyl)phenyl]-8-hydroxythieno[2,3-c]quinolin-4(5H)-one
0.00081



Hydrochloride



235
9-(4-{[4-(Aminomethyl)piperidin-1-yl]methyl}-3-fluorophenyl)-8-hydroxythieno
0.00057



[2,3-c]quinolin-4(5H)-one



254
N-[4-(8-Hydroxy-4-oxo-4,5-dihydrothieno[2,3-c]quinolin-9-yl)-2-methylphenyl]
0.003



methanesulfonamide



256
9-[4-(Aminomethyl)phenyl]-6-fluoro-8-hydroxythieno[2,3-c]quinolin-4(5H)-
0.0025



one Hydrochloride



257
9-[4-(Aminomethyl)phenyl]-6-fluoro-8-methoxythieno[2,3-c]quinolin-4(5H)-
0.026



one Hydrochloride



261
2-[2-Fluoro-4-(8-hydroxy-4-oxo-4,5-dihydrothieno[2,3-c]quinolin-9-yl)phenyl]
0.015



acetonitrile



262
8-Hydroxy-9-{4-[1-(piperidin-l-yl)ethyl]phenyl}thieno[2,3-c]quinolin-4(5H)-
0.0043



one Hydrochloride



265
9-[4-(2-Aminoethyl)-3-fluorophenyl]-8-methoxythieno[2,3-c]quinolin-4(5H)-
0.0038



one Hydrochloride



266
9-[5-(Aminomethyl)thiophen-2-yl]-8-hydroxythieno[2,3-c]quinolin-4(5H)-one
0.00078


267
9-{4-[(Ethylamino)methyl]phenyl}-8-hydroxythieno[2,3-c]quinolin-4(5H)-one
0.002



Hydrochloride



269
9-{4-[(Ethylamino)methyl]phenyl}-8-methoxythieno[2,3-c]quinolin-4(5H)-one
0.006



Hydrochloride



270
9-[4-(Aminomethyl)phenyl]-6-bromo-8-hydroxythieno[2,3-c]quinolin-4(5H)-
0.031



one Hydrochloride



272
(R)-9-{4-[1-(Dimethylamino)ethyl]phenyl}-8-hydroxythieno[2,3-c]quinolin-
0.00088



4(5H)-one Hydrochloride



273
9-[4-(3-Aminopropyl)phenyl]-8-hydroxythieno[2,3-c]quinolin-4(5H)-one
0.00074



Hydrochloride



274
(R)-9-[4-(1-Aminoethyl)phenyl]-8-methoxythieno[2,3-c]quinolin-4(5H)-one
0.0038



Hydrochloride



275
(R)-9-[4-(1-Aminoethyl)phenyl]-8-hydroxythieno[2,3-c]quinolin-4(5H)-one
0.00054



Hydrochloride



276
9-[4-(2-Aminoethyl)-3-fluorophenyl]-8-hydroxythieno[2,3-c]quinolin-4(5H)-one
0.0005



Hydrochloride



277
9-[4-(1-Amino-2-methylpropan-2-yl)phenyl]-8-hydroxythieno[2,3-c]quinolin-
0.00067



4(5H)-one Hydrochloride



278
9-{3-Fluoro-4-[(3-hydroxypyrrolidin-1-yl)methyl]phenyl}-8-hydroxythieno
0.00097



[2,3-c]quinolin-4(5H)-one Hydrochloride



290
3-[4-(8-Hydroxy-4-oxo-4,5-dihydrothieno[2,3-c]quinolin-9-yl)phenyl]
0.0032



propanenitrile



296
9-(4-Acetylphenyl)-8-hydroxythieno[2,3-c]quinolin-4(5H)-one
0.023


297
N-(2-Bromoethyl)-2-fluoro-4-(8-hydroxy-4-oxo-4,5-dihydrothieno[2,3-c]
0.013



quinolin-9-yl)benzenesulfonamide



298
9-{3-[3-(Dimethylamino)piperidin-1-yl]propyl}-8-hydroxythieno[2,3-c]
0.083



quinolin-4(5H)-one Dihydrochloride



301
(R)-N-{1-[4-(8-Hydroxy-4-oxo-4,5-dihydrothieno[2,3-c]quinolin-9-yl)phenyl]
0.0032



ethyl}methanesulfonamide



304
4-(8-Hydroxy-4-oxo-4,5-dihydrothieno[2,3-c]quinolin-9-yl)-N,N-
0.045



dimethylbenzenesulfonamide



308
9-{4-[1-(Dimethylamino)-2-methylpropan-2-yl]phenyl}-8-hydroxythieno[2,3-c]
0.0028



quinolin-4(5H)-one Hydrochloride



313
8-Hydroxy-9-[4-(1-hydroxyethyl)phenyl]thieno[2,3-c]quinolin-4(5H)-one
0.002


314
9-{4-[1-(Cyclopentylamino)ethyl]phenyl}-8-hydroxythieno[2,3-c]quinolin-4
0.0028



(5H)-one Hydrochloride



319
9-[4-(2-Aminopropan-2-yl)phenyl]-8-hydroxythieno[2,3-c]quinolin-4(5H)-one
0.00043



Hydrochloride



326
9-[4-(Aminomethyl)phenyl]-4-oxo-4,5-dihydrothieno[2,3-c]quinoline-8-
0.013



carbonitrile Hydrochloride



327
9-{4-[2-(Dimethylamino)ethyl]-3-fluorophenyl}-8-hydroxythieno[2,3-c]
0.0019



quinolin-4(5H)-one Hydrochloride



329
9-[4-(Aminomethyl)phenyl]-6-chloro-8-hydroxythieno[2,3-c]quinolin-4
0.016



(5H)-one Hydrochloride



332
N-(2-Chloroethyl)-4-(8-hydroxy-4-oxo-4,5-dihydrothieno[2,3-c]quinolin-9-yl)
0.023



benzenesulfonamide



333
N-(2-Fluoroethyl)-4-(8-methoxy-4-oxo-4,5-dihydrothieno[2,3-c]quinolin-9-yl)
0.031



benzenesulfonamide



334
9-[4-(2-Aminopropan-2-yl)phenyl]-6-chloro-8-hydroxythieno[2,3-c]quinolin-4
0.01



(5H)-one Hydrochloride



335
(S)-9-{4-[1-(Dimethylamino)ethyl]phenyl}-8-hydroxythieno[2,3-c]quinolin-4
0.0029



(5H)-one Hydrochloride



336
9-[4-(1-Aminopropyl)phenyl]-8-hydroxythieno[2,3-c]quinolin-4(5H)-one
0.00082



Hydrochloride



337
9-[4-(1-Aminopropyl)phenyl]-8-methoxythieno[2,3-c]quinolin-4(5H)-one
0.0052



Hydrochloride



338
9-{4-[1-(Diethylamino)propyl]phenyl}-8-hydroxythieno[2,3-c]quinolin-4(5H)-
0.0037



one Hydrochloride



339
9-{4-[1-(Dimethylamino)propyl]phenyl}-8-hydroxythieno[2,3-c]quinolin-4(5H)-
0.0019



one Hydrochloride



341
9-{4-[1-(Dimethylamino)ethyl]phenyl}-6,7-difluoro-8-hydroxythieno[2,3-c]
0.034



quinolin-4(5H)-one Hydrochloride



345
9-(2-Amino-2,3-dihydro-1H-inden-5-yl)-8-hydroxythieno[2,3-c]quinolin-4(5H)-
0.0012



one Hydrochloride



346
9-{4-[1-(Dimethylamino)ethyl]phenyl}thieno[2,3-c]quinolin-4(5H)-one
0.0092


347
(S)-N-{1-[4-(8-Hydroxy-4-oxo-4,5-dihydrothieno[2,3-c]quinolin-9-yl)phenyl]
0.002



ethyl}methanesulfonamide



348
9-{4-[1-(Aminomethyl)cyclopropyl]phenyl}-8-hydroxythieno[2,3-c]quinolin-4
0.0019



(5H)-one Hydrochloride



349
9-{4-[1-(Dimethylamino)ethyl]-3-fluorophenyl}-8-hydroxythieno[2,3-c]
0.0019



quinolin-4(5H)-one Hydrochloride



353
8-Hydroxy-9-(1,2,3,4-tetrahydroisoquinolin-7-yl)thieno[2,3-c]quinolin-4(5H)-
0.002



one Hydrochloride



356
9-{4-[1-(Diethylamino)ethyl]-3-fluorophenyl}-8-hydroxythieno[2,3-c]
0.0036



quinolin-4(5H)-one Hydrochloride



359
9-[4-(1-Aminoethyl)-3-fluorophenyl]-8-hydroxythieno[2,3-c]quinolin-4(5H)-
0.00092



one Hydrochloride



361
1-[4-(8-Hydroxy-4-oxo-4,5-dihydrothieno[2,3-c]quinolin-9-yl)phenyl]
0.032



cyclopropanecarbonitrile



373
9-(4-(1-aminopropan-2-yl)phenyl)-8-methoxythieno[2,3-c]quinolin-4(5H)-one
0.0032



hydrochloride



379
9-(4-(1-((dimethylamino)methyl)cyclopropyl)phenyl)-8-hydroxythieno[2,3-c]
0.0036



quinolin-4(5H)-one hydrochloride



385
9-(4-(1-(ethylamino)ethyl)phenyl)-8-hydroxythieno[2,3-c]quinolin-4(5H)-one
0.0039



hydrochloride



1032
9-(4-(1-aminoethyl)phenyl)-6-bromo-8-hydroxythieno[2,3-c]quinolin-4(5H)-
0.047



one hydrochloride



1041
9-(4-(1-aminoethyl)phenyl)-6-chloro-8-hydroxythieno[2,3-c]quinolin-4(5H)-
0.012



one hydrochloride



1052
(R)-8-hydroxy-9-(4-(1-(methylamino)ethyl)phenyl)thieno[2,3-c]quinolin-4(5H)-
0.0013



one hydrochloride



1062
N-(1-bromopropan-2-yl)-4-(8-hydroxy-4-oxo-4,5-dihydrothieno[2,3-c]quinolin-
0.031



9-yl)benzenesulfonamide



1064
(S)-8-methoxy-9-(4-(1-(methylamino)ethyl)phenyl)thieno[2,3-c]quinolin-4(5H)-
0.0025



one hydrochloride



1066
9-(4-(1-aminoethyl)phenyl)-8-hydroxy-6-methylthieno[2,3-c]quinolin-4(5H)-
0.012



one hydrochloride



1077
9-(4-(1-aminoethyl)phenyl)-4-oxo-4,5-dihydrothieno[2,3-c]quinolin-8-yl
0.076



isopropyl carbonate hydrochloride



1081
(R)-9-(4-(1-aminoethyl)phenyl)-6-chloro-8-hydroxythieno[2,3-c]quinolin-4
0.0086



(5H)-one hydrochloride



1082
(S)-8-hydroxy-9-(4-(1-(methylamino)ethyl)phenyl)thieno[2,3-c]quinolin-4(5H)-
0.0011



one hydrochloride



1087
(S)-6-chloro-8-hydroxy-9-(4-(1-(methylamino)ethyl)phenyl)thieno[2,3-c]
0.019



quinolin-4(5H)-one hydrochloride



1088
9-(4-(1-aminopropyl)phenyl)-6-chloro-8-hydroxythieno[2,3-c]quinolin-4(5H)-
0.016



one hydrochloride



1094
N-(2-bromoethyl)-4-(8-hydroxy-4-oxo-2,3,4,5-tetrahydro-1H-cyclopenta[c]
0.01



quinolin-9-yl)benzenesulfonamide



1095
9-(4-(2-aminopropyl)phenyl)-8-hydroxythieno[2,3-c]quinolin-4(5H)-one
0.0013



hydrochloride



1099
9-(4-(1-aminoethyl)phenyl)-4-oxo-4,5-dihydrothieno[2,3-c]quinolin-8-yl
0.033



acetate hydrochloride



1106
9-(4-(2-aminopropyl)phenyl)-6-chloro-8-hydroxythieno[2,3-c]quinolin-4(5H)-one
0.041



hydrochloride



1111
9-(4-(1-aminopropan-2-yl)phenyl)-8-hydroxythieno[2,3-c]quinolin-4(5H)-one
0.0013



hydrochloride



1112
9-(4-(1-(dimethylamino)propan-2-yl)phenyl)-8-hydroxythieno[2,3-c]quinolin-4
0.0033



(5H)-one hydrochloride



1116
9-(4-(1-(aminomethyl)cyclopropyl)phenyl)-6-chloro-8-hydroxythieno[2,3-c]
0.022



quinolin-4(5H)-one hydrochloride



1120
(S)-9-(4-(1-aminopropyl)phenyl)-8-hydroxythieno[2,3-c]quinolin-4(5H)-one
0.00088



hydrochloride



1121
(S)-9-(4-(1-aminopropyl)phenyl)-8-methoxythieno[2,3-c]quinolin-4(5H)-one
0.0029



hydrochloride



1122
(R)-9-(4-(1-aminoethyl)phenyl)-8-hydroxy-6-methylthieno[2,3-c]quinolin-4(5H)-
0.0059



one hydrochloride



1123
(R)-9-(4-(1-aminoethyl)phenyl)-6-bromo-8-hydroxythieno[2,3-c]quinolin-4(5H)-
0.033



one hydrochloride



1126
(R)-6-chloro-9-(4-(1-(dimethylamino)ethyl)phenyl)-8-hydroxythieno [2,3-c]
0.042



quinolin-4(5H)-one hydrochloride



1127
(S)-9-(4-(1-(ethylamino)propyl)phenyl)-8-hydroxythieno[2,3-c]quinolin-4(5H)-
0.0014



one hydrochloride



1128
(S)-9-(4-(1-(dimethylamino)propyl)phenyl)-8-hydroxythieno[2,3-c]quinolin-4
0.0022



(5H)-one hydrochloride



1131
(R)-9-(4-(1-aminopropyl)phenyl)-8-hydroxythieno[2,3-c]quinolin-4(5H)-one
0.0013



hydrochloride



1132
(R)-6-chloro-8-hydroxy-9-(4-(1-(methylamino)ethyl)phenyl)thieno[2,3-c]
0.014



quinolin-4(5H)-one hydrochloride



1133
9-(4-(2-aminoethyl)phenyl)-6-chloro-8-hydroxythieno[2,3-c]quinolin-4(5H)-
0.02



one hydrochloride



1135
(R)-6-bromo-8-hydroxy-9-(4-(1-(methylamino)ethyl)phenyl)thieno[2,3-c]
0.03



quinolin-4(5H)-one hydrochloride



1136
9-(4-(1-aminopropan-2-yl)phenyl)-6-chloro-8-hydroxythieno[2,3-c]quinolin-
0.0086



4(5H)-one hydrochloride



1139
N-(2-chloroethyl)-4-(8-methoxy-4-oxo-4,5-dihydrothieno[2,3-c]quinolin-9-yl)
0.07



benzenesulfonamide



1142
9-(4-(2-aminoethyl)phenyl)-6-bromo-8-hydroxythieno[2,3-c]quinolin-4(5H)-
0.045



one hydrochloride



1145
N-(2-chloroethyl)-4-(8-hydroxy-4-oxo-2,3,4,5-tetrahydro-1H-cyclopenta[c]
0.013



quinolin-9-yl)benzenesulfonamide



1148
(S)-8-hydroxy-9-(4-(1-(methylamino)propyl)phenyl)thieno[2,3-c]quinolin-4(5H)-
0.0013



one hydrochloride



1150
(R)-9-(4-(1-aminopropyl)phenyl)-6-bromo-8-hydroxythieno[2,3-c]quinolin-
0.047



4(5H)-one hydrochloride



1151
(R)-9-(4-(1-(dimethylamino)propyl)phenyl)-8-hydroxythieno[2,3-c]quinolin-
0.0025



4(5H)-one hydrochloride



1154
(S)-6-chloro-8-hydroxy-9-(4-(1-(methylamino)propyl)phenyl)thieno[2,3-c]
0.0094



quinolin-4(5H)-one hydrochloride



1157
(R)-9-(4-(1-aminopropyl)phenyl)-8-hydroxy-6-methylthieno[2,3-c]quinolin-4
0.018



(5H)-one hydrochloride



1159
(R)-9-(4-(1-aminopropyl)phenyl)-6-chloro-8-hydroxythieno[2,3-c]quinolin-4
0.026



(5H)-one hydrochloride



1160
(R)-9-(4-(1-aminopropan-2-yl)phenyl)-8-hydroxythieno[2,3-c]quinolin-4(5H)-
0.00064



one hydrochloride



1161
(R)-9-(4-(1-aminopropan-2-yl)phenyl)-8-methoxythieno[2,3-c]quinolin-4(5H)-
0.002



one hydrochloride



1162
2-(4-(8-hydroxy-4-oxo-4,5-dihydrothieno[2,3-c]quinolin-9-yl)phenyl)
0.013



butanenitrile



1163
(S)-9-(4-(1-aminopropan-2-yl)phenyl)-8-hydroxythieno[2,3-c]quinolin-4(5H)-
0.0013



one hydrochloride



1165
6-chloro-8-hydroxy-9-(4-(2-(methylamino)ethyl)phenyl)thieno[2,3-c]quinolin-4
0.058



(5H)-one hydrochloride



1166
(R)-9-(4-(1-aminopropan-2-yl)phenyl)-6-chloro-8-hydroxythieno[2,3-c]
0.0044



quinolin-4(5H)-one hydrochloride



1168
(R)-9-(4-(1-aminopropan-2-yl)phenyl)-8-hydroxy-6-methylthieno[2,3-c]
0.0026



quinolin-4(5H)-one hydrochloride



1169
(R)-9-(4-(1-aminopropan-2-yl)phenyl)-8-hydroxy-6-methylthieno[2,3-c]
0.0089



quinolin-4(5H)-one hydrobromide



1172
(S)-9-(4-(1-(dimethylamino)propan-2-yl)phenyl)-8-hydroxythieno[2,3-c]
0.004



quinolin-4(5H)-one hydrochloride



1174
9-(4-(1-aminopropan-2-yl)-3-fluorophenyl)-8-hydroxythieno[2,3-c]quinolin-4
0.0015



(5H)-one hydrochloride



1176
(R)-9-(4-(1-aminopropan-2-yl)phenyl)-6-bromo-8-hydroxythieno[2,3-c]
0.017



quinolin-4(5H)-one hydrochloride



1179
9-(4-(1-aminopropan-2-yl)-3-fluorophenyl)-8-methoxythieno[2,3-c]quinolin-
0.003



4(5H)-one hydrochloride



1181
(S)-9-(4-(1-aminopropan-2-yl)phenyl)-6-chloro-8-hydroxythieno[2,3-c]quinolin-
0.033



4(5H)-one hydrochloride



1187
(R)-8-hydroxy-9-(4-(1-(methylamino)propan-2-yl)phenyl)thieno[2,3-c]quinolin-
0.0013



4(5H)-one hydrochloride



1188
(R)-9-(4-(1-(dimethylamino)propan-2-yl)phenyl)-8-hydroxythieno[2,3-c]
0.0025



quinolin-4(5H)-one hydrochloride



1189
(R)-8-methoxy-9-(4-(1-(methylamino)propan-2-yl)phenyl)thieno[2,3-c]quinolin-
0.003



4(5H)-one hydrochloride



1190
9-(4-(1-aminopropan-2-yl)-3-fluorophenyl)-8-hydroxy-6-methylthieno[2,3-c]
0.0051



quinolin-4(5H)-one hydrochloride



1191
9-(4-(2-aminoethyl)phenyl)-8-hydroxy-6-methylthieno[2,3-c]quinolin-4(5H)-
0.019



one hydrochloride



1193
9-(4-(1-(dimethylamino)propan-2-yl)-3-fluorophenyl)-8-hydroxy-6-methylthieno
0.046



[2,3-c]quinolin-4(5H)-one hydrochloride



1197
(S)-8-hydroxy-9-(4-(1-(methylamino)propan-2-yl)phenyl)thieno[2,3-c]quinolin-4
0.0028



(5H)-one hydrochloride



1201
(R)-9-(4-(1-aminopropan-2-yl)phenyl)-6-chloro-8-methoxythieno[2,3-c]quinolin-
0.02



4(5H)-one hydrochloride



1204
N-(1-chloropropan-2-yl)-4-(8-hydroxy-4-oxo-4,5-dihydrothieno[2,3-c]quinolin-
0.015



9-yl)benzenesulfonamide



1209
9-(4-(3-(aminomethyl)pentan-3-yl)phenyl)-8-hydroxythieno[2,3-c]quinolin-4
0.0018



(5H)-one hydrochloride



1212
9-(4-(aminomethyl)phenyl)-8-hydroxy-6-methylthieno[2,3-c]quinolin-4(5H)-
0.016



one hydrochloride



1213
9-(4-(2-aminoethyl)-3-fluorophenyl)-6-bromo-8-hydroxythieno[2,3-c]quinolin-4
0.019



(5H)-one hydrochloride



1215
(S)-8-hydroxy-6-methyl-9-(4-(1-(methylamino)propan-2-yl)phenyl)thieno[2,3-c]
0.06



quinolin-4(5H)-one hydrochloride



1216
9-(4-(2-aminoethyl)-3-fluorophenyl)-8-methoxy-6-methylthieno[2,3-c]quinolin-
0.057



4(5H)-one hydrochloride



1217
9-(4-(2-aminoethyl)-3-fluorophenyl)-8-hydroxy-6-methylthieno[2,3-c]quinolin-4
0.0047



(5H)-one hydrochloride



1218
9-(4-(2-aminoethyl)-3-fluorophenyl)-6-chloro-8-methoxythieno[2,3-c]quinolin-4
0.087



(5H)-one hydrochloride



1219
9-(4-(2-aminoethyl)-3-fluorophenyl)-6-chloro-8-hydroxythieno[2,3-c]quinolin-4
0.0055



(5H)-one hydrochloride



1224
9-(4-(2-aminoethyl)-2-bromo-5-hydroxyphenyl)-8-hydroxythieno[2,3-c]quinolin-
0.0064



4(5H)-one hydrochloride



1225
(S)-9-(4-(1-aminoethyl)phenyl)-8-hydroxy-6-methylthieno[2,3-c]quinolin-4(5H)-
0.016



one hydrochloride



1226
3-(4-(8-hydroxy-6-methyl-4-oxo-4,5-dihydrothieno[2,3-c]quinolin-9-yl)phenyl)
0.092



propanenitrile



1228
9-(4-(1-amino-2-methylpropan-2-yl)phenyl)-8-hydroxy-6-methylthieno[2,3-c]
0.039



quinolin-4(5H)-one hydrochloride



1232
(S)-9-(4-(1-aminopropan-2-yl)phenyl)-8-hydroxy-6-methylthieno[2,3-c]quinolin-
0.016



4(5H)-one hydrochloride



1236
9-(4-(2-amino-1-cyclopentylethyl)phenyl)-8-hydroxythieno[2,3-c]quinolin-4(5H)-
0.0046



one



1239
9-(4-(2-amino-1-cyclopentylethyl)phenyl)-8-methoxythieno[2,3-c]quinolin-4(5H)-
0.023



one hydrochloride



1242
9-(4-(2-aminopropyl)phenyl)-8-hydroxy-6-methylthieno[2,3-c]quinolin-4(5H)-
0.037



one hydrochloride



1245
6-bromo-9-(3-fluoro-4-(2-(methylamino)ethyl)phenyl)-8-hydroxythieno[2,3-c]
0.045



quinolin-4(5H)-one hydrochloride



1247
9-(4-(1-amino-2-methylpropan-2-yl)phenyl)-6-bromo-8-hydroxythieno[2,3-c]
0.072



quinolin-4(5H)-one hydrochloride



1251
9-(4-(1-(aminomethyl)cyclopropyl)phenyl)-8-methoxy-6-methylthieno[2,3-c]
0.055



quinolin-4(5H)-one hydrochloride



1252
9-(4-(1-amino-3-methylbutan-2-yl)phenyl)-8-hydroxythieno[2,3-c]quinolin-4
0.0014



(5H)-one



1253
9-(4-(1-amino-3-methylbutan-2-yl)phenyl)-8-methoxythieno[2,3-c]quinolin-4
0.0041



(5H)-one hydrochloride



1254
9-(4-(1-(aminomethyl)cyclopropyl)phenyl)-8-hydroxy-6-methylthieno[2,3-c]
0.0096



quinolin-4(5H)-one hydrochloride



1258
9-(3-fluoro-4-(2-(methylamino)ethyl)phenyl)-8-hydroxy-6-methylthieno[2,3-c]
0.025



quinolin-4(5H)-one hydrochloride



1260
9-(4-(1-amino-2-methylpropan-2-yl)phenyl)-6-chloro-8-hydroxythieno[2,3-c]
0.075



quinolin-4(5H)-one hydrochloride



1262
(R)-8-hydroxy-6-methyl-9-(4-(1-(methylamino)ethyl)phenyl)thieno[2,3-c]
0.012



quinolin-4(5H)-one hydrochloride



1263
9-(4-(2-aminoethyl)-3-chlorophenyl)-8-methoxy-6-methylthieno[2,3-c]quinolin-
0.033



4(5H)-one hydrochloride



1264
9-(4-(2-aminoethyl)-3-chlorophenyl)-8-hydroxy-6-methylthieno[2,3-c]quinolin-
0.003



4(5H)-one hydrochloride



1265
(R)-8-methoxy-6-methyl-9-(4-(1-(methylamino)ethyl)phenyl)thieno[2,3-c]
0.067



quinolin-4(5H)-one hydrochloride



1268
9-(4-(2-aminoethyl)-3-chlorophenyl)-6-chloro-8-hydroxythieno[2,3-c]quinolin-
0.0039



4(5H)-one hydrochloride



1271
9-(4-(1-amino-2-methylpropan-2-yl)-3-fluorophenyl)-8-hydroxythieno[2,3-c]
0.001



quinolin-4(5H)-one hydrochloride



1273
9-(4-(1-aminopropan-2-yl)-3-fluorophenyl)-8-methoxy-6-methylthieno[2,3-c]
0.04



quinolin-4(5H)-one hydrochloride



1274
9-(4-(1-amino-3-methylbutan-2-yl)phenyl)-8-hydroxy-6-methylthieno[2,3-c]
0.018



quinolin-4(5H)-one



1277
9-(4-(1-aminobutan-2-yl)phenyl)-8-methoxy-6-methylthieno[2,3-c]quinolin-4
0.063



(5H)-one hydrochloride



1278
9-(4-(1-amino-2-methylpropan-2-yl)-3-fluorophenyl)-8-hydroxy-6-methylthieno
0.022



[2,3-c]quinolin-4(5H)-one hydrochloride



1280
9-(4-(1-aminopropan-2-yl)-3-chlorophenyl)-8-hydroxythieno[2,3-c]quinolin-4
0.01



(5H)-one hydrochloride



1283
9-(4-(1-amino-3-methylbutan-2-yl)-3-fluorophenyl)-8-methoxy-6-methylthieno
0.047



[2,3-c]quinolin-4(5H)-one hydrochloride



1285
8-hydroxy-6-methyl-9-(4-(3-methyl-1-(methylamino)butan-2-yl)phenyl)thieno
0.05



[2,3-c]quinolin-4(5H)-one



1286
9-(3-fluoro-4-(1-(methylamino)propan-2-yl)phenyl)-8-methoxy-6-methylthieno
0.043



[2,3-c]quinolin-4(5H)-one hydrochloride



1288
9-(4-(1-amino-3-methylbutan-2-yl)-3-fluorophenyl)-8-hydroxy-6-methylthieno
0.02



[2,3-c]quinolin-4(5H)-one



1290
9-(4-(1-(aminomethyl)cyclobutyl)phenyl)-8-hydroxy-6-methylthieno[2,3-c]
0.01



quinolin-4(5H)-one hydrochloride



1291
9-(4-(1-aminobutan-2-yl)phenyl)-8-hydroxy-6-methylthieno[2,3-c]quinolin-4
0.015



(5H)-one hydrochloride



1293
9-(3-fluoro-4-(1-(methylamino)propan-2-yl)phenyl)-8-hydroxy-6-methylthieno
0.0089



[2,3-c]quinolin-4(5H)-one



1294
9-(3-fluoro-4-(3-methyl-1-(methylamino)butan-2-yl)phenyl)-8-hydroxy-6-
0.017



methylthieno[2,3-c]quinolin-4(5H)-one



1297
9-(4-(1-(aminomethyl)cyclobutyl)phenyl)-8-methoxy-6-methylthieno[2,3-c]
0.035



quinolin-4(5H)-one hydrochloride



1298
(R)-8-methoxy-6-methyl-9-(4-(1-(methylamino)propan-2-yl)phenyl)thieno[2,3-c]
0.032



quinolin-4(5H)-one hydrochloride



1300
9-(4-(1-(aminomethyl)cyclobutyl)phenyl)-8-hydroxythieno[2,3-c]quinolin-4
0.0017



