Antibacterial agents

Abstract

Antibacterial compounds of formula I are provided: 1

Description

FIELD OF THE INVENTION

[0002] This invention pertains generally to treating infections caused by gram-negative bacteria. More specifically, the invention described herein pertains to treating gram-negative infections by inhibiting activity of UDP-3-O-(R-3-hydroxydecanoyl)-N-acetylglucosamine deacetylase (LpxC). The present invention provides small molecule inhibitors of LpxC, pharmaceutical formulations containing such inhibitors, methods of treating patients with such pharmaceutical formulations, and to methods of preparing such pharmaceutical formulations and inhibitors. The inhibitors can be used to treat Gram-negative infections of patients alone and in combination with other antibacterials.

BACKGROUND OF THE INVENTION

[0003] Over the past several decades, the frequency of antimicrobial resistance and its association with serious infectious diseases have increased at alarming rates. The increasing prevalence of resistance among nosocomial pathogens is particularly disconcerting. Of the over 2 million nosocomial infections occuriing each year in the United States, 50 to 60% are caused by antimicrobial-resistant strains of bacteria. This, high rate of resistance increases the morbidity, mortality, and costs associated with nosocomial infections. In the United States, nosocomial infections are thought to contribute to or cause more than 77,000 deaths per year and cost approximately $5 to $10 billion annually. Among Gram-positive organisms, the most important resistant pathogens are methicillin-(oxacillin-)resistant Staphylococcus aureus, β-lactam-resistant and multidrug-resistant pneumococci, and vancomycin-resistant enterococci. Important causes of Gram-negative resistance include extended-spectrum β-lactamases (ESBLs) in Klebsiella pneumoniae, Escherichia coli, and Proteus mirabilis, high-level third-generation cephalosporin (Amp C) β-lactamase resistance among Enterobacter species and Citrobacter freundii, and multidrug-resistance genes observed in Pseudomonas aeruginosa, Acinetobacter, and Stenotrophomonas maltophilia. (Jones RN 2001 Chest 119 (supplement), 397S-404S: Resistance patterns among nosocomial pathogens: Trends over the past few years.)

[0004] The problem of antibacterial resistance is compounded by the existence of bacterial strains resistant to multiple antibacterials. For example, Pseudomonas aeruginosa isolates resistant to fluoroquinolones are virtually all resistant to additional antibacterials (Sahm DF et al 2001 Antimicrobial Agents and Chemotherapy 45, 267-274: Evaluation of current activities of fluoroquinolones against gram-negative bacilli using centralized in vitro testing and electronic surveillance.)

[0005] Thus there is a need for new antibacterials, particularly antibacterials with novel mechanisms of action. Most of the antibacterial discovery effort in the pharmaceutical industry is aimed at development of drugs effective against gram-positive bacteria. However, there is also a need for new gram-negative antibacterials. Gram-negative bacteria are in general more resistant to a large number of antibacterials and chemotherapeutic agents than are gram-positive bacteria. A survey of recently reported antibacterials of natural origin showed that over 90% lacked activity against Escherichia coli, although they were active against gram-positive bacteria. The outer membrane of gram-negative bacteria contributes to this intrinsic resistance by acting as an efficient permeability barrier, because the narrow porin channels limit the penetration of hydrophilic solutes and the low fluidity of the lipopolysaccharide leaflet slows down the inward diffusion of lipophilic solutes. A second mechanism contributes to the intrinsic resistance of gram-negative bacteria. Recent studies showed that multiple drug efflux pumps, sometimes with unusually broad specificity, act as this second factor to create the general intrinsic resistance of gram-negative bacteria. When their expression levels are elevated as a consequence of physiological regulation or genetic alteration, they can frequently produce impressive levels of resistance to a wide variety of antimicrobial agents. (Nikaido H 1998 Clinical Infectious Diseases 27(Suppl 1), S32-41: Antibacterial resistance caused by gram-negative multidrug efflux pumps.)

[0006] Historically, most development of antimicrobial agents has been relatively empirical. Active compounds have generally been found via screening soil, sewage, water, and other natural substances to detect antimicrobial-producing organisms, or by screening various chemical compounds. Once a leading candidate has been found and its chemical structure determined, a series of analogs is made to identify an optimal compound for further clinical development. A more rational approach involves the defining of new targets, such as genes or enzymatic functions, responsible for a crucial cellular essential activity. Once this has been done, inhibitors or blockers of the function or gene product can be developed.

[0007] In order to identify potential targets for novel gram-negative antibacterial agents, studies aimed at identifying all essential and important genes in Pseudomonas aeruginosa have been performed. Among the essential genes identified was lpxC, that encodes the enzyme uridyldiphospho-3-O-(R-hydroxydecanoyl)-N-acetylglucosamine deacetylase (LpxC). This enzyme is the first committed step in the synthesis of lipid A, the lipid moiety of lipopolysaccharide, that is an essential component of all gram-negative bacteria. It therefore is an attractive target for novel antibacterials. In order to be useful as antibacterial agents, LpxC inhibitors would not only have to inhibit the enzymatic activity of LpxC from a variety of bacteria, but would have to defeat the intrinsic resistance mechanisms of gram- negative bacteria, as described above: they would have to penetrate the outer membrane and be relatively unsusceptible to multidrug efflux pumps.

[0008] Researchers have identified a few compounds with antibacterial activity that target lipid A biosynthesis. WO 97/42179 to Patchett et al. discloses compounds of the formula: 2

[0009] The compounds possess activity against certain gram-negative organisms, for example Escherichia coli, but are not active against other medically important gram-negative bacteria, for example Pseudomonas aeruginosa. Subsequent studies have found that the primary reason for their inactivity against particular, medically important gram-negative bacteria is their poor ability to inhibit P. aeruginosa LpxC; efflux by the major multidrug efflux pump or inability to penetrate the outer membrane were not the critical factors.

[0010] Jackrnan et al., in J.Biol.Chem. (vol. 275, no. 15, Apr. 14, 2000, pps. 11002-11009), discuss the mechanism of lipid A biosynthesis in the context of gram-negative bacteria and discloses a new class of hydroxamate-containing inhibitors of LpxC. Wyckoffet al., in Trends in Microbiology (vol. 6, no. 4, April 1998, pps. 154-159), discuss the role of LpxC in lipid A biosynthesis and its role in regulation. Wyckoff et al. disclose a few oxazoline hydroxamic acids that inhibit bacterial growth. However, Wyckoff et al. also discuss the shortcomings of the available deacetylase inhibitors as bactericidal agents against Pseudomonas and that more work is needed to be done in the area.

[0011] Thus, an increasing need exists for LpxC inhibitors that have activity as bactericidal agents against gram-negative bacteria. It is, accordingly, an object. of this invention to provide compounds and combinations of such compounds for use in the preparation of antibacterials and other pharmaceuticals capable of inhibiting Gram-negative bacterial infections.

[0012] U.S. Patent Publication No. 2001/0053555 (U.S. patent application Ser. No. 08/958,638) published Dec. 20, 2001, corresponding to WO 98/18754 published May 7, 1998 discloses a combinatorial library of hydroxylamine, hydroxamic acid, hydroxyurea and hydroxylsulfonamide compounds purported to be potentially useful as inhibitors of metalloproteases. U.S. Pat. No. 6,281,245, a continuation in part of U.S. Ser. No. 08/958,638 claims a method of inhibiting a deformylase enzyme by administering one of the hydroxylamine compounds from the combinatorial library as disclosed in U.S. Patent Publication No. 2001/0053555 and the corresponding WO 98/18754. Related to the above disclosed patent publications is WO 99/57097, published Nov. 11, 1999, that discloses a method of solid phase synthesis of the hydroxylamine library of compounds. WO 00/61134 (to British Biotech Pharmaceuticals Limited), published Oct. 19, 2000, discloses compounds of the formula below: 3

[0013] The compounds are useful as antimicrobial agents that are believed to have bactericidal activity at least in part to intracellular inhibition of bacterial polypeptide deformylase.

[0014] In an earlier to British Biotech Pharmaceuticals Limited, WO 99/39704, published Aug. 12, 1999, compounds of the formula below are disclosed: 4

[0015] The compounds are useful as antimicrobial agents useful against gram-negative and gram positive bacteria.

[0016] Recently, De Novo Pharmaceuticals LTD disclosed in WO 02/50081, published Jun. 27, 2002, antibacterial and antiprotozoal agents having the formulae shown below: 5

[0017] The patent publication discusses that the antibacterial activity is due, at least in part, to intracellular inhibition of bacterial polypeptide deformylase.

SUMMARY OF THE INVENTION

[0018] The present invention provides novel compounds, pharmaceutical formulations including the compounds, methods of inhibiting UDP-3-O-(R-3-hydroxydecanoyl)-N-acetylglucosamine deacetylase (LpxC), and methods of treating gram-negative bacterial infections.

[0019] In one embodiment, the present invention provides compounds of formula I: 6

[0020] or stereoisomers, pharmaceutically acceptable salts, esters, and prodrugs thereof, wherein E is absent or selected from the group consisting of

[0021] (1) H,

[0022] (2) substituted or unsubstituted C1-C6-alkyl,

[0023] (3) substituted or unsubstituted C2-C6-alkenyl,

[0024] (4) substituted or unsubstituted C2-C6-alkynyl,

[0025] (5) substituted-or unsubstituted aryl,

[0026] (6) substituted or unsubstituted heterocyclyl, and

[0027] (7) substituted or unsubstituted heteroaryl;

[0028] L is absent or selected from the group consisting of

[0029] (1) substituted or unsubstituted C1-C6-alkyl,

[0030] (2) —(NH)0-1—(CH2)j—NR3L—(CH2)k—,

[0031] (3) —(NH)0-1—C(R1L, R2)—NR3L—C(R1L, R2L)—,

[0032] (4) —C(R1L, R2L)—O—C(R1L, R2L)—,

[0033] (5) —(CH2)j—NR3L—C(R1L, R2L)—CONH—(CH2)k—,

[0034] (6) —CO—C(R1L, R2L)—NHCO—,

[0035] (7) —CONH—,

[0036] (8) —NHCO—,

[0037] wherein

[0038] R1L, R2L, and R3L are independently selected from the group consisting of

[0039] (a) H,

[0040] (b) substituted or unsubstituted C1-C6-alkyl,

[0041] (c) C1-C6-alkyl substituted with aryl,

[0042] (d) C1-C6-alkyl substituted with heterocyclyl, and

[0043] (e) C1-C6-alkyl substituted with heteroaryl,

[0044] or R1L and R3L, together with the atoms to which they are attached can form a substituted or unsubstituted heterocyclic ring, having from 3 to 8 ring atoms, wherein 1-2 ring atoms of the heterocyclic ring system are selected from N, O and S;

[0045] j is an integer of 0-4;

[0046] k is an integer of 0-4;

[0047] D is absent or selected from the group consisting of

[0048] (1) substituted or unsubstituted C3-C8-cycloalkyl,

[0049] (2) substituted or unsubstituted aryl,

[0050] (3) substituted or unsubstituted heterocyclyl, and

[0051] (4) substituted or unsubstituted heteroaryl;

[0052] G is absent or selected from the group consisting of

[0053] (1) —(CH2)i—O—(CH2)i—,

[0054] (2) —(CH2)i—S—(CH2)i—,

[0055] (3) —(CH2)i—NRg—(CH2)i—,

[0056] (4) —C(═O)—,

[0057] (5) —NHC(═O)—,

[0058] (6) —(═O)NH—,

[0059] (7) —(CH2)iNHCH2C(═O)NH—,

[0060] (8) —C≡C—,

[0061] (9) —C≡C—C═C—, and

[0062] (10) —C═C—;

[0063] wherein

[0064] Rg is H or substituted or unsubstituted C1-C6-alkyl;

[0065] i is an interger of 0-4;

[0066] Y is selected from the group consisting of

[0067] (1) substituted or unsubstituted C3-C8-cycloalkyl,

[0068] (2) substituted or unsubstituted aryl,

[0069] (3) substituted or unsubstituted heterocyclyl, and

[0070] (4) substituted or unsubstituted heteroaryl;

[0071] X is selected from the group consisting of

[0072] (1) —(C═O)—,

[0073] (2) —C1-C6-alkyl—(C═O)—,

[0074] (3) —C2-C6-alkenyl—(C═O)—,

[0075] (4) —C2-C6-alkyyl-(C═O)—, and

[0076] (5) —CH2—;

[0077] or when B is absent, X and A, together with the atoms to which they are attached can form a heterocyclic ring, having from 5 to 8 ring atoms, wherein 1-2 ring atoms of the heterocyclic ring system are selected from N, O and S;

[0078] B is a absent or 7

[0079] wherein R1b and R2b, are independently selected fromr the group consisting of

[0080] (a) H,

[0081] (b) substituted or unsubstituted C1-C6-alkyl,

[0082] (c) substituted or unsubstituted C2-C6-alkenyl,

[0083] (d) substituted or unsubstituted C2-C6-alkynyl,

[0084] (e) substituted or unsubstituted aryl,

[0085] (f) substituted or unsubstituted heterocyclyl,

[0086] (g) substituted or unsubstituted heteroaryl,

[0087] (h) C1-C6-alkyl substituted with aryl,

[0088] (i) C1-C6-alkyl substituted with heterocyclyl, and

[0089] (j) C1-C6-alkyl substituted with heteroaryl,

[0090] or R1b and R2b, together with the atoms to which they are attached can form a substituted or unsubstituted heterocyclic ring, having from 5 to 8 ring atoms, wherein 1-2 ring atoms of the heterocyclic ring system are selected from N, Q and S;

[0091] q is an integer of 0-4;

[0092] R3 is H or substituted or unsubstituted C1-C6-alkyl,

[0093] or R3 and A, together with the atoms to which they are attached can form a substituted or unsubstituted 3-10 membered cycloalkyl or a heterocyclic ring system, wherein the heterocyclic ring system may have from 3 to 10 ring atoms, with 1 to 2 rings being in the ring system and contain from 1-4 heteroatoms selected from N, O and S;

[0094] R4 is H or substituted or unsubstituted C1-C6-alkyl,

[0095] or R4 and A, together with the atoms to which they are attached can form a substituted or unsubstituted heterocyclic ring, having from 3 to 8 ring atoms, wherein 1-2 ring atoms of the heterocyclic ring system are selected from N, O and S;

[0096] n is an integer of 0-6;

[0097] A is selected from the group consisting of

[0098] (1) H,

[0099] (2) —(CH2)rC(R1a, R1a)(CH2)(CH2)sOR3a,

[0100] (3) —(CH2)rC(R1a, R2a)N(R4a, R5a),

[0101] (4) —(CH2)rC(R1a, R2a)N(R4a)COR3a,

[0102] (5) —(CH2)rC(R1a, R2a)NHCON(R4a, R5a),

[0103] (6) —(CH2)rC(R1a, R2a)NHC(═NH)N(R4a, R5a),

[0104] (7) —CH(R1a, R2a),

[0105] (8) —C≡CH,

[0106] (9) —(CH2)rC(R1a, R2a)CN,

[0107] (10) —(CH2)rC(R1a, R2a)CO2R3a, and

[0108] (11) —(CH2)rC(R1a, R2a)CON(R4a, R5a),

[0109] wherein R1a, R2a, R3a, R4a, and R5a are independently selected from the group consisting of

[0110] (a) H,

[0111] (b) substituted or unsubstituted C1-C6-alkyl,

[0112] (c) substituted or unsubstituted aryl,

[0113] (d) substituted or unsubstituted heterocyclyl,

[0114] (e) substituted or unsubstituted heteroaryl,

[0115] (f) C1-C6-alkyl substituted with aryl,

[0116] (g) C1-C6-alkyl substituted with, heterocyclyl, and

[0117] (h) C1-C6-alkyl substituted.with heteroaryl,

[0118] or R4a and R5a together with the N atom to which they are attached can form a substituted or unsubstituted heterocyclic ring, having from 5 to 8 ring atoms, wherein 1-2 ring atoms of the heterocyclic ring system are selected from N, O and S;

[0119] r is an integer of 0-4;

[0120] s is an integer of 0-4;

[0121] Q is absent or selected from the group consisting of

[0122] (1) —C(═O)N(R1, R2),

[0123] (2) —NHC(═O)N(R1, R2),

[0124] (3) 13 N(OH)C(═O)N(R1, R2),

[0125] (4) —CH(OH)C(═O)N(R1, R2),

[0126] (5) —CH[N(R2q, R3q)]C(═O)N(R1, R2),

[0127] (6) —CHR1qC(═O)N(R1, R2),

[0128] (7) —CO2H,

[0129] (8) —C(═O)NHSO2R4q,

[0130] (9) —SO2NH2,

[0131] (10) —N(OH)C(═O)R1q,

[0132] (11) —N(OH)SO2R4q,

[0133] (12) —NHSO2R4q,

[0134] (13) —SH,

[0135] (14) —CH(SH)(CH2)0-1C(═O)N(R1, R2),

[0136] (15) —CH(SH)(CH2)0-1CO2H,

[0137] (16) —CH(OH)(CH2)0-1CO2H,

[0138] (17) —CH(SH)CH2CO2R1q,

[0139] (18) —CH(OH)(CH2)SO2NH2,

[0140] (19) —CH(CH2SH)NHCOR1q,

[0141] (20) —CH(CH2SH)NHSO2R4q,

[0142] (21) —H(CH2SR5q)CO2H,

[0143] (22) —CH(CH2SH)NHSO2NH2,

[0144] (23) —H(CH2OH)CO2H,

[0145] (24) —CH(CH2OH)NHSO2NH2,

[0146] (25) —(═O)CH2CO2H,

[0147] (26) —C(═O)(CH2)0-1CONH2,

[0148] (27) —OSO2NHR5q,

[0149] (28) —SO2NHNH2,

[0150] (29) —P(═O)(OH)2, 8

[0151] (30)

[0152] (31)

[0153] (32)

[0154] wherein

[0155] R1 is selected from the group consisting of

[0156] (1) H,

[0157] (2) —OH,

[0158] (3) —OC1-6-alkyl,

[0159] (4) —N(R2q, R3q), and

[0160] (5) substituted or unsubstituted C1-6-alkyl;

[0161] R2 is selected from the group consisting of

[0162] (1) H,

[0163] (2) substituted or unsubstituted C1-C6-alkyl,

[0164] (3) substituted or unsubstituted C2-C6-alkenyl,

[0165] (4) substituted or unsubstituted C2-C6-alkenyl, (5) substituted or unsubstituted aryl,

[0166] (6) substituted or unsubstituted heterocyclyl,

[0167] (7) substituted or unsubstituted heteroaryl,

[0168] (8) C1-C6-alkyl substituted with aryl,

[0169] (9) C1-C6-alkyl substituted with heterocyclyl, and

[0170] (10) C1-C6-alkyl substituted with heteroaryl,

[0171] or R1 and R2, together with the N atom to which they are attached can form a substituted or unsubstituted heterocyclic ring, having from 3 to 10 ring atoms, wherein 1-4 ring atoms of the heterocyclic ring system are selected from N, O and S,

[0172] or R2 and R4, together with the N atoms to which they are attached can form a substituted or unsubstituted heterocyclic ring, having from 3 to 10 ring atoms, wherein 1-4 ring atoms of the heterocyclic ring system are selected from N, O and S;

[0173] R1q, R2q, R3q, R4q, and R5q are selected from H or C1-C6 alkyl,

[0174] wherein B is absent, or E, L, G, and B are absent, or E, L, and G are absent, or E, L, and B are absent, or E, L, D, G, and B are absent.

[0175] In one aspect, the invention provides a method of inhibiting a deacetylase enzyme in a gram-negative bacteria, thereby affecting bacterial growth, comprising administering to a patient in need of such inhibition a compound of formula I.

[0176] In another aspect, the invention provides a method of inhibiting LpxC, thereby modulating the virulence of a bacterial infection, comprising administering to a patient in need of such inhibition a compound of formula I.

[0177] In another aspect, the invention provides a method for treating a subject with a gram-negative bacterial infection comprising administering to the subject in need thereof an antibacterially effective amount of a compound of formula I with a pharmaceutically acceptable carrier. In a preferred embodiment of the method of treatment, the subject is a mammal and in some embodiments, a human.

[0178] In another aspect, the invention provides a method of administering an inhibitory amount of a compound of formula I to fermentative or non-fermentative gram-negative bacteria. In a preferred embodiment of the method of administering an inhibitory amount of a compound of formula I to fermentative or non-fermentative gram-negative bacteria, the gram-negative bacteria are selected from the group consisting of Pseudomonas aeruginosa, Stenotrophomonas maltophila, Burkholderia cepacia, Alcaligenes xylosoxidans, Acinetobacter, Enterobacteriaceae, Haemophilus, and Neisseria species.

[0179] In another embodiment, the invention provides a method of administering an inhibitory amount of a compound of formula I to gram-negative bacteria, such as Enterobacteriaceae which is selected from the group consisting of organisms such as Serratia, Proteus, Klebsiella, Enterobacter, Citrobacter, Salmonella, Providencia, Morganella, Cedecea, and Edwardsiella species and Escherichia coli.

[0180] Another embodiment of the invention provides a pharmaceutical composition comprising an effective amount of a compound of Formula I with a pharmaceutically acceptable carrier thereof.

[0181] Pharmaceutical formulations according to the present invention are provided which include any of the compounds described above in combination with a pharmaceutically acceptable carrier.

[0182] Another embodiment of the invention provides a method of co-administering the compound of formula I with other therapeutic agents that are selected for their particular usefulness against the condition that is being treated.

[0183] For example, the compound of formula I is useful in combination with other anti-bacterial agents. The compound of formula I augments the sensitivity of gram-negative bacteria to existing classes of antibacterials. Combinations of the presently disclosed compounds with other anti-bacterial. agents are within the scope of the invention. Such anti-bacterial agents include, but are not limited to, erythromycin, rifampicin, Nalidixic acid, carbenicillin, bacitracin, cycloserine, fosfomycin, and vancomycin.

DETAILED DESCRIPTION

[0184] The present invention provides novel compounds, methods for inhibiting LpxC in gram-negative bacteria, and novel methods for treating bacterial infections. The compounds provided herein can be formulated into pharmaceutical formulations and medicaments that are useful in the methods of the invention. The invention also provides for the use of the compounds in preparing medicaments and pharmaceutical formulations, for use of the compounds in inhibiting LpxC, and for use of the compounds in treating bacterial infections in a subject.

[0185] The following abbreviations and definitions are used throughout this application:

[0186] “LpxC” is an abbreviation that stands for UDP-3-O-(R-3-hydroxydecanoyl)-N-acetylglucosamine deacetylase.

[0187] Generally, reference to a certain element such as hydrogen or H is meant to include all isotopes of that element. For example, if an R group is defined to include hydrogen or H, it also includes deuterium and tritium.