(5H)-one hydrochloride



1302
8-hydroxy-6-methyl-9-(4-(piperidin-3-yl)phenyl)thieno[2,3-c]quinolin-4(5H)-
0.075



one hydrochloride



1303
(S)-9-(4-(1-aminopropan-2-yl)-3-fluorophenyl)-8-hydroxy-6-methylthieno[2,3-c]
0.014



quinolin-4(5H)-one



1304
(S)-9-(4-(1-aminopropan-2-yl)-3-fluorophenyl)-8-hydroxy-6-methylthieno[2,3-c]
0.013



quinolin-4(5H)-one hydrobromide



1305
(R)-9-(4-(1-aminopropan-2-yl)phenyl)-8-methoxy-6-methylthieno[2,3-c]
0.015



quinolin-4(5H)-one hydrochloride



1306
(R)-8-hydroxy-6-methyl-9-(4-(1-(methylamino)propan-2-yl)phenyl)thieno[2,3-c]
0.0073



quinolin-4(5H)-one hydrochloride



1307
(R)-8-hydroxy-6-methyl-9-(4-(1-(methylamino)propan-2-yl)phenyl)thieno[2,3-c]
0.018



quinolin-4(5H)-one hydrobromide



1309
9-(4-(1-aminobutan-2-yl)phenyl)-8-hydroxythieno[2,3-c]quinolin-4(5H)-one
0.00074



hydrochloride



1310
(S)-9-(4-(1-aminopropan-2-yl)-3-fluorophenyl)-8-methoxy-6-methylthieno[2,3-c]
0.054



quinolin-4(5H)-one hydrochloride



1311
(R)-9-(4-(1-(dimethylamino)propan-2-yl)-3-fluorophenyl)-8-hydroxy-6-
0.017



methylthieno[2,3-c]quinolin-4(5H)-one hydrochloride



1312
9-(4-(1-aminobutan-2-yl)phenyl)-6-chloro-8-hydroxythieno[2,3-c]quinolin-4(5H)-
0.019



one hydrochloride



1315
(R)-9-(3-fluoro-4-(1-(methylamino)propan-2-yl)phenyl)-8-hydroxy-6-
0.0081



methylthieno[2,3-c]quinolin4(5H)-one hydrochloride



1316
(R)-9-(3-fluoro-4-(1-(methylamino)propan-2-yl)phenyl)-8-methoxy-6-
0.033



methylthieno[2,3-c]quinolin-4(5H)-one hydrochloride



1317
(R)-9-(4-(1-aminopropan-2-yl)-3-fluorophenyl)-8-methoxy-6-methylthieno[2,3-c]
0.022



quinolin-4(5H)-one hydrochloride



1318
(R)-9-(4-(1-aminopropan-2-yl)-3-fluorophenyl)-8-hydroxy-6-methylthieno[2,3-c]
0.0036



quinolin-4(5H)-one hydrochloride



1319
(R)-9-(4-(1-aminopropan-2-yl)-3-fluorophenyl)-8-hydroxy-6-methylthieno[2,3-c]
0.0034



quinolin-4(5H)-one hydrobromide



1321
9-(4-(1-(aminomethyl)cyclobutyl)phenyl)-6-chloro-8-methoxythieno[2,3-c]
0.096



quinolin-4(5H)-one hydrochloride



1324
(R)-9-(4-(1-(dimethylamino)propan-2-yl)phenyl)-8-hydroxy-6-methylthieno
0.032



[2,3-c]quinolin-4(5H)-one hydrochloride



1330
9-(4-(2-aminopropan-2-yl)phenyl)-8-hydroxy-6-methylthieno[2,3-c]quinolin-4
0.0083



(5H)-one hydrochloride



1340
(R)-9-(4-(1-aminopropan-2-yl)phenyl)-8-hydroxy-2,6-dimethylthieno[2,3-c]
0.012



quinolin-4(5H)-one hydrochloride



1341
(R)-9-(4-(1-aminopropan-2-yl)phenyl)-8-methoxy-2,6-dimethylthieno[2,3-c]
0.038



quinolin-4(5H)-one hydrochloride



1347
(R)-6-chloro-9-(4-(1-(dimethylamino)propan-2-yl)phenyl)-8-hydroxythieno
0.043



[2,3-c]quinolin-4(5H)-one hydrochloride



1352
(R)-9-(4-(1-aminobutan-2-yl)phenyl)-8-hydroxy-6-methylthieno[2,3-c]
0.04



quinolin-4(5H)-one hydrochloride



1353
(R)-9-(4-(1-aminopropan-2-yl)phenyl)-2-chloro-8-hydroxy-6-methylthieno[2,3-c]
0.004



quinolin-4(5H)-one hydrochloride



1354
(R)-9-(4-(1-aminopropan-2-yl)phenyl)-2-chloro-8-methoxy-6-methylthieno
0.011



[2,3-c]quinolin-4(5H)-one hydrochloride



1364
8-hydroxy-6-methyl-9-(4-(2-(methylamino)ethyl)phenyl)thieno[2,3-c]quinolin-4
0.055



(5H)-one hydrochloride



1372
9-(4-(1-((dimethylamino)methyl)cyclobutyl)phenyl)-8-hydroxy-6-methylthieno
0.042



[2,3-c]quinolin-4(5H)-one hydrochloride



1375
(R)-9-(4-(1-aminopropan-2-yl)phenyl)-2-fluoro-8-methoxy-6-methylthieno[2,3-c]
0.022



quinolin-4(5H)-one hydrochloride



1379
(R)-9-(4-(1-(ethyl(methyl)amino)propan-2-yl)phenyl)-8-hydroxy-6-methylthieno
0.076



[2,3-c]quinolin-4(5H)-one hydrochloride



1380
(R)-8-hydroxy-6-methyl-9-(4-(1-(methylamino)butan-2-yl)phenyl)thieno[2,3-c]
0.085



quinolin-4(5H)-one hydrochloride



1383
(R)-9-(4-(1-aminopropan-2-yl)phenyl)-2-fluoro-8-hydroxy-6-methylthieno[2,3-c]
0.0037



quinolin-4(5H)-one hydrochloride



1391
9-(4-(1-(aminomethyl)cyclopropyl)phenyl)-6-bromo-8-methoxythieno[2,3-c]
0.07



quinolin-4(5H)-one hydrochloride



1399
(S)-9-(4-(1-(dimethylamino)propan-2-yl)-3-fluorophenyl)-8-hydroxy-6-
0.058



methylthieno[2,3-c]quinolin-4(5H)-one hydrochloride



1400
9-(4-((2-aminoethyl)(methyl)amino)phenyl)-8-hydroxy-6-methylthieno[2,3-c]
0.06



quinolin-4(5H)-one hydrochloride



1401
9-(4-(1-(aminomethyl)cyclopropyl)phenyl)-6-bromo-8-hydroxythieno[2,3-c]
0.051



quinolin-4(5H)-one hydrochloride



1419
2-(4-(8-hydroxy-6-methyl-4-oxo-4,5-dihydrothieno[2,3-c]quinolin-9-yl)phenyl)
0.082



propane-1-sulfonamide









Examples 508
Western Blot Analysis

To evaluate the expression status of PBK in several cell lines, western blot analysis was performed using crude cell lysate collected from those cells. Anti-PBK antibody (clone 31, BD Biosciences) was used to visualize the expression. Breast cancer cell lines, T47D and BT-549 expressed PBK significantly although Bladder cancer cell line and HT-1197 showed no expression of PBK.


Examples 509
Cell-Based Assay

Active candidate inhibitors against PBK were evaluated for their target-specific cytotoxicity using T47D, A549, BT-549, and HT-1197 cells was used for negative control. 100 micro-L of cell suspension was seeded onto 96-well microtiter plate (ViewPlate-96FTC, PerkinElmer). The initial cell concentration of T47D, BT-549 and HT-1197 were 3,000 cells/well, 2,000 cells/well and 2,500 cells/well, respectively. Cellular growth was determined using Cell Counting Kit-8 (DOJINDO) at 72 hours after the exposure of the candidate inhibitors. IC50 was used as an indicator of the anti-proliferative activity of the inhibitors, and calculated by serial dilution method (0, 1.5625, 3.125, 6.25, 12.5, 25, 50, and 100 micro-M). Accurate IC50 values were calculated as described previously.


IC50 values of the typical compounds of the present invention are shown in following table 3:














TABLE 3









IC50
IC50
IC50
IC50




(microM)
(microM)
(microM)
(microM)


ID
Compound
(BT549)
(T47D)
(A549)
(HT1197)





51
(S)-8-(3-Aminopyrrolidin-1-yl)-2-
14
2.1
21
62



(4-hydroxyphenyl)thieno[2,3-



c]quinolin-4(5H)-one Dihydrochloride


61
8-Hydroxy-9-(1H-indazol-6-
1.8
3.7
2.6
5.1



yl)thieno[2,3-c]quinolin-4(5H)-one


65
4-(8-Hydroxy-4-oxo-4,5-dihydrothieno[2,3-
3.3
4.4
100
100



c]quinolin-9-yl)benzenesulfonamide


72
9-[4-(Aminomethyl)phenyl]-8-
1.1
1.2
3.2
12



hydroxythieno[2,3-c]quinolin-4(5H)-one


73
9-[4-(Aminomethyl)phenyl]-8-hydroxy-
0.67
0.65
1.2
11



thieno[2,3-c]quinolin-4(5H)-one Hydrochloride


77
N-[4-(8-Hydroxy-4-oxo-4,5-dihydrothieno[2,3-
7.9
3.2
46
100



c]quinolin-9-yl)phenyl]methanesulfonamide


81
2-[4-(8-Hydroxy-4-oxo-4,5-dihydrothieno[2,3-
3.5
6.2
7.7
27



c]quinolin-9-yl)phenyl]acetonitrile


84
8-Hydroxy-9-(1,2,3,6-tetrahydropyridin-
5.4
4.8
11
7.1



4-yl)thieno[2,3-c]quinolin-4(5H)-one


93
9-{4-[2-(Dimethylamino)ethyl]phenyl}-
2.5
4.7
3
7



8-hydroxythieno[2,3-c]quinolin-4(5H)-one


95
9-[4-(Aminomethyl)phenyl]-8-hydroxy-2-
4.1
2.9
8.1
22



methylthieno[2,3-c]quinolin-4(5H)-one


112
8-Hydroxy-9-{4-[4-(methylsulfonyl)piperazin-
3.9
6.9
6.6
6.8



1-yl]phenyl}thieno[2,3-c]quinolin-4(5H)-one


139
tert-Butyl {1-[4-(8-Methoxy-4-oxo-4,5-
3.8
4.3
5
3.9



dihydrothieno[2,3-c]quinolin-9-



yl)benzyl]piperidin-4-yl}methylcarbamate


145
9-(4-{3-[2-(Diethylamino)ethyl-
7.7
4.8
8.2
9.2



amino]propoxy}phenyl)-8-methoxythieno[2,3-



c]quinolin-4(5H)-one


152
(E)-9-[3-(4-Aminopiperidin-1-yl)
5.8
4.4
12
6.5



prop-1-enyl]-8-methoxythieno[2,3-



c]quinolin-4(5H)-one


164
9-{4-[(Dimethylamino)methyl]phenyl}-8-
2.9
4.9
2.4
7



methoxythieno[2,3-c]quinolin-4(5H)-one


165
9-{4-[(Dimethylamino)methyl]phenyl}-8-
3.2
6.2
3
6.5



hydroxythieno[2,3-c]quinolin-4(5H)-one


169
9-[4-(2-Aminoethyl)phenyl]-8-me-
2.4
4.2
3.7
6.1



thoxythieno[2,3-c] quinolin-4(5H)-one


175
9-[4-(2-Aminoethyl)phenyl]-8-hydroxy-
0.7
0.67
0.85
1.5



thieno[2,3-c]quinolin-4(5H)-one


176
9-[4-(2-Aminoethyl)phenyl]-8-hydroxy-
0.64
0.49
0.64
1.1



thieno[2,3-c]quinolin-4(5H)-one Hydrochloride


184
9-{4-[(Diethylamino)methyl]phenyl}-8-
2.9
6.1
2.7
7.1



hydroxythieno[2,3-c]quinolin-4(5H)-one


187
8-Hydroxy-9-{4-[(methyl-
1.3
1.4
1.6
2



amino)methyl]phenyl}thieno[2,3-



c]quinolin-4(5H)-one


188
8-Methoxy-9-{4-[(methyl-
3.5
7.9
3.8
8



amino)methyl]phenyl}thieno[2,3-



c]quinolin-4(5H)-one


192
9-(4-(1-(dimethylamino)ethyl)phenyl)-8-
0.34
0.67
0.3
0.66



hydroxythieno[2,3-c]quinolin-4(5H)-one



Hydrochloride


191
9-{4-[1-(Dimethylamino)ethyl]phenyl}-8-
0.4
0.78
0.35
0.87



hydroxythieno[2,3-c]quinolin-4(5H)-one


193
N-{1-[4-(8-Hydroxy-4-oxo-4,5-di-
2.4
1.7
13
39



hydrothieno[2,3-c]quinolin-9-



yl)phenyl]ethyl}methanesulfonamide


194
8-Hydroxy-9-{4-[1-(pyrrolidin-1-
0.46
1
0.49
1.2



yl)ethyl]phenyl}thieno[2,3-c]quinolin-



4(5H)-one Hydrochloride


195
9-[4-(1-Aminoethyl)phenyl]-8-
0.37
0.4
0.61
2.4



hydroxythieno[2,3-c]quinolin-4(5H)-



one Hydrochloride


196
9-{4-[1-(Diethylamino)ethyl]phenyl}-8-
1.1
2.3
1
2.7



hydroxythieno[2,3-c]quinolin-4(5H)-one



Hydrochloride


210
N-(2-Bromoethyl)-4-(8-hydroxy-4-oxo-4,5-
0.006
0.25
0.028
14



dihydrothieno[2,3-c]quinolin-9-



yl)benzenesulfonamide


212
N-[4-(8-Hydroxy-4-oxo-4,5-dihydro-
5.5
1.4
17
40



thieno[2,3-c]quinolin-9-yl)benzyl]methane-



sulfonamide


216
8-Methoxy-9-{4-[1-(pyrrolidin-1-
2.9
5.8
2.6
7.4



yl)ethyl]phenyl}thieno[2,3-c]quinolin-



4(5H)-one Hydrochloride


217
9-(4-Amino-3-hydroxyphenyl)-8-
2.8
6.8
5.6
48



hydroxythieno[2,3-c]quinolin-4(5H)-one



Hydrochloride


222
9-{4-[1-(Dimethylamino)ethyl]phenyl}-
3.8
7
3.5
8.7



6-fluoro-8-methoxythieno[2,3-c]quinolin-



4(5H)-one Hydrochloride


225
9-{4-[2-(Dimethylamino)ethyl]phenyl}-
1.2
3
1.2
3.4



6-fluoro-8-hydroxythieno[2,3-c]quinolin-



4(5H)-one


229
8-Hydroxy-9-{4-[(isopropyl-
1.9
4
2.1
4.2



amino)methyl]phenyl}thieno[2,3-



c]quinolin-4(5H)-one Hydrochloride


232
(S)-9-[4-(1-Aminoethyl)phenyl]-8-me-
2.1
5
2
7.3



thoxythieno[2,3-c]quinolin-4(5H)-one



Hydrochloride


233
(S)-9-[4-(1-Aminoethyl)phenyl]-8-
0.28
0.38
0.36
1.1



hydroxythieno[2,3-c]quinolin-4(5H)-one



Hydrochloride


235
9-(4-{[4-(Aminomethyl)piperidin-1-
3.2
2.2
7.1
10



yl]methyl}-3-fluorophenyl)-8-



hydroxythieno[2,3-c]quinolin-4(5H)-one


254
N-[4-(8-Hydroxy-4-oxo-4,5-dihydro-
4.8
5.2
14
32



thieno[2,3-c]quinolin-9-yl)-2-methyl-



phenyl]methanesulfonamide


256
9-[4-(Aminomethyl)phenyl]-6-fluoro-8-
0.57
0.99
0.75
3.3



hydroxythieno[2,3-c]quinolin-4(5H)-one



Hydrochloride


257
9-[4-(Aminomethyl)phenyl]-6-fluoro-8-
3.4
8.2
3.7
100



methoxythieno[2,3-c]quinolin-4(5H)-



one Hydrochloride


261
2-[2-Fluoro-4-(8-hydroxy-4-oxo-4,5-
0.69
1.1
1.3
6.6



dihydrothieno[2,3-c]quinolin-9-



yl)phenyl]acetonitrile


262
8-Hydroxy-9-{4-[1-(piperidin-1-
1.2
2.7
1
2.6



yl)ethyl]phenyl}thieno[2,3-c]quinolin-



4(5H)-one Hydrochloride


265
9-[4-(2-Aminoethyl)-3-fluorophenyl]-8-
3
5.6
4.4
7.7



methoxythieno[2,3-c]quinolin-4(5H)-one



Hydrochloride


266
9-[5-(Aminomethyl)thiophen-2-yl]-8-
1.3
1.5
2.7
13



hydroxythieno[2,3-c]quinolin-4(5H)-one


267
9-{4-[(Ethylamino)methyl]phenyl}-8-
1.9
3.1
2
3.3



hydroxythieno[2,3-c]quinolin-4(5H)-one



Hydrochloride


269
9-{4-[(Ethylamino)methyl]phenyl}-8-
3
6.9
2.3
6.7



methoxythieno[2,3-c]quinolin-4(5H)-one



Hydrochloride


270
9-[4-(Aminomethyl)phenyl]-6-bromo-8-
0.36
0.65
0.44
2.4



hydroxythieno[2,3-c]quinolin-4(5H)-one



Hydrochloride


272
(R)-9-{4-[1-Dimethylamino)ethyl]phenyl}-
0.19
0.36
0.17
0.49



8-hydroxythieno[2,3-c]quinolin-4(5H)-one



Hydrochloride


273
9-[4-(3-Aminopropyl)phenyl]-8-hydroxy-
3.8
2.1
6.4
5.3



thieno[2,3-c]quinolin-4(5H)-one Hydrochloride


274
(R)-9-[4-(1-Aminoethyl)phenyl]-8-
1.3
2.8
1.6
5.1



methoxythieno[2,3-c]quinolin-4(5H)-one



Hydrochloride


275
(R)-9-[4-(1-Aminoethyl)phenyl]-8-
0.32
0.34
0.57
5.2



hydroxythieno[2,3-c] quinolin-4(5H)-one



Hydrochloride


276
9-[4-(2-Aminoethyl)-3-fluorophenyl]-8-
0.81
0.57
1.3
2.1



hydroxythieno[2,3-c]quinolin-4(5H)-one



Hydrochloride


277
9-[4-(1-Amino-2-methylpropan-2-yl)phenyl]-
0.53
0.74
0.69
2.1



8-hydroxythieno[2,3-c]quinolin-4(5H)-one



Hydrochloride


278
9-{3-Fluoro-4-[(3-hydroxypyrrolidin-1-
2.5
2.7
5
10



yl)methyl]phenyl}-8-hydroxythieno[2,3-



c]quinolin-4(5H)-one Hydrochloride


290
3-[4-(8-Hydroxy-4-oxo-4,5-dihydrothieno[2,3-
0.63
0.96
0.76
2.8



c]quinolin-9-yl)phenyl]propanenitrile


296
9-(4-Acetylphenyl)-8-hydroxythieno[2,3-
5.4
7.4
3.5
14



c]quinolin-4(5H)-one


297
N-(2-Bromoethyl)-2-fluoro-4-(8-hydroxy-4-oxo-
0.21
1.2
0.47
32



4,5-dihydrothieno[2,3-c]quinolin-9-



yl)benzenesulfonamide


298
9-{3-[3-(Dimethylamino)piperidin-1-
6.2
6.9
4.4
11



yl]propyl}-8-hydroxythieno[2,3-



c]quinolin-4(5H)-one Dihydrochloride


301
(R)-N-{1-[4-(8-Hydroxy-4-oxo-4,5-
7.2
3
14
28



dihydrothieno[2,3-c]quinolin-9-



yl)phenyl]ethyl}methanesulfonamide


304
4-(8-Hydroxy-4-oxo-4,5-dihydrothieno[2,3-
4.6
6.9
5.2
100



c]quinolin-9-yl)-N,N-dimethylbenzene-



sulfonamide


308
9-{4-[1-(Dimethylamino)-2-methylpropan-2-
1.8
3.8
1.4
4.2



yl]phenyl}-8-hydroxythieno[2,3-



c]quinolin-4(5H)-one Hydrochloride


313
8-Hydroxy-9-[4-(1-hydroxy-
1.7
3
2.6
11



ethyl)phenyl]thieno[2,3-c]quinolin-



4(5H)-one


314
9-{4-[1-(Cyclopentylamino)ethyl]
1.9
4.1
1.5
3.7



phenyl}-8-hydroxythieno[2,3-c]quinolin-



4(5H)-one Hydrochloride


319
9-[4-(2-Aminopropan-2-yl)phenyl]-8-
0.55
0.9
0.64
2.3



hydroxythieno[2,3-c]quinolin-4(5H)-



one Hydrochloride


326
9-[4-(Aminomethyl)phenyl]-4-oxo-4,5-
4.3
5.9
7.9
10



dihydrothieno[2,3-c]quinoline-8-



carbonitrile Hydrochloride


327
9-{4-[2-(Dimethylamino)ethyl]-3-
3.3
6.4
3.7
7.8



fluorophenyl}-8-hydroxythieno[2,3-



c]quinolin-4(5H)-one Hydrochloride


329
9-[4-(Aminomethyl)phenyl]-6-chloro-8-
0.32
0.63
0.36
1.4



hydroxythieno[2,3-c]quinolin-4(5H)-



one Hydrochloride


332
N-(2-Chloroethyl)-4-(8-hydroxy-4-oxo-4,5-
0.012
0.31
0.034
24



dihydrothieno[2,3-c]quinolin-9-



yl)benzenesulfonamide


333
N-(2-Fluoroethyl)-4-(8-methoxy-4-oxo-4,5-
2.5
9.3
2
24



dihydrothieno[2,3-c]quinolin-9-



yl)benzenesulfonamide


334
9-[4-(2-Aminopropan-2-yl)phenyl]-6-chloro-8-
0.48
1.1
0.49
1.3



hydroxythieno[2,3-c]quinolin-4(5H)-one



Hydrochloride


335
(S)-9-{4-[1-(Dimethylamino)ethyl]phenyl}-
1.1
2.4
1.2
3.3



8-hydroxythieno[2,3-c]quinolin-4(5H)-one



Hydrochloride


336
9-[4-(1-Aminopropyl)phenyl]-8-hydroxy-
0.21
0.35
0.32
0.97



thieno[2,3-c]quinolin-4(5H)-one Hydrochloride


337
9-[4-(1-Aminopropyl)phenyl]-8-
1.5
3.4
1.4
3.9



methoxythieno[2,3-c]quinolin-4(5H)-one



Hydrochloride


338
9-{4-[1-(Diethylamino)propyl]phenyl}-8-
2
7.1
1.8
4.5



hydroxythieno[2,3-c]quinolin-4(5H)-one



Hydrochloride


339
9-{4-[1-(Dimethylamino)propyl]phenyl}-8-
0.35
0.79
0.36
0.98



hydroxythieno[2,3-c]quinolin-4(5H)-one



Hydrochloride


341
9-{4-[1-(Dimethylamino)ethyl]phenyl}-6,7-
1.4
2.9
1.5
3.3



difluoro-8-hydroxythieno[2,3-c]quinolin-4(5H)-



one Hydrochloride


345
9-(2-Amino-2,3-dihydro-1H-inden-5-yl)-8-
3.1
4.4
5.7
7.1



hydroxythieno[2,3-c]quinolin-4(5H)-one



Hydrochloride


346
9-{4-[1-(Dimethyl-
2.5
7.2

6.8



amino)ethyl]phenyl}thieno[2,3-c]quinolin-



4(5H)-one


347
(S)-N-{1-[4-(8-Hydroxy-4-oxo-4,5-
1
0.75
5.6
29



dihydrothieno[2,3-c]quinolin-9-



yl)phenyl]ethyl}methanesulfonamide


348
9-{4-[1-(Aminomethyl)cyclopropyl]phenyl}-
0.31
3.2
0.38
1.2



8-hydroxythieno[2,3-c]quinolin-4(5H)-



one Hydrochloride


349
9-{4-[1-(Dimethylamino)ethyl]-3-
0.58
1.3
0.48
1.3



fluorophenyl}-8-hydroxythieno[2,3-



c]quinolin-4(5H)-one Hydrochloride


353
8-Hydroxy-9-(1,2,3,4-tetrahydroisoquinolin-7-
1.9
3.7
3.2
4.2



yl)thieno[2,3-c]quinolin-4(5H)-one



Hydrochloride


356
9-{4-[1-(Diethylamino)ethyl]-3-fluoro-
1.5
3.3
1.3
3.5



phenyl}-8-hydroxythieno[2,3-c]quinolin-



4(5H)-one Hydrochloride


359
9-[4-(1-Aminoethyl)-3-fluorophenyl]-8-
0.35
0.64
0.62
4



hydroxythieno[2,3-c]quinolin-4(5H)-one



Hydrochloride


361
1-[4-(8-Hydroxy-4-oxo-4,5-dihydrothieno[2,3-
0.94
2.5
0.96
2.7



c]quinolin-9-yl)phenyl]cyclopropanecarbonitrile


















IC50
IC50
IC50
IC50
IC50




(microM)
(microM)
(microM)
(microM)
(microM)


ID
Compound
(BT549)
(T47D)
(A549)
(HT1197)
(22Rv1)





373
9-(4-(1-aminopropan-2-yl)phenyl)-8-
0.46
0.82
0.58
1.5




methoxythieno[2,3-c]quinolin-



4(5H)-one hydrochloride


379
9-(4-(1-((dimethylamino)methyl)cyclo-
0.52
1
0.46
1.4




propyl)phenyl)-8-hydroxythieno[2,3-



c]quinolin-4(5H)-one hydrochloride


385
9-(4-(1-(ethylamino)ethyl)phenyl)-8-
0.8
1.8
0.94
2.6




hydroxythieno[2,3-c]quinolin-



4(5H)-one hydrochloride


1032
9-(4-(1-aminoethyl)phenyl)-6-bromo-8-
0.27
0.53
0.3
1.2




hydroxythieno[2,3-c]quinolin-



4(5H)-one hydrochloride


1041
9-(4-(1-aminoethyl)phenyl)-6-chloro-
0.19
0.34
0.16
0.65




8-hydroxythieno[2,3-c]quinolin-



4(5H)-one hydrochloride


1052
(R)-8-hydroxy-9-(4-(1-(methyl-
0.17
0.32
0.17
0.45




amino)ethyl)phenyl)thieno[2,3-



c]quinolin-4(5H)-one hydrochloride


1062
N-(1-bromopropan-2-yl)-4-(8-hydroxy-
0.15
1.9
0.88
12




4-oxo-4,5-dihydrothieno[2,3-



c]quinolin-9-yl)benzenesulfonamide


1064
(S)-8-methoxy-9-(4-(1-(methyl-
1
2.2
0.89
2.9




amino)ethyl)phenyl)thieno[2,3-



c]quinolin-4(5H)-one hydrochloride


1066
9-(4-(1-aminoethyl)phenyl)-8-hydroxy-
0.065
0.13
0.12
0.34




6-methylthieno[2,3-c]quinolin-



4(5H)-one hydrochloride


1077
9-(4-(1-aminoethyl)phenyl)-4-oxo-4,5-
0.41
0.45
0.66
2.5




dihydrothieno[2,3-c]quinolin-8-



yl isopropyl carbonate hydrochloride


1081
(R)-9-(4-(1-aminoethyl)phenyl)-6-
0.086
0.17
0.1
0.39




chloro-8-hydroxythieno[2,3-



c]quinolin-4(5H)-one hydrochloride


1082
(S)-8-hydroxy-9-(4-(1-(methyl-
0.36
0.6
0.43
1




amino)ethyl)phenyl)thieno[2,3-



c]quinolin-4(5H)-one hydrochloride


1087
(S)-6-chloro-8-hydroxy-9-(4-(1-(methyl-
0.23
0.5
0.26
0.66




amino)ethyl)phenyl)thieno[2,3-



c]quinolin-4(5H)-one hydrochloride


1088
9-(4-(1-aminopropyl)phenyl)-6-chloro-
0.24
0.52
0.24
0.66




8-hydroxythieno[2,3-c]quinolin-



4(5H)-one hydrochloride


1094
N-(2-bromoethyl)-4-(8-hydroxy-4-oxo-
0.0071
0.29
0.028
21




2,3,4,5-tetrahydro-1H-cyclo-



penta[c]quinolin-9-yl)benzene-



sulfonamide


1095
9-(4-(2-aminopropyl)phenyl)-8-
0.81
0.54
0.95
0.93




hydroxythieno[2,3-c]quinolin-



4(5H)-one hydrochloride


1099
9-(4-(1-aminoethyl)phenyl)-4-oxo-4,5-
0.46
0.37
0.54
1.9




dihydrothieno[2,3-c]quinolin-8-



yl acetate hydrochloride


1106
9-(4-(2-aminopropyl)phenyl)-6-chloro-
0.13
0.26
0.15
0.62




8-hydroxythieno[2,3-c]quinolin-



4(5H)-one hydrochloride


1111
9-(4-(1-aminopropan-2-yl)phenyl)-8-
0.12
0.072
0.12
0.37




hydroxythieno[2,3-c]quinolin-



4(5H)-one hydrochloride


1112
9-(4-(1-(dimethylamino)propan-2-
0.21
0.47
0.25
0.64




yl)phenyl)-8-hydroxythieno[2,3-



c]quinolin-4(5H)-one hydrochloride


1116
9-(4-(1-(aminomethyl)cyclo-
0.098
0.17
0.12
0.54




propyl)phenyl)-6-chloro-8-hydroxy-



thieno[2,3-c]quinolin-4(5H)-one



hydrochloride


1120
(S)-9-(4-(1-aminopropyl)phenyl)-8-
0.093
0.15
0.13
0.33




hydroxythieno[2,3-c]quinolin-



4(5H)-one hydrochloride


1121
(S)-9-(4-(1-aminopropyl)phenyl)-8-
0.42
0.7
0.36
1.5




methoxythieno[2,3-c]quinolin-



4(5H)-one hydrochloride


1122
(R)-9-(4-(1-aminoethyl)phenyl)-8-

0.065
0.049
0.17
0.065



hydroxy-6-methylthieno[2,3-



c]quinolin-4(5H)-one hydrochloride


1123
(R)-9-(4-(1-aminoethyl)phenyl)-6-
0.18
0.34
0.16
0.76




bromo-8-hydroxythieno[2,3-



c]quinolin-4(5H)-one hydrochloride


1126
(R)-6-chloro-9-(4-(1-(dimethyl-
0.14
0.29
0.11
0.32




amino)ethyl)phenyl)-8-hydroxy-



thieno [2,3-c]quinolin-4(5H)-one



hydrochloride


1127
(S)-9-(4-(1-(ethylamino)propyl)phenyl)-
0.3
0.63
0.22
0.65




8-hydroxythieno[2,3-c]quinolin-



4(5H)-one hydrochloride


1128
(S)-9-(4-(1-(dimethyl-
0.43
1
0.37
1.2




amino)propyl)phenyl)-8-hydroxy-



thieno[2,3-c]quinolin-4(5H)-one



hydrochloride


1131
(R)-9-(4-(1-aminopropyl)phenyl)-8-
0.51
0.71
0.68
4.8




hydroxythieno[2,3-c]quinolin-



4(5H)-one hydrochloride


1132
(R)-6-chloro-8-hydroxy-9-(4-(1-
0.097
0.19
0.09
0.32




(methylamino)ethyl)phenyl)thieno [2,3-



c]quinolin-4(5H)-one hydrochloride


1133
9-(4-(2-aminoethyl)phenyl)-6-chloro-8-
0.15
0.23
0.18
0.87




hydroxythieno[2,3-c]quinolin-



4(5H)-one hydrochloride


1135
(R)-6-bromo-8-hydroxy-9-(4-(1-
0.14
0.28
0.13
0.41




(methylamino)ethyl)phenyl)thieno[2,3-



c]quinolin-4(5H)-one hydrochloride


1136
9-(4-(1-aminopropan-2-yl)phenyl)-6-
0.032
0.057
0.035
0.18




chloro-8-hydroxythieno[2,3-



c]quinolin-4(5H)-one hydrochloride


1139
N-(2-chloroethyl)-4-(8-methoxy-4-oxo-
0.017
0.2
0.023
14




4,5-dihydrothieno[2,3-c]quinolin-



9-yl)benzenesulfonamide


1142
9-(4-(2-aminoethyl)phenyl)-6-bromo-8-
0.17
0.25
0.21
1




hydroxythieno[2,3-c]quinolin-



4(5H)-one hydrochloride


1145
N-(2-chloroethyl)-4-(8-hydroxy-4-oxo-
0.01
0.18
0.051
31




2,3,4,5-tetrahydro-1H-cyclo-



penta[c]quinolin-9-yl)benzene-



sulfonamide


1148
(S)-8-hydroxy-9-(4-(1-(methyl-
0.13
0.25
0.12
0.26




amino)propyl)phenyl)thieno[2,3-



c]quinolin-4(5H)-one hydrochloride


1150
(R)-9-(4-(1-aminopropyl)phenyl)-6-

1.1
0.51
1.3
0.88



bromo-8-hydroxythieno[2,3-



c]quinolin-4(5H)-one hydrochloride


1151
(R)-9-(4-(1-(dimethyl-
0.39
0.85
0.32
1




amino)propyl)phenyl)-8-



hydroxythieno[2,3-c]quinolin-



4(5H)-one hydrochloride


1154
(S)-6-chloro-8-hydroxy-9-(4-(1-(methyl-
0.14
0.29
0.13
0.32




amino)propyl)phenyl)thieno[2,3-



c]quinolin-4(5H)-one hydrochloride


1157
(R)-9-(4-(1-aminopropyl)phenyl)-8-
0.16
0.32
0.22
0.58




hydroxy-6-methylthieno[2,3-



c]quinolin-4(5H)-one hydrochloride


1159
(R)-9-(4-(1-aminopropyl)phenyl)-6-
0.38
0.76
0.4
1.1




chloro-8-hydroxythieno[2,3-



c]quinolin-4(5H)-one hydrochloride


1160
(R)-9-(4-(1-aminopropan-2-yl)phenyl)-
0.054
0.057
0.056
0.23
0.069



8-hydroxythieno[2,3-c]quinolin-



4(5H)-one hydrochloride


1161
(R)-9-(4-(1-aminopropan-2-yl)phenyl)-
0.22
0.45
0.27
0.82




8-methoxythieno[2,3-c]quinolin-



4(5H)-one hydrochloride


1162
2-(4-(8-hydroxy-4-oxo-4,5-di-
0.51
1.2
0.65
1.3




hydrothieno[2,3-c]quinolin-9-



yl)phenyl)butanenitrile


1163
(S)-9-(4-(1-aminopropan-2-yl)phenyl)-
0.33
0.24
0.32
0.96




8-hydroxythieno[2,3-c]quinolin-



4(5H)-one hydrochloride


1165
6-chloro-8-hydroxy-9-(4-(2-(methyl-
0.37
0.65
0.41
1.2




amino)ethyl)phenyl)thieno[2,3-



c]quinolin-4(5H)-one hydrochloride


1166
(R)-9-(4-(1-aminopropan-2-yl)phenyl)-
0.013
0.026
0.017
0.12




6-chloro-8-hydroxythieno[2,3-



c]quinolin-4(5H)-one hydrochloride


1168
(R)-9-(4-(1-aminopropan-2-yl)phenyl)-

0.0084
0.0065
0.027
0.008



8-hydroxy-6-methylthieno[2,3-



c]quinolin-4(5H)-one hydrochloride


1169
(R)-9-(4-(1-aminopropan-2-yl)phenyl)-
0.013
0.024
0.023
0.079
0.022



8-hydroxy-6-methylthieno [2,3-



c]quinolin-4(5H)-one hydrobromide


1172
(S)-9-(4-(1-(dimethylamino)propan-2-
0.31
0.65
0.33
0.65




yl)phenyl)-8-hydroxythieno [2,3-



c]quinolin-4(5H)-one hydrochloride


1174
9-(4-(1-aminopropan-2-yl)-3-
0.16
0.12
0.27
1.2




fluorophenyl)-8-hydroxythieno[2,3-



c]quinolin-4(5H)-one hydrochloride


1176
(R)-9-(4-(1-aminopropan-2-yl)phenyl)-
0.024
0.038
0.027
0.1




6-bromo-8-hydroxythieno[2,3-



c]quinolin-4(5H)-one hydrochloride


1179
9-(4-(1-aminopropan-2-yl)-3-
0.45
0.86
0.63
1.9




fluorophenyl)-8-methoxythieno[2,3-



c]quinolin-4(5H)-one hydrochloride


1181
(S)-9-(4-(1-aminopropan-2-yl)phenyl)-
0.1
0.21
0.11
0.6




6-chloro-8-hydroxythieno[2,3-



c]quinolin-4(5H)-one hydrochloride


1187
(R)-8-hydroxy-9-(4-(1-(methyl-
0.19
0.19
0.2
0.32




amino)propan-2-yl)phenyl)thieno[2,3-



c]quinolin-4(5H)-one hydrochloride


1188
(R)-9-(4-(1-(dimethylamino)propan-2-
0.16
0.29
0.16
0.43




yl)phenyl)-8-hydroxythieno [2,3-



c]quinolin-4(5H)-one hydrochloride


1189
(R)-8-methoxy-9-(4-(1-(methyl-
0.69
1.3
0.59
1.3




amino)propan-2-yl)phenyl)thieno[2,3-



c]quinolin-4(5H)-one hydrochloride


1190
9-(4-(1-aminopropan-2-yl)-3-
0.015
0.019
0.021
0.11




fluorophenyl)-8-hydroxy-6-methyl-



thieno [2,3-c]quinolin-4(5H)-one



hydrochloride


1191
9-(4-(2-aminoethyl)phenyl)-8-hydroxy-
0.064
0.073
0.12
0.48




6-methylthieno[2,3-c]quinolin-



4(5H)-one hydrochloride


1193
9-(4-(1-(dimethylamino)propan-2-yl)-3-
0.14
0.24
0.13
0.33




fluorophenyl)-8-hydroxy-6-methyl-



thieno[2,3-c]quinolin-4(5H)-one



hydrochloride


1197
(S)-8-hydroxy-9-(4-(1-(methyl-
0.43
0.54
0.62
1




amino)propan-2-yl)phenyl)thieno[2,3-



c]quinolin-4(5H)-one hydrochloride


1201
(R)-9-(4-(1-aminopropan-2-yl)phenyl)-
0.053
0.12
0.046
0.14




6-chloro-8-methoxythieno[2,3-



c]quinolin-4(5H)-one hydrochloride


1204
N-(1-chloropropan-2-yl)-4-(8-hydroxy-
0.16
1.9
0.71
15




4-oxo-4,5-dihydrothieno[2,3-



c]quinolin-9-yl)benzenesulfonamide


1209
9-(4-(3-(aminomethyl)pentan-3-
0.49
1
0.48
1.2




yl)phenyl)-8-hydroxythieno[2,3-



c]quinolin-4(5H)-one hydrochloride


1212
9-(4-(aminomethyl)phenyl)-8-hydroxy-
0.12
0.2
0.15
0.63




6-methylthieno[2,3-c]quinolin-



4(5H)-one hydrochloride


1213
9-(4-(2-aminoethyl)-3-fluorophenyl)-
0.23
0.38
0.36
1.7




6-bromo-8-hydroxythieno[2,3-



c]quinolin-4(5H)-one hydrochloride


1215
(S)-8-hydroxy-6-methyl-9-(4-(1-
0.14
0.26
0.15
0.5




(methylamino)propan-2-



yl)phenyl)thieno[2,3-c]quinolin-



4(5H)-one hydrochloride


1216
9-(4-(2-aminoethyl)-3-fluorophenyl)-
0.21
0.46
0.28
0.64




8-methoxy-6-methylthieno [2,3-



c]quinolin-4(5H)-one hydrochloride


1217
9-(4-(2-aminoethyl)-3-fluorophenyl)-
0.065
0.084
0.14
0.48




8-hydroxy-6-methylthieno[2,3-



c]quinolin-4(5H)-one hydrochloride


1218
9-(4-(2-aminoethyl)-3-fluorophenyl)-
0.55
1.2
0.62
1.3




6-chloro-8-methoxythieno[2,3-



c]quinolin-4(5H)-one hydrochloride


1219
9-(4-(2-aminoethyl)-3-fluorophenyl)-
0.1
0.18
0.17
0.88




6-chloro-8-hydroxythieno[2,3-



c]quinolin-4(5H)-one hydrochloride


1224
9-(4-(2-aminoethyl)-2-bromo-5-
0.98
0.77
0.49
1.5




hydroxyphenyl)-8-hydroxythieno[2,3-



c]quinolin-4(5H)-one hydrochloride


1225
(S)-9-(4-(1-aminoethyl)phenyl)-8-
0.091
0.16
0.1
0.38




hydroxy-6-methylthieno[2,3-



c]quinolin-4(5H)-one hydrochloride


1226
3-(4-(8-hydroxy-6-methyl-4-oxo-4,5-
0.59
1.2
0.49
1.3




dihydrothieno[2,3-c]quinolin-9-



yl)phenyl)propanenitrile


1228
9-(4-(1-amino-2-methylpropan-2-
0.15
0.33
0.16
0.81




yl)phenyl)-8-hydroxy-6-methyl-



thieno [2,3-c]quinolin-4(5H)-one



hydrochloride


1232
(S)-9-(4-(1-aminopropan-2-yl)phenyl)-
0.037
0.062
0.041
0.2




8-hydroxy-6-methylthieno[2,3-



c]quinolin-4(5H)-one hydrochloride


1236
9-(4-(2-amino-1-cyclopentyl-
0.51
0.8
0.46
1




ethyl)phenyl)-8-hydroxythieno[2,3-



c]quinolin-4(5H)-one


1239
9-(4-(2-amino-1-cyclopentyl-
1.5
1.1
0.89
1.7




ethyl)phenyl)-8-methoxythieno[2,3-



c]quinolin-4(5H)-one hydrochloride


1242
9-(4-(2-aminopropyl)phenyl)-8-hydroxy-
0.11
0.15
0.12
0.42




6-methylthieno[2,3-c]quinolin-



4(5H)-one hydrochloride


1245
6-bromo-9-(3-fluoro-4-(2-(methyl-
0.72
1.3
0.85
2.5




amino)ethyl)phenyl)-8-hydroxy-



thieno[2,3-c]quinolin-4(5H)-



one hydrochloride


1247
9-(4-(1-amino-2-methylpropan-2-
0.52
0.94
0.47
1.3




yl)phenyl)-6-bromo-8-hydroxy-



thieno[2,3-c]quinolin-4(5H)-one



hydrochloride


1251
9-(4-(1-(aminomethyl)cyclo-
0.26
0.52
0.2
0.65




propyl)phenyl)-8-methoxy-6-methyl-



thieno[2,3-c]quinolin-4(5H)-one



hydrochloride


1252
9-(4-(1-amino-3-methylbutan-2-
0.25
0.21
0.16
0.42




yl)phenyl)-8-hydroxythieno[2,3-



c]quinolin-4(5H)-one


1253
9-(4-(1-amino-3-methylbutan-2-
1.5
0.87
0.76
1.9




yl)phenyl)-8-methoxythieno[2,3-



c]quinolin-4(5H)-one hydrochloride


1254
9-(4-(1-(aminomethyl)cyclo-
0.035
0.053
0.039
0.24




propyl)phenyl)-8-hydroxy-6-methyl-



thieno[2,3-c]quinolin-4(5H)-one



hydrochloride


1258
9-(3-fluoro-4-(2-(methyl-
0.43
0.6
0.66
1.5




amino)ethyl)phenyl)-8-hydroxy-6-methyl-



thieno[2,3-c]quinolin-4(5H)-one



hydrochloride


1260
9-(4-(1-amino-2-methylpropan-2-
0.43
0.93
0.5
1.7




yl)phenyl)-6-chloro-8-hydroxy-



thieno[2,3-c]quinolin-4(5H)-one



hydrochloride


1262
(R)-8-hydroxy-6-methyl-9-(4-(1-
0.039
0.078
0.045
0.13




(methylamino)ethyl)phenyl)thieno[2,3-



c]quinolin-4(5H)-one hydrochloride


1263
9-(4-(2-aminoethyl)-3-chlorophenyl)-
0.2
0.41
0.23
0.58




8-methoxy-6-methylthieno[2,3-



c]quinolin-4(5H)-one hydrochloride


1264
9-(4-(2-aminoethyl)-3-chlorophenyl)-
0.032
0.046
0.075
0.17




8-hydroxy-6-methylthieno[2,3-



c]quinolin-4(5H)-one hydrochloride


1265
(R)-8-methoxy-6-methyl-9-(4-(1-
0.11
0.26
0.11
0.32




(methylamino)ethyl)phenyl)thieno[2,3-



c]quinolin-4(5H)-one hydrochloride


1268
9-(4-(2-aminoethyl)-3-chlorophenyl)-
0.077
0.12
0.13
0.38




6-chloro-8-hydroxythieno[2,3-



c]quinolin-4(5H)-one hydrochloride


1271
9-(4-(1-amino-2-methylpropan-2-yl)-
0.3
0.57
0.47
1.6




3-fluorophenyl)-8-hydroxy-



thieno[2,3-c]quinolin-4(5H)-one



hydrochloride


1273
9-(4-(1-aminopropan-2-yl)-3-
0.073
0.17
0.071
0.2




fluorophenyl)-8-methoxy-6-methyl-



thieno[2,3-c]quinolin-4(5H)-one



hydrochloride


1274
9-(4-(1-amino-3-methylbutan-2-
0.066
0.098
0.045
0.18




yl)phenyl)-8-hydroxy-6-methyl-



thieno[2,3-c]quinolin-4(5H)-one


1277
9-(4-(1-aminobutan-2-yl)phenyl)-8-
0.13
0.28
0.14
0.29




methoxy-6-methylthieno[2,3-



c]quinolin-4(5H)-one hydrochloride


1278
9-(4-(1-amino-2-methylpropan-2-yl)-3-
0.11
0.26
0.29
0.51




fluorophenyl)-8-hydroxy-6-



methylthieno[2,3-c]quinolin-



4(5H)-one hydrochloride


1280
9-(4-(1-aminopropan-2-yl)-3-
0.45
2.6
0.37
7




chlorophenyl)-8-hydroxy-



thieno[2,3-c]quinolin-4(5H)-one



hydrochloride


1283
9-(4-(1-amino-3-methylbutan-2-yl)-3-
0.25
0.56
0.56
0.53




fluorophenyl)-8-methoxy-6-



methylthieno[2,3-c]quinolin-



4(5H)-one hydrochloride


1285
8-hydroxy-6-methyl-9-(4-(3-methyl-1-
0.11
0.21
0.23
0.28




(methylamino)butan-2-



yl)phenyl)thieno[2,3-c]quinolin-



4(5H)-one


1286
9-(3-fluoro-4-(1-(methylamino)propan-
0.093
0.22
0.095
0.22




2-yl)phenyl)-8-methoxy-6-



methylthieno[2,3-c]quinolin-



4(5H)-one hydrochloride


1288
9-(4-(1-amino-3-methylbutan-2-yl)-3-
0.047
0.074
0.11
0.14




fluorophenyl)-8-hydroxy-6-methyl-



thieno[2,3-c]quinolin-4(5H)-one


1290
9-(4-(1-(aminomethyl)cyclobutyl)phenyl)-
0.025
0.044
0.021
0.096




8-hydroxy-6-methylthieno[2,3-



c]quinolin-4(5H)-one hydrochloride


1291
9-(4-(1-aminobutan-2-yl)phenyl)-8-
0.026
0.029
0.022
0.11




hydroxy-6-methylthieno[2,3-



c]quinolin-4(5H)-one hydrochloride


1293
9-(3-fluoro-4-(1-(methyl-
0.032
0.052
0.035
0.19




amino)propan-2-yl)phenyl)-8-hydroxy-6-



methylthieno[2,3-c]quinolin-



4(5H)-one


1294
9-(3-fluoro-4-(3-methyl-1-(methyl-
0.085
0.18
0.078
0.34




amino)butan-2-yl)phenyl)-8-hydroxy-6-



methylthieno[2,3-c]quinolin-



4(5H)-one


1297
9-(4-(1-(aminomethyl)cyclo-
0.26
0.62
0.22
0.52




butyl)phenyl)-8-methoxy-6-methyl-



thieno[2,3-c]quinolin-4(5H)-one



hydrochloride


1298
(R)-8-methoxy-6-methyl-9-(4-(1-
0.064
0.14
0.068
0.16




(methylamino)propan-2-



yl)phenyl)thieno [2,3-c]quinolin-



4(5H)-one hydrochloride


1300
9-(4-(l-(aminomethyl)cyclo-
0.1
0.12
0.077
0.23




butyl)phenyl)-8-hydroxythieno[2,3-



c]quinolin-4(5H)-one hydrochloride


1302
8-hydroxy-6-methyl-9-(4-(piperidin-3-
0.74
0.83
0.97
1.5




yl)phenyl)thieno[2,3-c]quinolin-



4(5H)-one hydrochloride


1303
(S)-9-(4-(1-aminopropan-2-yl)-3-
0.081
0.13
0.092
0.51




fluorophenyl)-8-hydroxy-6-methyl-



thieno[2,3-c]quinolin-4(5H)-one


1304
(S)-9-(4-(1-aminopropan-2-yl)-3-

0.12
0.099
0.34
0.074



fluorophenyl)-8-hydroxy-6-methyl-



thieno[2,3-c]quinolin-4(5H)-



one hydrobromide


1305
(R)-9-(4-(1-aminopropan-2-yl)phenyl)-
0.021
0.04
0.02
0.064




8-methoxy-6-methylthieno [2,3-



c]quinolin-4(5H)-one hydrochloride


1306
(R)-8-hydroxy-6-methyl-9-(4-(1-

0.035
0.02
0.073
0.033



(methylamino)propan-2-



yl)phenyl)thieno[2,3-c]quinolin-



4(5H)-one hydrochloride


1307
(R)-8-hydroxy-6-methyl-9-(4-(1-
0.042
0.085
0.057
0.15
0.073



(methylamino)propan-2-



yl)phenyl)thieno [2,3-c]quinolin-



4(5H)-one hydrobromide


1309
9-(4-(1-aminobutan-2-yl)phenyl)-8-
0.094
0.066
0.065
0.21




hydroxythieno[2,3-c]quinolin-



4(5H)-one hydrochloride


1310
(S)-9-(4-(1-aminopropan-2-yl)-3-
0.4
0.8
0.37
0.89




fluorophenyl)-8-methoxy-6-methyl-



thieno[2,3-c]quinolin-4(5H)-



one hydrochloride


1311
(R)-9-(4-(1-(dimethylamino)propan-2-
0.037
0.07
0.045
0.11




yl)-3-fluorophenyl)-8-hydroxy-6-



methylthieno[2,3-c]quinolin-4(5H)-



one hydrochloride


1312
9-(4-(1-aminobutan-2-yl)phenyl)-6-
0.058
0.076
0.054
0.23




chloro-8-hydroxythieno[2,3-



c]quinolin-4(5H)-one hydrochloride


1315
(R)-9-(3-fluoro-4-(1-(methyl-
0.024
0.041
0.034
0.1




amino)propan-2-yl)phenyl)-8-hydroxy-



6-methylthieno[2,3-c]quinolin-



4(5H)-one hydrochloride


1316
(R)-9-(3-fluoro-4-(1-(methyl-
0.083
0.16
0.086
0.23




amino)propan-2-yl)phenyl)-8-methoxy-



6-methylthieno[2,3-c]quinolin-



4(5H)-one hydrochloride


1317
(R)-9-(4-(1-aminopropan-2-yl)-3-
0.036
0.072
0.042
0.1




fluorophenyl)-8-methoxy-6-methyl-



thieno[2,3-c]quinolin-4(5H)-



one hydrochloride


1318
(R)-9-(4-(1-aminopropan-2-yl)-3-
0.0084
0.015
0.015
0.063




fluorophenyl)-8-hydroxy-6-methyl-



thieno[2,3-c]quinolin-4(5H)-



one hydrochloride


1319
(R)-9-(4-(1-aminopropan-2-yl)-3-

0.016
0.014
0.054
0.014



fluorophenyl)-8-hydroxy-6-methyl-



thieno[2,3-c]quinolin-4(5H)-



one hydrobromide


1321
9-(4-(1-(aminomethyl)cyclo-
1
2.2
0.8
2




butyl)phenyl)-6-chloro-8-methoxy-



thieno[2,3-c]quinolin-4(5H)-one



hydrochloride


1324
(R)-9-(4-(1-(dimethylamino)propan-
0.03
0.066
0.024
0.069




2-yl)phenyl)-8-hydroxy-6-



methylthieno[2,3-c]quinolin-



4(5H)-one hydrochloride


1330
9-(4-(2-aminopropan-2-yl)phenyl)-8-
0.19
0.43
0.18
0.76




hydroxy-6-methylthieno[2,3-



c]quinolin-4(5H)-one hydrochloride


1340
(R)-9-(4-(1-aminopropan-2-yl)phenyl)-
0.17
0.25
0.19
0.65




8-hydroxy-2,6-dimethylthieno[2,3-



c]quinolin-4(5H)-one hydrochloride


1341
(R)-9-(4-(1-aminopropan-2-yl)phenyl)-
0.86
0.98
0.57
0.88




8-methoxy-2,6-dimethylthieno[2,3-



c]quinolin-4(5H)-one hydrochloride


1347
(R)-6-chloro-9-(4-(1-(dimethyl-
0.11
0.26
0.1
0.26




amino)propan-2-yl)phenyl)-8-



hydroxythieno [2,3-c]quinolin-



4(5H)-one hydrochloride


1352
(R)-9-(4-(1-aminobutan-2-yl)phenyl)-8-
0.071
0.099
0.055
0.34




hydroxy-6-methylthieno[2,3-



c]quinolin-4(5H)-one hydrochloride


1353
(R)-9-(4-(1-aminopropan-2-yl)phenyl)-
0.079
0.087
0.045
0.11




2-chloro-8-hydroxy-6-



methylthieno[2,3-c]quinolin-



4(5H)-one hydrochloride


1354
(R)-9-(4-(1-aminopropan-2-yl)phenyl)-
0.29
0.53
0.15
0.23




2-chloro-8-methoxy-6-



methylthieno[2,3-c]quinolin-4(5H)-



one hydrochloride


1364
8-hydroxy-6-methyl-9-(4-(2-(methyl-
0.26
0.3
0.27
0.66




amino)ethyl)phenyl)thieno[2,3-



c]quinolin-4(5H)-one hydrochloride


1372
9-(4-(1-((dimethyl-

0.084
0.035
0.1
0.075



amino)methyl)cyclobutyl)phenyl)-8-



hydroxy-6-methylthieno[2,3-



c]quinolin-4(5H)-one hydrochloride


1375
(R)-9-(4-(1-aminopropan-2-yl)phenyl)-

0.42
0.16
0.37
0.35



2-fluoro-8-methoxy-6-



methylthieno[2,3-c]quinolin-



4(5H)-one hydrochloride


1379
(R)-9-(4-(1-(ethyl(methyl)amino)propan-

0.28
0.11
0.31
0.22



2-yl)phenyl)-8-hydroxy-6-methyl-



thieno[2,3-c]quinolin-4(5H)-



one hydrochloride


1380
(R)-8-hydroxy-6-methyl-9-(4-(1-

0.24
0.096
0.37
0.19



(methylamino)butan-2-



yl)phenyl)thieno[2,3-c]quinolin-



4(5H)-one hydrochloride


1383
(R)-9-(4-(1-aminopropan-2-yl)phenyl)-

0.057
0.029
0.1
0.048



2-fluoro-8-hydroxy-6-methylthieno[2,3-



c]quinolin-4(5H)-one hydrochloride


1391
9-(4-(1-(aminomethyl)cyclo-

1.2
0.67
1.4
0.99



propyl)phenyl)-6-bromo-8-methoxy-



thieno[2,3-c]quinolin-4(5H)-one



hydrochloride


1399
(S)-9-(4-(1-(dimethylamino)propan-2-

0.45
0.18
0.47
0.3



yl)-3-fluorophenyl)-8-hydroxy-6-



methylthieno[2,3-c]quinolin-



4(5H)-one hydrochloride


1400
9-(4-((2-amino-

1.4
0.9
2.8
1.1



ethyl)(methyl)amino)phenyl)-8-hydroxy-



6-methylthieno[2,3-c]quinolin-



4(5H)-one hydrochloride


1401
9-(4-(1-(aminomethyl)cyclo-

0.4
0.3
1.2
0.34



propyl)phenyl)-6-bromo-8-hydroxy-



thieno[2,3-c]quinolin-4(5H)-one



hydrochloride


1419
2-(4-(8-hydroxy-6-methyl-4-oxo-4,5-


0.72
6.4
0.28



dihydrothieno[2,3-c]quinolin-9-



yl)phenyl)propane-1-sulfonamide





“>100” in the table means over 100 micro M.