[0188] The phrase “alkyl” refers to alkyl groups that-do not contain heteroatoms. Thus the phrase includes straight chain alkyl groups such as methyl, ethyl, propyl, butyl, pentyl, hexyl, heptyl, octyl, nonyl, decyl, undecyl, dodecyl and the like. The phrase also includes branched chain isomers of straight chain alkyl groups, including but not limited to, the following that are provided by way of example: —CH(CH3)2, —CH(CH3)(CH2CH3), —CH(CH2CH3)2, —C(CH3)3, —C(CH2CH3)3, —CH2CH(CH3)2, —CH2CH(CH3)(CH2CH3), —CH2CH(CH2CH3)2, —CH2C(CH3)3, —CH2C(CH2CH3)3, —CH(CH3)CH(CH3)(CH2CH3), —CH2CH2CH(CH3)2, —CH2CH2CH(CH3)(CH2CH3), —CH2CH2CH(CH2CH3)2, —CH2CH2C(CH3)3, —CH2CH2C(CH2CH3)3, —CH(CH3)CH2CH(CH3)2, —CH(CH3)CH(CH3)CH(CH3)2, —CH(CH2CH3)CH(CH3)CH(CH3)(CH2CH3), and others. The phrase also includes cyclic alkyl groups such as cyclopropyl, cyclobutyl, cyclopentyl, cyclohexyl, cycloheptyl, and cyclooctyl and such rings substituted with straight and branched chain alkyl groups as defined above. Thus the phrase alkyl groups includes primary alkyl groups, secondary alkyl groups, and tertiary alkyl groups. Preferred alkyl groups include straight and branched chain alkyl groups and cyclic alkyl groups having 1 to 12 carbon atoms.

[0189] The phrase “substituted alkyl” refers to an alkyl group as defined above in which one or more bonds to a carbon(s) or hydrogen(s) are replaced by a bond to non-hydrogen and non-carbon atoms such as, but not limited to, a halogen atom such as F, Cl, Br, and I; an oxygen atom in groups such as hydroxyl groups, alkoxy groups, aryloxy groups, and ester groups; a sulfur atom in groups such as thiol groups, alkyl and aryl sulfide groups, sulfone groups, sulfonyl groups, and sulfoxide groups; a nitrogen atom in groups such as amines, amides, alkylamines, dialkylamines, arylamines, alkylarylamines, diarylamines, N-oxides, imides, and enamines; a silicon atom in groups such as in trialkylsilyl groups, dialkylarylsilyl groups, alkyldiarylsilyl groups, and triarylsilyl groups; and other heteroatoms in various other groups. Substituted alkyl groups also include groups in which one or more bonds to a carbon(s) or hydrogen(s) atom is replaced by a higher-order bond (e.g., a double- or triple-bond) to a heteroatom such as oxygen in oxo, carbonyl, carboxyl, and ester groups; nitrogen in groups such as imines, oximes, hydrazones, and nitriles. Substituted alkyl groups further include alkyl groups in which one or more bonds to a carbon(s) or hydrogen(s) atoms is replaced by a bond to an aryl, heterocyclyl group, or cycloalkyl group. Preferred substituted alkyl groups include, among others, alkyl groups in which one or more bonds to a carbon or hydrogen atom is/are replaced by one or more bonds to fluorine atoms. Another preferred substituted alkyl group is the trifluoromethyl group and other alkyl groups that contain the trifluoromethyl group. Other preferred substituted alkyl groups include those in which one or more bonds to a carbon or hydrogen atom is replaced by a bond to an oxygen atom such that the substituted alkyl group contains a hydroxyl, alkoxy, or aryloxy group. Still other preferred substituted alkyl groups include alkyl groups that have an amine, or a substituted or unsubstituted alkylamine, dialkylamine, arylamine, (alkyl)(aryl)amine, diarylamine, heterocyclylamine, diheterocyclylamine, (alkyl)(heterocyclyl)amine, or (aryl)(heterocyclyl)amine group.

[0190] The phrase “alkenyl” refers to straight and branched chain and cyclic groups such as those described with respect to alkyl groups as defined above, except that at least one double bond exists between two carbon atoms. Examples include, but are not limited to vinyl, —CH═C(H)(CH3), —CH═C(CH3)2, —C(CH3)═C(H)2, —C(CH3)═C(H)(CH3), —C(CH2CH3)═CH2, cyclohexenyl, cyclopentenyl, cyclohexadienyl, butadienyl, pentadienyl, and hexadienyl among others. The phrase “substituted alkenyl” has the same meaning with respect to alkenyl groups that substituted alkyl groups had with respect to unsubstituted alkyl groups. A substituted alkenyl group includes alkenyl groups in which a non-carbon or non-hydrogen atom is bonded to a carbon double bonded to another carbon and those in which one of the non-carbon or non-hydrogen atoms is bonded to a carbon not involved in a double bond to another carbon.

[0191] The phrase “alkynyl” refers to straight and branched chain groups such as those described with respect to alkyl groups as defined above, except that at least one triple bond exists between two carbon atoms. Examples include, but are not limited to —C≡C(H), —C≡C(CH3), —C≡C(CH2CH3), —C(H2)C≡C(H), —C(H)2C≡C(CH3), and —C(H)2C≡C(CH2CH3) among others. The phrase “substituted alkynyl” has the same meaning with respect to alkynyl groups that substituted alkyl groups had with respect to unsubstituted alkyl groups. A substituted alkynyl group includes alkynyl groups in which a non-carbon or non-hydrogen atom is bonded to a carbon triple bonded to another carbon and those in which a non-carbon or non-hydrogen atom is bonded to a carbon not involved in a triple bond to another carbon.

[0192] The phrase “heterocyclyl” refers to both aromatic and nonaromatic ring compounds including monocyclic, bicyclic, and polycyclic ring compounds such as, but not limited to, quinuclidinyl, containing 3 or more ring members of which one or more is a heteroatom such as, but not limited to, N, O, and S. Although the phrase “unsubstituted heterocyclyl” includes condensed heterocyclic rings such as benzimidazolyl, it does not include heterocyclyl groups that have other groups such as alkyl or halo groups bonded to one of the ring members as compounds such as 2-methylbenzimidazolyl are substituted heterocyclyl groups. Examples of heterocyclyl groups include, but are not limited to: unsaturated 3 to 8 membered rings containing 1 to 4 nitrogen atoms such as, but not limited to pyrrolyl, pyrrolinyl, imidazolyl, pyrazolyl, pyridyl, dihydropyridyl, pyrimidyl, pyrazinyl, pyridazinyl, triazolyl (e.g. 4H-1,2,4-triazolyl, 1H-1,2,3-triazolyl, 2H-1,2,3-triazolyl etc.), tetrazolyl, (e.g. 1H-tetrazolyl, 2H tetrazolyl, etc.); saturated 3 to 8 membered rings containing 1 to 4 nitrogen atoms such as, but not limited to, pyrrolidinyl, imidazolidinyl, piperidinyl, piperazinyl; condensed unsaturated heterocyclic groups containing 1 to 4 nitrogen atoms such as, but not limited to, indolyl, isoindolyl, indolinyl, indolizinyl, benzimidazolyl, quinolyl, isoquinolyl, indazolyl, benzotriazolyl; unsaturated 3 to 8 membered rings containing 1 to 2 oxygen atoms and 1 to 3 nitrogen atoms such as, but not limited to, oxazolyl, isoxazolyl, oxadiazolyl (e.g. 1,2,4-oxadiazolyl, 1,3,4-oxadiazolyl, 1,2,5-oxadiazolyl, etc.); saturated 3 to 8 membered rings containing 1 to 2 oxygen atoms and 1 to 3 nitrogen atoms such as, but not limited to, morpholinyl; unsaturated condensed heterocyclic groups containing 1 to 2 oxygen atoms and 1 to 3 nitrogen atoms, for example, benzoxazolyl, benzoxadiazolyl, benzoxazinyl (e.g. 2H-1,4-benzoxazinyl etc.); unsaturated 3 to 8 membered rings containing 1 to 3 sulfur atoms and 1 to 3 nitrogen atoms such as, but not limited to, thiazolyl, isothiazolyl, thiadiazolyl (e.g. 1,2,3-thiadiazolyl, 1,2,4-thiadiazolyl, 1,3,4-thiadiazolyl, 1,2,5-thiadiazolyl, etc.); saturated 3 to 8 membered rings containing 1 to 2 sulfur atoms and 1 to 3 nitrogen atoms such as, but not limited to, thiazolodinyl; saturated and unsaturated 3 to 8 membered rings containing 1 to 2 sulfur atoms such as, but not limited to, thienyl, dihydrodithiinyl, dihydrodithionyl, tetrahydrothiophene, tetrahydrothiopyran; unsaturated condensed heterocyclic rings containing 1 to 2 sulfur atoms and 1 to 3 nitrogen atoms such as, but not limited to, benzothiazolyl, benzothiadiazolyl, benzothiazinyl (e.g. 2H-1,4-benzothiazinyl, etc.), dihydrobenzothiazinyl (e.g. 2H-3,4-dihydrobenzothiazinyl, etc.), unsaturated 3 to 8 membered rings containing oxygen atoms such as, but not limited to furyl; unsaturated condensed heterocyclic rings containing 1 to 2 oxygen atoms such as benzodioxolyl (e.g. 1,3-benzodioxoyl, etc.); unsaturated 3 to 8 membered rings containing an oxygen atom and 1 to 2 sulfur atoms such as, but not limited to, dihydrooxathiinyl; saturated 3 to 8 membered rings containing 1 to 2 oxygen atoms and 1 to 2 sulfur atoms such as 1,4-oxathiane; unsaturated condensed rings containing 1 to 2 sulfur atoms such as benzothienyl, benzodithiinyl; and unsaturated condensed heterocyclic rings containing an oxygen atom and 1 to 2 oxygen atoms such as benzoxathiinyl. Heterocyclyl group also include those described above in which one or more S atoms in the ring is double-bonded to one or two oxygen atoms (sulfoxides and sulfones). For example, heterocyclyl groups include tetrahydrothiophene, tetrahydrothiophene oxide, and tetrahydrothiophene 1,1-dioxide. Preferred heterocyclyl groups contain 5 or 6 ring members. More preferred heterocyclyl groups include morpholine, piperazine, piperidine, pyrrolidine, imidazole, pyrazole, 1,2,3-triazole, 1,2,4-triazole, tetrazole, thiomorpholine, thiomorpholine in which the S atom of the thiomorpholine is bonded to one or more 0 atoms, pyrrole, homopiperazine, oxazolidin-2-one, pyrrolidin-2-one, oxazole, quinuclidine, thiazole, isoxazole, furan, and tetrahydrofuran.

[0193] The phrase “substituted heterocyclyl” refers to a heterocyclyl group as defined above in which one of the ring members is bonded to a non-hydrogen atom such as described above with respect to substituted alkyl groups and substituted aryl groups. Examples, include, but are not limited to, 2-methylbenzimidazolyl, 5-methylbenzimidazolyl, 5-chlorobenzthiazolyl, 1-methyl piperazinyl, and 2-chloropyridyl among others.

[0194] The phrase “aryl” refers to aryl groups that do not contain heteroatoms. Thus the phrase includes, but is not limited to, groups such as phenyl, biphenyl, anthracenyl, naphthenyl by way of example. Although the phrase “unsubstituted aryl” includes groups containing condensed rings such as naphthalene, it does not include aryl groups that have other groups such as alkyl or halo groups bonded to one of the ring members, as aryl groups such as tolyl are considered herein to be substituted aryl groups as described below. A preferred unsubstituted aryl group is phenyl. Unsubstituted aryl groups may be bonded to one or more carbon atom(s), oxygen atom(s), nitrogen atom(s), and/or sulfur atom(s) in the parent compound, however.

[0195] The phrase “substituted aryl group” has the same, meaning with respect to unsubstituted aryl groups that substituted alkyl groups had with respect to unsubstituted alkyl groups. However, a substituted aryl group also includes aryl groups in which one of the aromatic carbons is bonded to one of the non-carbon or non-hydrogen atoms described above and also includes aryl groups in which one or more aromatic carbons of the aryl group is bonded to a substituted and/or unsubstituted alkyl, alkenyl, or alkynyl group as defined herein. This includes bonding arrangements in which two carbon atoms of an aryl group are bonded to two atorns of an alkyl, alkenyl, or alkynyl group to define a fused ring system (e.g. dihydronaphthyl or tetrahydronaphthyl). Thus, the phrase “substituted aryl” includes, but is not limited to tolyl, and hydroxyphenyl among others. Preferred substituents include straight and branched chain alkyl groups, —CH3, —C2H5, —CH2OH, —OH, —OCH3, —OC2H5, —OCF3, —CN, —NO2, —CO2H, —CO2CH3, —CONH2, —NH2, —F, —Cl, Br, —CF3, —N(CH3)2, —NHSO2CH3, —NHCOCH3.

[0196] The term “heteroaryl”, as used herein, refers to a cyclic or bicyclic aromatic radical having from five to ten ring atoms in each ring of which one atom of the cyclic or bicyclic ring is selected from S, O and N; zero, one or two ring atoms are additional heteroatoms independently selected from S, O and N; and the remaining ring atoms are carbon, the radical being joined to the rest of the molecule via any of the ring atoms, such as, for example, pyridyl, pyrazinyl, pyrimidinyl, pyrrolyl, pyrazolyl, imidazolyl, thiazolyl, oxazolyl, isooxazolyl, thiadiazolyl, oxadiazolyl, thiophenyl, furanyl, quinolinyl, isoquinolinyl, and naphthyridinyl, and the like.

[0197] The term “substituted heteroaryl” as used herein refers to a heteroaryl group as defined herein substituted by independent replacement of one, two or three of the hydrogen atoms thereon with Cl, Br, F, I, OH, CN, C1-C3-alkyl, C1-C6-alkoxy, C1-C6-alkoxy substituted with aryl, haloalkyl, thioalkoxy, amino, alkylamino, dialkylamino, mercapto, nitro, carboxaldehyde, carboxy, alkoxycarbonyl and carboxamide. In addition, any one substituent may be an aryl, heteroaryl, or heterocycloalkyl group. Preferred substituents include straight and branched chain alkyl groups, —CH3, —C2H5, —CH2OH, —OH, —OCH3, —OC2H5, —OCF3, —CN, —NO2, —CO2H, —CO2CH3, —CONH2, —NH2, —F, —Cl, Br, —CF3, —N(CH3)2, —NHSO2CH3, —NHCOCH3.

[0198] The term “biaryl” refers to a group or substituent to which two aryl groups, which are not condensed to each other, are bound. Exemplary biaryl compounds include, for example, phenylbenzene, diphenyldiazene, 4-methylthio- 1 -phenylbenzene, phenoxybenzene, (2-phenylethynyl)benzene, diphenyl ketone, (4-phenylbuta-1,3-diynyl)benzene, phenylbenzylamine, (phenylmethoxy)benzene, and the like. Preferred optionally substituted biaryl groups include: 2-(phenylamino)-N-[4-(2-phenylethynyl)phenyl]acetamide, 1,4-diphenylbenzene, N-[4-(2-phenylethynyl)phenyl]-2-[benzylamino]acetamide, 2-amino-N-[4-(2-phenylethynyl)phenyl]propanamide, 2-amino-N-[4-(2-phenylethynyl)phenyl]acetamide, 2-(cyclopropylamino)-N-[4-(2-phenylethynyl)phenyl]acetamide, 2-(ethylamino)-N-[4-(2-phenylethynyl)phenyl]acetamide, 2-[(2-methylpropyl)amino]-N-[4-(2-phenylethynyl)phenyl]acetamide, 5-phenyl-2H-benzo[d]1,3-dioxolene, 2-chloro-1-methoxy4-phenylbenzene, 2-[(imidazolyhnethyl)amino]-N-[4-(2-phenylethynyl)phenyl]acetamide, 4-phenyl-1-phenoxybenzene, N-(2-aminoethyl)[4-(2-phenylethynyl)phenyl]carboxamide, 2-{[(4-fluorophenyl)methyl]amino}-N-[4-(2-phenylethynyl)phenyl]acetamide, 2-{[(4-methylphenyl)methyl]amino}-N-[4-(2-phenylethynyl)phenyl]acetamide, 4-phenyl-1-(trifluoromethyl)benzene, 1-butyl-4-phenylbenzene, 2-(cyclohexylamino)-N-[4-(2-phenylethynyl)phenyl]acetamide, 2-(ethylmethylamino)-N-[4-(2-phenylethynyl)phenyl]acetamide, 2-(butylamino)-N-[4-(2-phenylethynyl)phenyl]acetamide, N-[4-(2-phenylethynyl)phenyl]-2-(4-pyridylamino)acetamide, N-[4-(2-phenylethynyl)phenyl]-2-(quinuclidin-3-ylamino)acetamide, N-[4-(2-phenylethynyl)phenyl]pyrrolidin-2-ylcarboxamide, 2-amino-3-methyl-N-[4-(2-phenylethynyl)phenyl]butanamide, 4-(4-phenylbuta-1,3-diynyl)phenylamine, 2-(dimethylamino)-N-[4-(4-phenylbuta-1,3-diynyl)phenyl]acetamide, 2-(ethylamino)-N-[4-(4-phenylbuta- 1,3-diynyl)phenyl]acetamide, 4-ethyl-1-phenylbenzene, 1-[4-(2-phenylethynyl)phenyl]ethan-1-one, N-(1-carbamoyl-2-hydroxypropyl)[4-(4-phenylbuta-1,3-diynyl)phenyl]carboxamide, N-[4-(2-phenylethynyl)phenyl]propanamide, 4-methoxyphenyl phenyl ketone, phenyl-N-benzamide, (tert-butoxy)-N-[(4-phenylphenyl)methyl]carboxamide, 2-(3-phenylphenoxy)ethanehydroxamic acid, 3-phenylphenyl propanoate, 1-(4-ethoxyphenyl)-4-methoxybenzene, and [4-(2-phenylethynyl)phenyl]pyrrole.

[0199] The term “heteroarylaryl” refers to a biaryl group where one of the aryl groups. is a heteroaryl group. Exemplary heteroarylaryl groups include, for example, 2-phenylpyridine, phenylpyrrole, 3-(2-phenylethynyl)pyridine, phenylpyrazole, 5-(2-phenylethynyl)-1,3-dihydropyrimidine-2,4-dione, 4-phenyl-1,2,3-thiadiazole, 2-(2-phenylethynyl)pyrazine, 2-phenylthiophene, phenylimidazole, 3-(2-piperazinylphenyl)furan, 3-(2,4-dichlorophenyl)-4-methylpyrrole, and the like. Preferred optionally substituted heteroarylaryl groups include: 5-(2-phenylethynyl)pyrimidine-2-ylamine, 1-methoxy-4-(2-thienyl)benzene, 1-methoxy-3-(2-thienyl)benzene, 5-methyl-2-phenylpyridine, 5-methyl-3-phenylisoxazole, 2-[3-(trifluoromethyl)phenyl]furan, 3-fluoro-5-(2-furyl)-2-methoxy-1-prop-2-enylbenzene, (hydroxyimino)(5-phenyl(2-thienyl))methane, 5-[(4-methylpiperazinyl)methyl]-2-phenylthiophene, 2-(4-ethylphenyl)thiophene, 4-methylthio-1-(2-thienyl)benzene, 2-(3-nitrophenyl)thiophene, (tert-butoxy)-N-[(5-phenyl(3-pyridyl))methyl]carboxamide, hydroxy-N-[(5-phenyl(3-pyridyl))methyl]amide, 2-(phenylmethylthio)pyridine, and benzylimidazole.

[0200] The term “heteroarylheteroaryl” refers to a biaryl group where both of the aryl groups is a heteroaryl group. Exemplary heteroarylheteroaryl groups include, for example, 3-pyridylimidazole, 2-imidazolylpyrazine, and the like. Preferred optionally substituted heteroarylheteroaryl groups include: 2-(4-piperazinyl-3-pyridyl)furan, diethyl(3-pyrazin-2-yl(4-pyridyl))amine, and dimethyl{2-[2-(5-methylpyrazin-2-yl)ethynyl](4-pyridyl)}amine.

[0201] “Optionally substituted” refers to the optional replacement of hydrogen with one or more monovalent or divalent radicals. Optionally substituted groups include those described herein, for each group in which a distinct definition for substitution is supplied. Additionally, suitable substitution groups include, for example, hydroxyl, nitro, amino, imino, cyano, halo, thio, thioamido, amidino, imidino, oxo, oxamidino, methoxamidino, imidino, guanidino, sulfonamido, carboxyl, formyl, alkyl, substituted alkyl, haloloweralkyl, loweralkoxy, haloloweralkoxy, loweralkoxyalkyl, alkylcarbonyl, arylcarbonyl, aralkylcarbonyl, heteroarylcarbonyl, heteroaralkylcarbonyl, alkylthio, aminoalkyl, cyanoalkyl, benzyl, pyridyl, pyrazolyl, pyrrole, thiophene, imidazolyl, and the like.

[0202] Representative substituted amidino and heterocycloamidino groups include, for example, those shown below. These amidino and heterocycloamidino groups can be further substituted as will be apparent to those having skill in the organic and medicinal chemistry arts in conjunction with the disclosure herein. 9

[0203] Representative substituted alkylcarbonylamino, alkyloxycarbonylamino, aminoalkyloxycarbonylamino, and arylcarbonylamino groups include, for example, those shown below. These groups can be further substituted as will be apparent to those having skill in the organic and medicinal chemistry arts in conjunction with the disclosure herein. 10

[0204] Representative substituted aminocarbonyl groups include, for example, those shown below. These can be further substituted by heterocyclo groups and heteroaryl groups as will be apparent to those having skill in the organic and medicinal chemistry arts in conjunction with the disclosure herein. Prefered aminocarbonyl groups include: N-(2-cyanoethyl)carboxamide, N-(3-methoxypropyl)carboxamide, N-cyclopropylcarboxamide, N-(2-hydroxy-isopropyl)carboxamide, methyl 2-carbonylamino-3-hydroxypropanoate, N-(2-hydroxypropyl)carboxamide, N-(2-hydroxy-isopropyl)carboxamide, N-[2-hydroxy-1-(hydroxymethyl)ethyl]carboxamide, N-(2-carbonylaminoethyl)acetamide, N-(2-(2-pyridyl)ethyl)carboxamide, N-(2-pyridylmethyl)carboxamide, N-(oxolan-2-ylmethyl)carboxamide, N-(4-hydroxypyrrolidin-2-yl)carboxamide, N-[2-(2-hydroxyethoxy)ethyl]carboxamide, N-(4-hydroxycyclohexyl)carboxamide, N-[2-(2-oxo4-imidazolinyl)ethyl]carboxamide, N-(carbonylaminomethyl)acetamide, N-(3-pyrrolidinylpropyl)carboxamide, N-[1-(carbonylaminomethyl)pyrrolidin-3-yl]acetamide, N-(2-morpholin4-ylethyl)carboxamide, N-[3-(2-oxopyrrolidinyl)propyl]carboxamide, 4-methyl-2-oxopiperazinecarbaldehyde, N-(2-hydroxy-3-pyrrolidinylpropyl)carboxamide, N-(2-hydroxy-3-morpholin-4-ylpropyl)carboxamide, N-{2-[(5-cyano-2-pyridyl)atnino]ethyl}carboxamide, 3-(dimethylamino)pyrrolidinecarbaldehyde, N-[(5-methylpyrazin-2-yl)methyl]carboxamide, 2,2,2-trifluoro-N-(1-formylpyrrolidin-3-yl)acetamide, 11

[0205] Representative substituted alkoxycarbonyl groups include, for example, those shown below. These alkoxycarbonyl groups can be further substituted as will be apparent to those having skill in the organic and medicinal chemistry arts in conjunction with the disclosure herein. 12

[0206] The term “protected” with respect to hydroxyl groups, amine groups, and sulfhydryl groups refers to forms of these functionalities that are protected from undesirable reaction with a protecting group known to those skilled in the art such as those set forth in Protective Groups in Organic Synthesis, Greene, T. W.; Wuts, P. G. M., John Wiley & Sons, New York, NY, (3rd Edition, 1999) that can be added or removed using the procedures set forth therein. Examples of protected hydroxyl groups include, but are not limited to, silyl ethers such as those obtained by reaction of a hydroxyl group with a reagent such as, but not limited to, t-butyldimethyl-chlorosilane, trimethylchlorosilane, triisopropylchlorosilane, triethylchlorosilane; substituted methyl and ethyl ethers such as, but not limited to methoxymethyl ether, methythiomethyl ether, benzyloxymethyl ether, t-butoxymethyl ether, 2-methoxyethoxymethyl ether, tetrahydropyranyl ethers, 1-ethoxyethyl ether, allyl ether, benzyl ether; esters such as, but not limited to, benzoylformate, formate, acetate, trichloroacetate, and trifluoracetate. Examples of protected amine groups include, but are not limited to, amides such as, formamide, acetamide, trifluoroacetamide, and benzamide; imides, such as phthalimide, and dithiosuccinimide; and others. Examples of protected sulfhydryl groups include, but are not limited to, thioethers such as S-benzyl thioether, and S-4-picolyl thioether; substituted S-methyl derivatives such as hemithio, dithio and aminothio acetals; and others.