INDUSTRIAL APPLICABILITY

The present invention provides a novel Tricyclic compound having PBK inhibitory effect. The compounds of the present invention may be used for pharmaceutical composition for inhibiting PBK. Such pharmaceutical compositions are suitable for treating or preventing cancer.

Claims
  • 1. A compound represented by general formula I:
  • 2. The compound of claim 1, or a pharmaceutically acceptable salt thereof, wherein
  • 3. The compound of claim 2, or a pharmaceutically acceptable salt thereof, wherein R1 is hydrogen, cyano, C1-C6 alkyl optionally substituted with hydroxyl or halogen, C3-C10 cycloalkyl, C2-C6 alkenyl, C2-C6 alkynyl, or halogen.
  • 4. The compound of claim 2, or a pharmaceutically acceptable salt thereof, wherein R2 is hydrogen, hydroxyl, halogen, C1-C6 alkoxy, or C6-C10 aryl optionally substituted with hydroxyl.
  • 5. The compound of claim 2 or a pharmaceutically acceptable salt, wherein R2 is hydrogen, hydroxyl, halogen, C1-C6 alkoxy, or dihydroxyphenyl.
  • 6. The compound of claim 2, or a pharmaceutically acceptable salt thereof, wherein R3 is selected from the group consisting of: hydrogen; hydroxyl; C1-C6 alkyl optionally substituted with hydroxyl, halogen, or hydroxyethylamino; halogen; C1-C6 alkoxy optionally substituted with dimethylamino or morpholinyl; C1-C6 alkylphenyl, wherein the aliphatic carbons are optionally substituted with —NR51R52; cyano; nitro; amino; 3- to 8-membered heterocycloalkyl optionally substituted with amino; heteroaryl; —OSO2CH3; —OSO2CF3; —OCOR103, wherein R103 represents C1-C6 alkyl; —OCOOR104 wherein R104 represents C1-C6 alkyl; —OCONR101R102 wherein R101 and R102 each independently represent hydrogen or C1-C6 alkyl, or R101 and R102 taken together form morpholinyl; and —CONH2.
  • 7. The compound of claim 6, or a pharmaceutically acceptable salt thereof, wherein when R3 is a 3- to 8-membered heterocycloalkyl, the 3- to 8-membered heterocycloalkyl is selected from the group consisting of piperidyl, pyrrolidinyl, morpholinyl, or piperazinyl and optionally substituted with amino; and when R3 is heteroaryl, the heteroaryl is pyridyl.
  • 8. The compound of claim 2, or a pharmaceutically acceptable salt thereof, wherein R4 is selected from the group consisting of hydrogen, hydroxyl, halogen, amino, C1-C6 alkyl, C2-C6 alkenyl, C3-C10 cycloalkyl, C3-C10 cycloalkenyl, C1-C6 alkoxy, C6-C10 aryl, indanyl, heteroaryl, and 3- to 8-membered heterocycloalkyl, and R4 is optionally substituted with substituent A.
  • 9. The compound of claim 8, or a pharmaceutically acceptable salt thereof, wherein when R4 is heteroaryl, the heteroaryl is selected from the group consisting of pyridyl, 1H-indazolyl, 1H-tetrazolyl, [1,2,4]triazolo[1,5-a]pyridyl, benzoimidazolyl, 2,3-dihydrobenzooxazolyl, pyrazolyl, pyrrolo[2,3-b]pyridyl, pyrimidinyl, indolinyl, furyl, thienyl, and tetrahydroisoquinolyl); and wherein the 3- to 8-membered heterocycloalkyl is selected from the group consisting of aziridinyl, azetidinyl, pyrrolidinyl, imidazolidinyl, piperidyl, piperazinyl, azepanyl, morpholinyl, and 1,2,3,6-tetrahydropyridyl; wherein each of the groups of R4 is optionally substituted with substituent A-1; wherein substituent A-1 is selected from the group consisting of:hydroxyl;oxo;cyano;halogen;C1-C6 alkyl optionally substituted with a substituent selected from the group consisting of substituent B-1;C3-C10 cycloalkyl optionally substituted with cyano, or C1-C6 alkyl substituted with —NR31R32;—NR21AR22A, wherein R21A and R22A each independently represent hydrogen; C1-C6 alkyl optionally substituted with amino, di(C1-C6 alkyl)amino, —SO2 (C1-C6 alkyl), piperidyl, or cyano; or piperidyl optionally substituted with —COOR105;C1-C6 alkoxy optionally substituted with halogen; a 3- to 8-membered heterocycloalkyl selected from piperidyl and piperazinyl, either of which is optionally substituted with C1-C6 alkyl; or —NR33R34;—SO2NR23AR24A, wherein R23A and R24A each independently represent hydrogen, C1-C6 alkyl optionally substituted with hydroxyl, C1-C6 alkoxy, halogen, C3-C10 cycloalkyl, pyrazolyl, imidazolyl, or —NR35R36; C3-C10 cycloalkyl optionally substituted with C1-C6 hydroxyalkyl; azetidinyl; pyrrolidinyl, or R23A and R24A taken together form pyrrolidinyl optionally substituted with amino or halogen;C1-C6 alkylsulfonyl optionally substituted with hydroxyl;—NHSO2(C1-C6 alkyl), wherein the carbon atoms are optionally substituted with —NR37R38;3- to 8-membered heterocycloalkyl selected from the group consisting of azetidinyl, pyrrolidinyl, piperidyl, piperazinyl, and tetrahydropyridyl any of which is optionally substituted with —NR39R40; C1-C6 alkyl optionally substituted with —NR41R42; hydroxyl; or C1-C6 alkylsulfonyl;1H-tetrazolyl;aryl optionally substituted with C1-C6 alkyl, wherein C1-C6 is the aliphatic carbons are optionally substituted with cyano or amino;—COOR11; and—COR12A, wherein R12A represents piperazinyl optionally substituted with C1-C6 alkyl; C3-C10 cycloalkyl; cyanomethyl; aminomethyl; —NR25R26 wherein R25 and R26 each independently represent hydrogen or C1-C6 alkyl optionally substituted with hydroxyl or —NR43R44; or C1-C6 alkylsulfonyl;wherein substituent B-1 is selected from the group consisting of:halogen;hydroxyl;C1-C6 alkoxy;cyano;cycloalkyl;phenyl optionally substituted with cyano;heteroaryl selected from the group consisting of imidazolyl, pyrazolyl, and thiazolyl;3- to 8-membered heterocycloalkyl selected from the group consisting of pyrrolidinyl, piperidyl, piperazinyl, morpholinyl, and oxetanyl any of which are optionally substituted with hydroxyl, amino, C1-C6 aminoalkyl, or C1-C6 alkyl optionally substituted with C2-C7 alkyloxycarbonylamino;—NR51AR52A, wherein R51A and R52A each independently represent hydrogen; C1-C6 alkyl optionally substituted with C1-C6 alkylsulfonyl or piperidyl optionally substituted with —COOR53; piperidyl; C1-C6 alkylsulfonyl; C3-C10 cycloalkyl; —COR55, —COOR56, or —CONR57R58;—COOR54;—CONH2;—SO2NR106R107;C1-C6 alkylsulfinyl; andC1-C6 alkylysulfonyl.
  • 10. The compound of claim 9, or a pharmaceutically acceptable salt thereof, wherein R4 is a group selected from group (p): wherein group (p) is independently selected from the group consisting of: hydrogen,hydroxyl,halogen,amino optionally substituted with a substituent selected from the group consisting of substituent (g),C1-C6 alkyl optionally substituted with a substituent selected from the group consisting of substituent (a),C2-C6 alkenyl optionally substituted with a substituent selected from the group consisting of substituent (b),C3-C10 cycloalkyl,C3-C10 cycloalkenyl,C1-C6 alkoxy,C6-C10 aryl optionally substituted with a substituent selected from the group consisting of substituent (c),indanyl optionally substituted with a substituent selected from the group consisting of substituent (d),heteroaryl selected from the group consisting of pyridyl, 1H-indazolyl, 1H-tetrazolyl, [1,2,4]triazolo[1,5-a]pyridyl, benzoimidazolyl, 2,3-dihydrobenzooxazolyl, pyrazolyl, pyrrolo[2,3-b]pyridyl, pyrimidinyl, indolinyl, furyl, thienyl, and tetrahydroisoquinolyl any of which is optionally substituted with a substituent selected from the group consisting of substituent (e); and3- to 8-membered heterocycloalkyl selected from the group consisting of pyrrolidinyl, piperidyl, piperazinyl, morpholinyl, and 1,2,3,6-tetrahydropyridyl any of which is optionally substituted with a substituent selected from the group consisting of substituent (f);wherein substituent (a) is selected from the group consisting of: —NR21AR22A, wherein R21A and R22A each independently represent hydrogen; C1-C6 alkyl optionally substituted with piperidyl; or piperidyl optionally substituted with —COOR105;3- to 8-membered heterocycloalkyl selected from the group consisting of pyrrolidinyl and piperidyl either of which is optionally substituted with C1-C6 alkyl optionally substituted with —NR41R42 or —NR39R40 wherein R39 and R40 each independently represent hydrogen or C1-C6 alkyl; and—NHSO2(C1-C6 alkyl);wherein substituent (b) is selected from the group consisting of: —COOR11;—NR21aR22a, wherein R21a and R22a each independently represent hydrogen, or C1-C6 alkyl optionally substituted with di(C1-C6 alkyl)amino or C1-C6 alkylsulfonyl;3- to 8-membered heterocycloalkyl selected from the group consisting of azetidinyl, pyrrolidinyl, and piperidyl any of which are optionally substituted with —NR39R40, C1-C6 alkyl optionally substituted with —NR41R42, hydroxyl, or C1-C6 alkylsulfonyl;cyano; andC1-C6 alkoxy;wherein substituent (c) is selected from the group consisting of: hydroxyl;cyano;halogen;C1-C6 alkyl optionally substituted with a substituent selected from the group consisting of substituent B-c below;C3-C10 cycloalkyl optionally substituted with cyano, or C1-C6 alkyl substituted with —NR31R32;—NR21cR22c, wherein R21c and R22c each independently represent hydrogen or C1-C6 alkyl optionally substituted with amino or cyano;C1-C6 alkoxy optionally substituted with halogen, 3- to 8-membered heterocycloalkyl selected from the group consisting of piperidyl and piperazinyl either of which are optionally substituted with C1-C6 alkyl, or —NR33R34;—SO2NR23cR24c, wherein R23c and R24c each independently represent hydrogen, C1-C6 alkyl optionally substituted with hydroxyl, C1-C6 alkoxy, halogen, C3-C10 cycloalkyl, pyrazolyl, imidazolyl, or —NR35R36; C3-C10cycloalkyl optionally substituted with C1-C6 hydroxyalkyl; azetidinyl, pyrrolidinyl, or wherein R23c and R24c taken together form pyrrolidinyl which is optionally substituted with amino or halogen;C1-C6 alkylsulfonyl optionally substituted with hydroxyl;—NHSO2(C1-C6 alkyl), wherein the carbon atoms are optionally substituted with NR37R38;piperazinyl optionally substituted with C1-C6 alkyl or C1-C6 alkylsulfonyl;piperidyl optionally substituted with hydroxyl;1H-tetrazolyl;1,2,3,6-tetrahydropyridyl; and—COR12c, wherein R12c represents piperazinyl which is optionally substituted with C1-C6 alkyl, C3-C10 cycloalkyl, cyanomethyl, aminomethyl, —NR25R26, or C1-C6 alkyl; andwherein substituent B-c is selected from the group consisting of: halogen;hydroxyl;methoxy;cyano;C3-C10 cycloalkyl;3- to 8-membered heterocycloalkyl selected from the group consisting of pyrrolidinyl, piperidyl, piperazinyl, morpholinyl, and oxetanyl, any of which is optionally substituted with C1-C6 alkyl, hydroxyl, amino, C1-C6 aminoalkyl, or C1-C6 alkyl substituted with C2-C7 alkyloxycarbonylamino;—NR51CR52c, wherein R51c and R52c each independently represent hydrogen; C1-C6 alkyl optionally substituted with C1-C6 alkylsulfonyl, or piperidyl optionally substituted with —COOR53; piperidyl; C1-C6alkylsulfonyl; C3-C10 cycloalkyl; —COR55; or —CONR57R58;heteroaryl selected from the group consisting of imidazolyl, pyrazolyl, and thiazolyl;—COOR54;—CONH2;—SO2NR106R107;C1-C6 alkylsufinyl; andC1-C6 alkylsulfonyl; wherein substituent (d) is selected from the group consisting of: —NR21dR22d, wherein R21d and R22d each independently represent hydrogen or C1-C6 alkyl;wherein substituent (e) is selected from the group consisting of: hydroxyl;oxo;cyano;C3-C10 cycloalkyl optionally substituted with cyano;—NR21eR22e, wherein R21e and R22e each independently represent hydrogen or C1-C6 alkyl optionally substituted with amino;piperidyl;C1-C6 alkoxy optionally substituted with —NR33R34;C1-C6 alkyl optionally substituted with cyano; —NR51eR52e, wherein R51e and R52e each independently represent hydrogen, C1-C6 alkyl, or —COOR56; morpholinyl; or cyanophenyl;—CONH2;wherein substituent (f) is selected from the group consisting of: C1-C6 alkyl optionally substituted with —NR51fR52f, wherein R51f and R52f each independently represent hydrogen, C1-C6 alkyl, or —COOR56; andC1-C6 alkylsulfonyl;wherein substituent (g) is aryl optionally substituted with C1-C6 alkyl having the aliphatic carbons optionally substituted with cyano or amino.
  • 11. The compound of claim 2, or a pharmaceutically acceptable salt thereof, wherein R6 is hydrogen; hydroxyl; C1-C6 alkyl; phenyl optionally substituted with 1 to 3 hydroxyls; piperidyl optionally substituted with amino; or piperazinyl.
  • 12. The compound of claim 11, or a pharmaceutically acceptable salt thereof, wherein R7 is hydrogen; C1-C6 alkyl optionally substituted with hydroxyl or piperidyl; or halogen.
  • 13. The compound of claim 2, or a pharmaceutically acceptable salt thereof, wherein R7 is hydrogen;C1-C6 alkyl optionally substituted with hydroxyl; —NR71AR72A wherein R71A and R72A each independently represent hydrogen, C1-C6 alkyl optionally substituted with dimethylamino, C3-C10 cycloalkyl optionally substituted with amino, or piperidyl; or 3- to 8-membered heterocycloalkyl selected from the group consisting of piperidyl and morpholinyl either of which is optionally substituted with C1-C6 aminoalkyl;phenyl optionally substituted with 1 to 2 hydroxyls;phenylsulfonyl; or—COR73A, wherein R73A represents piperidyl optionally substituted with amino, or —NR74AR75A, wherein R74A and R75A each independently represent hydrogen, piperidyl, or C3-C10 cycloalkyl optionally substituted with amino.
  • 14. The compound of claim 1, or a pharmaceutically acceptable salt thereof, wherein
  • 15. The compound of claim 14, or a pharmaceutically acceptable salt thereof, wherein R1 and R2 are hydrogen.
  • 16. The compound of claim 14, or a pharmaceutically acceptable salt thereof, wherein R3 is hydroxyl or methoxy.
  • 17. The compound of claim 14, or a pharmaceutically acceptable salt thereof, wherein R4 is hydrogen; phenyl substituted with C1-C6 alkyl substituted with —NR51AR52A, wherein R51A and R52A each independently represent hydrogen or C1-C6 alkyl, or —SO2NR53AR54A, wherein R53A and R54A each independently represent hydrogen or C1-C6 alkyl optionally substituted with halogen or hydroxy; 1,2,3,6-tetrahydropyridyl; hydroxypyridyl; or methoxypyridyl.
  • 18. The compound of claim 1, or a pharmaceutically acceptable salt thereof, wherein
  • 19. The compound of claim 1, or a pharmaceutically acceptable salt thereof, wherein
  • 20. A compound selected from the group consisting of: (1): 8-methoxy-5-methylthieno[2,3-c]quinolin-4(5H)-one;(2): 8-hydroxy-5-methylthieno[2,3-c]quinolin-4(5H)-one;(3): 7,8-dihydroxythieno[2,3-c]quinolin-4(5H)-one;(4): 7,8-dimethoxythieno[2,3-c]quinolin-4(5H)-one;(5): 8-methoxythieno[2,3-c]quinolin-4(5H)-one;(6): 7,9-dimethoxythieno[2,3-c]quinolin-4(5H)-one;(7): 7,9-dihydroxythieno[2,3-c]quinolin-4(5H)-one;(8): 7,8,9-trimethoxythieno[2,3-c]quinolin-4(5H)-one;(9): 8-hydroxythieno[2,3-c]quinolin-4(5H)-one;(10): 7,8,9-trihydroxythieno[2,3-c]quinolin-4(5H)-one;(11): 9-(3-(2-aminoethyl)phenyl)-8-methoxythieno[2,3-c]quinolin-4(5H)-one;(12): 8-chlorothieno[2,3-c]quinolin-4(5H)-one;(13): 4-oxo-4,5-dihydrothieno[2,3-c]quinoline-8-carbonitrile;(14): thieno[2,3-c]quinolin-4(5H)-one;(15): 8-fluorothieno[2,3-c]quinolin-4(5H)-one;(16): 8-nitrothieno[2,3-c]quinolin-4(5H)-one;(17): 8-(3-aminopiperidin-1-yl)thieno[2,3-c]quinolin-4(5H)-one;(18): 1-(4-hydroxyphenyl)thieno[2,3-c]quinolin-4(5H)-one;(19): 1,8-dihydroxythieno[2,3-c]quinolin-4(5H)-one;(20): 8-hydroxy-1-(4-hydroxyphenyl)thieno[2,3-c]quinolin-4(5H)-one;(2H): (R)-8-(3-aminopyrrolidin-1-yl)thieno[2,3-c]quinolin-4(5H)-one;(22): (S)-8-(3-aminopyrrolidin-1-yl)thieno[2,3-c]quinolin-4(5H)-one;(23): 8-(pyridin-3-yl)thieno[2,3-c]quinolin-4(5H)-one;(24): 8-(4-hydroxyphenyl)thieno[2,3-c]quinolin-4(5H)-one;(25): 1-(3,4-dihydroxyphenyl)-8-hydroxythieno[2,3-c]quinolin-4(5H)-one;(26): 1-(3-aminopiperidin-1-yl)-8-hydroxythieno[2,3-c]quinolin-4(5H)-one;(27): 8-morpholinothieno[2,3-c]quinolin-4(5H)-one;(28): 8-hydroxy-2-methylthieno[2,3-c]quinolin-4(5H)-one;(29): 8-hydroxy-2-(hydroxymethyl)thieno[2,3-c]quinolin-4(5H)-one;(30): 8-hydroxy-4-oxo-N-(piperidin-3-yl)-4,5-dihydrothieno[2,3-c]quinoline-2-carboxamide;(31): 8-hydroxy-2-(4-hydroxyphenyl)thieno[2,3-c]quinolin-4(5H)-one;(32): 8-hydroxy-1-(piperazin-1-yl)thieno[2,3-c]quinolin-4(5H)-one;(33): N-((1R,4R)-4-aminocyclohexyl)-8-hydroxy-4-oxo-4,5-dihydrothieno[2,3-c]quinoline-2-carboxamide;(34): 2-(3-aminopiperidine-1-carbonyl)-8-hydroxythieno[2,3-c]quinolin-4(5H)-one;(35): 2-(3,4-dihydroxyphenyl)-8-hydroxythieno[2,3-c]quinolin-4(5H)-one;(36): 2-(((1R,4R)-4-aminocyclohexylamino)methyl)-8-hydroxythieno[2,3-c]quinolin-4(5H)-one;(37): 8-(piperazin-1-yl)thieno[2,3-c]quinolin-4(5H)-one;(38): 8-hydroxy-1-methylthieno[2,3-c]quinolin-4(5H)-one;(39): 2-((2-(dimethylamino)ethylamino)methyl)-8-hydroxythieno[2,3-c]quinolin-4(5H)-one;(40): 8-hydroxy-2-((piperidin-3-ylamino)methyl)thieno[2,3-c]quinolin-4(5H)-one;(41): 7-hydroxythieno[2,3-c]quinolin-4(5H)-one;(42): 9-bromo-8-hydroxythieno[2,3-c]quinolin-4(5H)-one;(43): 9-(3,4-dihydroxyphenyl)-8-hydroxythieno[2,3-c]quinolin-4(5H)-one;(44): 1-methyl-4-oxo-4,5-dihydrothieno[2,3-c]quinoline-8-carbonitrile;(45): 7-(3,4-dihydroxyphenyl)-8-hydroxythieno[2,3-c]quinolin-4(5H)-one;(46): 8-hydroxy-1-methyl-3H-pyrrolo[2,3-c]quinolin-4(5H)-one;(47): 9-(3,5-dihydroxyphenyl)-8-hydroxythieno[2,3-c]quinolin-4(5H)-one;(48): 8-hydroxy-9-(3-hydroxyphenyl)thieno[2,3-c]quinolin-4(5H)-one;(49): 8-hydroxy-9-(4-hydroxyphenyl)thieno[2,3-c]quinolin-4(5H)-one;(50): 9-(3,4-difluorophenyl)-8-methoxythieno[2,3-c]quinolin-4(5H)-one;(51): (S)-8-(3-aminopyrrolidin-1-yl)-2-(4-hydroxyphenyl)thieno[2,3-c]quinolin-4(5H)-one;(52): 5-(8-methoxy-4-oxo-4,5-dihydrothieno[2,3-c]quinolin-9-yl)picolinonitrile;(53): 9-(6-aminopyridin-3-yl)-8-hydroxythieno[2,3-c]quinolin-4(5H)-one;(54): 4-(8-hydroxy-4-oxo-4,5-dihydrothieno[2,3-c]quinolin-9-yl)benzamide;(55): 9-(3-fluoro-4-hydroxyphenyl)-8-hydroxythieno[2,3-c]quinolin-4(5H)-one;(56): 8-hydroxy-2-(3-hydroxyphenyl)thieno[2,3-c]quinolin-4(5H)-one;(57): (R)-8-(3-aminopyrrolidin-1-yl)-2-(3,4-dihydroxyphenyl)thieno[2,3-c]quinolin-4(5H)-one;(58): 9-(3,4-difluorophenyl)-8-hydroxythieno[2,3-c]quinolin-4(5H)-one;(59): 9-(4-fluoro-3-hydroxyphenyl)-8-hydroxythieno[2,3-c]quinolin-4(5H)-one;(60): 8-hydroxy-9-(3-hydroxy-5-(trifluoromethyl)phenyl)thieno[2,3-c]quinolin-4(5H)-one;(61): 8-hydroxy-9-(1H-indazol-6-yl)thieno[2,3-c]quinolin-4(5H)-one;(62): 8-hydroxy-9-(3,4,5-trihydroxyphenyl)thieno[2,3-c]quinolin-4(5H)-one;(63): 9-(4-hydroxyphenyl)-8-methoxythieno[2,3-c]quinolin-4(5H)-one;(64): 9-(4-(1H-tetrazol-5-yl)phenyl)-8-hydroxythieno[2,3-c]quinolin-4(5H)-one;(65): 4-(8-hydroxy-4-oxo-4,5-dihydrothieno[2,3-c]quinolin-9-yl)benzenesulfonamide;(66): 9-(3-chloro-4-fluorophenyl)-8-hydroxythieno[2,3-c]quinolin-4(5H)-one;(67): 9-(4-chloro-3-fluorophenyl)-8-hydroxythieno[2,3-c]quinolin-4(5H)-one;(68): 9-(3,4-dichlorophenyl)-8-hydroxythieno[2,3-c]quinolin-4(5H)-one;(69): 9-(4-fluorophenyl)-8-hydroxythieno[2,3-c]quinolin-4(5H)-one;(70): 8-hydroxy-9-phenylthieno[2,3-c]quinolin-4(5H)-one;(71): 9-(4-(difluoromethoxy)phenyl)-8-methoxythieno[2,3-c]quinolin-4(5H)-one;(72): 9-(4-(aminomethyl)phenyl)-8-hydroxythieno[2,3-c]quinolin-4(5H)-one;(73): 9-(4-(aminomethyl)phenyl)-8-hydroxythieno[2,3-c]quinolin-4(5H)-one;(74): 9-(3-aminophenyl)-8-hydroxythieno[2,3-c]quinolin-4(5H)-one;(75): 3-(8-hydroxy-4-oxo-4,5-dihydrothieno[2,3-c]quinolin-9-yl)benzenesulfonamide;(76): 8-hydroxy-9-(3,4,5-trifluorophenyl)thieno[2,3-c]quinolin-4(5H)-one;(77): N-(4-(8-hydroxy-4-oxo-4,5-dihydrothieno[2,3-c]quinolin-9-yl)phenyl)methanesulfonamide;(78): 8-methoxy-9-phenylthieno[2,3-c]quinolin-4(5H)-one;(79): 8-hydroxy-9-(naphthalen-2-yl)thieno[2,3-c]quinolin-4(5H)-one;(80): 8-hydroxy-9-(4-(hydroxymethyl)phenyl)thieno[2,3-c]quinolin-4(5H)-one;(81): 2-(4-(8-hydroxy-4-oxo-4,5-dihydrothieno[2,3-c]quinolin-9-yl)phenyl)acetonitrile;(82): 8-hydroxy-9-(4-(methylsulfonyl)phenyl)thieno[2,3-c]quinolin-4(5H)-one;(83): 8-hydroxy-9-(pyridin-4-yl)thieno[2,3-c]quinolin-4(5H)-one;(84): 8-hydroxy-9-(1,2,3,6-tetrahydropyridin-4-yl)thieno[2,3-c]quinolin-4(5H)-one;(85): 8-hydroxy-9-(4-hydroxy-3-methoxyphenyl)thieno[2,3-c]quinolin-4(5H)-one;(86): 9-(3-fluoro-4-(morpholinomethyl)phenyl)-8-hydroxythieno[2,3-c]quinolin-4(5H)-one;(87): 9-(3-(aminomethyl)phenyl)-8-hydroxythieno[2,3-c]quinolin-4(5H)-one;(88): 9-(4-(aminomethyl)phenyl)-8-methoxythieno[2,3-c]quinolin-4(5H)-one;(89): 9-(3-(difluoromethyl)phenyl)-8-methoxythieno[2,3-c]quinolin-4(5H)-one;(90): 9-(3-(aminomethyl)phenyl)-8-hydroxy-2-methylthieno[2,3-c]quinolin-4(5H)-one;(91): 9-cyclohexenyl-8-methoxythieno[2,3-c]quinolin-4(5H)-one;(92): 9-(3,5-difluorophenyl)-8-hydroxythieno[2,3-c]quinolin-4(5H)-one;(93): 9-(4-(2-(dimethylamino)ethyl)phenyl)-8-hydroxythieno[2,3-c]quinolin-4(5H)-one;(94): 9-(3-(aminomethyl)phenyl)-8-methoxythieno[2,3-c]quinolin-4(5H)-one;(95): 9-(4-(aminomethyl)phenyl)-8-hydroxy-2-methylthieno[2,3-c]quinolin-4(5H)-one;(96): 9-cyclopropyl-8-hydroxythieno[2,3-c]quinolin-4(5H)-one;(97): 9-([1,2,4]triazolo[1,5-a]pyridin-6-yl)-8-hydroxythieno[2,3-c]quinolin-4(5H)-one;(98): 8-methoxy-9-(1,2,3,6-tetrahydropyridin-4-yl)thieno[2,3-c]quinolin-4(5H)-one;(99): 9-cyclohexenyl-8-hydroxythieno[2,3-c]quinolin-4(5H)-one;(100): 8-methoxy-9-(4-(2-(piperidin-1-yl)ethylamino)phenyl)thieno[2,3-c]quinolin-4(5H)-one;(101): 9-(4-(aminomethyl)phenyl)-8-hydroxy-2-(morpholinomethyl)thieno[2,3-c]quinolin-4(5H)-one;(102): 9-(1H-benzo[d]imidazol-5-yl)-8-hydroxythieno[2,3-c]quinolin-4(5H)-one;(103): 9-(4-(difluoromethyl)phenyl)-8-methoxythieno[2,3-c]quinolin-4(5H)-one;(104): 9-(4-(aminomethyl)phenyl)-8-methoxy-2-(morpholinomethyl)thieno[2,3-c]quinolin-4(5H)-one;(105): 8-hydroxy-9-(4-(2-(piperidin-1-yl)ethylamino)phenyl)thieno[2,3-c]quinolin-4(5H)-one;(106): 8-hydroxy-9-(4-(piperazin-1-yl)phenyl)thieno[2,3-c]quinolin-4(5H)-one;(107): 8-methoxy-2,3-dihydro-1H-cyclopenta[c]quinolin-4(5H)-one;(108): 8-hydroxy-2,3-dihydro-1H-cyclopenta[c]quinolin-4(5H)-one;(109): 5-(8-hydroxy-4-oxo-4,5-dihydrothieno[2,3-c]quinolin-9-yl)benzo[d]oxazol-2(3H)-one;(110): tert-butyl 4-(2-(hydroxy-4-oxo-4,5-dihydrothieno[2,3-c]quinolin-9-yl)benzylamino)ethyl)piperidine-1-carboxylate;(111): 8-methoxy-9-(4-(piperazin-1-yl)phenyl)thieno[2,3-c]quinolin-4(5H)-one;(112): 8-hydroxy-9-(4-(4-(methylsulfonyl)piperazin-1-yl)phenyl)thieno[2,3-c]quinolin-4(5H)-one;(113): 8-hydroxy-9-(4-((piperidin-3-ylamino)methyl)phenyl)thieno[2,3-c]quinolin-4(5H)-one;(114): N-(2-(dimethylamino)ethyl)-4-(8-hydroxy-4-oxo-4,5-dihydrothieno[2,3-c]quinolin-9-yl)benzamide;(115): 9-(4-(3-(dimethylamino)propoxy)phenyl)-8-methoxythieno[2,3-c]quinolin-(5H)-one;(116): 8-methoxy-9-(1-(piperidin-4-yl)-1H-pyrazol-4-yl)thieno[2,3-c]quinolin-4(5H)-one;(117): 8-hydroxy-9-(1-(piperidin-4-yl)-1H-pyrazol-4-yl)thieno[2,3-c]quinolin-4(5H)-one;(118): 8-methoxythiazolo[4,5-c]quinolin-4(5H)-one;(119): 2-((4-(aminomethyl)piperidin-1-yl)methyl)-8-hydroxythieno[2,3-c]quinolin-4(5H)-one;(120): N-(2-(dimethylamino)ethyl)-4-(8-methoxy-4-oxo-4,5-dihydrothieno[2,3-c]quinolin-9-yl)benzamide;(121): 9-(4-(aminomethyl)phenyl)-8-hydroxy-2,3-dihydro-1H-cyclopenta[c]quinolin-4(5H)-one;(122): (E)-butyl 3-(8-hydroxy-4-oxo-4,5-dihydrothieno[2,3-c]quinolin-9-yl)acrylate;(123): 8-methoxy-9-(1H-pyrrolo[2,3-b]pyridin-5-yl)thieno[2,3-c]quinolin-4(5H)-one;(124): 8-hydroxy-9-(1H-pyrrolo[2,3-b]pyridin-5-yl)thieno[2,3-c]quinolin-4(5H)-one;(125): N-(methoxy-4-oxo-4,5-dihydrothieno[2,3-c]quinolin-9-yl)phenethyl)acetamide;(126): N-(2-aminoethyl)-4-(8-hydroxy-4-oxo-4,5-dihydrothieno[2,3-c]quinolin-9-yl)benzamide;(127): N-(2-aminoethyl)-4-(8-methoxy-4-oxo-4,5-dihydrothieno[2,3-c]quinolin-9-yl)benzamide;(128): N-(hydroxy-4-oxo-4,5-dihydrothieno[2,3-c]quinolin-9-yl)phenethyl)acetamide;(129): 4-(8-hydroxy-4 oxo-2,3,4,5-tetrahydro-1H-cyclopenta[c]quinolin-9-yl)benzenesulfonamide;(130): 8-hydroxy-9-(4-(4-methylpiperazine-1-carbonyl)phenyl)thieno[2,3-c]quinolin-4(5H)-one;(131): 8-methoxy-9-(4-(4-methylpiperazine-1-carbonyl)phenyl)thieno[2,3-c]quinolin-4(5H)-one;(132): 8-hydroxy-9-(4-((4-methylpiperazin-1-yl)methyl)phenyl)thieno[2,3-c]quinolin-4(5H)-one;(133): 8-methoxy-9-(4-((4-methylpiperazin-1-yl)methyl)phenyl)thieno[2,3-c]quinolin-4(5H)-one;(134): (E)-9-(3-(diethylamino)prop-1-enyl)-8-methoxythieno[2,3-c]quinolin-4(5H)-one;(135): (E)-9-(3-(4-(aminomethyl)piperidin-1-yl)prop-1-enyl)-8-methoxythieno[2,3-c]quinolin-4(5H)-one;(136): (E)-9-(3-(2-(diethylamino)ethylamino)prop-1-enyl)-8-hydroxythieno[2,3-c]quinolin-4(5H)-one;(137): N-(4-(8-hydroxy-4-oxo-2,3,4,5-tetrahydro-1H-cyclopenta[c]quinolin-9-yl)phenyl)methanesulfonamide;(138): 9-(2-(dimethylamino)pyrimidin-5-yl)-8-hydroxythieno[2,3-c]quinolin-4(5H)-one;(139): tert-butyl (1-(methoxy-4-oxo-4,5-dihydrothieno[2,3-c]quinolin-9-yl)benzyl)piperidin-4-yl)methylcarbamate;(140): 8-hydroxy-9-(4-(4-methylpiperazin-1-yl)phenyl)thieno[2,3-c]quinolin-4(5H)-one;(141): 8-methoxy-9-(4-(4-methylpiperazin-1-yl)phenyl)thieno[2,3-c]quinolin-4(5H)-one;(142): 8-methoxy-9-(1-(methylsulfonyl)-1,2,3,6-tetrahydropyridin-4-yl)thieno[2,3-c]quinolin-4(5H)-one;(143): (E)-9-(3-(diethylamino)prop-1-enyl)-8-hydroxythieno[2,3-c]quinolin-4(5H)-one;(144): 9-(3-(4-(aminomethyl)piperidin-1-yl)propyl)-8-methoxythieno[2,3-c]quinolin-4(5H)-one;(145): 9-(4-(3-(2-(diethylamino)ethylamino)propoxy)phenyl)-8-methoxythieno[2,3-c]quinolin-4(5H)-one;(146): 9-(4-(3-(diethylamino)propoxy)phenyl)-8-methoxythieno[2,3-c]quinolin-4(5H)-one;(147): 9-(4-(3-(2-(diethylamino)ethylamino)propoxy)phenyl)-8-hydroxythieno[2,3-c]quinolin-4(5H)-one;(148): (E)-9-(3-(4-(aminomethyl)piperidin-1-yl)prop-1-enyl)-8-hydroxythieno[2,3-c]quinolin-4(5H)-one;(149): 9-(4-(3-(dimethylamino)propoxy)phenyl)-8-hydroxythieno[2,3-c]quinolin-(5H)-one;(150): 8-hydroxy-9-(4-(2-(piperidin-1-yl)ethoxy)phenyl)thieno[2,3-c]quinolin-4(5H)-one;(151): 9-(4-(2-(ethylamino)ethoxy)phenyl)-8-hydroxythieno[2,3-c]quinolin-4(5H)-one;(152): (E)-9-(3-(4-aminopiperidin-1-yl)prop-1-enyl)-8-methoxythieno[2,3-c]quinolin-4(5H)-one;(153): 9-(1-(2-aminoethyl)-1,2,3,6-tetrahydropyridin-4-yl)-8-methoxythieno[2,3-c]quinolin-4(5H)-one;(154): 9-(4-(2-(ethylamino)ethoxy)phenyl)-8-methoxythieno[2,3-c]quinolin-4(5H)-one;(155): 9-(4-(2-(diethylamino)ethoxy)phenyl)-8-hydroxythieno[2,3-c]quinolin-4(5H)-one;(156): 9-(4-(2-(diethylamino)ethoxy)phenyl)-8-methoxythieno[2,3-c]quinolin-4(5H)-one;(157): 9-(4-(2-(dimethylamino)ethoxy)phenyl)-8-hydroxythieno[2,3-c]quinolin-4(5H)-one;(158): 9-(4-(2-(dimethylamino)ethoxy)phenyl)-8-methoxythieno[2,3-c]quinolin-4(5H)-one;(159): 8-methoxy-9-(4-(2-(piperidin-1-yl)ethoxy)phenyl)thieno[2,3-c]quinolin-4(5H)-one;(160): 8-methoxy-9-(3-(2-(4-methylpiperazin-1-yl)ethoxy)phenyl)thieno[2,3-c]quinolin-4(5H)-one;(161): 9-(3-(2-(diethylamino)ethoxy)phenyl)-8-methoxythieno[2,3-c]quinolin-4(5H)-one;(162): 9-(3-(3-(diethylamino)propoxy)phenyl)-8-methoxythieno[2,3-c]quinolin-4(5H)-one;(163): 9-(4-(2-(dimethylamino)ethyl)phenyl)-8-methoxythieno[2,3-c]quinolin-4(5H)-one;(164): 9-(4-((dimethylamino)methyl)phenyl)-8-methoxythieno[2,3-c]quinolin-4(5H)-one;(165): 9-(4-((dimethylamino)methyl)phenyl)-8-hydroxythieno[2,3-c]quinolin-4(5H)-one;(166): 9-(3-(2-(diethylamino)ethoxy)phenyl)-8-hydroxythieno[2,3-c]quinolin-4(5H)-one;(167): 8-hydroxy-9-(3-(2-(4-methylpiperazin-1-yl)ethoxy)phenyl)thieno[2,3-c]quinolin-4(5H)-one;(168): N-ethyl-N-(2-(4-(8-methoxy-4-oxo-4,5-dihydrothieno[2,3-c]quinolin-9-yl)phenylmethoxy-4-oxo-4,5-dihydrothieno[2,3-c]quinolin-9-yl)phenoxy)ethyl)methanesulfonamide;(169): 9-(4-(2-aminoethyl)phenyl)-8-methoxythieno[2,3-c]quinolin-4(5H)-one;(170): 2-(3-(8-hydroxy-4-oxo-4,5-dihydrothieno[2,3-c]quinolin-9-yl)phenyl)acetonitrile;(171): 2-(3-(8-methoxy-4-oxo-4,5-dihydrothieno[2,3-c]quinolin-9-yl)phenyl)acetonitrile;(172): 9-(1-(2-(dimethylamino)ethyl)-1,2,3,6-tetrahydropyridin-4-yl)-8-hydroxythieno[2,3-c]quinolin-4(5H)-one;(173): N-(hydroxy-4-oxo-4,5-dihydrothieno[2,3-c]quinolin-9-yl)phenethyl)methanesulfonamide;(174): 9-(1-(2-(diethylamino)ethyl)-1,2,3,6-tetrahydropyridin-4-yl)-8-hydroxythieno[2,3-c]quinolin-4(5H)-one;(175): 9-(4-(2-aminoethyl)phenyl)-8-hydroxythieno[2,3-c]quinolin-4(5H)-one;(176): 9-(4-(2-aminoethyl)phenyl)-8-hydroxythieno[2,3-c]quinolin-4(5H)-one;(177): N-(methoxy-4-oxo-4,5-dihydrothieno[2,3-c]quinolin-9-yl)phenethyl)methanesulfonamide;(178): N-(methoxy-4-oxo-4,5-dihydrothieno[2,3-c]quinolin-9-yl)phenethyl)methanesulfonamide;(179): N-(2-aminoethyl)-4-(8-hydroxy-4-oxo-4,5-dihydrothieno[2,3-c]quinolin-9-yl)benzenesulfonamide;(180): 8-hydroxy-9-(1,2,3,6-tetrahydropyridin-4-yl)-2,3-dihydro-1H-cyclopenta[c]quinolin-4(5H)-one;(181): 9-(4-(1-(dimethylamino)ethyl)phenyl)-8-hydroxy-2,3-dihydro-1H-cyclopenta[c]quinolin-4(5H)-one;(182): 9-(4-(2-(dimethylamino)ethyl)phenyl)-8-methoxy-2,3-dihydro-1H-cyclopenta[c]quinolin-4(5H)-one;(183): 9-(4-((diethylamino)methyl)phenyl)-8-methoxythieno[2,3-c]quinolin-4(5H)-one;(184): 9-(4-((diethylamino)methyl)phenyl)-8-hydroxythieno[2,3-c]quinolin-4(5H)-one;(185): 9-(3-(2-(dimethylamino)ethyl)phenyl)-8-hydroxythieno[2,3-c]quinolin-4(5H)-one;(186): 9-(3-(2-aminoethyl)phenyl)-8-hydroxythieno[2,3-c]quinolin-4(5H)-one;(187): 8-hydroxy-9-(4-((methylamino)methyl)phenyl)thieno[2,3-c]quinolin-4(5H)-one;(188): 8-methoxy-9-(4-((methylamino)methyl)phenyl)thieno[2,3-c]quinolin-4(5H)-one;(189): 9-(4-amino-3-methoxyphenyl)-8-methoxythieno[2,3-c]quinolin-4(5H)-one;(190): 3-(8-hydroxy-4 oxo-4,5-dihydrothieno[2,3-c]quinolin-9-yl)benzonitrile;(191): 9-(4-(1-(dimethylamino)ethyl)phenyl)-8-hydroxythieno[2,3-c]quinolin-4(5H)-one;(192): 9-(4-(1-(dimethylamino)ethyl)phenyl)-8-hydroxythieno[2,3-c]quinolin-4(5H)-one;(193): N-(1-(4-(8-hydroxy-4-oxo-4,5-dihydrothieno[2,3-c]quinolin-9-yl)phenyl)ethyl)methanesulfonamide;(194): 8-hydroxy-9-(4-(1-(pyrrolidin-1-yl)ethyl)phenyl)thieno[2,3-c]quinolin-4(5H)-one;(195): 9-(4-(1-aminoethyl)phenyl)-8-hydroxythieno[2,3-c]quinolin-4(5H)-one;(196): 9-(4-(1-(diethylamino)ethyl)phenyl)-8-hydroxythieno[2,3-c]quinolin-4(5H)-one;(197): N-(2-aminoethyl)-4-(8-methoxy-4-oxo-4,5-dihydrothieno[2,3-c]quinolin-9-yl)benzenesulfonamide;(198): N-(2-(dimethylamino)ethyl)-4-(8-methoxy-4-oxo-4,5-dihydrothieno[2,3-c]quinolin-9-yl)benzenesulfonamide;(199): 4-(8-hydroxy-4-oxo-4,5-dihydrothieno[2,3-c]quinolin-9-yl)-N-(pyrrolidin-3-yl)benzenesulfonamide;(200): N-(azetidin-3-yl)-4-(8-hydroxy-4-oxo-4,5-dihydrothieno[2,3-c]quinolin-9-yl)benzenesulfonamide;(201): 9-(4-(2-(diethylamino)ethyl)phenyl)-8-hydroxythieno[2,3-c]quinolin-4(5H)-one;(202): 2-amino-N-(3-(8-methoxy-4-oxo-4,5-dihydrothieno[2,3-c]quinolin-9-yl)phenyl)ethanesulfonamide;(203): 4-(8-hydroxy-4 oxo-4,5-dihydrothieno[2,3-c]quinolin-9-yl)benzonitrile;(204): 4-(8-methoxy-4 oxo-4,5-dihydrothieno[2,3-c]quinolin-9-yl)benzonitrile;(205): (E)-9-(3-(3-aminopyrrolidin-1-yl)prop-1-enyl)-8-methoxythieno[2,3-c]quinolin-4(5H)-one;(206): N-(2-hydroxyethyl)-4-(8-methoxy-4-oxo-4,5-dihydrothieno[2,3-c]quinolin-9-yl)benzensulfonamide;(207): 8-methoxy-9-(5-methoxypyridin-3-yl)thieno[2,3-c]quinolin-4(5H)-one;(208): 8-methoxy-9-(5-methoxypyridin-3-yl)-2,3-dihydro-1H-cyclopenta[c]quinolin-4(5H)-one;(209): 9-(4-(3-aminopyrrolidin-1-ylsulfonyl)phenyl)-8-hydroxythieno[2,3-c]quinolin-4(5H)-one;(210): N-(2-bromoethyl)-4-(8-hydroxy-4-oxo-4,5-dihydrothieno[2,3-c]quinolin-9-yl)benzensulfonamide;(211): 9-(4-((diisopropylamino)methyl)phenyl)-8-methoxythieno[2,3-c]quinolin-4(5H)-one;(212): N-(hydroxy-4-oxo-4,5-dihydrothieno[2,3-c]quinolin-9-yl)benzyl)methanesulfonamide;(213): 9-(4-((isopropylamino)methyl)phenyl)-8-methoxythieno[2,3-c]quinolin-4(5H)-one;(214): 2-(dimethylamino)-N-(3-(8-hydroxy-4-oxo-4,5-dihydrothieno[2,3-c]quinolin-9-yl)phenyl)ethanesulfonamide;(215): 2-amino-N-(3-(8-hydroxy-4-oxo-4,5-dihydrothieno[2,3-c]quinolin-9-yl)phenyl)ethanesulfonamide;(216): 8-methoxy-9-(4-(1-(pyrrolidin-1-yl)ethyl)phenyl)thieno[2,3-c]quinolin-4(5H)-one;(217): 9-(4-amino-3-hydroxyphenyl)-8-hydroxythieno[2,3-c]quinolin-4(5H)-one;(218): N-(2-methoxy-4-(8-methoxy-4-oxo-4,5-dihydrothieno[2,3-c]quinolin-9-yl)phenyl)methanesulfonamide;(219): 9-(3,5-difluoro-4-hydroxyphenyl)-8-methoxythieno[2,3-c]quinolin-4(5H)-one;(220): N-(2-hydroxy-4-(8-hydroxy-4-oxo-4,5-dihydrothieno[2,3-c]quinolin-9-yl)phenyl)methanesulfonamide;(221): 9-(4-((4-(aminomethyl)piperidin-1-yl)methyl)-3-fluorophenyl)-8-methoxythieno[2,3-c]quinolin-4(5H)-one;(222): 9-(4-(2-(dimethylamino)ethyl)phenyl)-6-fluoro-8-methoxythieno[2,3-c]quinolin-4(5H)-one;(223): 9-(3,5-difluoro-4-hydroxyphenyl)-8-hydroxythieno[2,3-c]quinolin-4(5H)-one;(224): 6-fluoro-8-methoxy-9-(1,2,3,6-tetrahydropyridin-4-yl)thieno[2,3-c]quinolin-4(5H)-one;(225): 9-(4-(1-(dimethylamino)ethyl)phenyl)-6-fluoro-8-hydroxythieno[2,3-c]quinolin-4(5H)-one;(226): 9-(4-((diethylamino)methyl)-3-fluorophenyl)-8-methoxythieno[2,3-c]quinolin-4(5H)-one;(227): (E)-9-(3-(3-hydroxypyrrolidin-1-yl)prop-1-enyl)-8-methoxythieno[2,3-c]quinolin-4(5H)-one;(228): (E)-8-hydroxy-9-(3-(3-hydroxypyrrolidin-1-yl)prop-1-enyl)thieno[2,3-c]quinolin-4(5H)-one;(229): 8-hydroxy-9-(4-((isopropylamino)methyl)phenyl)thieno[2,3-c]quinolin-4(5H)-one;(230): (E)-9-(3-(3-aminoazetidin-1-yl)prop-1-enyl)-8-hydroxythieno[2,3-c]quinolin-4(5H)-one;(231): (E)-8-methoxy-9-(3-(2-(methylsulfonyl)ethylamino)prop-1-enyl)thieno[2,3-c]quinolin-4(5H)-one;(232): (S)-9-(4-(1-aminoethyl)phenyl)-8-methoxythieno[2,3-c]quinolin-4(5H)-one;(233): (S)-9-(4-(1-aminoethyl)phenyl)-8-hydroxythieno[2,3-c]quinolin-4(5H)-one;(234): 8-hydroxy-9-(5-hydroxypyridin-3-yl)-2,3-dihydro-1H-cyclopenta[c]quinolin-4(5H)-one;(235): 9-(4-((4-(aminomethyl)piperidin-1-yl)methyl)-3-fluorophenyl)-8-hydroxythieno[2,3-c]quinolin-4(5H)-one;(236): 8-methoxy-9-(4-(1-(2-(methylsulfonyl)ethylamino)ethyl)phenyl)thieno[2,3-c]quinolin-4(5H)-one;(237): 9-(4-((3-aminopyrrolidin-1-yl)methyl)-3-fluorophenyl)-8-methoxythieno[2,3-c]quinolin-4(5H)-one;(238): (E)-9-(3-(3-aminoazetidin-1-yl)prop-1-enyl)-8-methoxythieno[2,3-c]quinolin-4(5H)-one;(239): (E)-9-(3-(ethylamino)prop-1-enyl)-8-hydroxythieno[2,3-c]quinolin-4(5H)-one;(240): 9-(4-((3-aminopiperidin-1-yl)methyl)-3-fluorophenyl)-8-hydroxythieno[2,3-c]quinolin-4(5H)-one;(241): 9-(4-((3-aminopyrrolidin-1-yl)methyl)-3-fluorophenyl)-8-hydroxythieno[2,3-c]quinolin-4(5H)-one;(242): 9-(4-((3-aminopiperidin-1-yl)methyl)-3-fluorophenyl)-8-methoxythieno[2,3-c]quinolin-4(5H)-one;(243): 8-hydroxy-9-(4-(1-(2-(methylsulfonyl)ethylamino)ethyl)phenyl)thieno[2,3-c]quinolin-4(5H)-one;(244): (E)-9-(3-(3-aminopiperidin-1-yl)prop-1-enyl)-8-methoxythieno[2,3-c]quinolin-4(5H)-one;(245): (E)-9-(3-(3-aminopyrrolidin-1-yl)prop-1-enyl)-8-hydroxythieno[2,3-c]quinolin-4(5H)-one;(246): (E)-9-(3-(3-aminopiperidin-1-yl)prop-1-enyl)-8-hydroxythieno[2,3-c]quinolin-4(5H)-one;(247): (E)-8-hydroxy-9-(3-(2-(methylsulfonyl)ethylamino)prop-1-enyl)thieno[2,3-c]quinolin-4(5H)-one;(248): 8-methoxy-9-(4-(2-(2-(methylsulfonyl)ethylamino)ethyl)phenyl)thieno[2,3-c]quinolin-(5H)-one;(249): 2-(2-fluoro-4-(8-methoxy-4-oxo-4,5-dihydrothieno[2,3-c]quinolin-9-yl)phenyl)acetonitrile;(250): (E)-N-(1-(3-(8-methoxy-4-oxo-4,5-dihydrothieno[2,3-c]quinolin-9-yl)allyl)azetidin-3-yl)methanesulfonamide;(251): 4-(8-methoxy-4-oxo-4,5-dihydrothieno[2,3-c]quinolin-9-yl)-N,N-dimethylbenzenesulfonamide;(252): 4-(8-hydroxy-4-oxo-4,5-dihydrothieno[2,3-c]quinolin-9-yl)-N-methylbenzenesulfonamide;(253): tert-butyl (5-(8-methoxy-4-oxo-4,5-dihydrothieno[2,3-c]quinolin-9-yl)furan-2-yl)methylcarbamate;(254): N-(4-(8-hydroxy-4-oxo-4,5-dihydrothieno[2,3-c]quinolin-9-yl)-2-methylphenyl)methanesulfonamide;(255): N-(4-(8-methoxy-4-oxo-4,5-dihydrothieno[2,3-c]quinolin-9-yl)-2-methylphenyl)methanesulfonamide;(256): 9-(4-(aminomethyl)phenyl)-6-fluoro-8-hydroxythieno[2,3-c]quinolin-4(5H)-one;(257): 9-(4-(aminomethyl)phenyl)-6-fluoro-8-methoxythieno[2,3-c]quinolin-4(5H)-one;(258): 