[0207] A “pharmaceutically acceptable salt” includes a salt with an inorganic base, organic base, inorganic acid, organic acid, or basic or acidic amino acid. As salts of inorganic bases, the invention includes, for example, alkali metals such as sodium or potassium; alkaline earth metals such as calcium and magnesium or aluminum; and ammonia. As salts of organic bases, the invention includes, for example, trimethylamine, triethylamine, pyridine, picoline, ethanolamine, diethanolamine, and triethanolamine. As salts of inorganic acids, the instant invention includes, for example, hydrochloric acid, hydroboric acid, nitric acid, sulfuric acid, and phosphoric acid. As salts of organic acids, the instant invention includes, for example, formic acid, acetic acid, trifluoroacetic acid, fumaric acid, oxalic acid, tartaric acid, maleic acid, citric acid, succinic acid, malic acid, methanesulfonic acid, benzenesulfonic acid, and p-toluenesulfonic acid. As salts of basic amino acids, the instant invention includes, for example, arginine, lysine and omithine. Acidic amino acids include, for example, aspartic acid and glutamic acid.

[0208] As used herein, the term “pharmaceutically acceptable ester” refers to esters that hydrolyze in vivo and include those that break down readily in the human body to leave the parent compound or a salt thereof. Suitable ester groups include, for example, those derived from pharmaceutically acceptable aliphatic carboxylic acids, particularly alkanoic, alkenoic, cycloalkanoic and alkanedioic acids, in which each alkyl or alkenyl moiety advantageously has not more than 6 carbon atoms. Representative examples of particular esters include, but are not limited to, formates, acetates, propionates, butyrates, acrylates and ethylsuccinates.

[0209] The term “pharmaceutically acceptable prodrugs” as used herein refers to those prodrugs of the compounds of the present invention that are, within the scope of sound medical judgment, suitable for use in contact with the tissues of humans and lower animals without undue toxicity, irritation, allergic response, and the like, commensurate with a reasonable benefit/risk ratio, and effective for their intended use, as well as the zwitterionic forms, where possible, of the compounds of the invention. The term “prodrug” refers to compounds that are rapidly transformed in vivo to yield the parent compound of the above formnula, for example by hydrolysis in blood. A thorough discussion is provided in T. Higuchi and V. Stella, Pro-drugs as Novel Delivery Systems, Vol. 14 of the A.C.S. Symposium Series, and in Edward B. Roche, ed., Bioreversible Carriers in Drug Design, American Pharmaceutical Association and Pergamon Press, 1987, both of which are incorporated herein by reference.

[0210] The term “antibacterial agent” refers to agents synthesized or modified in the laboratory that have either bactericidal or bacteriostatic activity. An “active” agent in this context will inhibit the growth of P. aeruginosa and other gram-negative bacteria. The term “inhibiting the growth” indicates that the rate of increase in the numbers of a population of a particular bacterium is reduced. Thus, the term includes situations in which the bacterial population increases but at a reduced rate, as well as situations where the growth of th& population is stopped, as well as situations where the numbers of the bacteria in the population are reduced or the population even eliminated. If an enzyme activity assay is used to screen for inhibitors, one can make modifications in uptake/efflux, solubility, half-life, etc. to compounds in order to correlate enzyme inhibition with growth inhibition. The activity of antibacterial agents is not necessarily limited to bacteria but may also encompass activity against parasites, virus, and fungi.

[0211] The subject invention also includes isotopically-labeled LpxC inhibitors, that are structurally identical to those disclosed above, but for the fact that one or more atoms are replaced by an atom having an atomic mass or mass number different from the atomic mass or mass number usually found in nature. Examples of isotopes that can be incorporated into compounds of the invention include isotopes of hydrogen, carbon, nitrogen, oxygen, phosphorous, sulfur, fluorine and chlorine, such as 2H, 3H, 13C, 14C, 15N, 18O, 17O, 31P, 32P, 35S, 18F and 36Cl, respectively. Compounds of the present invention, prodrugs thereof, and pharmaceutically acceptable salts of said compounds and of said prodrugs that contain the aforementioned isotopes and/or other isotopes of other atoms are within the scope of this invention. Certain isotopically labeled compounds of the present invention, for example those into which radioactive isotopes such as 3H and 14C are incorporated, are useful in drug and/or substrate tissue distribution assays. Tritiated, i.e., 3H, and carbon-14, i.e., 14C, isotopes are particularly preferred for their ease of preparation and detectability. Further, substitution with heavier isotopes such as deuterium, i.e., 2H, may afford certain therapeutic advantages resulting from greater metabolic stability, for example increased in vivo half-life or reduced dosage requirements and, hence, may be preferred in some circumstances. Isotopically labeled compounds of this invention and prodrugs thereof can generally be prepared by carrying out known or referenced procedures and by substituting a readily available isotopically labeled reagent for a non-isotopically labeled reagent.

[0212] The present invention provides novel compounds, pharmaceutical formulations including the compounds, methods of inhibiting UDP-3-O-(R-3-hydroxydecanoyl)-N-acetylglucosamine deacetylase (LpxC), and methods of treating gram-negative bacterial infections.

[0213] In one embodiment, the present invention provides compounds of formula I: 13

[0214] or stereoisomers, pharmaceutically acceptable salts, esters, and prodrugs thereof, wherein E is absent or selected from the group consisting of

[0215] (1) H,

[0216] (2) substituted or unsubstituted C1-C6-alkyl,

[0217] (3) substituted or unsubstituted C2-C6-alkenyl,

[0218] (4) substituted or unsubstituted C2-C6-alkynyl,

[0219] (5) substituted or unsubstituted aryl,

[0220] (6) substituted or unsubstituted heterocyclyl, and

[0221] (7) substituted or unsubstituted heteroaryl;

[0222] L is absent or selected from the group consisting of

[0223] (1) substituted or unsubstituted C1-C6-alkyl,

[0224] (2) —(NH)0-1—(CH2)j—NR3L—(CH2)k—,

[0225] (3) —(NH)0-1—C(R1L, R2L)—NR3L—C(R1L, R2L)—,

[0226] (4) —C(R1L, R2L)—O—C(R1L, R2L)—,

[0227] (5) —CH2)j—NR3L—C(R1L, R2L)—CONH—(CH2)k—,

[0228] (6) —CO—C(R1L, R2L)—NHCO—,

[0229] (7) —CONH—,

[0230] (8) —NHCO—,

[0231] wherein

[0232] R1L, R2L, and R3L are independently selected from the group consisting of

[0233] (a) H,

[0234] (b) substituted or unsubstituted C1-C6-alkyl,

[0235] (c) C1-C6-alkyl substituted with aryl,

[0236] (d) C1-C6-alkyl substituted with heterocyclyl, and

[0237] (e) C1-C6-alkyl substituted with heteroaryl,

[0238] or R1L and R3L, together with the atoms to which they are attached can form a substituted or unsubstituted heterocyclic ring, having from 3 to 8 ring atoms, wherein 1-2 ring atoms of the heterocyclic ring system are selected from N, O and S,

[0239] j is an integer of 0-4;

[0240] k is an integer of 0-4;

[0241] D is absent or selected from the group consisting of

[0242] (1) substituted or unsubstituted C3-C8-cycloalkyl,

[0243] (2) substituted or unsubstituted aryl,

[0244] (3) substituted or unsubstituted heterocyclyl, and

[0245] (4) substituted or-unsubstituted heteroaryl;

[0246] G is absent or selected from the group consisting of

[0247] (1) —(CH2)i—O—(CH2)i—,

[0248] (2) —(CH2)i—S—(CH2)i—,

[0249] (3) —(CH2)i—NRg—(CH2)i—,

[0250] (4) —C(═O)—,

[0251] (5) —NHC(═O)—,

[0252] (6) —C(═O)NH—,

[0253] (7) —CH2)iNHCH2C(═O)NH—,

[0254] (8) —C≡C—,

[0255] (9) —C≡C—C≡C—, and

[0256] (10) —C═C—;

[0257] wherein

[0258] Rg is H or substituted or unsubstituted C1-C6-alkyl; i is an interger of 0-4;

[0259] Y is selected from the group consisting of

[0260] (1) substituted or unsubstituted C3-C8-cycloalkyl,

[0261] (2) substituted or unsubstituted aryl,

[0262] (3) substituted or unsubstituted heterocyclyl, and

[0263] (4) substituted or unsubstituted heteroaryl;

[0264] X is selected from the group consisting of

[0265] (1) —(C═O)—,

[0266] (2) —C1-C6-alkyl-(C═O)—,

[0267] (3) —C2-C6-alkenyl-(C═O)—,

[0268] (4) —C2-C6-alkynyl-(C═O)—, and

[0269] (5) —CH2—;

[0270] or when B is absent, X and A, together with the atoms to which they are attached can form a heterocyclic ring, having from 5 to 8 ring atoms, wherein 1-2 ring atoms of the heterocyclic ring system are selected from N, O and S;

[0271] B is a absent or 14

[0272] wherein R1b and R2b, are independently selected from the group consisting of

[0273] (a) H,

[0274] (b) substituted or unsubstituted C1-C6-alkyl,

[0275] (c) substituted or unsubstituted C2-C6-alkenyl,

[0276] (d) substituted or unsubstituted C2-C6-allynyl,

[0277] (e) substituted or unsubstituted aryl,

[0278] (f) substituted or unsubstituted heterocyclyl,

[0279] (g) substituted or unsubstituted heteroaryl,

[0280] (h) C1-C6-alkyl substituted with aryl,

[0281] (i) C1-C6-alkyl substituted with heterocyclyl, and

[0282] (j) C1-C6-alkyl substituted with heteroaryl,

[0283] or R1b and R2b, together with the atoms to which they are attached can form a substituted or unsubstituted heterocyclic ring, having from 3 to 8 ring atoms, wherein 1-2 ring atoms of the heterocyclic: ring system are selected from N, O and S;

[0284] q is an integer of 0-4;

[0285] R3 is H or substituted or unsubstituted C1-C6-alkyl, or R3 and A, together with the atoms to which they are attached can form a substituted or unsubstituted 3-10 membered cycloalkyl or a heterocyclic ring system, wherein the heterocyclic ring system may have from 3 to 10 ring atoms, with 1 to 2 rings being in the ring system and contain from 1-4 heteroatoms selected from N, O and S;

[0286] R4 is H or substituted or unsubstituted C1-C6-alkyl, or R4 and A, together with the atoms to which they are attached can form a substituted or unsubstituted heterocyclic ring, having from 3 to 8 ring atoms, wherein 1-2 ring atoms of the heterocyclic ring system are selected from N, O and S;

[0287] n is an integer of 0-2;

[0288] A is selected from the group consisting of

[0289] (1) H,

[0290] (2) —(CH2)rC(R1a, R2a)(CH2)sOR3a,

[0291] (3) —(CH2)rC(R1a, R2a)N(R4a, R5a),

[0292] (4) —(CH2)rC(R1a, R2a)N(R4a)COR3a,

[0293] (5) —(CH2)rC(R1a, R2a)NHCON(R4a, R5a),

[0294] (6) —(CH2)rC(R1a, R2a)NHC(═NH)N(R4a, R5a),

[0295] (7) —CH(R1a, R2a),

[0296] (8) —C≡CH,

[0297] (9) —CH2)rC(R1a, R2a)CN,

[0298] (10) —CH2)rC(R1a, R2a)CO2R3a, and

[0299] (11) —CH2)rC(R1a, R2a)CN(R4a, R5a),

[0300] wherein R1a, R2a, R3a, R4a, and R5a are independently selected from the group consisting of

[0301] (a) H,

[0302] (b) substituted or unsubstituted C1-C6-alkyl,

[0303] (c) substituted or unsubstituted aryl,

[0304] (d) substituted or unsubstituted heterocyclyl,

[0305] (e) substituted or unsubstituted heteroaryl,

[0306] (f) C1-C6-alkyl substituted with aryl,

[0307] (g) C1-C6-alkyl substituted with heterocyclyl, and

[0308] (h) C1-C6-alkyl substituted with heteroaryl,

[0309] or R4a and R5a together with the N atom to which they are attached can form a substituted or unsubstituted heterocyclic ring, having from 3 to 8 ring atoms, wherein 1-2 ring atoms of the heterocyclic ring system are selected from N, O and S;

[0310] r is an integer of 0-4;

[0311] s is an integer of 0-4;

[0312] Q is absent or selected from the group consisting of

[0313] (1) —C(═O)N(R1, R2),

[0314] (2) —NHC(═O)N(R1, R2),

[0315] (3) —N(OH)C(═O)N(R1, R2),

[0316] (4) —CH(OH)C(═O)N(R1, R2),

[0317] (5) —CH[NR2q, R3q)]C(═O)N(R1, R2),

[0318] (6) —CHR1qC(═O)N(R1, R2),

[0319] (7) —CO2H,

[0320] (8) —C(═O)NHSO2R4q,

[0321] (9) —SO2NH2,

[0322] (10) —N(OH)C(═O)R1q,

[0323] (11) —N(OH)SO2R4q,

[0324] (12) —NHSO2R4q,

[0325] (13) —SH,

[0326] (14) —CH(SH)(CH2)0-1C(═O)N(R1, R2),

[0327] (15) —CH(SH)(CH2)0-1CO2H,

[0328] (16) —CH(OH)(CH2)0-1CO2H,

[0329] (17) —CH(SH)CH2CO2R1q,

[0330] (18) —CH(OH)(CH2)SO2NH2,

[0331] (19) —CH(CH2SH)NHCOR1q,

[0332] (20) —CH(CH2SH)NHSO2R4q,

[0333] (21) —CH(CH2SR5q)CO2H,

[0334] (22) —CH(CH2SH)NHSO2NH2,

[0335] (23) —CH(CH2OH)CO2H,

[0336] (24) —CH(CH2OH)NHSO2NH2,

[0337] (25) —C(═O)CH2CO2H,

[0338] (26) —C(═O)(CH2)0-1CONH2,

[0339] (27) —OSO2NHR5q,

[0340] (28) —SO2NHNH2,

[0341] (29) —P(═O)(OH)2, 15

[0342] (30)

[0343] (31)

[0344] (32)

[0345] R1 is selected from the group consisting of

[0346] (1) —H,

[0347] (2) —OH,

[0348] (3) —OC1-6-alkyl,

[0349] (4) —N(R2q, R3q), and

[0350] (5) substituted or unsubstituted C1-6-alkyl;

[0351] R2 is selected from the group consisting of

[0352] (1) H,

[0353] (2) substituted or unsubstituted C1-C6-alkyl,

[0354] (3) substituted or unsubstituted C2-C6-alkenyl,

[0355] (4) substituted or unsubstituted C2-C6-alkenyl,

[0356] (5) substituted or unsubstituted aryl,

[0357] (6) substituted or unsubstituted heterocyclyl,

[0358] (7) substituted or unsubstituted heteroaryl,

[0359] (8) C1-C6-alkyl substituted with aryl,

[0360] (9) C1-C6-alkyl substituted with heterocyclyl, and

[0361] (10) C1-C6-alkyl substituted with heteroaryl,

[0362] or R1 and R2, together with the N atom to which they are attached can form a substituted or unsubstituted heterocyclic ring, having from 3 to 10 ring atoms, wherein 1-4 ring atoms of the heterocyclic ring system are selected from N, O and S,

[0363] R1q, R2q, R3q, R4q, and R5q are selected from H or C1-C6 alkyl,

[0364] wherein B is absent, or E, L, G, and B are absent, or E, L, and G are absent, or E, L, and B are absent, or E, L, D, G, and B are absent.

[0365] In another embodiment, the present invention provides compounds of formula I: 16

[0366] or stereoisomers, pharmaceutically acceptable salts, esters, and prodrugs thereof, wherein

[0367] E is absent or selected from the group consisting of

[0368] (1) H,

[0369] (2) substituted or unsubstituted C1-C6-alkyl,

[0370] (3) substituted or unsubstituted aryl,

[0371] (4) substituted or unsubstituted heterocyclyl, and

[0372] (5) substituted or unsubstituted heteroaryl;

[0373] L is absent or selected from the group consisting of

[0374] (1) —(CH2)j—NR3L—(CH2)k—,

[0375] (2) —C(R1L, R2L)j—NR3L—C(R1L, R2L)k—,

[0376] (3) —C(R1L, R2L)j—O—C(R1L, R2L)k—,

[0377] (4) —(CH2)j—NR3L—C(R1L, R2L)k—CONH—(CH2)k—,

[0378] (5) —CO—C(R1L, R2L)—NHCO—,

[0379] (6) —CONH—, and

[0380] (7) —NHCO—,

[0381] wherein

[0382] R1L, R2L, R3L are independently selected from the group consisting of

[0383] (a) H,

[0384] (b) substituted or unsubstituted C1-C6-alkyl,

[0385] (c) C1-C6-alkyl substituted with aryl,

[0386] (d) C1-C6-alkyl substituted with heterocyclyl,

[0387] (e) C1-C6-alkyl substituted with heteroaryl,

[0388] or R1L and R3L, together with the atoms to which they are attached can form a substituted or unsubstituted heterocyclic ring, having from 5 to 8 ring atoms, wherein 1-2 ring atoms of the heterocyclic ring system are selected from N, O and S;

[0389] j is an integer of 0-4;

[0390] k is an integer of 0-4;

[0391] D is absent or selected from the group consisting of

[0392] (1) substituted or unsubstituted C3-C8-cycloalkyl,

[0393] (2) substituted or unsubstituted aryl,

[0394] (3) substituted or unsubstituted heterocyclyl,

[0395] (4) substituted or unsubstituted heteroaryl, and

[0396] G is absent or selected from the group consisting of

[0397] (1) —C(═O)—,

[0398] (2) —NHC(═O)—,

[0399] (3) —C(═O)NH—,

[0400] (4) —(CH2)iNHCH2C(═O)NH—,

[0401] (5) —C≡C—, and

[0402] (6) —C≡C—C≡C—,

[0403] wherein i is an interger of 0-4;

[0404] Y is selected from the group consisting of

[0405] (1) substituted or unsubstituted C3-C8-cycloalkyl,

[0406] (2) substituted or unsubstituted aryl,

[0407] (3) substituted or unsubstituted heterocyclyl, and

[0408] (4) substituted or unsubstituted heteroaryl;

[0409] X is selected from the group consisting of

[0410] (1) —(C═O)—,

[0411] (2) —C1-C6-alkyl-(C═O)—,

[0412] (3) —C2-C26-alkenyl-(C═O)—,

[0413] (4) —C2-C6-alkynyl-(C═O), and

[0414] (5) —CH2—;

[0415] or when B is absent, X and A, together with the atoms to which they are attached can form a heterocyclic ring, having from 5 to 8 ring atoms, wherein 1-2 ring atoms of the heterocyclic ring system are selected from N, O and S;

[0416] B is absent or 17

[0417] wherein R1b and R2b are independently selected from the group consisting of

[0418] (a) H

[0419] (b) substituted or unsubstituted C1-C6-alkyl,

[0420] (c) substituted or unsubstituted C2-C6-alkenyl,

[0421] (d) substituted or unsubstituted C2-C6-alkenyl,

[0422] (e) substituted or unsubstituted aryl,

[0423] (f) substituted or unsubstituted heterocyclyl,

[0424] (g) substituted or unsubstituted heteroaryl,

[0425] (h) C1-C6-alkyl substituted with aryl,

[0426] (i) C1-C6-alkyl substituted with heterocyclyl, and

[0427] (i) C1-C6-alkyl substituted with heteroaryl,

[0428] or R1b and R2b, together with the atoms to which they are attached can form a substituted or unsubstituted.heterocyclic ring, having from 5 to 8 ring atoms, wherein 1-2 ring atoms of the heterocyclic ring system are selected from N, O and S;

[0429] q is an integer of 0-2;

[0430] R3 is H or substituted or unsubstituted C1-C6-alkyl,

[0431] or R3 and A, together with the atoms to which they are attached can form a substituted or unsubstituted 3-10 membered cycloalkyl or a heterocyclic ring system, wherein the heterocyclic ring system may have from 3 to 10 ring atoms, with 1 to 2 rings being in the ring system and contain from 1-4 heteroatoms selected from N, O and S;

[0432] R4 is H or substituted or unsubstituted C1-C6-alkyl,

[0433] or R4 and A, together with the atoms to which they are attached can form a substituted or unsubstituted heterocyclic ring, having from 5 to 8 ring atoms, wherein 1-2 ring atoms of the heterocyclic ring system are selected from N, O and S;

[0434] A is selected from the group consisting of

[0435] (1) H,

[0436] (2) —(CH2)rC(R1a, R2a)(CH2)sOR3a,

[0437] (3) —(CH2)rC(R1a, R2a)N(R4a, R5a),

[0438] (4) —(CH2)rC(R1a, R2a)N(R4a)COR3a,

[0439] (5) —(CH2)rC(R1a, R2a)NHCON(R4a, R5a),

[0440] (6) —(CH2)rC(R1a, R2a)NHC(═NH)N(R4a, R5a),

[0441] (7) —(CH(R1a, R2a),

[0442] (8) —C≡CH,

[0443] (9) —(CH2)rC(R1a, R2a)CN, and

[0444] (10) —(CH2)rC(R1a, R2a)CO2R3a,

[0445] wherein R1a, R2a, R3a, R4a, and R5a, are independently selected from the group consisting of

[0446] (a) H,

[0447] (b) substituted or unsubstituted C1-C6-alkyl,

[0448] (c) C -C6-alkyl substituted with aryl,

[0449] (d) C1-C6-alkyl substituted with heterocyclyl, and

[0450] (e) C1-C6-alkyl substituted with heteroaryl,

[0451] or R4a and R5a, together with the N atom to which they are attached can form a substituted or unsubstituted heterocyclic ring, having from 5 to 8 ring atoms, wherein 1-2 ring atoms of the heterocyclic ring system are selected from N, O and S;

[0452] r is an integer of 0-4;

[0453] Q is absent or selected from the group consisting of

[0454] (1) —C(═O)N(R1, R2),

[0455] (2) —NHC(═O)N(R1, R2),

[0456] (3) —N(OH)C(═O)N(R1, R2),

[0457] (4) —CH(OH)C(═O)N(R1, R2),

[0458] (5) —CHR2q, R3q)]C(═O)N(R1, R2), and

[0459] (6) —CHR1qC(═O)N(R1, R2),

[0460] R1 is selected from the group consisting of

[0461] (1) H,

[0462] (2) OH,

[0463] (3) OC1-6-alkyl,

[0464] (4) N(R2q, R3q), and

[0465] (5) substituted or unsubstituted C1-6-alkyl;

[0466] R2 is selected from the group consisting of

[0467] (1) H,

[0468] (2) substituted or unsubstituted C1-C6-alkyl,

[0469] (3) substituted or unsubstituted aryl,

[0470] (4) substituted or unsubstituted heterocyclyl,

[0471] (5) substituted or unsubstituted heteroaryl,

[0472] (6) C1-C6-alkyl substituted with aryl,

[0473] (7) C1-C6-alkyl substituted with heterocyclyl, and

[0474] (8) C1-C6-alkyl substituted with heteroaryl,

[0475] or R1 and R2, together with the N atom to which they are attached can form a substituted or unsubstituted heterocyclic ring, having from 3 to 10 ring atoms, wherein 1-4 ring atoms of the heterocyclic ring system are selected from N, O and S,

[0476] R1q, R2q, and R3q are selected from H or C1-C6 alkyl,

[0477] wherein B is absent, or E, L, G, and B are absent, or E, L, and G are absent, or E, L, and B are absent, or E, L, D, G, and B are absent.