6-fluoro-8-hydroxy-9-(1,2,3,6-tetrahydropyridin-4-yl)thieno[2,3-c]quinolin-4(5H)-one;(259): 9-(4-((diethylamino)methyl)-3-fluorophenyl)-8-hydroxythieno[2,3-c]quinolin-4(5H)-one;(260): 8-methoxy-9-(4-(1-(piperidin-1-yl)ethyl)phenyl)thieno[2,3-c]quinolin-4(5H)-one;(261): 2-(2-fluoro-4-(8-hydroxy-4-oxo-4,5-dihydrothieno[2,3-c]quinolin-9-yl)phenyl)acetonitrile;(262): 8-hydroxy-9-(4-(1-(piperidin-1-yl)ethyl)phenyl)thieno[2,3-c]quinolin-4(5H)-one;(263): (E)-9-(3-(3-(dimethylamino)piperidin-1-yl)prop-1-enyl)-8-hydroxythieno[2,3-c]quinolin-4(5H)-one;(264): (E)-9-(3-(3-(dimethylamino)pyrrolidin-1-yl)prop-1-enyl)-8-hydroxythieno[2,3-c]quinolin-4(5H)-one;(265): 9-(4-(2-aminoethyl)-3-fluorophenyl)-8-methoxythieno[2,3-c]quinolin-4(5H)-one;(266): 9-(5-(aminomethyl)thiophen-2-yl)-8-hydroxythieno[2,3-c]quinolin-4(5H)-one;(267): 9-(4-((ethylamino)methyl)phenyl)-8-hydroxythieno[2,3-c]quinolin-4(5H)-one;(268): (E)-9-(3-(4-aminopiperidin-1-yl)prop-1-enyl)-8-hydroxythieno[2,3-c]quinolin-4(5H)-one;(269): 9-(4-((ethylamino)methyl)phenyl)-8-methoxythieno[2,3-c]quinolin-4(5H)-one;(270): 9-(4-(aminomethyl)phenyl)-6-bromo-8-hydroxythieno[2,3-c]quinolin-4(5H)-one;(271): 9-(3-chloro-4-((diethylamino)methyl)phenyl)-8-methoxythieno[2,3-c]quinolin-4(5H)-one;(272): (R)-9-(4-(1-(dimethylamino)ethyl)phenyl)-8-hydroxythieno[2,3-c]quinolin-4(5H)-one;(273): 9-(4-(3-aminopropyl)phenyl)-8-hydroxythieno[2,3-c]quinolin-(5H)-one;(274): (R)-9-(4-(1-aminoethyl)phenyl)-8-methoxythieno[2,3-c]quinolin-4(5H)-one;(275): (R)-9-(4-(1-aminoethyl)phenyl)-8-hydroxythieno[2,3-c]quinolin-4(5H)-one;(276): 9-(4-(2-aminoethyl)-3-fluorophenyl)-8-hydroxythieno[2,3-c]quinolin-4(5H)-one;(277): 9-(4-(1-amino-2-methylpropan-2-yl)phenyl)-8-hydroxythieno[2,3-c]quinolin-4(5H)-one;(278): 9-(3-fluoro-4-((3-hydroxypyrrolidin-1-yl)methyl)phenyl)-8-hydroxythieno[2,3-c]quinolin-4(5H)-one;(279): 9-(3-fluoro-4-((3-hydroxypyrrolidin-1-yl)methyl)phenyl)-8-methoxythieno[2,3-c]quinolin-4(5H)-one;(280): 4-(8-methoxy-4-oxo-4,5-dihydrothieno[2,3-c]quinolin-9-yl)-N-(2,2,2-trifluoroethyl)benzenesulfonamide;(281): 4-(8-hydroxy-4-oxo-4,5-dihydrothieno[2,3-c]quinolin-9-yl)-N-(2,2,2-trifluoroethyl)benzenesulfonamide;(282): N-(2-(dimethylamino)ethyl)-4-(8-hydroxy-4-oxo-4,5-dihydrothieno[2,3-c]quinolin-9-yl)benzenesulfonamide;(283): 8-hydroxy-9-(4-((2-(methylsulfonyl)ethylamino)methyl)phenyl)thieno[2,3-c]quinolin-4(5H)-one;(284): 9-(3-(3-(dimethylamino)pyrrolidin-1-yl)propyl)-8-hydroxythieno[2,3-c]quinolin-4(5H)-one;(285): 9-(1-(2-aminoethyl)-1H-pyrazol-4-yl)-8-methoxythieno[2,3-c]quinolin-4(5H)-one;(286): 9-(3-chloro-4-((diethylamino)methyl)phenyl)-8-hydroxythieno[2,3-c]quinolin-4(5H)-one;(287): 4-(7-fluoro-8-methoxy-4-oxo-4,5-dihydrothieno[2,3-c]quinolin-9-yl)-N-(2-hydroxyethyl)benzenesulfonamide;(288): 9-(3-acetylphenyl)-8-methoxythieno[2,3-c]quinolin-4(5H)-one;(289): 2-fluoro-4-(8-hydroxy-4-oxo-4,5-dihydrothieno[2,3-c]quinolin-9-yl)-N-(2-hydroxyethyl)benzamide;(290): 3-(4-(8-hydroxy-4-oxo-4,5-dihydrothieno[2,3-c]quinolin-9-yl)phenyl)propanenitrile;(291): 9-(4-acetylphenyl)-8-methoxythieno[2,3-c]quinolin-4(5H)-one;(292): 2-fluoro-N-(2-hydroxyethyl)-4-(8-methoxy-4-oxo-4,5-dihydrothieno[2,3-c]quinolin-9-yl)benzamide;(293): 4-(8-hydroxy-4-oxo-4,5-dihydrothieno[2,3-c]quinolin-9-yl)-N-(2-hydroxyethyl)benzamide;(294): 1,1-diethyl-3-(hydroxy-4-oxo-4,5-dihydrothieno[2,3-c]quinolin-9-yl)benzyl)urea;(295): N-(2-hydroxyethyl)-4-(8-methoxy-4-oxo-4,5-dihydrothieno[2,3-c]quinolin-9-yl)benzamide;(296): 9-(4-acetylphenyl)-8-hydroxythieno[2,3-c]quinolin-4(5H)-one;(297): N-(2-bromoethyl)-2-fluoro-4-(8-hydroxy-4-oxo-4,5-dihydrothieno[2,3-c]quinolin-9-yl)benzenesulfonamide;(298): 9-(3-(3-(dimethylamino)piperidin-1-yl)propyl)-8-hydroxythieno[2,3-c]quinolin-4(5H)-one;(299): N-(2-fluoro-4-(8-hydroxy-4-oxo-4,5-dihydrothieno[2,3-c]quinolin-9-yl)phenethyl)methanesulfonamide;(300): 9-(3-fluoro-4-(2-(methylsulfonamido)ethyl)phenyl)-4-oxo-4,5-dihydrothieno[2,3-c]quinolin-8-yl methanesulfonate;(301): (R)—N-(1-(4-(8-hydroxy-4-oxo-4,5-dihydrothieno[2,3-c]quinolin-9-yl)phenyl)ethyl)methanesulfonamide;(302): (R)-9-(4-(1-(methylsulfonamido)ethyl)phenyl)-4-oxo-4,5-dihydrothieno[2,3-c]quinolin-8-yl methanesulfonate;(303): 2-fluoro-N-(2-hydroxyethyl)-4-(8-methoxy-4-oxo-4,5-dihydrothieno[2,3-c]quinolin-9-yl)benzenesulfonamide;(304): 4-(8-hydroxy-4-oxo-4,5-dihydrothieno[2,3-c]quinolin-9-yl)-N,N-dimethylbenzenesulfonamide;(305): 9-(4-(2-(dimethylamino)ethyl)phenyl)-7-fluoro-8-methoxythieno[2,3-c]quinolin-(5H)-one;(306): N-(2-bromoethyl)-4-(7-fluoro-8-hydroxy-4-oxo-4,5-dihydrothieno[2,3-c]quinolin-9-yl)benzenesulfonamide;(307): 4-(7-fluoro-8-hydroxy-4-oxo-4,5-dihydrothieno[2,3-c]quinolin-9-yl)-N-(2-hydroxyethyl)benzenesulfonamide;(308): 9-(4-(1-(dimethylamino)-2-methylpropan-2-yl)phenyl)-8-hydroxythieno[2,3-c]quinolin-4(5H)-one;(309): N-(2-chloro-4-(8-methoxy-4-oxo-4,5-dihydrothieno[2,3-c]quinolin-9-yl)benzyl)-N-methyl methanesulfonamide;(310): 4-(8-hydroxy-4-oxo-4,5-dihydrothieno[2,3-c]quinolin-9-yl)-N-(2-methoxyethyl)benzenesulfonamide;(311): (E)-3-(8-methoxy-4-oxo-4,5-dihydrothieno[2,3-c]quinolin-9-yl)-2-methylacrylonitrile;(312): N-(2-fluoro-4-(8-methoxy-4-oxo-4,5-dihydrothieno[2,3-c]quinolin-9-yl)phenethyl)methanesulfonamide;(313): 8-hydroxy-9-(4-(1-hydroxyethyl)phenyl)thieno[2,3-c]quinolin-4(5H)-one;(314): 9-(4-(1-(cyclopentylamino)ethyl)phenyl)-8-hydroxythieno[2,3-c]quinolin-4(5H)-one;(315): 9-(4-(1-(cyclopentylamino)ethyl)phenyl)-8-methoxythieno[2,3-c]quinolin-4(5H)-one;(316): 4-(8-hydroxy-4 oxo-4,5-dihydrothieno[2,3-c]quinolin-9-yl)-N-(2-hydroxyethyl)benzenesulfonamide;(317): 9-(5-(aminomethyl)furan-2-yl)-8-hydroxythieno[2,3-c]quinolin-4(5H)-one;(318): 9-(3-chloro-4-((methylamino)methyl)phenyl)-8-methoxythieno[2,3-c]quinolin-4(5H)-one;(319): 9-(4-(2-aminopropan-2-yl)phenyl)-8-hydroxythieno[2,3-c]quinolin-4(5H)-one;(320): N-(3-hydroxypropyl)-4-(8-methoxy-4-oxo-4,5-dihydrothieno[2,3-c]quinolin-9-yl)benzenesulfonamide;(321): 2-fluoro-4-(8-hydroxy-4-oxo-4,5-dihydrothieno[2,3-c]quinolin-9-yl)-N-(2-hydroxyethyl)benzenesulfonamide;(322): 4-(8-hydroxy-4-oxo-4,5-dihydrothieno[2,3-c]quinolin-9-yl)-N-(3-hydroxypropyl)benzensulfonamide;(323): N-(3-bromopropyl)-4-(8-hydroxy-4-oxo-4,5-dihydrothieno[2,3-c]quinolin-9-yl)benzenesulfonamide;(324): 2-fluoro-4-(8-hydroxy-4-oxo-4,5-dihydrothieno[2,3-c]quinolin-9-yl)-N-(2-methoxyethyl)benzenesulfonamide;(325): 9-(3-chloro-4-((methylamino)methyl)phenyl)-8-hydroxythieno[2,3-c]quinolin-4(5H)-one;(326): 9-(4-(aminomethyl)phenyl)-4 oxo-4,5-dihydrothieno[2,3-c]quinoline-8-carbonitrile;(327): 9-(4-(2-(dimethylamino)ethyl)-3-fluorophenyl)-8-hydroxythieno[2,3-c]quinolin-(5H)-one;(328): 9-(4-(aminomethyl)phenyl)-6,7-dichloro-8-hydroxythieno[2,3-c]quinolin-4(5H)-one;(329): 9-(4-(aminomethyl)phenyl)-6-chloro-8-hydroxythieno[2,3-c]quinolin-4(5H)-one;(330): 9-(4-(aminomethyl)phenyl)-4-oxo-4,5-dihydrothieno[2,3-c]quinolin-8-yl trifluoromethanesulfonate;(331): 9-(4-(2-(dimethylamino)ethyl)phenyl)-8-methoxythieno[2,3-c]quinolin-4(5H)-one;(332): N-(2-chloroethyl)-4-(8-hydroxy-4-oxo-4,5-dihydrothieno[2,3-c]quinolin-9-yl)benzensulfonamide;(333): N-(2-fluoroethyl)-4-(8-methoxy-4-oxo-4,5-dihydrothieno[2,3-c]quinolin-9-yl)benzensulfonamide;(334): 9-(4-(2-aminopropan-2-yl)phenyl)-6-chloro-8-hydroxythieno[2,3-c]quinolin-4(5H)-one;(335): (S)-9-(4-(1-(dimethylamino)ethyl)phenyl)-8-hydroxythieno[2,3-c]quinolin-4(5H)-one;(336): 9-(4-(1-aminopropyl)phenyl)-8-hydroxythieno[2,3-c]quinolin-4(5H)-one;(337): 9-(4-(1-aminopropyl)phenyl)-8-methoxythieno[2,3-c]quinolin-4(5H)-one;(338): 9-(4-(1-(diethylamino)propyl)phenyl)-8-hydroxythieno[2,3-c]quinolin-4(5H)-one;(339): 9-(4-(1-(dimethylamino)propyl)phenyl)-8-hydroxythieno[2,3-c]quinolin-4(5H)-one;(340): 9-amino-8-methoxythieno[2,3-c]quinolin-4(5H)-one;(341): 9-(4-(1-(dimethylamino)ethyl)phenyl)-6,7-difluoro-8-hydroxythieno[2,3-c]quinolin-(5H)-one;(342): 9-(4-(1-(dimethylamino)ethyl)phenyl)-6,7-difluoro-8-methoxythieno[2,3-c]quinolin-4(5H)-one;(343): N-cyclopropyl-4-(8-methoxy-4-oxo-4,5-dihydrothieno[2,3-c]quinolin-9-yl)benzenesulfonamide;(344) N-cyclopropyl-4-(8-hydroxy-4-oxo-4,5-dihydrothieno[2,3-c]quinolin-9-yl)benzenesulfonamide;(345): 9-(2-amino-2,3-dihydro-1H-inden-5-yl)-8-hydroxythieno[2,3-c]quinolin-4(5H)-one;(346): 9-(4-(1-(dimethylamino)ethyl)phenyl)thieno[2,3-c]quinolin-4(5H)-one;(347): (S)—N-(1-(4-(8-hydroxy-4-oxo-4,5-dihydrothieno[2,3-c]quinolin-9-yl)phenyl)ethyl)methanesulfonamide;(348): 9-(4-(1-(aminomethyl)cyclopropyl)phenyl)-8-hydroxythieno[2,3-c]quinolin-4(5H)-one;(349): 9-(4-(1-(dimethylamino)ethyl)-3-fluorophenyl)-8-hydroxythieno[2,3-c]quinolin-(5H)-one;(350): N-(1-(hydroxymethyl)cyclopentyl)-4-(8-methoxy-4-oxo-4,5-dihydrothieno[2,3-c]quinolin-9-yl)benzenesulfonamide;(351): 9-(2-(diethylamino)-2,3-dihydro-1H-inden-5-yl)-8-hydroxythieno[2,3-c]quinolin-4(5H)-one(352): 9-(2-(dimethylamino)-2,3-dihydro-1H-inden-5-yl)-8-hydroxythieno[2,3-c]quinolin-4(5H)-one;(353): 8-hydroxy-9-(1,2,3,4-tetrahydroisoquinolin-7-yl)thieno[2,3-c]quinolin-4(5H)-one;(354): 8-methoxy-9-(1,2,3,4-tetrahydroisoquinolin-7-yl)thieno[2,3-c]quinolin-4(5H)-one;(355): 3-(3-(8-hydroxy-4-oxo-4,5-dihydrothieno[2,3-c]quinolin-9-yl)phenyl)propanenitrile;(356): 9-(4-(1-(diethylamino)ethyl)-3-fluorophenyl)-8-hydroxythieno[2,3-c]quinolin-4(5H)-one;(357): 1-(4-(8-methoxy-4-oxo-4,5-dihydrothieno[2,3-c]quinolin-9-yl)phenyl)cyclopropanecarbonitrile;(358): 9-(2-ethyl-1,2,3,4-tetrahydroisoquinolin-7-yl)-8-hydroxythieno[2,3-c]quinolin-4(5H)-one;(359): 9-(4-(1-aminoethyl)-3-fluorophenyl)-8-hydroxythieno[2,3-c]quinolin-4(5H)-one;(360): 3-(3-(8-methoxy-4-oxo-4,5-dihydrothieno[2,3-c]quinolin-9-yl)phenyl)propanenitrile;(361): 1-(4-(8-hydroxy-4-oxo-4,5-dihydrothieno[2,3-c]quinolin-9-yl)phenyl)cyclopropanecarbonitrile;(362): 9-(2-amino-2,3-dihydro-1H-inden-5-yl)-8-methoxythieno[2,3-c]quinolin-4(5H)-one;(363): N-isopentyl-4-(8-methoxy-4-oxo-4,5-dihydrothieno[2,3-c]quinolin-9-yl)benzenesulfonamide;(364): 9-(2-(dimethylamino)-2,3-dihydro-1H-inden-5-yl)-8-methoxythieno[2,3-c]quinolin-4(5H)-one;(365): 9-(4-(1-(ethylamino)ethyl)phenyl)-8-methoxythieno[2,3-c]quinolin-4(5H)-one;(366): 6-chloro-9-(4-(1-(dimethylamino)ethyl)phenyl)-8-hydroxythieno[2,3-c]quinolin-4(5H)-one;(367): 9-(4-(cyclopropanecarbonyl)phenyl)-8-methoxythieno[2,3-c]quinolin-4(5H)-one;(368): 9-(4-(aminomethyl)phenyl)-4-oxo-4,5-dihydrothieno[2,3-c]quinoline-8-carboxamide;(369): 9-(2-aminoethyl)-8-methoxythieno[2,3-c]quinolin-4(5H)-one;(370): 8-hydroxy-9-(4-(2-hydroxyethylsulfonyl)phenyl)thieno[2,3-c]quinolin-4(5H)-one;(371): 9-(4-(2-hydroxyethylsulfonyl)phenyl)-8-methoxythieno[2,3-c]quinolin-4(5H)-one;(372): 9-(1-ethylindolin-5-yl)-8-hydroxythieno[2,3-c]quinolin-4(5H)-one;(373): 9-(4-(1-aminopropan-2-yl)phenyl)-8-methoxythieno[2,3-c]quinolin-4(5H)-one;(374): 8-hydroxy-9-(2-methyl-1,2,3,4-tetrahydroisoquinolin-7-yl)thieno[2,3-c]quinolin-4(5H)-one;(375): 9-(4-(1-aminoethyl)-3-fluorophenyl)-8-methoxythieno[2,3-c]quinolin-4(5H)-one;(376): 8-hydroxy-9-(1-methylindolin-5-yl)thieno[2,3-c]quinolin-4(5H)-one;(377): 8-hydroxy-9-(indolin-5-yl)thieno[2,3-c]quinolin-4(5H)-one;(378): 9-(indolin-5-yl)-8-methoxythieno[2,3-c]quinolin-4(5H)-one;(379): 9-(4-(1-((dimethylamino)methyl)cyclopropyl)phenyl)-8-hydroxythieno[2,3-c]quinolin-4(5H)-one;(380): 4-(8-methoxy-4-oxo-4,5-dihydrothieno[2,3-c]quinolin-9-yl)-N-propylbenzenesulfonamide;(381): N-(cyclopropylmethyl)-4-(8-methoxy-4-oxo-4,5-dihydrothieno[2,3-c]quinolin-9-yl)benzenesulfonamide;(382): N-(3,3-dimethylbutyl)-4-(8-methoxy-4-oxo-4,5-dihydrothieno[2,3-c]quinolin-9-yl)benzenesulfonamide;(383): 4-(8-hydroxy-4-oxo-4,5-dihydrothieno[2,3-c]quinolin-9-yl)-N-isopentylbenzenesulfonamide;(384): N-(3,3-dimethylbutyl)-4-(8-hydroxy-4-oxo-4,5-dihydrothieno[2,3-c]quinolin-9-yl)benzenesulfonamide;(385): 9-(4-(1-(ethylamino)ethyl)phenyl)-8-hydroxythieno[2,3-c]quinolin-4(5H)-one;(386): 3-(4-(8-methoxy-4-oxo-4,5-dihydrothieno[2,3-c]quinolin-9-yl)phenyl)-3-oxopropanenitrile;(387): (E)-9-(2-ethoxyvinyl)-8-methoxythieno[2,3-c]quinolin-4(5H)-one;(388): N-(1-(4-(8-hydroxy-4-oxo-4,5-dihydrothieno[2,3-c]quinolin-9-yl)phenyl)ethyl)acetamide;(389): 4-(8-methoxy-4-oxo-4,5-dihydrothieno[2,3-c]quinolin-9-yl)-N-(3,3,3-trifluoropropyl)benzenesulfonamide;(390): 4-(8-hydroxy-4-oxo-4,5-dihydrothieno[2,3-c]quinolin-9-yl)-N-(1-(hydroxymethyl)cyclopentyl)benzenesulfonamide;(391): N-(2,2-difluoroethyl)-4-(8-methoxy-4-oxo-4,5-dihydrothieno[2,3-c]quinolin-9-yl)benzenesulfonamide;(1031): 8-methoxy-9-(4-(1-methoxyethyl)phenyl)thieno[2,3-c]quinolin-4(5H)-one;(1032): 9-(4-(1-aminoethyl)phenyl)-6-bromo-8-hydroxythieno[2,3-c]quinolin-4(5H)-one;(1033): 8-methoxy-9-(2-((piperidin-3-ylmethyl)amino)ethyl)thieno[2,3-c]quinolin-4(5H)-one;(1034): 9-(2-(4-((dimethylamino)methyl)piperidin-1-yl)ethyl)-8-methoxythieno[2,3-c]quinolin-4(5H)-one;(1035): tert-butyl 4-((2-(8-methoxy-4-oxo-4,5-dihydrothieno[2,3-c]quinolin-9-yl)ethyl)amino)piperidine-1-carboxylate;(1036): 8-methoxy-9-(2-(piperidin-4-ylamino)ethyl)thieno[2,3-c]quinolin-4(5H)-one;(1037): 4-(8-hydroxy-4-oxo-4,5-dihydrothieno[2,3-c]quinolin-9-yl)-N-(3,3,3-trifluoropropyl)benzenesulfonamide;(1038): 3H-pyrrolo[2,3-c]quinolin-4(5H)-one;(1039): 9-(4-(1-aminoethyl)phenyl)-6-cyclopropyl-8-hydroxythieno[2,3-c]quinolin-4(5H)-one;(1040): 9-(4-(1-aminoethyl)phenyl)-8-hydroxy-4-oxo-4,5-dihydrothieno[2,3-c]quinoline-6-carbonitrile;(1041): 9-(4-(1-aminoethyl)phenyl)-6-chloro-8-hydroxythieno[2,3-c]quinolin-4(5H)-one;(1042): 8-hydroxy-9-(2-(4-((methylamino)methyl)piperidin-1-yl)ethyl)thieno[2,3-c]quinolin-4(5H)-one;(1043): 8-methoxy-9-(2-(4-((methylamino)methyl)piperidin-1-yl)ethyl)thieno[2,3-c]quinolin-4(5H)-one;(1044): 9-(2-(4-((dimethylamino)methyl)piperidin-1-yl)ethyl)-8-hydroxythieno[2,3-c]quinolin-4(5H)-one;(1045): 9-(4-(1-hydroxypropyl)phenyl)-8-methoxythieno[2,3-c]quinolin-4(5H)-one;(1046): (R)-8-methoxy-9-(4-(1-(methylamino)ethyl)phenyl)thieno[2,3-c]quinolin-4(5H)-one;(1047): (R)-8-(4-(1-aminoethyl)phenyl)thieno[2,3-c]quinolin-4(5H)-one;(1048): (R)-tert-butyl(1-(4-(4-oxo-4,5-dihydrothieno[2,3-c]quinolin-8-yl)phenyl)ethyl)carbamate;(1049): 9-(4-(4-hydroxypiperidin-4-yl)phenyl)-8-methoxythieno[2,3-c]quinolin-4(5H)-one;(1050): (R)-8-(4-(1-(dimethylamino)ethyl)phenyl)thieno[2,3-c]quinolin-4(5H)-one;(1051): 8-hydroxy-9-(4-(1,2,3,6-tetrahydropyridin-4-yl)phenyl)thieno[2,3-c]quinolin-4(5H)-one;(1052): (R)-8-hydroxy-9-(4-(1-(methylamino)ethyl)phenyl)thieno[2,3-c]quinolin-4(5H)-one;(1053): 8-hydroxy-9-(4-(1-hydroxypropyl)phenyl)thieno[2,3-c]quinolin-4(5H)-one;(1054): (R)-8-hydroxy-9-(4-(1-hydroxyethyl)phenyl)thieno[2,3-c]quinolin-4(5H)-one;(1055): 8-hydroxy-9-(4-(4-hydroxypiperidin-4-yl)phenyl)thieno[2,3-c]quinolin-4(5H)-one;(1056): (S)-8-hydroxy-9-(4-(1-hydroxyethyl)phenyl)thieno[2,3-c]quinolin-4(5H)-one;(1057): N-(1-hydroxypropan-2-yl)-4-(8-methoxy-4-oxo-4,5-dihydrothieno[2,3-c]quinolin-9-yl)benzenesulfonamide;(1058): 9-(4-(hydroxy(thiazol-2-yl)methyl)phenyl)-8-methoxythieno[2,3-c]quinolin-4(5H)-one;(1059): 9-(6-(1-aminoethyl)pyridin-3-yl)-8-hydroxythieno[2,3-c]quinolin-4(5H)-one;(1060): 9-(4-(4-hydroxybutyl)phenyl)-8-methoxythieno[2,3-c]quinolin-4(5H)-one;(1061): 2-(4-(8-hydroxy-4-oxo-4,5-dihydrothieno[2,3-c]quinolin-9-yl)phenyl)-2-methylpropanamide;(1062): N-(1-bromopropan-2-yl)-4-(8-hydroxy-4-oxo-4,5-dihydrothieno[2,3-c]quinolin-9-yl)benzenesulfonamide;(1063): 8-hydroxy-9-(4-(hydroxy(thiazol-2-yl)methyl)phenyl)thieno[2,3-c]quinolin-4(5H)-one;(1064): (S)-8-methoxy-9-(4-(1-(methylamino)ethyl)phenyl)thieno[2,3-c]quinolin-4(5H)-one;(1065): 9-(6-(1-(diethylamino)ethyl)pyridin-3-yl)-8-hydroxythieno[2,3-c]quinolin-4(5H)-one;(1066): 9-(4-(1-aminoethyl)phenyl)-8-hydroxy-6-methylthieno[2,3-c]quinolin-4(5H)-one;(1067): 9-(6-(1-aminoethyl)pyridin-3-yl)-8-methoxythieno[2,3-c]quinolin-4(5H)-one;(1068): 8-hydroxy-9-(4-(4-hydroxybutyl)phenyl)thieno[2,3-c]quinolin-4(5H)-one;(1069): 9-(4-(3-amino-1-hydroxypropyl)phenyl)-8-methoxythieno[2,3-c]quinolin-4(5H)-one;(1070): 9-(6-(1-(dimethylamino)ethyl)pyridin-3-yl)-8-hydroxythieno[2,3-c]quinolin-(5H)-one;(1071): 9-(6-(1-(dimethylamino)ethyl)pyridin-3-yl)-8-methoxythieno[2,3-c]quinolin-4(5H)-one;(1072): 4-((4-(8-methoxy-4-oxo-4,5-dihydrothieno[2,3-c]quinolin-9-yl)-1H-pyrazol-1-yl)methyl)benzonitrile;(1073): 8-aminothieno[2,3-c]quinolin-4(5H)-one;(1074): 9-(4-((1H-pyrazol-1-yl)methyl)phenyl)-8-methoxythieno[2,3-c]quinolin-4(5H)-one;(1075): 9-(6-(1-aminoethyl)pyridin-3-yl)-8-methoxythieno[2,3-c]quinolin-4(5H)-one;(1076): 9-(4-(1-aminoethyl)phenyl)-4-oxo-4,5-dihydrothieno[2,3-c]quinolin-8-yl dimethylcarbamate;(1077): 9-(4-(1-aminoethyl)phenyl)-4-oxo-4,5-dihydrothieno[2,3-c]quinolin-8-yl isopropyl carbonate;(1078): 9-(4-((1H-imidazol-1-yl)methyl)phenyl)-8-methoxythieno[2,3-c]quinolin-4(5H)-one;(1079): N-(2-bromopropyl)-4-(8-hydroxy-4-oxo-4,5-dihydrothieno[2,3-c]quinolin-9-yl)benzenesulfonamide;(1080): (R)-9-(4-(1-aminoethyl)phenyl)-6,7-dichloro-8-hydroxythieno[2,3-c]quinolin-4(5H)-one;(1081): (R)-9-(4-(1-aminoethyl)phenyl)-6-chloro-8-hydroxythieno[2,3-c]quinolin-4(5H)-one;(1082): (S)-8-hydroxy-9-(4-(1-(methylamino)ethyl)phenyl)thieno[2,3-c]quinolin-4(5H)-one;(1083): 9-(4-(1-aminoethyl)phenyl)-4-oxo-4,5-dihydrothieno[2,3-c]quinolin-8-yl diethylcarbamate;(1084): 4-(8-hydroxy-4-oxo-4,5-dihydrothieno[2,3-c]quinolin-9-yl)-N-(2-hydroxyethyl)-N-methylbenzenesulfonamide;(1085): N-(2-hydroxyethyl)-4-(8-methoxy-4-oxo-4,5-dihydrothieno[2,3-c]quinolin-9-yl)-N-methylbenzenesulfonamide;(1086): 9-(4-((1H-pyrazol-1-yl)methyl)phenyl)-8-hydroxythieno[2,3-c]quinolin-4(5H)-one;(1087): (S)-6-chloro-8-hydroxy-9-(4-(1-(methylamino)ethyl)phenyl)thieno[2,3-c]quinolin-4(5H)-one;(1088): 9-(4-(1-aminopropyl)phenyl)-6-chloro-8-hydroxythieno[2,3-c]quinolin-4(5H)-one;(1089): 9-(4-(1-aminoethyl)phenyl)-4-oxo-4,5-dihydrothieno[2,3-c]quinolin-8-yl