[0478] In another embodiment, the present invention provides compounds of formula II: 18

[0479] or stereoisomers, pharmaceutically acceptable salts, esters, and prodrugs thereof, wherein D-G-Y taken together, is selected from the group consisting of 1920212223

[0480] Wherein

[0481] R is selected from the group consisting of —CH3, —C2H5, —CH2OH, —OH, —OCH3, —OC2H5, —OCF3, —CN, —NO2, —CO2, —CO2CH3, —CONH2, —NH2, —F, —Cl, —Br, —CF3, —N(CH3)2, —NHSO2CH3, and —NHCOCH3;

[0482] X is selected from the group consisting of

[0483] (1) —(C═O)—,

[0484] (2) —C1-C6-alkyl-(C═O)—, and

[0485] (3) —C2-C6-alkenyl-(C═O)—.

[0486] In another embodiment, the present invention provides compounds of formula III: 24

[0487] or stereoisomers, pharmaceutically acceptable salts, esters, and prodrugs thereof, wherein D-G-Y taken together, is selected from the group consisting of 2526272829

[0488] Wherein

[0489] R is selected from the group consisting of —CH3, —C2H5, —CH2OH, —OH, —OCH3, —OC2H5, —OCF3, —CN, —NO2, —CO2H, —CO2CH3, —CONH2, —NH2, —F, —Cl, —Br, —CF3, —N(CH3)2, —NHSO2CH3, and —NHCOCH3;

[0490] X is selected from the groups consisting of

[0491] (1) —(C═O)—,

[0492] (2) —C1-C6-alkyl-(C═O)—, and

[0493] (3) —C2-C6-alkenyl-(C═O)—.

[0494] In another embodiment, the present invention provides compounds of formula IV: 30

[0495] or stereoisomers, pharmaceutically acceptable salts, esters, and prodrugs thereof, wherein D-G-Y taken together, is selected from the group consisting of 3132333435

[0496] Wherein

[0497] R is selected from the group consisting of —CH3, —C2H5, —CH2OH, —OH, —OCH3, —OC2H5, —OCF3, —CN, —NO2, —CO2H, —CO2CH3, —CONH2, —NH2, —F, —Cl, —Br, —CF3, —N(CH3)2, —NHSO2CH3, and —NHCOCH3;

[0498] X is selected from the groups consisting of

[0499] (1) —(C═O)—,

[0500] (2) —C1-C6-alkyl-(C═O)—, and

[0501] (3) —C2-C6-alkenyl-(C═O)—.

[0502] In another embodiment, the present invention provides compounds of formula V: 36

[0503] or stereoisomers, pharmaceutically acceptable salts, esters, and prodrugs thereof, wherein D-G-Y taken together, is selected from the group consisting of 3738394041

[0504] Wherein

[0505] R is selected from the group consisting of —CH3, —C2H5, —CH2OH, —OH, —OCH3, —OC2H5, —OCF3, —CN, —NO2, —CO2H, —CO2CH3, CONH2, —NH2, —F, —Cl, —Br, —CF3, —N(CH3)2, —NHSO2CH3, and —NHCOCH3;

[0506] X is selected from the groups consisting of

[0507] (1) —(C═O)—,

[0508] (2) —C1-C6-alkyl-(C═O)—, and

[0509] (3) —C2-C6-alkenyl-(C═O)—.

[0510] In another embodiment, the present invention provides compounds of formula VI: 42

[0511] or stereoisomers, pharmaceutically acceptable salts, esters, and prodrugs thereof, wherein E is absent or selected from the group consisting of

[0512] (1) H,

[0513] (2) substituted or unsubstituted C1-C6-alkyl,

[0514] (3) substituted or unsubstituted aryl,

[0515] (4) substituted or unsubstituted heterocyclyl, and

[0516] (5) substituted or unsubstituted heteroaryl,

[0517] or E and R3L, together with the atoms to which they are attached can form a substituted or unsubstituted heterocyclic ring, having from 3 to 10 ring atoms, wherein 1-4 ring atoms of the heterocyclic ring system are selected from N, O and S,

[0518] R1L, R3L are independently selected from the group consisting of

[0519] (1) H,

[0520] (2) substituted or unsubstituted C1-C6-alkyl,

[0521] (3) C1-C6-alkyl substituted with aryl,

[0522] (4) C1-C6-alkyl substituted with heterocyclyl, and

[0523] (5) C1-C6-alkyl substituted with heteroaryl,

[0524] or R1L and R3L, together with the atoms to which they are attached can form a substituted or unsubstituted heterocyclic ring, having from 3 to 8 ring atoms, wherein 1-2 ring atoms of the heterocyclic ring system are selected from N, O and S.

[0525] In another embodiment, the present invention provides compounds of formula VII: 43

[0526] or stereoisomers, pharmaceutically acceptable salts, esters, and prodrugs thereof, wherein E is absent or selected from the group consisting of

[0527] (1) H,

[0528] (2) substituted or unsubstituted C1-C6-alkyl,

[0529] (3) substituted or unsubstituted aryl,

[0530] (4) substituted or unsubstituted heterocyclyl, and

[0531] (5) substituted or unsubstituted heteroaryl,

[0532] or E and R3L, together with the atoms to which they are attached can form a substituted or unsubstituted heterocyclic ring, having from 3 to 10 ring atoms, wherein 1-4 ring atoms of the heterocyclic ring system are selected from N, O and S;

[0533] R1L, R3L are independently selected from the group consisting of

[0534] (1) H,

[0535] (2) substituted or unsubstituted C1-C6-alkyl,

[0536] (3) C1-C6-alkyl substituted with aryl,

[0537] (4) C1-C6-alkyl substituted with heterocyclyl, and

[0538] (5) C1-C6-alkyl substituted with heteroaryl,

[0539] or R1L and R3L, together with the atoms to which they are attached can form a substituted or unsubstituted heterocyclic ring, having from 3 to 8 ring atoms, wherein 1-2 ring atoms of the heterocyclic ring system are selected from N, O and S.

[0540] In another embodiment, the present invention provides compounds of formula VIII: 44

[0541] or stereoisomers, pharmaceutically acceptable salts, esters, and prodrugs thereof, wherein

[0542] E is absent or selected from the group consisting of

[0543] (1) H,

[0544] (2) substituted or unsubstituted C1-C6-alkyl,

[0545] (3) substituted or unsubstituted aryl,

[0546] (4) substituted or unsubstituted heterocyclyl, and

[0547] (5) substituted or unsubstituted heteroaryl,

[0548] or E and R3L, together with the atoms to which they are attached can form a substituted or unsubstituted heterocyclic ring, having from 3 to 10 ring atoms, wherein 1-4 ring atoms of the heterocyclic ring system are selected from N, O and S;

[0549] R1L, R3L are independently selected from the group consisting of

[0550] (1) H,

[0551] (2) substituted or unsubstituted C1-C6-alkyl,

[0552] (3) C1-C6-alkyl substituted with aryl,

[0553] (4) C1-C6-alkyl substituted with heterocyclyl, and

[0554] (5) C1-C6-alkyl substituted with heteroaryl,

[0555] or R1L and R3L, together with the atoms to which they are attached can form a substituted or unsubstituted heterocyclic ring, having from 3 to 8 ring atoms, wherein 1-2 ring atoms of the heterocyclic ring system are selected from N, O and S.

[0556] In another embodiment, the present invention provides compounds of formula IX: 45

[0557] or stereoisomers, pharmaceutically acceptable salts, esters, and prodrugs thereof, wherein E is absent or selected from the group consisting of

[0558] (1) H,

[0559] (2) substituted or unsubstituted C1-C6-alkyl,

[0560] (3) substituted or unsubstituted aryl,

[0561] (4) substituted or unsubstituted heterocyclyl, and

[0562] (5) substituted or unsubstituted heteroaryl,

[0563] or E and R3L, together with the atoms to which, they are attached can form a substituted or unsubstituted heterocyclic ring, having from 3 to 10 ring atoms, wherein 1-4 ring atoms of the heterocyclic ring system are selected from N, O and S;

[0564] R1L, R3L are independently selected from the group consisting of

[0565] (1) H,

[0566] (2) substituted or unsubstituted C1-C6-alkyl,

[0567] (3) C1-C6-alkyl substituted with aryl,

[0568] (4) C1-C6-alkyl substituted with heterocyclyl, and

[0569] (5) C1-C6-alkyl substituted with heteroaryl,

[0570] or R1L and R3L, together with the atoms to which they are attached can form a substituted or unsubstituted heterocyclic ring, having from 3 to 8 ring atoms, wherein 1-2 ring atoms of the heterocyclic ring system are selected from N, O and S.

[0571] In another embodiment, the present invention provides compounds of formula X: 46

[0572] or stereoisomers, pharmaceutically acceptable salts, esters, and prodrugs thereof, wherein E is absent or selected from the group consisting of

[0573] (1) H1,

[0574] (2) substituted or unsubstituted C1-C6-alkyl,

[0575] (3) substituted or unsubstituted aryl,

[0576] (4) substituted or unsubstituted heterocyclyl, and

[0577] (5) substituted or unsubstituted heteroaryl,

[0578] or E and R3L, together with the atoms to which they are attached can form a substituted or unsubstituted heterocyclic ring, having from 3 to 10 ring atoms, wherein 1-4 ring atoms of the heterocyclic ring system are selected from N, O and S;

[0579] R1L, R3L are independently selected from the group consisting of

[0580] (1) H,

[0581] (2) substituted or unsubstituted C1-C6-alkyl,

[0582] (3) C1-C6-alkyl substituted with aryl,

[0583] (4) C1-C6-alkyl substituted with heterocyclyl, and

[0584] (5) C1-C6-alkyl substituted with heteroaryl,

[0585] or R1L and R3L, together with the atoms to which they are attached can form a substituted or unsubstituted-heterocyclic ring, having from 3 to 8 ring atoms, wherein 1-2 ring atoms of the heterocyclic ring system are selected from N, O and S.

[0586] In another embodiment, the present invention provides compounds of formula XI: 47

[0587] or stereoisomers, pharmaceutically acceptable salts, esters, and prodrugs thereof, wherein Y—X taken together, is selected from the group consisting of 4849

[0588] In another embodiment, the present invention provides compounds of formula XII: 50

[0589] or stereoisomers, pharmaceutically acceptable salts, esters, and prodrugs thereof, wherein R1b and R2b are independently selected from the group consisting of

[0590] (1) H,

[0591] (2) substituted or unsubstituted C1-C6-alkyl,

[0592] (3) substituted or unsubstituted C2-C6-alkenyl,

[0593] (4) substituted or unsubstituted C2-C6-alkenyl,

[0594] (5) substituted or unsubstituted aryl,

[0595] (6) substituted or unsubstituted heterocyclyl,

[0596] (7) substituted or unsubstituted heteroaryl,

[0597] (8) C1-C6-alkyl substituted with aryl,

[0598] (9) C1-C6-alkyl substituted with heterocyclyl, and

[0599] (10) C1-C6-alkyl substituted with heteroaryl;

[0600] q is an integer of 0-2;

[0601] In another embodiment, the present invention provides compounds of formula XIII: 51

[0602] or stereoisomers, pharmaceutically acceptable salts, esters, and prodrugs thereof, wherein

[0603] R4 is selected from the group consisting of

[0604] (1) H,

[0605] (2) substituted or unsubstituted C1-C6-alkyl,

[0606] (3) C1-C6-alkyl substituted with aryl,

[0607] (4) C1-C6-alkyl substituted with heterocyclyl, and

[0608] (5) C1-C6-alkyl substituted with heteroaryl;

[0609] A is H or —CH(CH3)OH—;

[0610] R1 is H or substituted or unsubstituted C1-6-alkyl;

[0611] R2 is selected from the group consisting of

[0612] (1) H,

[0613] (2) substituted or unsubstituted C1-C6-alkyl,

[0614] (3) substituted or unsubstituted aryl,

[0615] (4) substituted or unsubstituted heterocyclyl,

[0616] (5) substituted or unsubstituted heteroaryl,

[0617] (6) C1-C6-alkyl substituted with aryl,

[0618] (7) C1-C6-alkyl substituted with heterocyclyl,

[0619] (8) C1-C6-alkyl substituted with heteroaryl,

[0620] or R1 and R2 together with the N atom to which they are attached can form a substituted or unsubstituted heterocyclic ring, having from 3 to 10 ring atoms, wherein 1-2 ring atoms of the heterocyclic ring system are selected from N, O and S.

[0621] In another embodiment, the present invention provides compounds of formula XIV: 52

[0622] or stereoisomers, pharmaceutically acceptable salts, esters, and prodrugs thereof, wherein D-G-Y taken together is selected from the group consisting of 5354555657

[0623] Wherein

[0624] R is selected from the group consisting of —CH3, —C2H5, —CH2OH, —OH, —OCH3, —OC2H5, —OCF3, —CN, —NO2, —CO2H, —CO2CH3, —CONH2, —NH2, —F, —Cl, —Br, —CF3, —N(CH3)2, —NHSO2CH3, and —NHCOCH3;

[0625] R4 is selected from the group consisting of

[0626] (1) H,

[0627] (2) substituted or unsubstituted C1-C6-alkyl,

[0628] (3) C1-C6-alkyl substituted with aryl,

[0629] (4) C1-C6-alkyl substituted with heterocyclyl, and

[0630] (5) C1-C6-alkyl substituted with heteroaryl.

[0631] In another embodiment, the present invention provides compounds of formula XV: 58

[0632] or stereoisomers, pharmaceutically acceptable salts, esters, and prodrugs thereof, wherein D-G-Y taken together, is selected from the group consisting of 5960616263

[0633] Wherein

[0634] R is selected from the group consisting of —CH3, —C2H5, —CH2OH, —OH, —OCH3,—OC2H5, —OCF3, —CN, —NO2, —CO2H, —CO2CH3, —CONH2, —NH2, —F, —Cl, —Br, —CF3, —N(CH3)2, —NHSO2CH3, and —NHCOCH3;

[0635] In another embodiment, the present invention provides compounds of formula XVI: 64

[0636] or stereoisomers, pharmaceutically acceptable salts, esters, and prodrugs thereof, wherein D-G-Y taken together, is selected from the group consisting of 6566676869

[0637] Wherein

[0638] R is selected from the group consisting of —CH3, —C2H5, —CH2OH, —OH, —OCH3, —OC2H5, —OCF3, —CN, —NO2, —CO2H, —CO2CH3, —CONH2, —NH2, —F, —Cl, —Br, —CF3, —N(CH3)2, —NHSO2CH3, and —NHCOCH3;

[0639] R4 is selected from the group consisting of

[0640] (1) H,

[0641] (2) substituted or unsubstituted C1-C6-alkyl,

[0642] (3) C1-C6-alkyl substituted with aryl,

[0643] (4) C1-C6-alkyl substituted with heterocyclyl, and

[0644] (5) C1-C6-alkyl substituted with heteroaryl;

[0645] In another embodiment, the present invention provides compounds of formula XVII: 70

[0646] or stereoisomers, pharmaceutically acceptable salts, esters, and prodrugs thereof, wherein D-G-Y taken together, is selected from the group consisting of 7172737475

[0647] Wherein

[0648] R is selected from the group consisting of —CH3, —C2H5, —CH2OH, —OH, —OCH3, —OC2H5, —OCF3, —CN, —NO2, —CO2H, —CO2CH3, —CONH2, —NH2, —F, —Cl, —Br, —CF3, —N(CH3)2, —NHSO2CH3, and —NHCOCH3;

[0649] In one aspect, the invention provides a method of inhibiting a deacetylase enzyme in a gram-negative bacteria, thereby affecting bacterial growth, comprising administering to a patient in need of such inhibition a compound of formula I.

[0650] In another aspect, the invention provides a method of inhibiting LpxC, thereby modulating the virulence of a bacterial infection, comprising administering to a patient in need of such inhibition a compound of formula I.

[0651] In some embodiments of the method of inhibiting LpxC using a compound of formula I, the IC50 value of the compound is less than or equal to 10 μM with respect to LpxC. In other such embodiments, the IC50 value is less than or equal to 1 μM, is less than or equal to 0.1 μM, is less than or equal to 0.050 μM, is less than or equal to 0.030 μM, is less than or equal to 0.025 μM, or is less than or equal to 0.010 μM.

[0652] In one aspect of the invention, methods for treating a subject comprising administering to the subject an antibacterially effective amount of a compound of formula I, together with a pharmaceutically acceptable carrier is provided. In a preferred embodiment of the method of treatment, the subject is a mammal and some embodiments, a human.

[0653] In another aspect, the invention provides a method of administering an inhibitory amount of a compound of formula I to fermentative or non-fermnentative gram-negative bacteria. In a preferred embodiment of the method of administering an inhibitory amount of a compound of formula I to fermentative or non-fermentative gram-negative bacteria, the gram-negative bacteria are selected from the group consisting of Pseudomonas aeruginosa, Stenotrophomonas maltophila, Burkholderia cepacia, Alcaligenes xylosoxidans, Acinetobacter, Enterobacteriaceae, Haemophilus, Neisseria species.

[0654] In another embodiment, the invention provides a method of administering an inhibitory amount of a compound of formula I to gram-negative bacteria, such as Enterobacteriaceae that is selected from the group consisting of organisms such as Serratia, Proteus, Klebsiella, Enterobacter, Citrobacter, Salmonella, Providencia, Morganella, Cedecea, and Edwardsiella species and Escherichia coli.

[0655] Another embodiment of the invention provides a pharmaceutical composition comprising an effective amount of a compound of Formula I with a pharmaceutically acceptable carrier thereof.

[0656] Pharmaceutical formnulations according to the present invention are provided which include any of the compounds described above in combination with a pharmaceutically acceptable carrier.

[0657] Another embodiment of the invention provides a method of co-administering the compound of formula I with other therapeutic agents that are selected for their particular usefulness against the condition that is being treated.

[0658] For example, the compound of formula I is useful in combination with other anti-bacterial agents. The compound of formula I augments the sensitivity of gram-negative bacteria to existing classes of antibacterials. Combinations of the presently disclosed compounds with other anti-bacterial agents are within the scope of the invention. Such anti-bacterial agents include, but are not limited to, erythromycin, rifampicin, Nalidixic acid, carbenicillin, bacitracin, cycloserine, fosfomycin, and vancomycin.

[0659] A further aspect of the invention is the use of LpxC inhibitors for the treatment of an infection, particularly a bacterial infection. A bacterial infection treated with the compounds of the invention can be a primary infection or a co-infection caused by a species of bacteria and one or more additional infectious agents selected from the group consisting of bacteria, virus, parasite and fungus.

[0660] The term “treating”, as used herein, refers to reversing, alleviating, inhibiting the progress of, or preventing the disorder or condition to which such term applies, or one or more symptoms of such disorder or condition. The term “treatment”, as used herein, refers to the act of treating, as “treating” is defined immediately above.

[0661] The compounds of the invention can be used for treating conditions caused by the bacterial production of endotoxin and, in particular, by gram-negative bacteria and bacteria that use LpxC in the biosynthesis of lipopolysaccharide (LPS) or endotoxin.

[0662] The compounds of the invention also are useful in the conditions that are caused or exacerbated by the bacterial production of lipid A and LPS or endotoxin, such as sepsis, septic shock, systemic inflammation, localized inflammation, chronic obstructive pulmonary disease (COPD) and acute exacerbations of chronic bronchitis (AECB). For these conditions, treatment includes the administration of a compound of the invention, or a combination of compounds of the invention, optionally with a second agent wherein the second agent is a second antibacterial agent or a second non-antibacterial agent.

[0663] For sepsis, septic shock, systemic inflammation, localized inflammation, chronic obstructive pulmonary disease (COPD) and acute exacerbations of chronic bronchitis (AECB), preferred second non-antibacterial agents include antiendotoxins including endotoxin receptor-binding antibodies, endotoxin-binding antibodies, antiCD14-binding protein antibodies antilipopolysaccharide-binding protein antibodies and tyrosine kinase inhibitors.

[0664] In treatment of serious or chronic respiratory tract infections, the compounds of the present invention may also be used with second non-antibacterial agents administered via inhalation. Preferred non-antibacterial agents used in this treatment include anti-inflammatory steroids, non-steroidal anti-inflammatory agents, bronchiodilators, mucolytics, anti-asthma therapeutics and lung fluid surfactants. In particular, the non-antibacterial agent may be selected from a group consisting of albuterol, salbuterol, budesonide, beclomethasone, dexamethasone, nedocromil, beclomethasone, fluticasone, flunisolide, triamcinolone, ibuprofin, rofecoxib, naproxen, celecoxib, nedocromil, ipratropium, metaproterenol, pirbuterol, salneterol, bronchiodilators, mucolytics, calfactant, beractant, poractant alfa, surfaxin and pulmozyme (also called domase alfa).

[0665] The compounds of the invention can be used, alone or in combination with a second antibacterial agent for the treatment of a serious or chronic respiratory tract infection including serious lung and nosocomial infections such as those caused by Enterobacter aerogenes, Enterobacter cloacae, Escherichia coli, Klebsiella pneumoniae, Klebsiella oxytoca, Prbteus mirabilis, Serratia marcescens, Stenotrophomonas maltophilia, Pseudomonas aeruginosa, Burkholderia cepacia, Acinetobacter calcoaceticus, Alcaligenes xylosoxidans, Flavobacterium meningosepticum, Providencia stuartii and Citrobacter freundi, community lung infections such as those caused by Haemophilus Influenzae, Legionella species, Moraxella catarrhalis, Branhamella catarrhalis, Enterobacter species, Acinetobacter species, Klebsiella species, and Proteus species, and infections caused by other bacterial species such as Neisseria species, Shigella species, Salmonella species, Helicobacter pylori, Vibrionaceae and Bordetella species as well as the infections is caused by a Brucella species, Francisella tularensis and/or Yersinia Pestis.

[0666] When used for treating Gram-negative bacteria, the compounds of the present invention can be used to sensitize gram-negative bacteria to the effects of a second agent.