morpholine-4-carboxylate;(1090): N-(2-hydroxyethyl)-4-(8-methoxy-4-oxo-2,3,4,5-tetrahydro-1H-cyclopenta[c]quinolin-9-yl)benzenesulfonamide;(1091): 8-bromothieno[2,3-c]quinolin-4(5H)-one;(1092): 9-(4-(2-(dimethylamino)propyl)phenyl)-8-hydroxythieno[2,3-c]quinolin-4(5H)-one;(1093): 9-(4-(2-aminopropyl)phenyl)-8-methoxythieno[2,3-c]quinolin-4(5H)-one;(1094): N-(2-bromoethyl)-4-(8-hydroxy-4 oxo-2,3,4,5-tetrahydro-1H-cyclopenta[c]quinolin-9-yl)benzenesulfonamide;(1095): 9-(4-(2-aminopropyl)phenyl)-8-hydroxythieno[2,3-c]quinolin-4(5H)-one;(1096): 8-methoxy-9-(1-(2-morpholinoethyl)-1H-pyrazol-4-yl)thieno[2,3-c]quinolin-4(5H)-one;(1097): 9-(4-(2-(diethylamino)propyl)phenyl)-8-hydroxythieno[2,3-c]quinolin-4(5H)-one;(1098): 9-(4-(1-aminoethyl)phenyl)-8-hydroxy-6-(hydroxymethyl)thieno[2,3-c]quinolin-4(5H)-one;(1099): 9-(4-(1-aminoethyl)phenyl)-4-oxo-4,5-dihydrothieno[2,3-c]quinolin-8-yl acetate;(1100): 9-(1-(1-(dimethylamino)propan-2-yl)-1H-pyrazol-4-yl)-8-methoxythieno[2,3-c]quinolin-4(5H)-one;(1101): 9-(4-((1H-imidazol-1-yl)methyl)phenyl)-8-hydroxythieno[2,3-c]quinolin-4(5H)-one;(1102): 9-(4-(aminomethyl)phenyl)-8-(2-morpholinoethoxy)thieno[2,3-c]quinolin-4(5H)-one;(1103): 8-hydroxy-9-(1-(2-morpholinoethyl)-1H-pyrazol-4-yl)thieno[2,3-c]quinolin-4(5H)-one;(1104): N-(2-(1H-pyrazol-1-yl)ethyl)-4-(8-hydroxy-4-oxo-4,5-dihydrothieno[2,3-c]quinolin-9-yl)benzenesulfonamide;(1105): 8-hydroxy-9-(4-(2,2,2-trifluoro-1-hydroxyethyl)phenyl)thieno[2,3-c]quinolin-4(5H)-one;(1106): 9-(4-(2-aminopropyl)phenyl)-6-chloro-8-hydroxythieno[2,3-c]quinolin-4(5H)-one;(1107): N-(2-(4-(8-hydroxy-4-oxo-4,5-dihydrothieno[2,3-c]quinolin-9-yl)phenyl)-2-methylpropyl)methanesulfonamide;(1108): 9-(4-(2-(dimethylamino)propyl)phenyl)-8-methoxythieno[2,3-c]quinolin-4(5H)-one;(1109): 9-(4-(1-aminoethyl)phenyl)thieno[2,3-c]quinolin-4(5H)-one;(1110): 9-(1-(1-(dimethylamino)propan-2-yl)-1H-pyrazol-4-yl)-8-hydroxythieno[2,3-c]quinolin-4(5H)-one;(1111): 9-(4-(1-aminopropan-2-yl)phenyl)-8-hydroxythieno[2,3-c]quinolin-4(5H)-one;(1112): 9-(4-(1-(dimethylamino)propan-2-yl)phenyl)-8-hydroxythieno[2,3-c]quinolin-4(5H)-one;(1113): 8-methoxy-9-(4-(2,2,2-trifluoro-1-hydroxyethyl)phenyl)thieno[2,3-c]quinolin-4(5H)-one;(1114): N-(2-bromoethyl)-4-(8-hydroxy-4-oxo-4,5-dihydrothieno[2,3-c]quinolin-9-yl)-N-methylbenzenesulfonamide;(1115): N-(2-(1H-imidazol-1-yl)ethyl)-4-(8-hydroxy-4-oxo-4,5-dihydrothieno[2,3-c]quinolin-9-yl)benzenesulfonamide;(1116): 9-(4-(1-(aminomethyl)cyclopropyl)phenyl)-6-chloro-8-hydroxythieno[2,3-c]quinolin-4(5H)-one;(1117): 3-(4-(8-(2-(dimethylamino)ethoxy)-4-oxo-4,5-dihydrothieno[2,3-c]quinolin-9-yl)phenyl)propanenitrile;(1118): (R)-9-(4-(1-aminopropyl)phenyl)-8-methoxythieno[2,3-c]quinolin-4(5H)-one;(1119): N-(2-chloroethyl)-4-(8-hydroxy-4-oxo-4,5-dihydrothieno[2,3-c]quinolin-9-yl)-N-methylbenzenesulfonamide;(1120): (S)-9-(4-(1-aminopropyl)phenyl)-8-hydroxythieno[2,3-c]quinolin-4(5H)-one;(1121): (S)-9-(4-(1-aminopropyl)phenyl)-8-methoxythieno[2,3-c]quinolin-4(5H)-one;(1122): (R)-9-(4-(1-aminoethyl)phenyl)-8-hydroxy-6-methylthieno[2,3-c]quinolin-4(5H)-one;(1123):(R)-9-(4-(1-aminoethyl)phenyl)-6-bromo-8-hydroxythieno[2,3-c]quinolin-4(5H)-one;(1124): 9-(4-(1-aminoethyl)phenyl)-4-oxo-4,5-dihydrothieno[2,3-c]quinoline-8-carbonitrile;(1125): 9-(4-(1-aminoethyl)phenyl)-8-(hydroxymethyl)thieno[2,3-c]quinolin-4(5H)-one;(1126):(R)-6-chloro-9-(4-(1-(dimethylamino)ethyl)phenyl)-8-hydroxythieno[2,3-c]quinolin-4(5H)-one;(1127): (S)-9-(4-(1-(ethylamino)propyl)phenyl)-8-hydroxythieno[2,3-c]quinolin-4(5H)-one;(1128):(S)-9-(4-(1-(dimethylamino)propyl)phenyl)-8-hydroxythieno[2,3-c]quinolin-4(5H)-one;(1129):6-chloro-9-(4-(1-(dimethylamino)propan-2-yl)phenyl)-8-hydroxythieno[2,3-c]quinolin-4(5H)-one;(1130): 9-(4-(1-aminoethyl)phenyl)-6-ethynyl-8-hydroxythieno[2,3-c]quinolin-4(5H)-one;(1131): (R)-9-(4-(1-aminopropyl)phenyl)-8-hydroxythieno[2,3-c]quinolin-4(5H)-one;(1132): (R)-6-chloro-8-hydroxy-9-(4-(1-(methylamino)ethyl)phenyl)thieno[2,3-c]quinolin-4(5H)-one;(1133): 9-(4-(2-aminoethyl)phenyl)-6-chloro-8-hydroxythieno[2,3-c]quinolin-(5H)-one;(1134): 9-(4-(1-aminoethyl)phenyl)-8-(difluoromethyl)thieno[2,3-c]quinolin-4(5H)-one;(1135): (R)-6-bromo-8-hydroxy-9-(4-(1-(methylamino)ethyl)phenyl)thieno[2,3-c]quinolin-4(5H)-one;(1136): 9-(4-(1-aminopropan-2-yl)phenyl)-6-chloro-8-hydroxythieno[2,3-c]quinolin-4(5H)-one;(1137): 9-(4-butylphenyl)-8-methoxythieno[2,3-c]quinolin-4(5H)-one;(1138): 9-(4-butylphenyl)-8-hydroxythieno[2,3-c]quinolin-4(5H)-one;(1139): N-(2-chloroethyl)-4-(8-methoxy-4-oxo-4,5-dihydrothieno[2,3-c]quinolin-9-yl)benzenesulfonamide;(1140): 9-(4-((3-bromopyrrolidin-1-yl)sulfonyl)phenyl)-8-hydroxythieno[2,3-c]quinolin-4(5H)-one;(1141): (S)-9-(4-(1-(methylsulfonamido)propyl)phenyl)-4-oxo-4,5-dihydrothieno[2,3-c]quinolin-8-yl methanesulfonate;(1142): 9-(4-(2-aminoethyl)phenyl)-6-bromo-8-hydroxythieno[2,3-c]quinolin-4(5H)-one;(1143): 9-(4-(3-(dimethylamino)-1-hydroxypropyl)phenyl)-8-methoxythieno[2,3-c]quinolin-4(5H)-one;(1144): N-(2-bromoethyl)-4-(6-chloro-8-hydroxy-4-oxo-4,5-dihydrothieno[2,3-c]quinolin-9-yl)benzenesulfonamide;(1145): N-(2-chloroethyl)-4-(8-hydroxy-4-oxo-2,3,4,5-tetrahydro-1H-cyclopenta[c]quinolin-9-yl)benzenesulfonamide;(1146): N-(2-bromoethyl)-4-(5-ethyl-8-hydroxy-4-oxo-4,5-dihydrothieno[2,3-c]quinolin-9-yl)benzenesulfonamide;(1147): (S)-8-methoxy-9-(4-(1-(methylamino)propyl)phenyl)thieno[2,3-c]quinolin-4(5H)-one;(1148): (S)-8-hydroxy-9-(4-(1-(methylamino)propyl)phenyl)thieno[2,3-c]quinolin-4(5H)-one;(1149): 9-(4-(1-aminoethyl)phenyl)-8-(((2-hydroxyethyl)amino)methyl)thieno[2,3-c]quinolin-4(5H)-one;(1150): (R)-9-(4-(1-aminopropyl)phenyl)-6-bromo-8-hydroxythieno[2,3-c]quinolin-4(5H)-one;(1151): (R)-9-(4-(1-(dimethylamino)propyl)phenyl)-8-hydroxythieno[2,3-c]quinolin-4(5H)-one;(1152): 8-hydroxy-9-(4-pentylphenyl)thieno[2,3-c]quinolin-4(5H)-one;(1153): 9-(4-(2-aminoacetyl)phenyl)-8-hydroxythieno[2,3-c]quinolin-4(5H)-one;(1154): (S)-6-chloro-8-hydroxy-9-(4-(1-(methylamino)propyl)phenyl)thieno[2,3-c]quinolin-4(5H)-one;(1155): 8-hydroxy-9-(4-(2-(methylamino)ethyl)phenyl)thieno[2,3-c]quinolin-4(5H)-one;(1156): 8-methoxy-9-(4-(2-(methylamino)ethyl)phenyl)thieno[2,3-c]quinolin-4(5H)-one;(1157): (R)-9-(4-(1-aminopropyl)phenyl)-8-hydroxy-6-methylthieno[2,3-c]quinolin-4(5H)-one;(1158): (R)-9-(4-(1-aminopropyl)phenyl)-8-methoxy-6-methylthieno[2,3-c]quinolin-4(5H)-one;(1159): (R)-9-(4-(1-aminopropyl)phenyl)-6-chloro-8-hydroxythieno[2,3-c]quinolin-4(5H)-one;(1160): (R)-9-(4-(1-aminopropan-2-yl)phenyl)-8-hydroxythieno[2,3-c]quinolin-4(5H)-one;(1161): (R)-9-(4-(1-aminopropan-2-yl)phenyl)-8-methoxythieno[2,3-c]quinolin-4(5H)-one;(1162): 2-(4-(8-hydroxy-4-oxo-4,5-dihydrothieno[2,3-c]quinolin-9-yl)phenyl)butanenitrile;(1163): (S)-9-(4-(1-aminopropan-2-yl)phenyl)-8-hydroxythieno[2,3-c]quinolin-4(5H)-one;(1164): (S)-9-(4-(1-aminopropan-2-yl)phenyl)-8-methoxythieno[2,3-c]quinolin-4(5H)-one;(1165): 6-chloro-8-hydroxy-9-(4-(2-(methylamino)ethyl)phenyl)thieno[2,3-c]quinolin-4(5H)-one;(1166): (R)-9-(4-(1-aminopropan-2-yl)phenyl)-6-chloro-8-hydroxythieno[2,3-c]quinolin-4(5H)-one;(1167): 9-(4-(2-aminoethyl)-3,5-difluorophenyl)-8-hydroxythieno[2,3-c]quinolin-4(5H)-one;(1168): (R)-9-(4-(1-aminopropan-2-yl)phenyl)-8-hydroxy-6-methylthieno[2,3-c]quinolin-4(5H)-one;(1169): (R)-9-(4-(1-aminopropan-2-yl)phenyl)-8-hydroxy-6-methylthieno[2,3-c]quinolin-4(5H)-one;(1170): 6-chloro-8-methoxy-9-(4-(2-(methylamino)ethyl)phenyl)thieno[2,3-c]quinolin-4(5H)-one;(1171): 9-(4-(2-aminoethyl)-3-chlorophenyl)-8-hydroxythieno[2,3-c]quinolin-4(5H)-one;(1172): (S)-9-(4-(1-(dimethylamino)propan-2-yl)phenyl)-8-hydroxythieno[2,3-c]quinolin-4(5H)-one;(1173): 6-bromo-8-methoxy-9-(4-(2-(methylamino)ethyl)phenyl)thieno[2,3-c]quinolin-4(5H)-one;(1174): 9-(4-(1-aminopropan-2-yl)-3-fluorophenyl)-8-hydroxythieno[2,3-c]quinolin-4(5H)-one;(1175): (R)-9-(4-(1-aminopropyl)phenyl)-6-chloro-8-methoxythieno[2,3-c]quinolin-4(5H)-one;(1176): (R)-9-(4-(1-aminopropan-2-yl)phenyl)-6-bromo-8-hydroxythieno[2,3-c]quinolin-4(5H)-one;(1177): 9-(4-(2-aminoethyl)-3,5-difluorophenyl)-8-methoxythieno[2,3-c]quinolin-(5H)-one;(1178): 9-(4-(2-(dimethylamino)ethyl)-3,5-difluorophenyl)-8-hydroxythieno[2,3-c]quinolin-4(5H)-one;(1179): 9-(4-(1-aminopropan-2-yl)-3-fluorophenyl)-8-methoxythieno[2,3-c]quinolin-4(5H)-one;(1180): (S)-9-(4-(1-aminopropan-2-yl)phenyl)-6,7-dichloro-8-methoxythieno[2,3-c]quinolin-4(5H)-one;(1181): (S)-9-(4-(1-aminopropan-2-yl)phenyl)-6-chloro-8-hydroxythieno[2,3-c]quinolin-4(5H)-one;(1182): (S)-6-chloro-9-(4-(1-(dimethylamino)propan-2-yl)phenyl)-8-hydroxythieno[2,3-c]quinolin-4(5H)-one;(1183): 6-bromo-8-hydroxy-9-(4-(2-(methylamino)ethyl)phenyl)thieno[2,3-c]quinolin-4(5H)-one;(1185): N-(2-hydroxyethyl)-4-(8-methoxy-5-methyl-4-oxo-4,5-dihydrothieno[2,3-c]quinolin-9-yl)benzenesulfonamide;(1186): methyl 3-(4-(8-hydroxy-4-oxo-4,5-dihydrothieno[2,3-c]quinolin-9-yl)phenyl)propanoate;(1187): (R)-8-hydroxy-9-(4-(1-(methylamino)propan-2-yl)phenyl)thieno[2,3-c]quinolin-4(5H)-one;(1188): (R)-9-(4-(1-(dimethylamino)propan-2-yl)phenyl)-8-hydroxythieno[2,3-c]quinolin-4(5H)-one;(1189): (R)-8-methoxy-9-(4-(1-(methylamino)propan-2-yl)phenyl)thieno[2,3-c]quinolin-4(5H)-one;(1190): 9-(4-(1-aminopropan-2-yl)-3-fluorophenyl)-8-hydroxy-6-methylthieno[2,3-c]quinolin-4(5H)-one;(1191): 9-(4-(2-aminoethyl)phenyl)-8-hydroxy-6-methylthieno[2,3-c]quinolin-4(5H)-one;(1192): 9-(4-(2-aminoethyl)phenyl)-8-methoxy-6-methylthieno[2,3-c]quinolin-4(5H)-one;(1193): 9-(4-(1-(dimethylamino)propan-2-yl)-3-fluorophenyl)-8-hydroxy-6-methylthieno[2,3-c]quinolin-4(5H)-one;(1194): (S)-6-chloro-8-hydroxy-9-(4-(1-(methylamino)propan-2-yl)phenyl)thieno[2,3-c]quinolin-4(5H)-one;(1195): (S)-6-chloro-9-(4-(1-(diethylamino)propan-2-yl)phenyl)-8-hydroxythieno[2,3-c]quinolin-4(5H)-one;(1196): (S)-8-methoxy-9-(4-(1-(methylamino)propan-2-yl)phenyl)thieno[2,3-c]quinolin-4(5H)-one;(1197): (S)-8-hydroxy-9-(4-(1-(methylamino)propan-2-yl)phenyl)thieno[2,3-c]quinolin-4(5H)-one;(1198): 4-(8-hydroxy-5-methyl-4-oxo-4,5-dihydrothieno[2,3-c]quinolin-9-yl)-N-(2-hydroxyethyl)benzenesulfonamide;(1199): N-(2-bromoethyl)-4-(8-hydroxy-5-methyl-4-oxo-4,5-dihydrothieno[2,3-c]quinolin-9-yl)benzenesulfonamide;(1200): (R)-6-chloro-9-(4-(1-(dimethylamino)propan-2-yl)phenyl)-8-methoxythieno[2,3-c]quinolin-4(5H)-one;(1201): (R)-9-(4-(1-aminopropan-2-yl)phenyl)-6-chloro-8-methoxythieno[2,3-c]quinolin-4(5H)-one;(1202): 9-(4-(1-aminobutan-2-yl)phenyl)-8-methoxythieno[2,3-c]quinolin-4(5H)-one;(1203): 9-(4-(2-aminopropan-2-yl)phenyl)-8-hydroxy-2-(phenylsulfonyl)thieno[2,3-c]quinolin-4(5H)-one;(1204): N-(1-chloropropan-2-yl)-4-(8-hydroxy-4-oxo-4,5-dihydrothieno[2,3-c]quinolin-9-yl)benzenesulfonamide;(1205): N-(1-chloropropan-2-yl)-4-(8-methoxy-4-oxo-4,5-dihydrothieno[2,3-c]quinolin-9-yl)benzenesulfonamide;(1206): 9-(4-(2-aminoethyl)-3-hydroxyphenyl)-8-hydroxythieno[2,3-c]quinolin-4(5H)-one;(1207): 9-(4-(2-aminoethyl)-3-methoxyphenyl)-8-methoxythieno[2,3-c]quinolin-4(5H)-one;(1208): 9-(4-(2-aminoethyl)-2-chloro-5-methoxyphenyl)-8-methoxythieno[2,3-c]quinolin-4(5H)-one;(1209): 9-(4-(3-(aminomethyl)pentan-3-yl)phenyl)-8-hydroxythieno[2,3-c]quinolin-4(5H)-one;(1210): (R)-9-(4-(1-aminopropyl)phenyl)-8-hydroxy-5,6-dimethylthieno[2,3-c]quinolin-4(5H)-one;(1211): 9-(4-(2-aminoethyl)-2-chloro-5-hydroxyphenyl)-6-chloro-8-hydroxythieno[2,3-c]quinolin-4(5H)-one;(1212): 9-(4-(aminomethyl)phenyl)-8-hydroxy-6-methylthieno[2,3-c]quinolin-4(5H)-one;(1213): 9-(4-(2-aminoethyl)-3-fluorophenyl)-6-bromo-8-hydroxythieno[2,3-c]quinolin-4(5H)-one;(1214): 9-(4-(2-aminoethyl)-3-fluorophenyl)-6-bromo-8-methoxythieno[2,3-c]quinolin-4(5H)-one;(1215): (S)-8-hydroxy-6-methyl-9-(4-(1-(methylamino)propan-2-yl)phenyl)thieno[2,3-c]quinolin-4(5H)-one;(1216): 9-(4-(2-aminoethyl)-3-fluorophenyl)-8-methoxy-6-methylthieno[2,3-c]quinolin-4(5H)-one;(1217): 9-(4-(2-aminoethyl)-3-fluorophenyl)-8-hydroxy-6-methylthieno[2,3-c]quinolin-4(5H)-one;(1218): 9-(4-(2-aminoethyl)-3-fluorophenyl)-6-chloro-8-methoxythieno[2,3-c]quinolin-(5H)-one;(1219): 9-(4-(2-aminoethyl)-3-fluorophenyl)-6-chloro-8-hydroxythieno[2,3-c]quinolin-(5H)-one;(1220): 9-(4-(2-aminoethyl)-3-fluorophenyl)-6-cyclopropyl-8-methoxythieno[2,3-c]quinolin-4(5H)-one;(1221): 9-(4-(2-aminoethyl)-3-fluorophenyl)-6-cyclopropyl-8-hydroxythieno[2,3-c]quinolin-4(5H)-one;(1222): (S)-8-methoxy-6-methyl-9-(4-(1-(methylamino)propan-2-yl)phenyl)thieno[2,3-c]quinolin-4(5H)-one;(1223): (S)-9-(4-(1-aminopropan-2-yl)phenyl)-8-methoxy-6-methylthieno[2,3-c]quinolin-4(5H)-one;(1224): 9-(4-(2-aminoethyl)-2-bromo-5-hydroxyphenyl)-8-hydroxythieno[2,3-c]quinolin-4(5H)-one;(1225): (S)-9-(4-(1-aminoethyl)phenyl)-8-hydroxy-6-methylthieno[2,3-c]quinolin-4(5H)-one;(1226): 3-(4-(8-hydroxy-6-methyl-4-oxo-4,5-dihydrothieno[2,3-c]quinolin-9-yl)phenyl)propanenitrile;(1227): 9-(4-(1-amino-2-methylpropan-2-yl)phenyl)-8-methoxy-6-methylthieno[2,3-c]quinolin-4(5H)-one;(1228): 9-(4-(1-amino-2-methylpropan-2-yl)phenyl)-8-hydroxy-6-methylthieno[2,3-c]quinolin-4(5H)-one;(1229): 2-(2-fluoro-4-(8-hydroxy-6-methyl-4-oxo-4,5-dihydrothieno[2,3-c]quinolin-9-yl)phenyl)propanenitrile;(1230): 6-cyclopropyl-9-(4-(2-(dimethylamino)ethyl)-3-fluorophenyl)-8-hydroxythieno[2,3-c]quinolin-4(5H)-one;(1231): 6-cyclopropyl-9-(4-(2-(dimethylamino)ethyl)-3-fluorophenyl)-8-methoxythieno[2,3-c]quinolin-4(5H)-one;(1232): (S)-9-(4-(1-aminopropan-2-yl)phenyl)-8-hydroxy-6-methylthieno[2,3-c]quinolin-4(5H)-one;(1233): (S)-9-(4-(1-(dimethylamino)propan-2-yl)phenyl)-8-hydroxy-6-methylthieno[2,3-c]quinolin-4(5H)-one;(1234): 9-(3-fluoro-4-(2-(methylamino)ethyl)phenyl)-8-methoxythieno[2,3-c]quinolin-4(5H)-one;(1235): 9-(3-fluoro-4-(2-(methylamino)ethyl)phenyl)-8-hydroxythieno[2,3-c]quinolin-4(5H)-one;(1236): 9-(4-(2-amino-1-cyclopentylethyl)phenyl)-8-hydroxythieno[2,3-c]quinolin-4(5H)-one;(1237): 9-(4-(2-amino-1,1-dicyclopentylethyl)phenyl)-8-methoxythieno[2,3-c]quinolin-4(5H)-one;(1238): 3-(4-(8-methoxy-6-methyl-4-oxo-4,5-dihydrothieno[2,3-c]quinolin-9-yl)phenyl)propanenitrile;(1239): 9-(4-(2-amino-1-cyclopentylethyl)phenyl)-8-methoxythieno[2,3-c]quinolin-4(5H)-one;(1240): 9-(4-(1-amino-2-methylpropan-2-yl)phenyl)-6-cyclopropyl-8-hydroxythieno[2,3-c]quinolin-4(5H)-one;(1241): 9-(4-(3-aminopropyl)phenyl)-8-methoxy-6-methylthieno[2,3-c]quinolin-4(5H)-one;(1242): 9-(4-(2-aminopropyl)phenyl)-8-hydroxy-6-methylthieno[2,3-c]quinolin-4(5H)-one;(1243): 9-(4-(2-aminopropyl)phenyl)-8-methoxy-6-methylthieno[2,3-c]quinolin-4(5H)-one;(1244): 9-(4-(1-amino-2-methylpropan-2-yl)phenyl)-6-cyclopropyl-8-methoxythieno[2,3-c]quinolin-4(5H)-one;(1245): 6-bromo-9-(3-fluoro-4-(2-(methylamino)ethyl)phenyl)-8-hydroxythieno[2,3-c]quinolin-4(5H)-one;(1246): 6-bromo-9-(3-fluoro-4-(2-(methylamino)ethyl)phenyl)-8-methoxythieno[2,3-c]quinolin-4(5H)-one;(1247): 9-(4-(1-amino-2-methylpropan-2-yl)phenyl)-6-bromo-8-hydroxythieno[2,3-c]quinolin-4(5H)-one;(1248): 9-(4-(1-amino-2-methylpropan-2-yl)phenyl)-6-bromo-8-methoxythieno[2,3-c]quinolin-4(5H)-one;(1249): (R)-9-(4-(1-aminopropan-2-yl)phenyl)-6-methyl-4-oxo-4,5-dihydrothieno[2,3-c]quinoline-8-carbonitrile;(1250): (R)-9-(4-(1-aminoethyl)phenyl)-8-hydroxy-6-vinylthieno[2,3-c]quinolin-4(5H)-one;(1251): 9-(4-(1-(aminomethyl)cyclopropyl)phenyl)-8-methoxy-6-methylthieno[2,3-c]quinolin-4(5H)-one;(1252): 9-(4-(1-amino-3-methylbutan-2-yl)phenyl)-8-hydroxythieno[2,3-c]quinolin-4(5H)-one;(1253): 9-(4-(1-amino-3-methylbutan-2-yl)phenyl)-8-methoxythieno[2,3-c]quinolin-4(5H)-one;(1254): 9-(4-(1-(aminomethyl)cyclopropyl)phenyl)-8-hydroxy-6-methylthieno[2,3-c]quinolin-4(5H)-one;(1255): (R)-9-(4-(1-aminoethyl)phenyl)-6-ethyl-8-hydroxythieno[2,3-c]quinolin-4(5H)-one;(1256): (R)-9-(4-(1-aminoethyl)phenyl)-6-(difluoromethyl)-8-hydroxythieno[2,3-c]quinolin-4(5H)-one;(1257): 9-(3-fluoro-4-(2-(methylamino)ethyl)phenyl)-8-methoxy-6-methylthieno[2,3-c]quinolin-4(5H)-one;(1258): 9-(3-fluoro-4-(2-(methylamino)ethyl)phenyl)-8-hydroxy-6-methylthieno[2,3-c]quinolin-4(5H)-one;(1259): 6-bromo-9-(4-(1-(dimethylamino)-2-methylpropan-2-yl)phenyl)-8-hydroxythieno[2,3-c]quinolin-4(5H)-one;(1260): 9-(4-(1-amino-2-methylpropan-2-yl)phenyl)-6-chloro-8-hydroxythieno[2,3-c]quinolin-4(5H)-one;(1261): 9-(4-(3-aminopropyl)phenyl)-8-hydroxy-6-methylthieno[2,3-c]quinolin-4(5H)-one;(1262): (R)-8-hydroxy-6-methyl-9-(4-(1-(methylamino)ethyl)phenyl)thieno[2,3-c]quinolin-4(5H)-one;(1263): 9-(4-(2-aminoethyl)-3-chlorophenyl)-8-methoxy-6-methylthieno[2,3-c]quinolin-4(5H)-one;(1264): 9-(4-(2-aminoethyl)-3-chlorophenyl)-8-hydroxy-6-methylthieno[2,3-c]quinolin-4(5H)-one;(1265): (R)-8-methoxy-6-methyl-9-(4-(1-(methylamino)ethyl)phenyl)thieno[2,3-c]quinolin-4(5H)-one;(1266): 9-(4-(2-aminopropyl)phenyl)-6-ethyl-8-hydroxythieno[2,3-c]quinolin-4(5H)-one;(1267): (R)-9-(4-(1-aminoethyl)phenyl)-6-butyl-8-hydroxythieno[2,3-c]quinolin-4(5H)-one;(1268): 9-(4-(2-aminoethyl)-3-chlorophenyl)-6-chloro-8-hydroxythieno[2,3-c]quinolin-(5H)-one;(1269): 9-(4-(2-aminopropyl)phenyl)-6-ethyl-8-methoxythieno[2,3-c]quinolin-4(5H)-one;(1270): 2-(4-(8-methoxy-4-oxo-4,5-dihydrothieno[2,3-c]quinolin-9-yl)phenyl)-2-(oxetan-3-yl)acetonitrile;(1271): 9-(4-(1-amino-2-methylpropan-2-yl)-3-fluorophenyl)-8-hydroxythieno[2,3-c]quinolin-4(5H)-one;(1272): (R)-6-ethyl-8-hydroxy-9-(4-(1-(methylamino)ethyl)phenyl)thieno[2,3-c]quinolin-4(5H)-one;(1273): 9-(4-(1-aminopropan-2-yl)-3-fluorophenyl)-8-methoxy-6-methylthieno[2,3-c]quinolin-4(5H)-one;(1274): 9-(4-(1-amino-3-methylbutan-2-yl)phenyl)-8-hydroxy-6-methylthieno[2,3-c]quinolin-4(5H)-one;(1275): 9-(4-(1-aminopropan-2-yl)-3-chlorophenyl)-8-methoxy-6-methylthieno[2,3-c]quinolin-4(5H)-one;(1276): 9-(4-(1-aminopropan-2-yl)-3-chlorophenyl)-8-methoxythieno[2,3-c]quinolin-4(5H)-one;(1277): 9-(4-(1-aminobutan-2-yl)phenyl)-8-methoxy-6-methylthieno[2,3-c]quinolin-4(5H)-one;(1278): 