[0667] When the compounds of the present invention are used in combination with a second antibacterial agent, non-limiting examples of antibacterial agents may be selected from the following groups:

[0668] (1) Macrolides or ketolides such as erythromycin, azithromycin, clarithromycin and telithromycin;

[0669] (2) Beta-lactams including penicillin, cephalosporin, and carbapenems such as carbapenem, imipenem, and meropenem;

[0670] (3) Monobactams such as penicillin G, penicillin V, methicillin, oxacillin, cloxacillin, dicloxacillin, nafcillin, ampicillin, amoxicillin, carbenicillin, ticarcillin, mezlocillin, piperacillin, azlocillin, temocillin, cepalothin, cephapirin, cephradine, cephaloridine, cefazolin, cefamandole, cefuroxime, cephalexin, cefprozil, cefaclor, loracarbef, cefoxitin, cefinetazole, cefotaxime, ceftizoxime, ceftriaxone, cefoperazone, ceftazidime, cefixime, cefpodoxime, ceftibuten, cefdinir, cefpirome, cefepime, and astreonam;

[0671] (4) Quinolones such as nalidixic acid, oxolinic acid, norfloxacin, pefloxacin, enoxacin, ofloxacin, levofloxacin, ciprofloxacin, temafloxacin, lomefloxacin, fleroxacin, grepafloxacin, sparfloxacin, trovafloxacin, clinafloxacin, gatifloxacin, moxifloxacin, sitafloxacin, ganefloxacin, gemifloxacin and pazufloxacin;

[0672] (5) Antibacterial sulfonanmides and antibacterial sulphanilamides, including para-aminobenzoic acid, sulfadiazine, sulfisoxazole, sulfamethoxazole and sulfathalidine;

[0673] (6) Aminoglycosides such as streptomycin, neomycin, kanamycin, paromycin, gentamicin, tobramycin, amikacin, netilmicin, spectinomycin, sisomicin, dibekalin and isepamicin;

[0674] (7) Tetracyclines such as tetracycline, chlortetracycline, demeclocycline, minocycline, oxytetracycline, methacycline, doxycycline;

[0675] (8) Rifamycins such as rifampicin (also called rifampin), rifapentine, rifabutin, bezoxazinorifamycin and rifaximin;

[0676] (9) Lincosamides such as lincomycin and clindamycin;

[0677] (10) Glycopeptides such as vancomycin and teicoplanin;

[0678] (11) Streptogramins such as quinupristin and daflopristin;

[0679] (12) Oxazolidinones such as linezolid;

[0680] (13) Polymyxin, colistin and colymycin;

[0681] (14) Trimethoprim and bacitracin.

[0682] The second antibacterial agent may be administered in combination with the compounds of the present inventions wherein the second antibacterial agent is administered prior to, simultaneously, or after the compound or compounds of the present invention. When simultaneous administration of a compound of the invention with a second agent is desired and the route of administration is the same, then a compound of the invention may be formulated with a second agent into the same dosage form. An example of a dosage form containing a compound of the invention and a second agent is a tablet or a capsule.

[0683] When used for treating a serious or chronic respiratory tract infections, the compounds of the invention may be used alone or in combination with a second antibacterial agent administered via inhalation. In the case of inhalation, a preferred second antibacterial agent is selected from a group consisting of tobramycin, gentamicin, aztreonam, ciprofloxacin, polymyxin, colistin, colymycin, azithromycin and clarithromycin.

[0684] Pharmaceutical Compositions

[0685] Pharmaceutical compositions of the present invention comprise a therapeutically effective amount of a compound of the present invention formulated together with one or more pharmaceutically acceptable carriers. As used herein, the term “pharmaceutically acceptable carrier” means a non-toxic, inert solid, semi-solid or liquid filler, diluent, encapsulating material or formulation auxiliary of any type. Some examples of materials that can serve as pharmaceutically acceptable carriers are sugars such as lactose, glucose and sucrose; starches such as corn starch and potato starch; cellulose and its derivatives such as sodium carboxymethyl cellulose, ethyl cellulose and cellulose acetate; powdered tragacanth; malt; gelatin; talc; excipients such as cocoa butter and suppository waxes; oils such as peanut oil, cottonseed oil; safflower oil; sesame oil; olive oil; corn oil and soybean oil; glycols; such a propylene glycol; esters such as ethyl oleate and ethyl laurate; agar; buffering agents such as magnesium hydroxide and aluminum hydroxide; alginic acid; pyrogen-free water; isotonic saline; Ringer's solution; ethyl alcohol, and phosphate buffer solutions, as well as other non-toxic compatible lubricants such as sodium lauryl sulfate and magnesium stearate, as well as coloring agents, releasing agents, coating agents, sweetening, flavoring and perfuming agents, preservatives and antioxidants can also be present in the composition, according to the judgment of the formulator. The pharmaceutical compositions of this invention can be administered to humans and other animals orally, rectally, parenterally, intracisternally, intravaginally, intraperitoneally, topically (as by powders, ointments, or drops), bucally, or as an oral or nasal spray, or a liquid aerosol or dry powder formulation for inhalation.

[0686] Liquid dosage forms for oral administration include pharmaceutically acceptable emulsions, microemulsions, solutions, suspensions, syrups and elixirs. In addition to the active compounds, the liquid dosage forms may contain inert diluents commonly used in the art such as, for example, water or other solvents, solubilizing agents and emulsifiers such as ethyl alcohol, isopropyl alcohol, ethyl carbonate, ethyl acetate, benzyl alcohol, benzyl benzoate, propylene glycol, 1,3-butylene glycol, dimethylformamide, oils (in particular, cottonseed, groundnut, corn, germ, olive, castor, and sesame oils), glycerol, tetrahydrofurfuryl alcohol, polyethylene glycols and fatty acid esters of sorbitan, and mixtures thereof. Besides inert diluents, the oral compositions can also include adjuvants such as wetting agents, emulsifying and suspending agents, sweetening, flavoring, and perfuming agents.

[0687] Injectable preparations, for example, sterile injectable aqueous or oleaginous suspensions may be formulated according to the known art using suitable dispersing or wetting agents and suspending agents. The sterile injectable preparation may also be a sterile injectable solution, suspension or emulsion in a nontoxic parenterally acceptable diluent or solvent, for example, as a solution in 1,3-butanediol. Among the acceptable vehicles and solvents that may be employed are water, Ringer's solution, U.S.P. and isotonic sodium chloride solution. In addition, sterile, fixed oils are conventionally employed as a solvent or suspending medium. For this purpose any bland fixed oil can be employed including synthetic mono- or diglycerides. In addition, fatty acids such as oleic acid are used in the preparation of injectables.

[0688] The injectable formulations can be sterilized, for example, by filtration through a bacterial-retaining filter, or by incorporating sterilizing agents in the form of sterile solid compositions that can be dissolved or dispersed in sterile water or other sterile injectable medium prior to use.

[0689] In order to prolong the effect of a drug, it is often desirable to slow the absorption of the drug from subcutaneous or intramuscular injection. This may be accomplished by the use of a liquid suspension of crystalline or amorphous material with poor water solubility. The rate of absorption of the drug then depends upon its rate of dissolution that, in turn, may depend upon crystal size and crystalline form. Alternatively, delayed absorption of a parenterally administered drug form may be accomplished by dissolving or suspending the drug in an oil vehicle. Injectable depot forms are made by forming microencapsule matrices of the drug in biodegradable polymers such as polylactide-polyglycolide. Depending upon the ratio of drug to polymer and the nature of the particular polymer employed, the rate of drug release can be controlled. Examples of other biodegradable polymers include poly(orthoesters) and poly(anhydrides). Depot injectable formulations may also be prepared by entrapping the drug in liposomes or microemulsions that are compatible with body tissues.

[0690] Compositions for rectal or vaginal administration are preferably suppositories that can be prepared by mixing the compounds of this invention with suitable non-irritating excipients or carriers such as cocoa butter, polyethylene glycol or a suppository wax which are solid at ambient temperature but liquid at body temperature and therefore melt in the rectum or vaginal cavity and release the active compound.

[0691] Solid dosage forms for oral administration include capsules, tablets, pills, powders, and granules. In such solid dosage forms, the active compound is mixed with at least one inert, pharmaceutically acceptable excipient or carrier such as sodium citrate or dicalcium phosphate and/or a) fillers or extenders such as starches, lactose, sucrose, glucose, mannitol, and silicic acid, b) binders such as, for example, carboxymethylcellulose, alginates, gelatin, polyvinylpyrrolidinone, sucrose, and acacia, c) humectants such as glycerol, d) disintegrating agents such as agar-agar, calcium carbonate, potato or tapioca starch, alginic acid, certain silicates, and sodium carbonate, e) solution retarding agents such as paraffin, f) absorption accelerators such as quaternary ammonium compounds, g) wetting agents such as, for example, acetyl alcohol and glycerol monostearate, h) absorbents such as kaolin and bentonite clay, and i) lubricants such as talc, calcium stearate, magnesium stearate, solid polyethylene glycols, sodium lauryl sulfate, and mixtures thereof. In the case of capsules, tablets and pills, the dosage form may also comprise buffering agents.

[0692] Solid compositions of a similar type may also be employed as fillers in soft and hard-filled gelatin capsules using such excipients as lactose or milk sugar as well as high molecular weight polyethylene glycols and the like.

[0693] The solid dosage forms of tablets, dragees, capsules, pills, and granules can be prepared with coatings and shells such as enteric coatings and other coatings well known in the pharmaceutical formulating art. They may optionally contain opacifying agents and can also be of a composition that they release the active ingredient(s) only, or preferentially, in a certain part of the intestinal tract, optionally, in a delayed manner. Examples of embedding compositions that can be used include polymeric substances and waxes.

[0694] Solid compositions of a similar type may also be employed as fillers in soft and hard-filled gelatin capsules using such excipients as lactose or milk sugar as well as high molecular weight polyethylene glycols and the like.

[0695] The active compounds can also be in micro-encapsulated form with one or more excipients as noted above. The solid dosage forms of tablets, dragees, capsules, pills, and granules can be prepared with coatings and shells such as enteric coatings, release controlling coatings and other coatings well known in the pharmaceutical formulating art. In such solid dosage forms the active compound may be admixed with at least one inert diluent such as sucrose, lactose or starch. Such dosage forms may also comprise, as is normal practice, additional substances other than inert diluents, e.g., tableting lubricants and other tableting aids such a magnesium stearate and microcrystalline cellulose. In the case of capsules, tablets and pills, the dosage forms may also comprise buffering agents. They may optionally contain opacifying agents and can also be of a composition that they release the active ingredient(s) only, or preferentially, in a certain part of the intestinal tract, optionally, in a delayed manner. Examples of embedding compositions that can be used include polymeric substances and waxes.

[0696] Dosage forms for topical or transdermal administration of a compound of this invention include ointments, pastes, creams, lotions, gels, powders, solutions, sprays, inhalants or patches. The active component is admixed under sterile conditions with a pharmaceutically acceptable carrier and any needed preservatives or buffers as may be required. Ophthalmic formulations, ear drops, and the like arealso contemplated as being within the scope of this invention.

[0697] The ointments, pastes, creams and gels may contain, in addition to an active compound of this invention, excipients such as animal and vegetable fats, oils, waxes, paraffins, starch, tragacanth, cellulose derivatives, polyethylene glycols, silicones, bentonites, silicic acid, talc and zinc oxide, or mixtures thereof.

[0698] Compositions of the invention may also be formulated for delivery as a liquid aerosol or inhalable dry powder. Liquid aerosol formulations may be nebulized predominantly into particle sizes that can be delivered to the terminal and respiratory bronchioles where bacteria reside in patients with bronchial infections, such as chronic bronchitis and pneumonia. Pathogenic bacteria are commonly present throughout airways down to bronchi, bronchioli and lung parenchema, particularly in terminal and respiratory bronchioles. During exacerbation of infection, bacteria can also be present in alveoli. Liquid aerosol and inhalable dry powder formulations are preferably delivered throughout the endobronchial tree to the terminal bronchioles and eventually to the parenchymal tissue.

[0699] Aerosolized formulations of the invention may be delivered using an aerosol forming device, such as a jet, vibrating porous plate or ultrasonic nebulizer, preferably selected to allow the formation of a aerosol particles having with a mass medium average diameter predominantly between 1 to 5 μm. Further, the formulation preferably has balanced osmolarity ionic strength and chloride concentration, and the smallest aerosolizable volume able to deliver effective dose of the compounds of the invention to the site of the infection. Additionally, the aerosolized formulation preferably does not impair negatively the functionality of the airways and does not cause undesirable side effects.

[0700] Aerosolization devices suitable for administration of aerosol formulations of the invention include, for example, jet, vibrating porous plate, ultrasonic nebulizers and energized dry powder inhalers, that are able to nebulize the formulation of the invention into aerosol particle size predominantly in the size range from 1-5 pm. Predominantly in this application means that at least 70% but preferably more than 90% of all generated aerosol particles are 1 to 5 μm range. A jet nebulizer works by air pressure to break a liquid solution into aerosol droplets. Vibrating porous plate nebulizers work by using a sonic vacuum produced by a rapidly vibrating porous plate to extrude a solvent droplet through a porous plate. An ultrasonic nebulizer works by a piezoelectric crystal that shears a liquid into small aerosol droplets. A variety of suitable devices are available, including, for example, AeroNeb and AeroDose vibrating porous plate nebulizers (AeroGen, Inc., Sunnyvale, Calif.), Sidestream7 nebulizers (Medic-Aid Ltd., West Sussex, England), Pari LC7 and Pari LC Star7 jet nebulizers (Pari Respiratory Equipment, Inc., Richmond, Va.), and Aerosonic (DeVilbiss Medizinische Produkte (Deutschland) GmbH, Heiden, Germany) and UltraAire7 (Omron Healthcare, Inc., Vernon Hills, Ill.) ultrasonic nebulizers.

[0701] Compounds of the invention may also be formulated for use as topical powders and sprays that can contain, in addition to the compounds of this invention, excipients such as lactose, talc, silicic acid, aluminum hydroxide, calcium silicates and polyamide powder, or mixtures of these substances. Sprays can additionally contain customary propellants such as chlorofluorohydrocarbons.

[0702] Transdermal patches have the added advantage of providing controlled delivery of a compound to the body. Such dosage forms can be made by dissolving or dispensing the compound in the proper medium. Absorption enhancers can also be used to increase the flux of the compound across the skin. The rate can be controlled by either providing a rate controlling membrane or by dispersing the compound in a polymer matrix or gel.

[0703] According to the methods of treatment of the present invention, bacterial infections are treated or prevented in a patient such as a human or lower mammal by administering to the patient a therapeutically effective amount of a compound of the invention, in such amounts and for such time as is necessary to achieve the desired result. By a “therapeutically effective amount” of a compound of the invention is meant a sufficient amount of the compound to treat bacterial infections, at a reasonable benefit/risk ratio applicable to any medical treatment. It will be understood, however, that the total daily usage of the compounds and compositions of the present invention will be decided by the attending physician within the scope of sound medical judgment. The specific therapeutically effective dose level for any particular patient will depend upon a variety of factors including the disorder being treated and the severity of the disorder; the activity of the specific compound employed; the specific composition employed; the age, body weight, general health, sex and diet of the patient; the time of administration, route of administration, and rate of excretion of the specific compound employed; the duration of the treatment; drugs used in combination or coincidental with the specific compound employed; and like factors well known in the medical arts.

[0704] The total daily dose of the compounds of this invention administered to a human or other mammal in single or in divided doses can be in amounts, for example, from 0.01 to 50 mg/kg body weight or more usually from 0.1 to 25 mg/kg body weight. Single dose compositions may contain such amounts or submultiples thereof to make up the daily dose. In general, treatment regimens according to the present invention comprise administration to a patient in need of such treatment from about 10 mg to about 2000 mg of the compound(s) of this invention per day in single or multiple doses.

[0705] Methods of formulation are well known in the art and are disclosed, for example, in Remington: The Science and Practice of Pharmacy, Mack Publishing Company, Easton, Pa., 19th Edition (1995). Pharmaceutical compositions for use in thepresent invention can be in the form of sterile, non-pyrogenic liquid solutions or suspensions, coated capsules, suppositories, lyophilized powders, transdermal patches or other forms known in the art.

[0706] A “kit” as used in the instant application includes a container for containing the pharmaceutical compositions and may also include divided containers such as a divided bottle or a divided foil packet. The container can be in any conventional shape or form as known in the art that is made of a pharmaceutically acceptable material, for example a paper or cardboard box, a glass or plastic bottle or jar, a resealable bag (for example, to hold a “refill” of tablets for placement into a different container), or a blister pack with individual doses for pressing out of the pack according to a therapeutic schedule. The container employed can depend on the exact dosage form involved, for example a conventional cardboard box would not generally be used to hold a liquid suspension. It is feasible that more than one container can be used together in a single package to market a single dosage form. For example, tablets may be contained in a bottle that is in turn contained within a box.

[0707] An example of such a kit is a so-called blister pack. Blister packs are well known in the packaging industry and are being widely used for the packaging of pharmaceutical unit. dosage forms (tablets, capsules, and the like). Blister packs generally consist of a sheet of relatively stiff material covered with a foil of a preferably transparent plastic material. During the packaging process, recesses are formed in the plastic foil. The recesses have the size and shape of individual tablets or capsules to be packed or may have the size and shape to accommodate multiple tablets and/or capsules to be packed. Next, the tablets or capsules are placed in the recesses accordingly and the sheet of relatively stiff material is sealed against the plastic foil at the face of the foil that is opposite from the direction in which the recesses were formed. As a result, the tablets or capsules are individually sealed or collectively sealed, as desired, in the recesses between the plastic foil and the sheet. Preferably the strength of the sheet is such that the tablets or capsules can be removed from the blister pack by manually applying pressure on the recesses whereby an opening is formed in the sheet at the place of the recess. The tablet or capsule can then be removed via said opening.

[0708] It maybe desirable to provide a written memory aid, where the written memory aid is of the type containing information and/or instructions for the physician, pharmacist or other health care provider, or subject, e.g., in the form of numbers next to the tablets or capsules whereby the numbers correspond with the days of the regimen that the tablets or capsules so specified should be ingested or a card that contains the same type of information. Another example of such a memory aid is a calendar printed on the card e.g., as follows “First Week, Monday, Tuesday,”. . . etc . . . “Second Week, Monday, Tuesday, . . . ” etc. Other variations of memory aids will be readily apparent. A “daily dose” can be a single tablet or capsule or several tablets or capsules to be taken on a given day. When the kit contains separate compositions, a daily dose of one or more compositions of the kit can consist of one tablet or capsule while a daily dose of another one or more compositions of the kit can consist of several tablets or capsules.

[0709] Another specific embodiment of a kit is a dispenser designed to dispense the daily doses one at a time in the order of their intended use. Preferably, the dispenser is equipped with a memory-aid, so as to further facilitate compliance with the regimen. An example of such a memory-aid is a mechanical counter, that indicates the number of daily doses that has been dispensed. Another example of such a memory-aid is a battery-powered micro-chip memory coupled with a liquid crystal readout, or audible reminder signal that, for example, reads out the date that the last daily dose has been taken and/or reminds one when the next dose is to be taken.

[0710] The kits of the present invention may also include, in addition to LpxC inhibitors, one or more additional pharmaceutically active compounds. Preferably, the additional compound is another LpxC inhibitor or another compound useful to bacterial infections. The additional compounds may be administered in the same dosage form as the LpxC inhibitor or in different dosage forms. Likewise, the additional compounds can be administered at the same time as the LpxC inhibitor or at different times.

[0711] Compositions of the present compounds may also be used in combination with other known antibacterial agents of similar spectrum to (1) synergistically enhance treatment of severe Gram-negative infections covered by the spectrum of this compound or (2) add coverage in severe infections in which multiple organisms are suspected in which another agent of a different spectrum may be required in addition to this compound. Potential agents include members of the aminoglycosides, penicillins, cephalosporins, fluoroquinolones, macrolides, glycopeptides, lipopeptides and oxazolidinones. The treatment can involve administering a composition having both active agents or administration of the inventive compounds followed by or preceded by administration of an additional active antibacterial agent.

[0712] Characterization and Purification Methods

[0713] Referring to the examples that follow, compounds of the present invention were characterized by high performance liquid chromatography (HPLC) using a Waters Millenium chromatography system with a 2690 Separation Module (Milford, Mass.). The analytical columns were Alltima C-18 reversed phase, 4.6×250 mm from Alltech (Deerfield, Ill.). A gradient elution was used, typically starting with 5% acetonitrile/95% water and progressing to 100% acetonitrile over a period of 40 minutes. All solvents contained 0.1% trifluoroacetic acid (TFA). Compounds were detected by ultraviolet light (UV) absorption at either 220 or 254 nm. HPLC solvents were from Burdick and Jackson (Muskegan, Mich.), or Fisher Scientific (Pittsburg, Pa.). In some instances, purity was assessed by thin layer chromatography (TLC) using glass or plastic backed silica gel plates, such as, for example, Baker-Flex Silica Gel 1 B2-F flexible sheets. TLC results were readily detected visually under ultraviolet light, or by employing well known iodine vapor and other various staining techniques.

[0714] Mass spectrometric analysis was performed on one of two LCMS instruments: a Waters System. (Alliance HT HPLC and a Micromass ZQ mass spectrometer; Column: Eclipse XDB-C-18, 2.1×50 mm; solvent system: 5-95% (or 35-95%, or 65-95% or 95-95%) acetonitrile in water with 0.05%TFA; flow rate 0.8 mL/min; molecular weight range 500-1500; cone Voltage 20 V; column temperature 40° C.) or a Hewlett Packard System (Series 1100 HPLC; Column: Eclipse XDB-C18, 2.1×50 mm; solvent system: 1-95% acetonitrile in water with 0.05% TFA; flow rate 0.4 mL/min; molecular weight range 150-850; cone Voltage 50 V; column temperature 30° C). All masses are reported as those of the protonated parent ions.

[0715] GCMS analysis was performed on a Hewlet Packard instrument (HP6890 Series gas chromatograph with a Mass Selective Detector 5973; injector volume: 1 μL; initial column temperature: 50° C.; final column temperature: 250C; ramp time: 20 minutes; gas flow rate: 1 mL/min; column: 5% phenyl methyl siloxane, Model #HP 190915-443, dimensions: 30.0 m×25 m×0.25 m).

[0716] Nuclear magnetic resonance (NMR) analysis was performed with a Varian 300 Mhz NMR (Palo Alto, Calif.). The spectral reference was either TMS or the known chemical shift of the solvent. Some compound samples were run at elevated temperatures (e.g. 75° C.) to promote increased sample solubility.

[0717] The purity of some of the invention compounds was assessed by elemental analysis (Desert Analytics, Tuscon, Ariz.)

[0718] Melting points were determined on a Laboratory Devices Mel-Temp apparatus (Holliston, Mass.).

[0719] Preparative separations were carried out using a Flash 40 chromatography system and KP-Sil, 60A (Biotage, Charlottesville, Va.), or by flash column chromatography using silica gel (230-400 mesh) packing material, or by HPLC using a C-18 reversed phase column. Typical solvents employed for the Flash 40 Biotage system and flash column chromatography were dichloromethane, methanol, ethyl acetate, hexane, acetone, aqueous hydroxyamine and triethyl amine. Typical solvents employed for the reverse phase HPLC were varying concentrations of acetonitrile and water with 0.1% trifluoroacetic acid.

[0720] Compounds of the present invention can be readily synthesized using the methods described herein, or other methods, that are well known in the art. For example, the synthesis of hxdroxamic acids or similar scaffolds having a wide variety of substituents are comprehensively reviewed in Kline T, Andersen N H, Harwood E A, Bowman J, Malanda A, Endsley S, Erwin A L, Doyle M, Fong S, Harris A L, Mendelsohn B,. Mdluli K, Raetz C R, Stover C K, Witte P R, Yabannavar A, Zhu S., “Potent, novel in vitro inhibitors of the Pseudomonas aeruginosa deacetylase LpxC,” J. Med Chem 2002 July 4;45(14):3112-29; Patchett, A. A., Nargund, R., Chen, M.-H., Nishi, H. R., U. S. Pat. No. 5,925,659, 1999; Pirrung, M. C., Chau, J. H., “A Convenient Procedure for the Preparation of Amino Acid Hydrokamates from Esters,” J. Org. Chem. 1995, 60, 8084-8085; Nhu, K., Patel, D. V., “A New and Efficient Solid Phase Synthesis of Hydroxamic Acids,” J. Org. Chem. 1997, 62, 7088-7089; Patel, D., Nhu, K., “Methods for Solid-phase Synthesis of Hydroxylamine Compounds and Derivatives, and Combinatorial Libraries Thereof,” PCT WO 98/18754, 1998, Mellor, S. L., McGuire, C., Chan, W. C., “N-Fmoc-aminoxy-2-chlortrityl Polystyrene Resin: A Facile Solid-phase Methodology for the Synthesis of Hydroxamic Acids,” Tetrahedron Lett., 1997, 38, 3311-3314; Khan, S. I., Grinstaff, M. W., “A Facile and Convenient Solid-phase Procedure for Synthesizing Nucleoside Hydroxamic Acids,” Terahedron. Lett., 1998, 39, 8031-8034; Zhang, Y., Li, D., Houtman, J. C., Witiak, D. T., Seltzer, J., Bertics, P. J., Lauhon, C. T., “Design, Combinatorial Chemical Synthesis, and in vitro Characterization of Novel Urea Based Gelatinase Inhibitors,” Bioorg. Med. Chem. Lett., 1999, 9, 2823-2826; Ito, Y., Inubushi, Y., Zenbayashi, M., Tomita, S., Saegusa, T., “Synthetic Reactions by Complex Catalysts. XXXI, A Novel and Versatile Method of Heterocycle Synthesis,” J. Am Chem. Soc., 1973, 95, 4447-4448; Ito, Y., Ito, I., Hirao, T., Saegus, T., “Synthetic Reactions by Complex Catalysts XXXV,” Syn. Commun. 1974, 4, 97-103; Witte, H., Seliger, W., “Cyclische Imidsaurester aus Nitrilen und Aminoalkoholen,” Liebigs Ann. Chem, 1974, 996-1009; Pattenden, G., Thom. S. M., “Naturally Occurring Linear Fused Thiazoline-Thiazole Containing Metabolites: Total Synthesis of (−) Didehydromirabazole A, a Cytotoxic Alkaloid from Blue-Green Algae,” J. Chem. Soc. Perkin Trans 1, 1993, 1629-1636; Boyce, R. J., Mulqueen, G. C., Pattenden, G., “Total Synthesis of Thiangazole, A Novel Naturally Occurring HIV-1 Inhibitor from Polyangium sp.,” Tetrahedron, 1995, 51, 7321-7330; Galeotti, N., Plagnes, E., Jouin, P., “Synthesis of Peptidyl Aldehydes from Thiazolines,” Tetrahedron. Lett. 1997, 38, 2459-2462; Charette, A. B., Chua, P., “Mild Method for the Synthesis of Thiazolines from Secondary and Tertiary Amides,” J. Org. Chem., 1998, 63, 908-909; Bergeron, R. J., Wiegand, J., McManis, J. S., McCosar, B. H., Weimar, W. R., Brittenham, G. M., Smith, R. E., “Effects of C-4 Stereochemistry and C-4′ Hydroxylation on the Iron Clearing Efficiency and Toxicity of Desferrithiocin Analogues,” J. Med. Chem. 1999, 42, 2432-2440; Raman, P., Razavik H., Kelly, J. W., “Titanium (IV)-mediated Tandem Deprotection-cyclodehydration of Protected Cysteine N-Amides: Biomimetic Synthesis of Thiazoline- and Thiazole-containing Heterocycles,” Org. Lett., 2000, 2, 3289-3292; Fernandez, X., Fellous, R., Dunach, E., “Novel Synthesis of 2-Thioazolines,” Tetrahedron Lett., 2000, 41, 3381-3384. Wipf, P., Miller, C. P., Venkatraman, S., Fritch, P., “C. Thiolysis of Oxazolinenes: A New, Selective Method for the Direct Conversion of Peptide Oxazolines into Thiazolines,” Tetrahedron Lett., 1995, 36, 6395-6398, which are incorporated herein by reference.

[0721] The synthesis of other non-hydroxamates compounds or more generally zinc binding groups are reviewed in Pirrung, M. C., Tumey, L. N., Raetz, C. R. H., Jackman, J. E., Snehalatha, K., McClerren, A. L., Fierke, C. A., Gantt, S. L., Rusche, K. M., “Inhibition of the Antibacterial Target UDP-(3-O-acyl)-N-acetylglucosamine Deacetylase (LpxC): Isoxazoline Zinc Amidase Inhibitors Bearing Diverse Metal Binding Groups,” Journal of Medicinal Chemistry (2002), 45(19), 4359-4370; Jackman, J. E., Fierke, C. A., Tumey, L. N., Pirrung, M., Uchiyama, T., Tahir, S. H., Hindsgaul, O., Raetz, C. R. H., “Antibacterial agents that target lipid A biosynthesis in gram-negative bacteria: inhibition of diverse UDP-3-O-(R-3-hydroxymyristoyl)-N-acetylglucosamine deacetylases by substrate analogs containing zinc binding motifs,” Journal of Biological Chemistry (2000), 275(15), 11002-11009; Brooks, C. D. W., Summers, J. B., “Modulators of Leukotriene Biosynthesis and Receptor Activation,” Journal of Medicinal Chemistry (1996), 39(14), 2629-2654; Jeng, A. Y., De Lombaert, S., “Endothelin converting enzyme inhibitors,” Current Pharmaceutical Design (1997), 3(6), 597-614; Zask, A., Levin, J. I., Killar, L. M., Skotnicki, J. S., “Inhibition of matrix metalloproteinases: structure based design,” Current Pharmaceutical Design (1996), 2(6), 624-661; Skotnicki, J. S., DiGrandi, M. J., Levin, J. I., Chemical and Screening Sciences, Wyeth Research, New York, N.Y., USA. Current Opinion in Drug Discovery & Development (2003), 6(5), 742-759.

[0722] The foregoing may be better understood by reference to the following examples, that are presented for illustration and not to limit the scope of the inventive concepts.

EXAMPLES

[0723] The following are abbreviations used in the examples:

AcOH:           Acetic acid
aq:             Aqueous
ATP:            Adenosine triphosphate
Boc:            tert-butoxycarbonyl
Boc-Thr(OBn)-OH 3-(R)-Benzyloxy-2-(S)-tert-butoxycarbonylamino-
                butyric acid.
DAP or Dap:     Diaminopropionate
DCM:            4-(Dicyanomethylene)-2-methyl-6-
                (4-dimethylaminostyryl)-4H-pyran
DEAD:           Diethyl azodicarboxylate
DIEA:           Diisopropylethylamine
DME:            1,2-dimethoxyethane
DMF:            N,N-Dimethylformamide
DMSO:           Dimethyl sulfoxide
DPPA:           Diphenyl phosphoryl azide
Et3N:           Triethylamine
EDC:            N-(3-Dimethylaminopropyl)-N′-ethylcarbodiimide
EDCI:           1-(3-dimethylaminopropyl)3-ethylcarbodiimide
EtOAc:          Ethyl acetate
EtOH:           Ethanol
Fmoc:           9-fluorenylmethoxycarbonyl
Gly-OH:         glycine
HATU:           O-(7-azabenzotriaazol-1-yl)-N,N,N′N′=
                tetramethyluronium
                hexafluorophophate
HBTU:           2-(1H-benzotriazol-1-yl)-1,1,3,3-tetramethyluronium
                hexafluorophosphate
Hex:            hexane
HOBt:           butyl alcohol
HOBT:           1-Hydroxybenzotriazole
HPLC:           High Pressure Liquid Chromatography
IC50 value:     The concentration of an inhibitor that causes
                a 50% reduction
                in a measured activity.
iPrOH:          Isopropanol
LC/MS:          Liquid Chromatography/Mass Spectrometry
LRMS:           Low Resolution Mass Spectrometry
MeOH:           Methanol
NaOMe:          sodium methoxide
nm:             Nanometer
NMP:            N-Methylpyrrolidone
PPh3:           triphenyl phosphine
RP-HPLC:        Reversed-phase high-pressure liquid
                chromatography
RT:             Room temperature
sat:            Saturated
TEA:            Triethylamine
TFA:            Trifluoroacetic acid
THF:            Tetrahydrofuran
Thr:            Threonine
TLC:            Thin Layer Chromatography
Trt-Br:         Tert-butyl bromide

[0724] Nomenclature for the Example compounds was provided using ACD Name version 5.07 software (Nov. 14, 2001) available from Advanced Chemistry Development, Inc. Some of the compounds and starting materials were named using standard IUPAC nomenclature.

SYNTHESIS OD N-AROYL THREONINE ANALOGUES AND FORMATION OF HYDROXAMATE

Example 1

[0725] Synthesis of 3-bromo4-fluoro-N-{(1S,2R)-2-hydroxy-1-[(hydroxyamino)carbonyl]propyl}benzamide (3)

76
77
78
	Reagent	MW	Eq.	g/ml	mmol
	Benzoic acid (1)	219.02	1.0	2.152 g	9.83
	L-Thr-OMe—HCl	169.61	1.2	1.968 g	11.6
	EDCI	191.71	1.2	2.218 g	11.6
	HOBt	135.13	1.1	1.410 g	10.4
	DIEA	129.25	4.0	6.8 mL	39.0
	DMF			60 mL

[0726] Preparation of (2S,3R)-2-(3-bromo-4-fluoro-benzoylamino)-3-hydroxy-butyric Acid Methyl Ester (2)

[0727] Diisopropylethylamine (6.8 mL, 39.0 mmol) was added to a stirred solution of 3-bromo-4-fluorobenzoic acid 1 (2.152 g, 9.83 mmol), L-threonine methyl ester hydrochloride (1.968 g, 11.6 mmol), EDCI (2.218 g, 11.6 mmol) and HOBt (1.410 g, 10.4 mmol) in anhydrous DMF (60 mL) at 0° C. under N2. The solution was stirred at 0° C. for 1 h and at room temperature for 20 h. The solution was diluted with EtOAc (300 mL) and washed with 1.0 M HCl (2×80 mL), saturated NaHCO3 (2×80 mL), H2O (4×80 mL), dried over MgSO4, filtered and concentrated in vacuo to give a colorless syrup which solidified on standing to afford 3.280 g (100%) of (2S,3R)-2-(3-bromo-4-fluoro-benzoylamino)-3-hydroxy-butyric acid methyl ester 2 as a white solid, mp 73-74° C. MS(ES+) m/z 333.9 (C12H13BrFNO4+H requires 334.00).

[0728] Preparation of 3-bromo-4-fluoro-N-{(1S,2R)-2-hydroxy-1-[(hydroxyamino)carbonyl]propyl}benzamide (3) 79

[0729] To a solution of hydroxylamine hydrochloride (66 mg, 0.95 mmol) in anhydrous MeOH (2.0 mL) at 0° C. under N2 atmosphere was added sodium methoxide (25 wt % in MeOH, 360 mg, 1.67 mmol). A precipitate formed immediately and the cloudy white solution was stirred for 10 minutes at 0° C. A solution of methyl (2S,3R)-2-[(3-bromo-4-fluorophenyl)carbonylamino]-3-hydroxybutanoate (2) (284 mg, 0.850 mmol) in MeOH (2.0 mL) was added and the reaction stirred 2 h at 0° C. and then warmed gradually to room temperature overnight (17 h total). Aqueous 1.0 M HCl (10 mL) was added and the solution extracted with 4:1 chloroform/isopropyl alcohol (4×20 mL). The organic layers were combined, dried over Na2SO4 and concentrated to give a pink foam. The crude solid was triturated with diethyl ether (2×8 mL) and dried in vacuo to give 3-bromo4-fluoro-N-{(1S,2R)-2-hydroxy-1-[(hydroxyamino)carbonyl]propyl}benzamide 3 as a white foam: mp 152-153° C. Rf (10:1 CH2Cl2/MeOH on silica gel)=0.53.

Preparation of Hydroxamates

Example 2

[0730] Synthesis of 4-benzoyl-N-{(1S,2R)-2-hydroxy-1-[(hydroxyamino)carbonyl]propyl}benzamide 80

[0731] Procedure:

[0732] To a solution of hydroxylamine hydrochloride (121 mg, 1.74 mmol) in anhydrous MeOH (2.0 mL) at 0° C. under N2 atmosphere was added sodium methoxide (25 wt % in MeOH, 680 mg, 3.14 mmol). A precipitate was immediately observed and the cloudy white solution was stirred for 10 minutes at 0° C. A solution of methyl (2S,3R)-3-hydroxy-2-{[4-(phenylcarbonyl)phenyl]carbonylamino}butanoate (1) (534 mg, 1.56 mmol) in MeOH (3.0 nL) was added and the reaction stirred 3 h at 0° C., then warmed gradually to ambient temperature overnight (18 h total). Aqueous 0.5 M HCl (20 mL) was added and the solution extracted with 5:1 chloroform/isopropyl alcohol (4×40 mL). The organic layers were combined, dried over Na2SO4 and concentrated to give an orange foam. Purification by silica gel chromatography (increasing eluant polarity from 30:1 CH2Cl2/MeOH to 15:1 CH2Cl2/MeOH) afforded 228 mg (43%) of 4-benzoyl-N-{1S,2R)-2-hydroxy-1-[(hydroxyamino)carbonyl]propyl}benzamide.

Example 3

[0733] Synthesis of (2R, 3R)-3-hydroxy-1-{[4-(trifluoromethoxy)phenyl]carbonyl}pyrrolidine-2-carbohydroxamic acid

[0734] Preparafion of ((2R,3R)-3-hydroxy-1-{[4-(trifluoromethoxy)phenyl]carbonyl)}pyrrolidin-2-yl)-N-(phenylmethoxy)carboxamide (2) 81

[0735] Procedure:

[0736] To a solution of (2R,3R)-3-hydroxy-1-{[4-(trifluoromethoxy)phenyl]carbonyl}pyrrolidine-2-carboxylic acid (1) (405 mg, 1.27 mmol), benzylhydroxylamine hydrochloride (243 mg, 1.52 mmol), HATU (556 mg, 1.46 mmol), and HOBt (178 mg, 1.32 mmol) in DMF (10 mL) at 0° C. was added diisopropylethylamine (710 μL, 4.07 mmol) with stirring. The cooling bath was removed after one hour and the reaction mixture stirred at ambient temperature for 18 h and then diluted with EtOAc (200 mL). The organic layer was washed with 1.0 M HCl (2×60 mL), sat. NaHCO3 (2×60 mL) and H2O (5×60 mL), dried over MgSO4 and concentrated to give 493 mg (92%) of ((2R,3R)-3-hydroxy-1-{[4-(trifluoromethoxy)phenyl]carbonyl}pyrrolidin-2-yl)-N-(phenylmethoxy)carboxamide (2), a colorless oil that slowly crystallized upon standing. Rf (25:1 CH2Cl2/MeOH)=0.35.

[0737] Prepartion of (2R,3R)-3-hydroxy-1-{[4-(trifluoromethoxy)phenyl]carbonyl}pyrrolidine-2-carbohydroxamic acid (2) 82

[0738] Procedure:

[0739] To a solution of ((2R,3R)-3-hydroxy-1-{[4-(trifluoromethoxy)phenyl]carbonyl}pyrrolidin-2-yl)-N-(phenylmethoxy)carboxamide (1) (143 mg, 0.337 mmol) in EtOH (10 mL) was added 20% Pd(OH)2/C (50 mg). The solution was purged with hydrogen gas (approx. 0.5 L from a 1 L balloon) and then stirred under an atmosphere of H2 (balloon pressure). TLC analysis showed no starting material after one hour. The solution was diluted with EtOAc (10 mL) and filtered through celite, washing with 20:1 EtOAc/EtOH (50 mL). The solution was concentrated and dried in vacuo to afford 90 mg (80%) of (2R,3R)-3-hydroxy-1-{[4-(trifluoromethoxy)phenyl]carbonyl}pyrrolidine-2-carbohydroxamic acid (2) as a sticky white foam: mp 64-65° C. Rf (10: 1 CH2Cl2/MeOH)=0.29.

Synthesis of N-Benzyl Threonine Analogues by Reductive Amination

Example 4

[0740] Synthesis of (2S,3R-3-hydroxy-2-{[(4-phenylphenyl)methyl]amino}butanehydroxamic acid (3).

83
84
85
Reagent	MW	Eq.	g/ml	mmol
4-biphenylcarboxaldehyde	182.22	1.0	1.104 g	6.06
L-Thr-OMe—HCl	169.61	1.0	1.030 g	6.07
NaBH(OAc)3	211.94	1.4	1.800 g	8.49
Et3N	101.19	2.0	1.70 mL	12.1
THF			25 mL

[0741] Triethylamine (1.70 mL, 12.1 mmol) was added to a stirred suspension of L-threonine methyl ester hydrochloride (1.030 g, 6.07 mmol) and 4-biphenylcarboxaldehyde (1.104 g, 6.06 mmol) in THF (25 mL). After 20 min, NaBH(OAc)3 was added and the suspension stirred for 20 h. The reaction was monitored by TLC (50:1 DCM/MeOH, Rf=0.4). The reaction mixture was quenched with saturated NaHCO3 (50 mL), extracted with EtOAc (2×120 mL), dried over MgSO4, filtered and concentrated to give a yellow oil. Purification by silica gel chromatography (150:1 DCM/MeOH) afforded 1.220 g (67% yield, 98% pure) of (2S,3R)-2-[(biphenyl-4-ylmethyl)-amino]-3-hydroxy-butyric acid methyl ester 2 as a pale yellow oil.

[0742] HPLC (260 nm, 34 min run) 14.2 min; LRMS(ES+) m/z 299.9 (C18H21NO3+H requires 300.10). Compound 3 was then formed by the addition of NH2OH in MeOH/NaOMe at 0° C., warming to ambient temparture of the period of several hours. LCMS MH+301.15.

[0743] General Methods for Making Phenyl-benzoic Acids and Phenyl-benzoate Esters(see Example 5 Below) 86

[0744] Suzuki Procedures Using Pd(dppf)Cl2-DCM Catalyst and a THF/H2O Mixture

87
Reagent	MW	EQ	g/ml	mmol
BromoArene #1	˜300	1	100 mg	˜0.33
Boromc Acid #2	—	1.2	—	˜0.40
Na2CO3	105.99	3	104 m	˜0.99
Pd(dppf)Cl2	816.63	0.1-0.2	27-54 mg	˜0.033-0.066
THF (3) (sparged			0.75 ml
with argon for 5 min.)
water (1) (sparged			0.25 ml
with argon for 5 min.)

[0745] Standard Procedure

[0746] 1 eq aryl halide (1) was added to 1.2 eq. (2) and Pd(dppf)Cl2 in Th, followed by addition of water and stirred 8 hours at RT. Upon completion (usually over night), the reactions are diluted with ethyl acetate (5-10 ml) and water (1 ml). The organic layer is separated and washed with NaHCO3 (2×3 ml), water (1×3 ml), brine (1×3 ml), dried with Na2SO4, filtered and concentrated in an 8 ml glass vial. The residue is dissolved in DMSO and injected on a preparatory HPLC reverse phase column to afford >80% yield.

[0747] Suzuki Procedures Using Pd(dppf)Cl-DCM Catalyst and DMF Solvent

88
Reagent	MW	EQ	g/ml	mmol
BromoArene #1	˜500	1	20 mg	˜0.04
Boronic Acid #2	˜200	2	˜14 mg	˜0.08
Pd(dppf)Cl2	816.63	0.25	10 mg	˜0.01-0.02
TEA	101.19	5	28 μL	˜0.2
DMF (dry & sparged			0.5 ml
with argon for 5 min.)

[0748] Standard Procedure

[0749] The haloarene 1 and boronic acid 2 were weighed out and placed in the reaction flask. The DMF was sparged with argon for 5-10 minutes, followed by TEA addition, and the reaction was lightly bubbled with argon. The solid Pd(dppf)Cl2 catalyst was added in one portion. The vial was flushed with argon, capped tight and stirred or shaken at ˜80° C. Upon reaching completion (over night), the reaction was filtered and injected on a preparatory HPLC reverse phase column (80% yield).

Synthesis of Methyl DAP Analogues

Example 5

[0750] 3-(R)-Amino-2-(S)-[(4′-ethyl-biphenyl-4-carbonyl)-amino]-butyl-hydroxamic acid (8) 89

[0751] Preparation of N-triphenylmethyl allo-threonine Methyl Ester (2).

90
	Reagent	MW	EQ	g/ml	mmol
	H-allo-Thr-OMe.HCl (1)	169.7	1.2	2.0 g	12.0
	Trt-Br	323.24	1.0	3.23 g	10.0
	DIEA	129.25	3.0	5.2 ml	30.0
	CHCl3 (dry)			100 ml

[0752] For similar-procedures see: Righi, P.; Scardovi, N.; Marotta, E.; ten Holte, P.; Zwanenburg, B. Organic Letters 2002, 4(4), 497-500.

[0753] A solution of trityl bromide (3.2 g, 10.0 mmol) in CHCl3 (40 ml) was added dropwise to a stirred solution of allo-threonine methyl ester HCl salt (1) (2.0 g, 12.0 mmol) and DIEA (5.2 ml, 30.0 mmol) in CHCl3 (60 ml) at rt under N2. The reaction could be followed by TLC eluting with EtOAc/Hex (40:60) (Rf=0.3). After stirring 12 h, the reaction was concentrated to a brown oil. The crude product was diluted with EtOAc (170 ml) and washed with 0.2 N citric acid (2×50 ml), water (2×50 ml), brine (50 ml), dried (Na2SO4), filtered and concentrated under reduced pressure to yield 3.73 g (85% yield, 95% pure) of a yellow solid.

[0754] HPLC(220 nm, 41 min. run) 30.90 min.; HPLC(220 nm, 17 min. run) 14.86 min.; LCMS: LC(214 nm) 3.06 min., MS(ES+) m/z 376.2 (C24H25NO3 +H requires 376.18).

[0755] Preparation of 3-(R)-Azido-2-(S)-(trityl-amino)-butyric Acid Methyl Ester (3).

91
	Reagent	MW	Eq.	g/ml	mmol
	Trt-allo-Thr-OMe (2)	375.46	1.0	4.08 g	10.88
	PPh3	262.29	1.0	2.85 g	10.88
	DEAD (neat)	174.16	1.6	2.93 ml	17.82
	DPPA	275.7	2.7	6.40 ml	29.7
	THF (dry)			50 ml

[0756] For similar procedures see: Matsuda, A.; Yasuoka, J.; Sasaki, T.; Ueda, T. J.Med.Chem. 1991, 34, 999-1002.