9-(4-(1-amino-2-methylpropan-2-yl)-3-fluorophenyl)-8-hydroxy-6-methylthieno[2,3-c]quinolin-4(5H)-one;(1279): 9-(4-(1-aminopropan-2-yl)-3-chlorophenyl)-8-hydroxy-6-methylthieno[2,3-c]quinolin-4(5H)-one;(1280): 9-(4-(1-aminopropan-2-yl)-3-chlorophenyl)-8-hydroxythieno[2,3-c]quinolin-4(5H)-one;(1281): 9-(4-(2-amino-2-methylpropyl)phenyl)-8-methoxythieno[2,3-c]quinolin-4(5H)-one;(1282): 9-(4-(2-amino-2-methylpropyl)phenyl)-8-hydroxythieno[2,3-c]quinolin-4(5H)-one;(1283): 9-(4-(1-amino-3-methylbutan-2-yl)-3-fluorophenyl)-8-methoxy-6-methylthieno[2,3-c]quinolin-4(5H)-one;(1284): 8-methoxy-6-methyl-9-(4-(3-methyl-1-(methylamino)butan-2-yl)phenyl)thieno[2,3-c]quinolin-4(5H)-one;(1285): 8-hydroxy-6-methyl-9-(4-(3-methyl-1-(methylamino)butan-2-yl)phenyl)thieno[2,3-c]quinolin-4(5H)-one;(1286): 9-(3-fluoro-4-(1-(methylamino)propan-2-yl)phenyl)-8-methoxy-6-methylthieno[2,3-c]quinolin-4(5H)-one;(1287): 9-(4-(1-amino-2-methylpropan-2-yl)-3-fluorophenyl)-8-methoxythieno[2,3-c]quinolin-4(5H)-one;(1288): 9-(4-(1-amino-3-methylbutan-2-yl)-3-fluorophenyl)-8-hydroxy-6-methylthieno[2,3-c]quinolin-4(5H)-one;(1289): 9-(4-(2-amino-2-methylpropyl)phenyl)-6-bromo-8-methoxythieno[2,3-c]quinolin-4(5H)-one;(1290): 9-(4-(1-(aminomethyl)cyclobutyl)phenyl)-8-hydroxy-6-methylthieno[2,3-c]quinolin-4(5H)-one;(1291): 9-(4-(1-aminobutan-2-yl)phenyl)-8-hydroxy-6-methylthieno[2,3-c]quinolin-4(5H)-one;(1292): 9-(4-(2-amino-2-methylpropyl)phenyl)-6-bromo-8-hydroxythieno[2,3-c]quinolin-4(5H)-one;(1293): 9-(3-fluoro-4-(1-(methylamino)propan-2-yl)phenyl)-8-hydroxy-6-methylthieno[2,3-c]quinolin-4(5H)-one;(1294): 9-(3-fluoro-4-(3-methyl-1-(methylamino)butan-2-yl)phenyl)-8-hydroxy-6-methylthieno[2,3-c]quinolin-4(5H)-one;(1295): 9-(4-(1-(dimethylamino)-3-methylbutan-2-yl)phenyl)-8-methoxy-6-methylthieno[2,3-c]quinolin-4(5H)-one;(1296): 9-(4-(1-(dimethylamino)-3-methylbutan-2-yl)-3-fluorophenyl)-8-hydroxy-6-methylthieno[2,3-c]quinolin-4(5H)-one;(1297): 9-(4-(1-(aminomethyl)cyclobutyl)phenyl)-8-methoxy-6-methylthieno[2,3-c]quinolin-4(5H)-one;(1298): (R)-8-methoxy-6-methyl-9-(4-(1-(methylamino)propan-2-yl)phenyl)thieno[2,3-c]quinolin-4(5H)-one;(1299): 9-(4-(1-(aminomethyl)cyclobutyl)phenyl)-8-methoxythieno[2,3-c]quinolin-4(5H)-one;(1300): 9-(4-(1-(aminomethyl)cyclobutyl)phenyl)-8-hydroxythieno[2,3-c]quinolin-4(5H)-one;(1301): 8-methoxy-6-methyl-9-(4-(piperidin-3-yl)phenyl)thieno[2,3-c]quinolin-4(5H)-one;(1302): 8-hydroxy-6-methyl-9-(4-(piperidin-3-yl)phenyl)thieno[2,3-c]quinolin-4(5H)-one;(1303): (S)-9-(4-(1-aminopropan-2-yl)-3-fluorophenyl)-8-hydroxy-6-methylthieno[2,3-c]quinolin-4(5H)-one;(1304): (S)-9-(4-(1-aminopropan-2-yl)-3-fluorophenyl)-8-hydroxy-6-methylthieno[2,3-c]quinolin-4(5H)-one;(1305): (R)-9-(4-(1-aminopropan-2-yl)phenyl)-8-methoxy-6-methylthieno[2,3-c]quinolin-4(5H)-one;(1306): (R)-8-hydroxy-6-methyl-9-(4-(1-(methylamino)propan-2-yl)phenyl)thieno[2,3-c]quinolin-4(5H)-one;(1307): (R)-8-hydroxy-6-methyl-9-(4-(1-(methylamino)propan-2-yl)phenyl)thieno[2,3-c]quinolin-4(5H)-one;(1308): 8-methoxy-3-methyl-3H-pyrrolo[2,3-c]quinolin-4(5H)-one;(1309): 9-(4-(1-aminobutan-2-yl)phenyl)-8-hydroxythieno[2,3-c]quinolin-4(5H)-one;(1310): (S)-9-(4-(1-aminopropan-2-yl)-3-fluorophenyl)-8-methoxy-6-methylthieno[2,3-c]quinolin-4(5H)-one;(1311): (R)-9-(4-(1-(dimethylamino)propan-2-yl)-3-fluorophenyl)-8-hydroxy-6-methylthieno[2,3-c]quinolin-4(5H)-one;(1312): 9-(4-(1-aminobutan-2-yl)phenyl)-6-chloro-8-hydroxythieno[2,3-c]quinolin-4(5H)-one;(1313): 8-hydroxy-3-methyl-3H-pyrrolo[2,3-c]quinolin-4(5H)-one;(1314): 9-amino-8-methoxy-6-methylthieno[2,3-c]quinolin-4(5H)-one;(1315): (R)-9-(3-fluoro-4-(1-(methylamino)propan-2-yl)phenyl)-8-hydroxy-6-methylthieno[2,3-c]quinolin-4(5H)-one;(1316): (R)-9-(3-fluoro-4-(1-(methylamino)propan-2-yl)phenyl)-8-methoxy-6-methylthieno[2,3-c]quinolin-4(5H)-one;(1317): (R)-9-(4-(1-aminopropan-2-yl)-3-fluorophenyl)-8-methoxy-6-methylthieno[2,3-c]quinolin-4(5H)-one;(1318): (R)-9-(4-(1-aminopropan-2-yl)-3-fluorophenyl)-8-hydroxy-6-methylthieno[2,3-c]quinolin-4(5H)-one;(1319): (R)-9-(4-(1-aminopropan-2-yl)-3-fluorophenyl)-8-hydroxy-6-methylthieno[2,3-c]quinolin-4(5H)-one;(1320): 9-((4-(2-aminoethyl)phenyl)amino)-8-methoxy-6-methylthieno[2,3-c]quinolin-4(5H)-one;(1321): 9-(4-(1-(aminomethyl)cyclobutyl)phenyl)-6-chloro-8-methoxythieno[2,3-c]quinolin-(5H)-one;(1322): (R)-1-(4-(1-aminopropan-2-yl)phenyl)-8-methoxy-3-methyl-3H-pyrrolo[2,3-c]quinolin-4(5H)-one;(1323): 8-hydroxy-3-(hydroxymethyl)-3H-pyrrolo[2,3-c]quinolin-4(5H)-one;(1324): (R)-9-(4-(1-(dimethylamino)propan-2-yl)phenyl)-8-hydroxy-6-methylthieno[2,3-c]quinolin-4(5H)-one;(1325): 9-((4-(aminomethyl)phenyl)amino)-8-hydroxy-6-methylthieno[2,3-c]quinolin-4(5H)-one;(1326): 9-((4-(aminomethyl)phenyl)amino)-8-methoxy-6-methylthieno[2,3-c]quinolin-4(5H)-one;(1327): 9-((4-(1-aminopropan-2-yl)phenyl)amino)-8-methoxy-6-methylthieno[2,3-c]quinolin-4(5H)-one;(1328): 9-((4-(1-aminopropan-2-yl)phenyl)amino)-8-hydroxy-6-methylthieno[2,3-c]quinolin-4(5H)-one;(1329): 9-(4-(2-aminopropan-2-yl)phenyl)-8-methoxy-6-methylthieno[2,3-c]quinolin-4(5H)-one;(1330): 9-(4-(2-aminopropan-2-yl)phenyl)-8-hydroxy-6-methylthieno[2,3-c]quinolin-4(5H)-one;(1331): 9-(4-(3-(aminomethyl)pentan-3-yl)phenyl)-8-methoxy-6-methylthieno[2,3-c]quinolin-4(5H)-one;(1332): 9-(4-((R)-1-aminopropan-2-yl)phenyl)-8-hydroxy-2-(1-hydroxyethyl)thieno[2,3-c]quinolin-4(5H)-one;(1333): 9-(4-((R)-1-aminopropan-2-yl)phenyl)-2-(1-hydroxyethyl)-8-methoxythieno[2,3-c]quinolin-4(5H)-one;(1334): 3-(4-((8-methoxy-6-methyl-4-oxo-4,5-dihydrothieno[2,3-c]quinolin-9-yl)amino)phenyl)propanenitrile;(1335): 9-((3-(2-aminoethyl)phenyl)amino)-8-methoxy-6-methylthieno[2,3-c]quinolin-4(5H)-one;(1336): 9-((4-(2-aminoethyl)phenyl)amino)-8-hydroxy-6-methylthieno[2,3-c]quinolin-4(5H)-one;(1337): 9-(4-(2-(ethylamino)propyl)phenyl)-8-hydroxy-6-methylthieno[2,3-c]quinolin-4(5H)-one;(1338): 9-(4-(3-(aminomethyl)pentan-3-yl)phenyl)-8-methoxythieno[2,3-c]quinolin-4(5H)-one;(1339): 9-(4-(3-(aminomethyl)pentan-3-yl)phenyl)-8-hydroxy-6-methylthieno[2,3-c]quinolin-(5H)-one;(1340): (R)-9-(4-(1-aminopropan-2-yl)phenyl)-8-hydroxy-2,6-dimethylthieno[2,3-c]quinolin-4(5H)-one;(1341): (R)-9-(4-(1-aminopropan-2-yl)phenyl)-8-methoxy-2,6-dimethylthieno[2,3-c]quinolin-4(5H)-one;(1342): 9-(4-((R)-1-aminopropan-2-yl)phenyl)-2-(1-hydroxyethyl)-8-methoxy-6-methylthieno[2,3-c]quinolin-4(5H)-one;(1343): 2-((4-(8-methoxy-6-methyl-4-oxo-4,5-dihydrothieno[2,3-c]quinolin-9-yl)phenyl)amino)acetonitrile;(1344): (R)-9-(4-(1-aminobutan-2-yl)phenyl)-8-methoxy-6-methylthieno[2,3-c]quinolin-4(5H)-one;(1345): 9-(3-chloro-4-(2-(ethylamino)ethyl)phenyl)-8-methoxythieno[2,3-c]quinolin-4(5H)-one;(1346): 9-(4-(3-((dimethylamino)methyl)pentan-3-yl)phenyl)-8-hydroxy-6-methylthieno[2,3-c]quinolin-4(5H)-one;(1347): (R)-6-chloro-9-(4-(1-(dimethylamino)propan-2-yl)phenyl)-8-hydroxythieno[2,3-c]quinolin-4(5H)-one;(1348): 9-(4-(2-(ethylamino)ethyl)phenyl)-8-hydroxy-6-methylthieno[2,3-c]quinolin-4(5H)-one;(1349): 9-(4-(2-(ethylamino)ethyl)phenyl)-8-methoxy-6-methylthieno[2,3-c]quinolin-4(5H)-one;(1350): 9-(4-(2-(ethyl(methyl)amino)propyl)phenyl)-8-hydroxy-6-methylthieno[2,3-c]quinolin-4(5H)-one;(1351): 2-(hydroxy(piperidin-4-yl)methyl)-8-methoxy-6-methylthieno[2,3-c]quinolin-4(5H)-one;(1352): (R)-9-(4-(1-aminobutan-2-yl)phenyl)-8-hydroxy-6-methylthieno[2,3-c]quinolin-4(5H)-one;(1353): (R)-9-(4-(1-aminopropan-2-yl)phenyl)-2-chloro-8-hydroxy-6-methylthieno[2,3-c]quinolin-4(5H)-one;(1354): (R)-9-(4-(1-aminopropan-2-yl)phenyl)-2-chloro-8-methoxy-6-methylthieno[2,3-c]quinolin-4(5H)-one;(1355): 8-methoxy-6-methyl-9-(4-(2-(methylamino)ethyl)phenyl)thieno[2,3-c]quinolin-4(5H)-one;(1356): 9-(4-(2-(ethyl(methyl)amino)ethyl)phenyl)-8-hydroxy-6-methylthieno[2,3-c]quinolin-4(5H)-one;(1357): 9-(4-(3-(aminomethyl)pentan-3-yl)phenyl)-6-chloro-8-methoxythieno[2,3-c]quinolin-4(5H)-one;(1358): 9-(4-(3-((dimethylamino)methyl)pentan-3-yl)phenyl)-8-hydroxythieno[2,3-c]quinolin-4(5H)-one;(1359): 9-(6-(dimethylamino)pyridin-3-yl)-8-methoxy-6-methylthieno[2,3-c]quinolin-4(5H)-one;(1360): (R)-9-(4-(1-(dimethylamino)butan-2-yl)phenyl)-8-hydroxy-6-methylthieno[2,3-c]quinolin-4(5H)-one;(1361): (R)-8-methoxy-6-methyl-9-(4-(1-(methylamino)butan-2-yl)phenyl)thieno[2,3-c]quinolin-4(5H)-one;(1362): 9-(4-(3-((diethylamino)methyl)pentan-3-yl)phenyl)-8-hydroxy-6-methylthieno[2,3-c]quinolin-4(5H)-one;(1363): 9-(3-chloro-4-(2-(ethylamino)ethyl)phenyl)-8-hydroxythieno[2,3-c]quinolin-4(5H)-one;(1364): 8-hydroxy-6-methyl-9-(4-(2-(methylamino)ethyl)phenyl)thieno[2,3-c]quinolin-4(5H)-one;(1365): (R)-9-(4-(1-(dimethylamino)butan-2-yl)phenyl)-8-methoxy-6-methylthieno[2,3-c]quinolin-4(5H)-one;(1366): (R)-9-(4-(1-(ethyl(methyl)amino)butan-2-yl)phenyl)-8-methoxy-6-methylthieno[2,3-c]quinolin-4(5H)-one;(1367): (R)-9-(4-(1-(diethylamino)butan-2-yl)phenyl)-8-hydroxy-6-methylthieno[2,3-c]quinolin-4(5H)-one;(1368): (R)-9-(4-(1-(ethyl(methyl)amino)butan-2-yl)phenyl)-8-hydroxy-6-methylthieno[2,3-c]quinolin-4(5H)-one;(1369): 2-((4-(8-methoxy-6-methyl-4-oxo-4,5-dihydrothieno[2,3-c]quinolin-9-yl)phenyl)(methyl)amino)acetonitrile;(1370): 2-((4-(8-hydroxy-6-methyl-4-oxo-4,5-dihydrothieno[2,3-c]quinolin-9-yl)phenyl)(methyl)amino)acetonitrile;(1371): 9-(3-chloro-4-(2-(ethyl(methyl)amino)ethyl)phenyl)-8-hydroxythieno[2,3-c]quinolin-4(5H)-one;(1372): 9-(4-(1-((dimethylamino)methyl)cyclobutyl)phenyl)-8-hydroxy-6-methylthieno[2,3-c]quinolin-4(5H)-one;(1373): (R)-9-(4-(1-aminopropyl)phenyl)-6-bromo-8-methoxythieno[2,3-c]quinolin-4(5H)-one;(1374): 9-(6-(2-aminoethoxy)pyridin-3-yl)-8-hydroxy-6-methylthieno[2,3-c]quinolin-4(5H)-one;(1375): (R)-9-(4-(1-aminopropan-2-yl)phenyl)-2-fluoro-8-methoxy-6-methylthieno[2,3-c]quinolin-4(5H)-one;(1376): 9-(6-(2-aminoethoxy)pyridin-3-yl)-8-methoxy-6-methylthieno[2,3-c]quinolin-4(5H)-one;(1377): 9-(4-(1-amino-2,2,2-trifluoroethyl)phenyl)-8-hydroxy-6-methylthieno[2,3-c]quinolin-4(5H)-one;(1378): 9-(4-(1-amino-2,2,2-trifluoroethyl)phenyl)-8-methoxy-6-methylthieno[2,3-c]quinolin-4(5H)-one;(1379): (R)-9-(4-(1-(ethyl(methyl)amino)propan-2-yl)phenyl)-8-hydroxy-6-methylthieno[2,3-c]quinolin-4(5H)-one;(1380): (R)-8-hydroxy-6-methyl-9-(4-(1-(methylamino)butan-2-yl)phenyl)thieno[2,3-c]quinolin-4(5H)-one;(1381): 9-(4-(1-amino-2,2,2-trifluoroethyl)phenyl)-8-methoxythieno[2,3-c]quinolin-4(5H)-one;(1382): (R)-1-(4-(1-aminopropan-2-yl)phenyl)-8-hydroxy-3-methyl-3H-pyrrolo[2,3-c]quinolin-4(5H)-one;(1383): (R)-9-(4-(1-aminopropan-2-yl)phenyl)-2-fluoro-8-hydroxy-6-methylthieno[2,3-c]quinolin-4(5H)-one;(1384): 9-(6-((2-aminoethyl)amino)pyridin-3-yl)-8-hydroxy-6-methylthieno[2,3-c]quinolin-(5H)-one;(1385): 9-(6-((2-aminoethyl)amino)pyridin-3-yl)-8-methoxy-6-methylthieno[2,3-c]quinolin-4(5H)-one;(1386): (S)-6-chloro-9-(4-(1-(ethyl(methyl)amino)propan-2-yl)phenyl)-8-hydroxythieno[2,3-c]quinolin-4(5H)-one;(1387): (S)-9-(4-(1-(dimethylamino)propan-2-yl)-3-fluorophenyl)-8-methoxy-6-methylthieno[2,3-c]quinolin-4(5H)-one;(1388): (R)-9-(4-(1-(diethylamino)propan-2-yl)phenyl)-8-hydroxy-6-methylthieno[2,3-c]quinolin-4(5H)-one;(1389): 9-(4-(1-amino-2,2,2-trifluoroethyl)phenyl)-8-hydroxythieno[2,3-c]quinolin-4(5H)-one;(1390): 9-(4-(1-amino-2,2,2-trifluoroethyl)phenyl)-6-bromo-8-methoxythieno[2,3-c]quinolin-4(5H)-one;(1391): 9-(4-(1-(aminomethyl)cyclopropyl)phenyl)-6-bromo-8-methoxythieno[2,3-c]quinolin-4(5H)-one;(1392): (4-(8-hydroxy-6-methyl-4-oxo-4,5-dihydrothieno[2,3-c]quinolin-9-yl)phenyl)methanesulfonamide;(1393): 8-methoxy-6-methyl-9-(4-(2-(methylsulfinyl)ethyl)phenyl)thieno[2,3-c]quinolin-4(5H)-one;(1394): 8-hydroxy-6-methyl-9-(4-((methylsulfonyl)methyl)phenyl)thieno[2,3-c]quinolin-4(5H)-one;(1395): (4-(8-methoxy-6-methyl-4-oxo-4,5-dihydrothieno[2,3-c]quinolin-9-yl)phenyl)methanesulfonamide;(1396): 9-(4-((2-aminoethyl)(methyl)amino)phenyl)-8-methoxy-6-methylthieno[2,3-c]quinolin-4(5H)-one;(1397): (R)—N-(2-(2-fluoro-4-(8-hydroxy-6-methyl-4-oxo-4,5-dihydrothieno[2,3-c]quinolin-9-yl)phenyl)propyl)methanesulfonamide;(1398): (R)—N-(2-(2-fluoro-4-(8-methoxy-6-methyl-4-oxo-4,5-dihydrothieno[2,3-c]quinolin-9-yl)phenyl)propyl)methanesulfonamide;(1399): (S)-9-(4-(1-(dimethylamino)propan-2-yl)-3-fluorophenyl)-8-hydroxy-6-methylthieno[2,3-c]quinolin-4(5H)-one;(1400): 9-(4-((2-aminoethyl)(methyl)amino)phenyl)-8-hydroxy-6-methylthieno[2,3-c]quinolin-4(5H)-one;(1401): 9-(4-(1-(aminomethyl)cyclopropyl)phenyl)-6-bromo-8-hydroxythieno[2,3-c]quinolin-4(5H)-one;(1402): 2-(6-(8-methoxy-6-methyl-4-oxo-4,5-dihydrothieno[2,3-c]quinolin-9-yl)pyridin-3-yl)acetonitrile;(1403): 8-hydroxy-6-methyl-9-(4-(2-(methylsulfinyl)ethyl)phenyl)thieno[2,3-c]quinolin-4(5H)-one;(1404): 8-methoxy-6-methyl-9-(4-((methylsulfonyl)methyl)phenyl)thieno[2,3-c]quinolin-4(5H)-one(1405): 5-(8-methoxy-6-methyl-4-oxo-4,5-dihydrothieno[2,3-c]quinolin-9-yl)nicotinamide;(1406): 2-(5-(8-hydroxy-4-oxo-4,5-dihydrothieno[2,3-c]quinolin-9-yl)pyridin-2-yl)propanenitrile;(1407): 2-(4-(8-methoxy-6-methyl-4-oxo-4,5-dihydrothieno[2,3-c]quinolin-9-yl)phenyl)propanamide;(1408): 9-(6-(1-aminopropan-2-yl)pyridin-3-yl)-8-methoxy-6-methylthieno[2,3-c]quinolin-4(5H)-one;(1409): 2-(5-(8-methoxy-6-methyl-4-oxo-4,5-dihydrothieno[2,3-c]quinolin-9-yl)pyridin-2-yl)-2-methylpropanenitrile;(1410): 2-hydroxy-2-(4-(8-hydroxy-4-oxo-4,5-dihydrothieno[2,3-c]quinolin-9-yl)phenyl)propane-1-sulfonamide;(1411): N-(tert-butyl)-2-hydroxy-2-(4-(8-methoxy-4-oxo-4,5-dihydrothieno[2,3-c]quinolin-9-yl)phenyl)propane-1-sulfonamide;(1412): 2-(4-(8-hydroxy-6-methyl-4-oxo-4,5-dihydrothieno[2,3-c]quinolin-9-yl)phenyl)propanamide;(1413): 2-(4-(8-hydroxy-4-oxo-4,5-dihydrothieno[2,3-c]quinolin-9-yl)phenyl)propane-1-sulfonamide;(1414): 9-(4-(2-amino-1-fluoroethyl)phenyl)-8-methoxy-6-methylthieno[2,3-c]quinolin-4(5H)-one;(1415): 9-(6-(1-aminopropan-2-yl)pyridin-3-yl)-8-hydroxy-6-methylthieno[2,3-c]quinolin-4(5H)-one;(1416): 2-(5-(8-hydroxy-6-methyl-4-oxo-4,5-dihydrothieno[2,3-c]quinolin-9-yl)pyridin-2-yl)-2-methylpropanenitrile;(1417): 2-(5-(8-hydroxy-4-oxo-4,5-dihydrothieno[2,3-c]quinolin-9-yl)pyridin-2-yl)-2-methylpropanenitrile;(1418): 2-(5-(8-methoxy-4-oxo-4,5-dihydrothieno[2,3-c]quinolin-9-yl)pyridin-2-yl)-2-methylpropanenitrile;(1419): 2-(4-(8-hydroxy-6-methyl-4-oxo-4,5-dihydrothieno[2,3-c]quinolin-9-yl)phenyl)propane-1-sulfonamide;(1420): 9-(4-(2-amino-1-hydroxyethyl)phenyl)-8-methoxy-6-methylthieno[2,3-c]quinolin-4(5H)-one;(1421): 9-(6-(1-amino-2-methylpropan-2-yl)pyridin-3-yl)-8-hydroxythieno[2,3-c]quinolin-4(5H)-one;(1422): N-cyclopropyl-1-(4-(8-methoxy-6-methyl-4-oxo-4,5-dihydrothieno[2,3-c]quinolin-9-yl)phenyl)methanesulfonamide;(1423): 2-(5-(8-methoxy-4-oxo-4,5-dihydrothieno[2,3-c]quinolin-9-yl)pyridin-2-yl)propanenitrile;(1424): (R)—N-(2-(4-(8-methoxy-6-methyl-4-oxo-4,5-dihydrothieno[2,3-c]quinolin-9-yl)phenyl)propyl)methanesulfonamide;(1425): N-ethyl-1-(4-(8-methoxy-6-methyl-4-oxo-4,5-dihydrothieno[2,3-c]quinolin-9-yl)phenyl)methanesulfonamide;(1426): 9-(6-(1-aminopropan-2-yl)pyridin-3-yl)-8-methoxythieno[2,3-c]quinolin-4(5H)-one;(1427): N-cyclopropyl-1-(4-(8-hydroxy-6-methyl-4-oxo-4,5-dihydrothieno[2,3-c]quinolin-9-yl)phenyl)methanesulfonamide;(1428): 1-(5-(8-methoxy-4-oxo-4,5-dihydrothieno[2,3-c]quinolin-9-yl)pyridin-2-yl)cyclopropanecarbonitrile;(1429): N-ethyl-1-(4-(8-hydroxy-6-methyl-4-oxo-4,5-dihydrothieno[2,3-c]quinolin-9-yl)phenyl)methanesulfonamide;(1430): 1-(4-(8-methoxy-6-methyl-4-oxo-4,5-dihydrothieno[2,3-c]quinolin-9-yl)phenyl)ethanesulfonamide;(1431): 1-(4-(8-methoxy-4-oxo-4,5-dihydrothieno[2,3-c]quinolin-9-yl)phenyl)ethanesulfonamide;(1432): (R)—N-(2-(4-(8-methoxy-4-oxo-4,5-dihydrothieno[2,3-c]quinolin-9-yl)phenyl)propyl)methanesulfonamide;(1433): (R)—N-(2-(4-(8-hydroxy-4-oxo-4,5-dihydrothieno[2,3-c]quinolin-9-yl)phenyl)propyl)-N-methylmethanesulfonamide;(1434): (R)—N-(2-(4-(8-hydroxy-6-methyl-4-oxo-4,5-dihydrothieno[2,3-c]quinolin-9-yl)phenyl)propyl)methanesulfonamide;(1435): (R)—N-(2-(4-(8-hydroxy-4-oxo-4,5-dihydrothieno[2,3-c]quinolin-9-yl)phenyl)propyl)methanesulfonamide;(1436): (R)—N-(2-(4-(8-methoxy-4-oxo-4,5-dihydrothieno[2,3-c]quinolin-9-yl)phenyl)propyl)-N-methylmethanesulfonamide;(1437): (R)—N-(2-(4-(8-hydroxy-6-methyl-4-oxo-4,5-dihydrothieno[2,3-c]quinolin-9-yl)phenyl)propyl)-N-methylmethanesulfonamide;(1438): (R)—N-(2-(4-(8-methoxy-6-methyl-4-oxo-4,5-dihydrothieno[2,3-c]quinolin-9-yl)phenyl)propyl)-N-methylmethanesulfonamide; or a pharmaceutically acceptable salt thereof.
  • 21. A pharmaceutical composition comprising at least one compound of claim 1 or 2 or a pharmaceutically acceptable salt thereof, and a pharmaceutically acceptable carrier.
  • 22. The pharmaceutical composition of claim 21 which is available for preventing or treating a PBK dependent disease.
  • 23. The pharmaceutical composition of claim 22, wherein the PBK dependent disease is cancer.
  • 24. A PBK inhibitor comprising at least one compound of claim 1 or 2, or a pharmaceutically acceptable salt thereof.
  • 25. A method for treating a PBK dependent disease in a subject, comprising administering to said subject an effective amount of a compound or a pharmaceutically acceptable salt thereof of claim 1 or 2.
  • 26. A compound or pharmaceutically acceptable salt thereof of claim 1 or 2 for use in treatment of a PBK dependent disease.
  • 27. Use of a compound of claim 1 or 2 or a pharmaceutically acceptable salt thereof in manufacturing a pharmaceutical composition for treating a PBK dependent disease.
PRIORITY

The present application claims the benefit of U.S. Provisional Applications No. 61/318,606, filed on Mar. 29, 2010, the contents of which are hereby incorporated herein by reference in their entirety for all purposes.

PCT Information
Filing Document Filing Date Country Kind 371c Date
PCT/US11/30278 3/29/2011 WO 00 8/19/2011
Provisional Applications (1)
Number Date Country
61318606 Mar 2010 US