[0757] A solution of pure DEAD (2.9 ml, 17.8 mmol) in THF (5 ml) was added slowly dropwise to a stirred solution of trt-allo-threonine methyl ester (2) (4. 1 g, 10.9 mmol) and PPh3 (2.9 g, 10.9 mmol) in THF (40 ml) at 0° C. under N2. After 3 min., a solution of DPPA (6.4 ml, 29.7 mmol) in THF (5 ml) was added to the orange-yellow reaction solution at 0° C. After 1 h, the reaction was allowed to warm to rt. After 40h, the reaction had reached completion by TLC (Hexane/DCM/EtOAc (64:20:16) (Rf=0.6)) and LCMS. The yellow solution was concentrated to give 18 g of crude material that was purified by column chromatography eluting with Hexane/EtOAc (88:12) giving 3.5 g of 70% pure product after evaporation. The product was purified again (to remove trityl alcohol and a crotyl side-product formed during the reaction by elimination) by column chromatography eluting with Hexane/DCM/EtOAc (76:20:4) giving 1.65 g (38% yield) of a pale yellow oil after concentration and drying in vacuo. Note that the trityl protecting group would hydrolyze when exposed to TFA while running the sample on HPLC.

[0758] Alternately, the reaction could be carried out in dry DCM. A reaction using 5.44 g (14.5 mmol) of trt-allo-threonine methyl ester (2) in DCM (100 ml) with PPh3 (3.8 g, 14.5 mmol), pure DEAD (3.4 ml, 21.8 mmol) in DCM (5 ml) and DPPA (6.3 ml, 24.0 mmol) in DCM (10 ml) were combined following the procedure above. After 3 days, the reaction did not progress further by TLC and LCMS. After the same work up, 2.97 g of the product was obtained in 51% yield.

[0759] HPLC(220 nm, 41 min. run) 40.5 min.; HPLC(220 nm, 17 min. run) 16.32 min.; LCMS: LC(214 nm) 3.7 min., MS(ES+) m/z 401.2 (C24H25N3O2+H requires 401.15).

[0760] Preparation of 2-(S)-Amino-3-(R)-azido-butyric acid methyl ester HCl salt (4).

92
	Reagent	MW	EQ	g/ml	mmol
	Trt-Azido-Thr-OMe (3)	400.47	1.0	4.79 g	11.98
	TFA			57 ml
	CHCl3 (dry)			3 ml

[0761] A solution of Trt-Azido-Thr-OMe (3) (4.8 g, 12.0 mmol) was dissolved in a 95% TFA/DCM solution (60 ml) at rt with stirring. After 2.5 h, the reaction was complete by LCMS. The bright yellow solution was diluted with 0.5 N aq. HCl (300 ml). The aqueous layer was extracted with DCM (2×30 ml) and then lyophilized to dryness. The white solid was dissolved in AcCN/water (50:50) (100 ml) and again lyophilized to dryness to produce a consistent powder and remove as much of the TFA as possible. The azido-Thr′product (4), 2.26 g (97% yield, 95% pure) of a white solid, was obtained as the HCl salt.

[0762] HPLC(220 nm, 41 min. run) 7.91 min.; HPLC(220 nm, 17 min.run) 3.36 min; LCMS: LC(214 nm) 0.48 min., MS(ES+) m/z 159.3 (C5H10N4O2+H requires 159.08).

[0763] Preparation of 3-(R)-Azido-2-(S-[(4′-ethyl-biphenyl-4-carbonyl)-amino]-butyric acid methyl ester (6).

93
94
	Reagent	MW	EQ	g/ml	mmol
	Azido-Thr-OMe.HCl (4)	194.62	1.0	195 mg	1.0
	Biphenyl Acid (5)	226.27	1.0	226 mg	1.0
	HOBT	153	1.0	158 mg	1.0
	EDC.HCl	191.17	1.3	249 mg	1.3
	DIEA	129.25	2.5	0.44 ml	2.5
	DCM (dry)			10 ml

[0764] A EDC.HCl (249 mg, 1.3 mmol) was added to a stirred colorless solution of azido-Thr-OMe.HCl (4) (195 mg, 1.0 mmol), HOBT (158 mg, 1.0 mmol), 4′-Ethyl-biphenyl-4-carboxylic acid (5) (226 mg, 1.0 mmol) and DIEA (0.44 ml, 2.5 mmol) in DCM (10 ml) at rt under N2. After 24 h, the reaction had reached completion by TLC (Hexane/EtOAc (60:40) (Rf=0.3)) and LCMS. The reaction was evaporated under reduced pressure to a brown tar. The crude product was dissolved in EtOAc (100 ml) and washed with 0.2N aq. HCl (2×50 ml), aq. sat. NaHCO3 (50 ml), brine (50 ml), dried (Na2SO4), filtered and concentrated under reduced pressure to yield a crude brown solid. The crude material was further purified by column chromatography eluting with Hexane/EtOAc (70:30) giving 245 mg (67% yield) of pure product after evaporation and drying in vacuo.

[0765] HPLC(220 nn, 41 min. run) 33.87 min.; HPLC(220 nm, 17 min. run) 15.61 min; LCMS: LC(214 nm) 3.25 min., MS(ES+) m/z 367.2(C20H22N4O3 +H requires 367.17).

[0766] Preparation of 3-(R)-Amino-2-(S)-[(4′-ethyl-biphenyl-4-carbonyl)-amino]-butyric acid methyl ester (7).

95
96
Reagent	MW	EQ	g/ml	mmol
Biphenyl Azido-Thr (6)	366.41	1.0	244 mg	0.67
10% Pd/C			200 mg
H2 (gas)			12″ balloon
MeOH (dry)			10 ml

[0767] A solution of biphenyl azido-Thr methyl ester (6) (244 mg, 0.67 mmol) in MeOH (10 ml) was made by sonicating until the milky precipitate cleared. After bubbling nitrogen through the reaction solution for 30 sec., 10% Pd/C was added in one portion. The reaction was stirred under nitrogen at RT. The reaction was exposed to aspirator vacuum to remove the nitrogen and then opened to the hydrogen gas at balloon pressure (˜1 atm). The reaction stirred for 3 h at which time the hydrogen was exchanged for nitrogen. The reaction was filtered through a pad of celite to remove the palladium. The celite pad was washed with MeOH (30 ml). The combined fractions of MeOH were evaporated under reduced pressure and dried in vacuo to give 225 mg (99% yield) of pure produce (7) as a white solid.

[0768] HPLC(220 nm, 17 min. run) 10.79 min.; LCMS: LC(214 nm) 2.21 min., MS(ES+) m/z 341.2 (C20H24N2O2+H requires 341.18).

[0769] Preparafion of 3-(R)-Amino-2-(S)-[(4′-ethyl-biphenyl-4-carbonyl)-amino]-butyl-hydroxamic acid (8)

97
98
	Reagent	MW	EQ	g/ml	mmol
	Amino-Thr-OMe (7)	340.42	1.0	225 mg	0.66
	H2NOH.HCl	69.49	10.0	460 mg	6.6
	NaOMe	54.02	˜12.0	˜430 mg	7.92
	MeOH (dry)			7 ml
	DCM (dry)			5 ml

[0770] To a stirred suspension of biphenyl-amino-Thr methyl ester (7) (225 mg, 0.6 mmol) and hydroxylamine HCl salt (460 mg, 6.6 mmol) in MeOH (7 ml) and DCM (5 ml) was added fresh solid NaOMe powder (430 mg, 7.92 mmol) in one portion. After strrring for 2 min. at rt under nitrogen, the pH of the reaction on wet pH paper was approximately 7-8. The suspension had change from larger particles of white solid to a finely-divided milky consistency. The pH of the reaction was checked after adding small portions of NaOMe (50-100 mg) and allowing 2 min. for the reaction to equilibrate. The pH of the reaction reached a stable 11-12 after the final portion of NaOMe was added (250 mg total). The reaction was initiated at pH 11 and proceeded quickly. After 30 min., the reaction reached 85% completion as determined by LCMS, and the reaction was placed in a −10° C. bath. The cold mixture filtered over fine filter paper on a Büchner funnel. The white residue was washed with MeOH (15 ml). The organic fractions were collected and concentrated under reduced pressure to give crude product (750 mg). The crude product (only one 150 mg portion) was dissolved in DMSO (1 ml), AcCN (100 μl) and water (100 μl ), passed through a Teflon syringe filter, and the clear filtrate was injected on a preparative HPLC. The purification used a 20×50 mm Ultro 120 C18 column running a 22 ml/min 2% gradient (AcCN/water, 0.1% TFA) for 16 min. The purified fractions were lyophilized to dryness. The product as the TFA salt was dissolved in AcCN/water (50:50) (5 ml), 1N aq. HCl (1 equivalent) and lyophilized again to give 11.5 mg of white powder as an HCl salt (23% yield).

[0771] HPLC(220 nm, 41 min. run) 19.31 min.; HPLC(220 nm, 17 min. run) 9.39 min; LCMS: LC(214 nm) 1.98 min., MS(ES+) m/z 342.2 (C19H23N3O3+H requires 342.17).

Synthesis of 4′Benzamide Biphenyl Threonine Hydroxamic Acid

Example 6

[0772] Biphenyl-4,4′-dicarboxylic acid 4′-[(3-Boc-amino-propyl)-amide] 4-[((2R)-hydroxy-(1S)-hydroxycarbamoyl-propyl)-amide] (6), and

Example 7

[0773] Biphenyl-4,4′-dicarboxylic acid 4′-[(3-amino-propyl)-amide] 4-[((2R)-hydroxy-(1S)-hydroxycarbamoyl-propyl)-amide] (7) 99

[0774] Synthesis of (2S,3R)-2-amino-3-(phenylmethoxys)-N-(phenylmethoxy)butanamide (1) 100

[0775] Procedure:

[0776] To a suspension of benzylhydroxylamine hydrochloride (8.310 g, 52.06 mmol), Boc-Thr(OBn)-OH (14.01 g, 45.28 mmol), EDCI (10.01 g, 52.21 mmol), and HOBt (6.90 g, 51.06 mmol) in CH2Cl2 (300 mL) at 0° C. was added diisopropylethylamine (28.3 mL, 162 mmol) with stirring. The cooling bath was removed after one hour and the reaction mixture stirred at ambient temperature for 20 h and was then diluted with Ch2Cl2 (300 mL). The organic layer was washed with 1.0 M HCl (2×200 mL), sat. NaHCO3 (2×200 mL) and brine (200 mL), dried over MgSO4 and concentrated to give 14.5 g of a white solid. The crude solid was treated with a solution of trifluoroacetic acid (90 riL) in CH2Cl2 (90 mL) and stirred for 2.5 h. The reaction mixture was concentrated by rotary evaporation and then diluted with CH2Cl2 (600 mL). The organic layer was washed with sat. NaHCO3 (2×200 mL), dried over MgSO4 and concentrated to give a dark orange oil. Purification by silica gel chromatography (50:1 CH2Cl2/MeOH) afforded (2S,3R)-2-amino-3-(phenylmethoxy)-N-(phenylmethoxy)butanamide (A) (8.9 g,) as a pale yellow oil. Rf(50:1 CH2Cl2/MeOH on silica gel)=0.2.

[0777] Preparation of (1S,2R)-4′-(2-benzyloxy-1-benzyloxycarbamoyl-propylcarbamoyl)-biphenyl-4-carboxylic acid (3).

	Reagent	MW	Eq.	g/mL	mmol
	Amine (1)	314.38	1.0	0.944 g	3.00
	Dicarboxylic acid (2)	242.23	1.9	1.360 g	5.61
	BOP	442.3	1.5	2.007 g	4.54
	DIEA	129.25	3.3	1.7 mL	9.76
	DMF			200 mL

[0778] To a suspension of 4,4′-biphenyldicarboxylic acid 2 (1.360 g, 5.61 mmol) in DMF (180 mL) was added BOP (2.007 g, 4.54 mmol) and DIEA (1.7 mL, 9.8 mrmol). A solution of (IS,2R)-2-amino-3,N-bis-benzyloxy-butyramide 1 (944 mg, 3.00 mmol) in DMF (20 mL) was added and the reaction stirred for 18 h. The solution was diluted with EtOAc (250 mL) and washed with 1.0 M HCl (500 mL). The aqueous layer was extracted with EtOAc (250 mL) and the organic layers combined. The organic layer was washed with 1.0 M HCl (250 mL), dried over MgSO4, and concentrated to give a crude yellow solid. Purification by silica gel chromatography (60:1 CH2Cl2/MeOH) gave 210 mg (1S,2R)-4′-(2-benzyloxy-1-benzyloxycarbamoyl-propylcarbamoyl)-biphenyl-4-carboxylic acid 3. (13% yield) as a yellow solid. Rf=0.80 (10:1 CH2Cl2/MeOH); LRMS (ES+) m/z 539.1 (C32H30N2O6+H requires 539.22).

[0779] Preparation of biphenyl-4,4′-dicarboxylic acid 4′-[(3-(Boc)-amino-propyl)-amide]4-[(2R)-benzyloxy-(1S)-benzyloxycarbamoyl-propyl)-amide] (5).

Reagent	MW	Eq.	g/mL	mmol
Biphenylcarboxylic acid (3)	538.59	1.0	0.200 g	0.371
Amine (4)	174.24	1.1	0.071 g	0.407
EDCI	191.71	1.1	0.078 g	0.407
HOBt	135.13	1.0	0.052 g	0.385
DIEA	129.25	2.7	180 μL	1.0
DMF			2 mL

[0780] To a solution of biphenylcarboxylic acid 3 (200 mg, 0.371 mmol), EDCI (78 mg, 0.407 mmol), and HOBt (52 mg, 0.385 mmol) in DMF (-2 mL) was added t-Butyl N-(3-aminopropyl)carbamate 4 (71 mg, 0.407 mmol) and DIEA (180 μL, 1.0 mmol). The reaction mixture was stirred 24 h, diluted with EtOAc (150 mL), washed with 1.0 M HCl (2×60 mL), saturated NaHCO3 (2×60 mL), H2O (3×60 mL), dried over MgSO4 and concentrated to give a crude white solid. Purification by silica gel chromatography (25:1 CH2Cl2/MeOH) afforded 194 mg (75% yield) of biphenyl-4,4′-dicarboxylic acid 4′-[(3-(Boc)-amino-propyl)-amide]4-[(2R)-benzyloxy-(1S)-benzyloxycarbamoyl-propyl)-amide] 5 as a white solid. Rf=0.15 (50:1 CH2Cl2/MeOH); LRMS (ES+) m/z 695.2 (C40H46N4O7+H requires 695.35).

[0781] Preparation of Biphenyl-4,4′-dicarboxylic acid 4′-[(3-Boc-amino-propyl)-amide] 4-[((2R)-hydroxy-(1S)-hydroxycarbamoyl-propyl)-amide] (6).

	Reagent	MW	Eq.	g/mL	mmol
	Biphenyl diamide (5)	694.82	1.00	0.190 g	0.273
	Pd(OH)2 (20%/C)	106.42	0.15	0.020 g	0.040
	H2 (g)			balloon
	THF			5.0 mL
	MeOH			3.0 mL

[0782] A solution of dibenzyl-protected threonine hydroxamic acid 5 (190 mg, 0.273 mrnol) in THF (5 mL) and MeOH (3 mL) was charged with Pd(OH)2 (20%/C, 20 mg, 0.04 mmol) and stirred under a hydrogen atmosphere (balloon pressure) for 16 h. The crude mixture was filtered through a plug of celite eluting with 2:1 MeOH/THF (15 mL) and concentrated to give an orange syrup. Purification by silica gel chromatography (5:1:1 THF/MeOH/CH2Cl2 afforded 110 mg (78% yield) of biphenyl-4,4′-dicarboxylic acid 4′-[(3-Boc-amino-propyl)-amide] 4-[((2R)-hydroxy-(1S)-hydroxycarbamoyl-propyl)-amide] as a white foam, mp 75-77° C. Rf=0.20 (10:1 CH2Cl2/MeOH); LRMS (ES+) m/z 515.4 (C26H34N4O7+H requires 515.26).

[0783] Preparation of Biphenyl-4,4′-dicarboxylic acid 4′-[(3-amino-propyl)-amide] 4-[((2R)-hydroxy-(1S)-hydroxycarbamoyl-propyl)-amide] (7).

	Reagent	MW	Eq.	g/mL	mmol
	Boc-protected	514.57	1.00	0.080 g	0.155
	amine (6)
	TFA			3.0 mL
	CH2Cl2			3.0 mL

[0784] A flask containing Boc-protected amine 6 (80 mg, 0.155 mmol) was treated with 50% TFA/CH2Cl2 (6.0 mL) and stirred for 2.5 h. The reaction mixture was concentrated by rotary evaporation to give a brown syrup. Purification by RP-HPLC (C18 column, CH3CN gradient 5-70%, 0.1% TFA, UV analysis 300 nm, 36 min) and lyophilization of the collected fractions afforded 14 mg (21% yield) of biphenyl-4,4′-dicarboxylic acid 4′-[(3-amino-propyl)-amide] 4-[((2R)-hydroxy-(1S)-hydroxycarbamoyl-propyl)-amide] as a white solid. LRMS (ES+) m/z 415.3 (C21H26N4O5 +H requires 415.20); RP-HPLC (300 nm, 36 min run) 18.2 min.

Example 8

[0785] Synthesis of N-(2-(N-hydroxycarbamoyl)(2S)-2-{[4-(4-ethylphenyl)phenyl]carbonylamino}ethyl)acetamide (4) 101

[0786] Preparation of 3-Acetylamino-2-(9H-fluoren-9-ylmethoxycarbonylamino)-propionic acid (2).

102
Reagent	MW	EQ	g/ml	mmol
Fmoc—DAP—H (1)	326.4	1.0	980 mg	3.0
Acetic anhydride	102.09	1.5	425 uL	4.5
Pyridine	79.1	2.0	483 uL	6.0
THF			20 ml

[0787] Acetic anhydride in THF (5 ml) was added to a cloudy mixture of Fmoc-DAP-H (1) (980 mg, 3.0 mmol) and pyridine (483 uL, 6.0 mmol) in THF (15 ml) with stirring at rt. After 4 hours, the clear pale yellow solution had reacted completely by LCMS. The reaction was evaporated under reduced pressure. The residue was dissolved in EtOAc (150 ml) and washed with 0.1M NaHSO4 (50 ml), water (50 ml), sat. brine (50 ml), dried with Na2SO4, filtered and concentrated under reduced pressure to give 1.1 g of crude product as a white solid. The crude product was purified by prep. HPLC to give 0.99 g (90% yield) of acyl-DAP (2).

[0788] Preparation of (2-Acetylamino-1-hydroxycarbamoyl-ethyl)-carbamic acid 9H-fluoren-9-ylmethyl ester trityl resin (3).

103
104
	Reagent	MW	EQ	g/ml	mmol
	H2N—O—Trt Resin		1.0	120 mg	0.113
	Fmoc—DAP(Ac)—H (1)	368.4	5.0	980 mg	0.564
	HATU	380	5.0	0.146 g	0.564
	DIEA	129.25	10.0	196 ul	1.13
	NMP			1.7 ml

[0789] A solution of Fmoc-DAP(Ac)-H (1) (980 mg, 0.56 mmol), HATU (0.146 g, 0.56 mmol) in NMP (1.7 ml) was made. After 2 min. of shaking, the activated acid was added to the deprotected H2N-O-Trt Resin (120 mg, 0.113 mmol) at rt with shaking. [Deprotection of the Fmoc group from the resin was accomplished using 20% piperizine in DMF (4 ml) for 2 hours twice. The resin was drained and washed with DMF (2×5 ml) and DCM (2×5 ml).] After shaking for 20 hours, the reaction was drained and washed with DMF (2×5 ml) and DCM (2×5 ml). The resin was dried and used as is in the next reaction.

[0790] Preparation of N-(2-(N-hydroxycarbamoyl)(2S)-2-{[4-(4-ethylphenyl)phenyl]carbonylamino}ethyl)acetamide (4)

[0791] Preparation of (2-Acetylamino-1-hydroxycarbamoyl-ethyl)-carbamic acid 9H-fluoren-9-ylmethyl ester trityl resin (3).

105
106
Reagent	MW	EQ	g/ml	mmol
Fmoc—DAP(Ac)—Trt Resin (3)		1.0	120 mg	0.113
4′-Etbiphenyl 4-carboxy acid	226.3	5.0	91 mg	0.4
HATU	380	5.0	152 mg	0.4
DIEA	129.25	10.0	140 ul	0.8
NMP			1.0 ml

[0792] The resin was treated with 20% piperizine in DMF (4 ml) for 2 hours twice. The resin was drained and washed with DMF (2×5 ml) and DCM (2×5 ml). The resin was dried in vacuo. A solution of 4′-Ethyl-biphenyl-4-carboxylic acid (9lmg, 0.4 mmol), HATU (152 g, 0.4 mmol) in NMP (1.0 ml) was made. After 2 min. of shaking, the activated acid was added to the deprotected H-DAP(Ac)-Trt resin (120 mg, 0.113 mmol) at rt with shaking. After shaking for 18 hours, the reaction was drained and washed with DMF (2×5 ml) and DCM (2×5 ml). The resin was dried in. vacuo. The product was cleaved from the resin through treatment with a solution of TFA (500 uL), DCM (500 uL) and water (50 uL) for 25 min. The resin was filtered and washed with fresh DCM (2 ml). The combined TFA and DCM fractions are evaporated under reduced pressure. The residue was diluted with CH3CN/water (1:1) (10 ml) and lyophilized. The crude product was purified by prep. HPLC. The crude product was dissolved in DMSO (1 ml), passed through a Teflon syringe filter, and the clear filtrate was injected on a preparative HPLC. The purification used a 20×50 mm Ultro 120 C18 column running a 22 ml/min 2% gradient (AcCN/water, 0.1% TFA) for 16 min. The purified fractions were lyophilized to dryness. The solid residue was lyophilized again from CH3CN/water (1:1) (5 ml) give 8.6 mg of pure product (4) (˜21% yield).

Example 9

[0793] Synthesis of 4′-Ethyl-biphenyl-4-carboxylic acid (1-hydroxycarbamoyl-2-methanesulfonylamino-ethyl)-amide (3)

[0794] Preparation of 4′-Ethyl-biphenyl-4-carboxylic acid (2-amino-1-hydroxycarbamoyl-ethyl)-amide. trityl resin (2).

107
108
Reagent	MW	EQ	g/ml	mmol
Biphenyl-DAP(Alloc)—Trt Resin (1)		1.0	500 mg	0.35
Dimethyl barbituric acid	156.14	10.0	600 mg	3.5
Pd(PPh3)4	1135.6	1.0	438 mg	0.35
PPh3	262.3	2.0	202 mg	0.7
DCM			11.0 ml

[0795] Pd(Ph3)4 (438 mg, 0.35 mmol) was added to a vial containing biphenyl-DAP(Alloc)-Trt Resin (1) (500 mg, 0.35 mmol), Dimethyl barbituric acid (600 mg, 3.5 mmol) and PPh3 (438 mg, 0.35 mmol) in DCM (11 ml) at rt under argon. The mixture was sparged with argon and shaken for 16 hours. The bright yellow mixture was drained and washed with DMF (8×10 ml) and DCM (8×10). The resin was dried in vacuo to give the deprotected DAP resin 2.

[0796] Preparation of 4′-Ethyl-biphenyl-4-carboxylic acid (1-hydroxycarbamoyl-2-methane sulfonylamino-ethyl)-amide (3).

109
110
Reagent	MW	EQ	g/ml	mmol
Biphenyl-DAP—Trt Resin (2)		1.0	160 mg	0.11
Methanesulfonyl chloride	114.55	10.0	85 uL	1.1
Lutidine	107.16	15.0	190 uL	1.6
DCM			1.5 ml

[0797] Methanesulfonyl chloride (85 uL, 1.1 mmol) was added to a mixture of deprotected DAP resin (2) (160 mg, 0.11 mmol) and lutidine (190 uL, 1.6 mmol) in DCM (1.5 ml). After shaking for 16 hours, the mixture was drained and washed with DMF 10×2 ml) and DCM (5×2 ml). The product was cleaved from the resin through treatment with TFA/water (4:1) (1.5 ml). After shaking for 45 min., the TFA solution was collected from the resin by filtration, and the resin was washed with TFA (1 ml) and TFA/water (1:1) (10 ml). The combined TFA fractions were concentrated under reduced pressure to a reddish-brown solid. The product, identified by LCMS, was purified by prep. HPLC using a 20×50 mm Ultro 120 C18 column running a 22 ml/min 4% gradient (AcCN/water, 0.1% TFA) for 16 min. The purified fractions were lyophilized to dryness. The solid residue was lyophilized again from CH3CN/water (1:1) (5 ml) give 4 mg of pure product as a white solid (3) (˜9% yield).

Example 10

[0798] Synthesis of 4′-Ethyl-biphenyl-4-carboxylic acid [2-(3,3-dimethyl-ureido)-1-hydroxycarbamoyl-ethyl]-amide (3) (Continued from compound 2 of Example 9 above)

111
112
Reagent	MW	EQ	g/ml	mmol
Biphenyl-DAP—Trt Resin (2)		1.0	125 mg	0.096
Dimethylcarbamyl chloride	107.5	10.0	103 mg	0.96
Lutidine	107.16	20.0	225 uL	1.92
DCM			1.5 ml

[0799] Dimethylcarbamyl chloride (103 mg, 0.96 mmol) was added to a mixture of deprotected DAP resin (2) (125 mg, 0.096 mmol) and lutidine (225 uL, 1.92 mmol) in DCM (1.5 ml). After shaking at rt for 5 hours, the mixture was drained and washed with DCM (5×2 ml), DMF (5×2 ml) and DCM (5×2 ml). The product was cleaved from the resin through treatment with TFA/water (4:1) (1.5 ml). After shaking for 45 min., the TFA solution was collected from the resin by filtration, and the resin was washed with TFA/water (1:1) (2 ml). The combined TFA fractions were concentrated under reduced pressure to a reddish-brown solid. The product, identified by LCMS, was purified by prep. HPLC using a 20×50 mm Ultro 120 C18 column running a 22 mvmin 4% gradient (AcCN/water, 0.1% TFA) for 16 min. The purified fractions were lyophilized to dryness. The solid residue was lyophilized again from CH3CN/water (1:1) (5 ml) give 5 mg of pure product as a white solid (3) (˜13% yield).

Example 11

[0800] Synthesis of 4′-Ethyl-biphenyl-4-carboxylic acid [2-(2-amino-ethylamino)-1-hydroxycarbamoyl-ethyl]-amide (2).

113
114
Reagent	MW	EQ	g/ml	mmol
Biphenyl-DAP-hydroxamate (1)	327.4	1.0	20 mg	0.096
Boc-amino-acetaldehyde	159.19	4.0	6.4 mg	0.4
NaBH3CN	62.84	10.0	3.1 mg	0.05
Acetic acid	60.05	20.0	6 uL	1.00
DCM			1.5 ml

[0801] NaBH3CN (3.1 mg, 0.05 mmol) followed by acetic acid (6 uL, 1.0 mmol) were sequentially added to a stirred suspension of biphenyl-DAP-hydroxamate (1) (20 mg, 0.096 mmol) and Boc-amino-acetaldehyde (6.4 mg, 0.4 mmol) in MeOH (1.5 ml) in a 4 ml vial. The reaction was followed by LCMS. After stirring 12 hours, the cloudy reaction was only 50% complete. The reaction was concentrated under reduced pressure to a thick slurry that was dissolved in DMSO. The product was purified by prep. HPLC using a 20×50 mm Ultro 120 C18 column running a 22 ml/min 3% gradient (AcCN/water, 0.1% TFA) for 16 min. The purified fractions were lyophilized to dryness. The dried powder was dissolved in CH3CN/water (1:1) (1 ml) and 1M HCl (700 uL). After heating at 50° C. for 75 min., the reaction mixture was again lyophilized to dryness to produce 7.1 mg of product (2) as a 2xHCl salt white powder (˜17% yield).

Example 12

[0802] Synthesis of N-(1-(N-hydroxycarbamoyl)1S,2R)-2-hydroxypropyl)[4-(2-phenylethynyl)phenyl]carboxamide 115

[0803] Preparation of 4-Phenylethynyl-benzoic acid (3)

116
117
	Reagent	MW	EQ	g/ml	mmol
	Iodo-benzoate 1	262	1.0	20.0 g	76.34
	Ethynyl-benzene 2	102	1.1	8.56 g	83.96
	PdCl2(PPh3)2	702	0.012	0.65 g	0.92
	CuI	190	0.024	0.35 g	1.83
	TEA	101	1.5	16 ml	114.5
					d = 0.726
	THF (dry & sparged			110 ml
	with argon for
	5 min.)

[0804] The 4-iodo-benzoic acid methyl ester 1 (20.0 g, 76.34 mmol), ethynyl-benzene 2 (8.56 g, 83.96 mmol), PdCl2(PPh3)2 (0.65 g, 0.92 mmol), and CuI (0.35 g, 1.83 mmol) were mixed with THF (110 ml) in a round bottom under argon. The dry THF was sparged with dry, oxygen-free argon for at least 5 min. immediately before use. The reaction was cooled to 10° C. and TEA (16 ml) was added. The cooling bath was removed and the reaction was stirred at RT under argon. After 2.5 h, the reaction was diluted with EtOAc (400 ml) and the solids were filtered off through a pad of celite. The organic filtrate was washed with 1M HCl (60 ml), sat. aq. NaHCO3 (60 ml), water (60 ml), brine (60 ml), dried with Na2SO4, filtered and concentrated under reduced pressure. The crude solid methyl ester was dissolved in MeOH (400 ml), 6M NaOH (30 ml) and water (50 ml). The reaction was stirred at 70° C. until a clear solution was formed (about 1 h). The reaction could be followed by LCMS. The reaction was cooled and diluted with water (500 ml) and hexane (100 ml). The pH was adjusted to pH 6-7. The white solid that formed was collected and washed with water (3×60 ml) and hexane (3×60 ml). The solid 3 was dried in vacuo yielding 17.3 g (approximately quantitative yield in 99% purity).

[0805] Preperation of 3-Hydroxy-2-(4-phenylethynyl-benzoylamino)-butyric acid methyl ester (4)

118
119
Reagent	MW	EQ	g/ml	mmol
4-Phenylethynyl-benzoic acid (3)	222	1.0	1.55 g	7.0
Threonine methyl ester.HCl	169.65	1.4	1.66 g	9.8
HBTU	380	1.0	2.66 g	7.0
DIEA	125.28	2.5	3.05 ml	17.5
DMF			21 ml

[0806] A solution of threonine (1.66 g, 9.8 mmol) and DIEA (1.53 ml, 8.8 mmol) in DMF (10 ml) was added to a stirred solution of 4-phenylethynyl-benzoic acid 3 (1.55 g, 7.0 mmol) and DIEA (1.53 ml, 8.8 mmol) in DMF (11 ml) at rt. After 12 h, the reaction was diluted with EtOAc (300 ml) and washed with 0.5M HCl (2×60 ml), sat. aq. NaHCO3 (60 ml), 50% diluted brine (60 ml), sat. brine (60 ml), dried with Na2SO4, filtered and concentrated under reduced pressure. Upon drying in vacuo, 2.34 g of white solid was obtained (approximately quantitative yield in 99% purity).

[0807] Preperation of N-(2-Hydroxy-1- hydroxycarbamoyl-propyl)-4-phenylethynyl-benzamide (5)

120
121
	Reagent	MW	EQ	g/ml	mmol
	Tolanoic-Thr—OMe (4)	340.42	1.0	2.34 g	7.0
	H2NOH.HCl	69.49	10.0	4.81 g	70.0
	NaOMe	54.02	>11.0	>4.16 g	>77.0
	MeOH (dry)			50 ml
	DCM (dry)			30 ml

[0808] A solution of tolanoic-Thr methyl ester (4) (2.34 g, 7.0 mmol) in MeOH (20 ml) and DCM (30 ml) was added to a cooled (−10° C. bath) suspension of hydroxylamine HCl salt (4.81 g, 70.0 mmol) and NaOMe (4.16 g, 77.0 mmol) in MeOH (30 ml). Follow reaction by LCMS. After stirring for 2 hours, the reaction seems to stall at 50% completion. Add an additional 1 equivalent of NaOMe (0.416 g). After 3 hours, the reaction was 75% complete. Add an additional 0.5 equivalent of NaOMe (0.21 g). After 4 hours, the reaction was 90% complete. Add an additional 0.15 equivalent of NaOMe (0.064 g) for a total of 12.65 equivalents of NaOMe. The pH of the reaction was between 11-12 and had reacted about 95% completion. The reaction was diluted with EtOAc (500 ml) and washed with sat. aq. NaHCO3 (2×60 ml), 50% diluted brine (60 ml), sat. brine (60 ml), dried with Na2SO4, filtered and concentrated under reduced pressure. The residue was dissolved in minimal DMA. The product was purified by prep. HPLC using a reverse phase Ultro 120 C18 column running a 2% gradient (AcCN/water, 0.1% TFA). The purified fractions were lyophilized to dryness. The product as the TFA salt dissolved in AcCN/water (50:50) (80 ml), 1N aq. HCl (13 equivalent) and lyophilized again to give 1.3 g of white powder in 55% yield and >97% purity.

Example 13

[0809] Synthesis of 3-(R)-Amino-2-(S)-(3-phenylethynyl-benzoylamino)-butyl-hydroxamic acid (10)

[0810] Preparation of 3-(R)-Azido-2-(S)-(3-phenylethynyl-benzoylamino)-butyric acid methyl ester (9). 122

[0811] The synthesis of compound 4 is described above. The tolanyl compound (9) was made by the same procedures as for compound (6). The product (9) was obtained in 92% yield (952 mg).

[0812] HPLC(220 nm, 41 min. run) 32.64 min.; HPLC(220 nm, 17 min. run) 15.08 min LCMS: LC(214 nm) 3.16 min., MS(ES+) m/z 363.1 (C20H18N4O3+H requires 363.14).

[0813] Preparation of 3-(R)-Amino-2-(S)-(3-phenylethynyl-benzoylamino)-butyl-hydroxamic acid (10)

123
124
	Reagent	MW	Eq.	g/ml	mmol
	Amino-Thr-OMe (9)	362.38	1.0	726	mg	2.0
	PPh3	262.29	1.0	526	mg	2.0
	H2NOH.HCl	69.49	10.0	1.4	g	20.0
	NaOMe	54.02	˜12.0	1.3	g	24.0
	THF (dry)			20	ml
	MeOH (dry)			20	ml

[0814] Triphenylphosphine (526 mg, 2.0 mmol) was added to a stirred solution of tolanyl-azido-Thr methyl ester (9) (726 mg, 2.0 mmol) at rt. After 3 days the reaction reached completion as judged by TLC (EtOAc/Hex (2:1)) and LCMS. The reaction was concentrated under reduced pressure to give an ivory colored solid. The crude amino-phosphine was dissolved in MeOH (20 ml) to give a pale yellow solution. To the solution of amino-phosphine was added sequentially hydroxylamine HCl salt (1.4 g, 20.0 mmol) followed by fresh solid NaOMe powder (1.3 g, 24.0 mmol) to make a milky pH 10 suspension. After 36 h, the reaction was complete by LCMS. The reaction was evaporated under reduced pressure to give a yellow solid that was dried in vacuo. The crude product (2.75 g) was triturated with ether (3×50 ml) to remove impurities (P(O)Ph3) and then was dissolved in abs. EtOH (120 ml) with sonication for 15 min. A fine white powder was suction filtered off, and the clear yellow ethanolic portion was concentrated to a small volume. The crude product was dissolved in DMSO (8 ml) and purified by preparative HPLC (Ultro 120 C18 75×300 mm column) running a gradient (AcCN/water, 0.1% TFA) from 5 to 70% for 55 min. The purified fractions were pooled together and lyophilized to dryness. The product as the TFA salt was dissolved in AcCN/water (50:50) (100 ml), 1N aq. HCl (1 equivalent) and lyophilized again to give 325 mg of light yellow powder as the HCl salt (43% yield).

[0815] HPLC(220 nm, 41 min.run) 18.31 min.; HPLC(220 nm, 17 min.run) 9.11 min; LCMS: LC(214 nm) 1.91 min., MS(ES+)m/z 338.1 (Cl19H19N3O3+H requires 338.14).

Synthesis of 4′-(N-Acylamnino)-Tolan Dap Analogs

Example 14

[0816] Synthesis of 4-({4-[(aminoacetyl)amino]phenyl}ethynyl)-N-[(1S)-1-(aminomethyl)-2-(hydroxyamino)-2-oxoethyl]benzamide 125

[0817] Preparation of 2-N-Boc-amino-N-(4-iodo-phenyl)-acetamide (2).

126
127
	Reagent	MW	Eq.	g/mL	mmol
	Boc-Gly-OH	175.19	1.00	1.752	g	10.0
	4-Iodoaniline (1)	219.03	1.04	2.290	g	10.4
	EDCI	191.71	1.04	1.994	g	10.4
	HOBt	135.13	1.00	1.351	g	10.0
	DCM			18	mL
	DMF			1	mL

[0818] A solution of Boc-Gly-OH (1.752 g, 10.0 mmol) in DCM (18 mL) and DMF (1 mL) was treated with EDCI (1.994 g, 10.4 mmol) and HOBt (1.351 g, 10.0 mmol). After stirring 15 min, 4-iodoaniline 1 (2.290 g, 10.4 mmol) was added and the reaction monitored by TLC (25:1 DCM/MeOH (Rf=0.6)). After 24 h the solution was diluted with EtOAc (250 mL), washed with 1.0 M HCl (3×100 mL), sat. NaHCO3 (3×100 mL), brine (3×100 mL), dried over MgSO4, filtered and concentrated in vacuo to afford 2.900 g (77% yield) of a white solid.

[0819] Preparation of (2S)-3-N-Boc-amino-(4-ethynyl-benzoylamino)-propionic acid methyl ester (4).

128
129
Reagent	MW	Eq.	g/mL	mmol
4-Ethynylbenzoic acid (3)	146.14	1.0	0.910	g	6.22
H-Dap(Boc)—OMe—HCl	254.71	1.2	1.903	g	7.47
EDCI	191.71	1.2	1.432	g	7.47
HOBt	135.13	1.1	0.910	g	6.73
DIEA	129.25	3.2	3.5	mL	20.0
DMF			50	mL

[0820] Triethylamine (3.5 mL, 20.0 mmol) was added to a stirred solution of 4-ethynylbenzoic acid 3 (910 mg, 6.22 mmol), H-Dap(Boc)-OMe hydrochloride (1.903 g, 7.47 nmnol), EDCI (1.432 g, 7.47 mmol), and HOBt (910 mg, 6.73 mmol) in DMF (50.0 mL). After stirring 20 h, the reaction mixture was diluted with EtOAc (400 mL), washed with 1.0 M HCl (2×100 mL), saturated NaHCO3 (2×100 mL), H2O (4×100 mL), dried over MgSO4, filtered and concentrated in vacuo to give 2.140 g (99% yield) of a tan solid, mp=110-111° C. LRMS (ES+) m/z 346.9 (Cl8H22N2O5 +H requires 347.10). 130

[0821] To a suspension of methyl (2S)-3-[(tert-butoxy)carbonylamino]-2-[(4-ethynylphenyl)carbonylamino]propanoate (4) (200 mg, 0.577 mmol) and 2-[(tert-butoxy)carbonylamino]-N-(4-iodophenyl)acetamide (2) (476 mg, 1.26 mmol) was added Et3N (350 μL, 2.5 mmol). The solution was purged with a stream of N2 for several minutes and PdCl2(PPh3)2 (20 mg, 0.028 mmol) and CuI (10.6 mg, 0.055 mmol) were added. The reaction mixture was stirred at ambient temperature for 22 h and then concentrated by rotary evaporation. The crude black residue was chromatographed twice by silica gel chromatography (30:1 CH2Cl2/MeOH) to give 285 mg (83%) of methyl (2S)-3-[(tert-butoxy)carbonylamino]-2-({4-[2-(4-{2-[(tert-butoxy)carbonylamino]acetylamino}phenyl)ethynyl]phenyl}carbonylamino) propanoate (5) as a yellow foam. 131

[0822] To a solution of hydroxylamine hydrochloride (98 mg, 1.41 nimol) in MeOH (1.3 mL) at 0° C was added 25 wt % NaOMe (460 mg, 2.13 mmol). The solution was stirred at 0° C. for 15 min and then charged with a solution of methyl (2S)-3-[(tert-butoxy)carbonylamino]-2-({4-[2-(4-{2-[(tert-butoxy)carbonylamino]acetylamino}phenyl)ethynyl]phenyl}carbonylamino) propanoate (4) (279 mg, 0.469 mmol) in THF (1.5 mL) and MeOH (0.6 mL). The reaction was stirred at 0° C. for 30 min and at room temperature for 2.5 h. The reaction mixture was diluted with 4:1 CHCl3/iPrOH (50 ml) and washed with 0.1 M HCl (30 mL). The layers were separated and the aqueous layer extracted once more with 4:1 CHCl3/iPrOH (30 ml). The organic layers were combined, dried over Na2SO4, filtered and concentrated. The crude residue was suspended in 10:1 CH2Cl2/MeOH (4 mL), filtered, and washed with 50:1 CH2Cl2/MeOH (2 mL) and Et2O (10 mL) to afford 180 mg (64%) of N-(4-{2-[4-(N-{1-(N-hydroxycarbamoyl)(1S)-2-[(tert-butoxy)carbonylamino]ethyl}carbamoyl)phenyl]ethynyl}phenyl)-2-[(tert-butoxy)carbonylamino]acetamide (6) as a white powder.

[0823] To an oven-dried flask containing N-(4-{2-[4-(N-{1-(N-hydroxycarbamoyl)(1S)-2-[(tert-butoxy)carbonylamino]ethyl}carbamoyl)phenyl]ethynyl}phenyl)-2-[(tert-butoxy)carbonylamino]acetamide (6) (130 mg, 0.218 mmol) was added 1:1 TFA/CH2Cl2 (2.5 mL). The resulting pink solution was stirred for 2 h and concentrated to give a pink gum. The crude residue was rinsed with CH2Cl2 (4 mL), concentrated by rotary evaporation and dissolved in THF (2 mL) and MeOH (0.4 mL). A solution of 4 M HCl in dioxane (200 μL) was added and the resulting precipitate filtered and washed with Et2O (10 mL) to afford 90 mg of 4-({4-[(aminoacetyl)amino]phenyl}ethynyl)-N-[(1S)-1-(aminomethyl)-2-(hydroxyamino)-2-oxoethyl]benzamide as a pale tan powder.

Reaction of Iodoaniline with Bromoacetyl Bromide

[0824] 132

[0825] Bromoacetyl bromide (175 μL, 2.00 mmol) was added dropwise over 5 minutes to a solution of 4-iodoaniline (438 mg, 2.00 mmol) and Et3N (280 μL, 2.00 mmol) in benzene (5 mL). The reaction was stirred 1 hour, treated with morpholine (1.0 mL, 11.5 mmol) and stirred overnight. The reaction mixture was diluted with EtOAc (200 mL), washed with aqueous 0.1 M KOH (50 nmL), H2O (50 mL), dried over MgSO4 and concentrated to give a yellow oil. Purification by silica gel chromatography (100:1 CH2Cl2/MeOH) afforded 630 mg (91%) of N-(4-iodophenyl)-2-morpholin4-ylacetamide as a waxy tan solid. This product was converted to analogues in a similar manner as Example 14.

Example A

[0826] Preparation of 4-[4-(6-Chloro-pyridin-3-yl)-buta-1,3-diynyl]-benzoic acid methyl ester.

133
134
135
Reagent	MW	EQ	g/ml	mmol
H—DAP(Boc)—OMe (1)	254	1.05	5.93	g	23.3
4-Iodo-benzoic acid	248	1.0	5.49	g	22.2
HOAT	136.1	1.02	3.08	g	22.6
EDC	191.71	1.02	4.33	g	22.6
DIEA	129.25	2.5	9.7	ml	55.1
DMF			85	ml

[0827] DIEA (9.7 ml, 55.1 mmol) was added to a stirred solution of 4-iodo-benzoic acid (5.49 g, 22.2 mmol), HOAT (3.08 g, 22.6 mmol), EDC (4.33 g, 22.6 mmol) in DMF (85 ml). After 2 min., the H-DAP(Boc)-OMe (1) was added in one portion. After 12 hours, the reaction was found complete by LCMS. The reaction was diluted with EtOAc/hexane (1:1) (500 ml). The organic phase-was washed with 1N HCl (2×80 ml), IN NaOH (2×80 ml), water (2×80 ml), sat. brine (80 ml), dried with Na2SO4, filtered and concentrated under reduced pressure to give crude product. The residue was filtered through a filter plug of silica eluting with EtOAc/hexane (1:1). The fractions with product were evaporated to give 9.3 g of product (3-tert-Butoxycarbonylamino-2-(4-iodo-benzoylamino)-propionic acid methyl ester) in 93% yield. This product was converted to analogues in a similar manner as the aforementioned Examples.

Example 15

[0828] N-(1-(N-hydroxycarbamoyl)(1S,2R)-2-hydroxypropyl)(4-{2-[4-(morpholin4-ylmethyl)phenyl]ethynyl}phenyl)carboxamide (5) 136

Preparation of (2S, 3R)-2-[4-(4-formyl-phenylethynyl)-benzoylaminol-3-hydroxy-butyric acid methyl ester (3).

[0829]

137
138
	Reagent	MW	Eq.	g/ml	mmol
	Ethynylbenzene (1)	261.27	1.0	0.745	g	2.85
	4-Iodobenzaldehyde (2)	232.00	1.4	0.902	g	3.89
	PdCl2(PPh3)2	701.89	0.03	0.070	g	0.10
	CuI	190.44	0.06	0.034	g	0.18
	Et3N	101.19	2.3	0.90	mL	6.5
	THF			50	mL

[0830] A solution of alkyne 1 (745 mg, 2.85 mmol), 4-iodobenzaldehyde 2 (902 mg, 3.89 mmol), and Et3N (900 μL, 6.5 mmol) in THF (50 mL) was purged with a stream of N2 for two minutes and then treated with PdCl2(PPh3)2 (70 mg, 0.10 mmol) and CuI (34 mg, 0.18 mmol). The reaction mixture was stirred 40 h, concentrated by rotary evaporation and purified by silica gel chromatography (40:1 DCM/MeOH) to give 0.833 g (80% yield) of (2S, 3R)-2-[4-(4-formyl-phenylethynyl)-benzoylamino]-3-hydroxy-butyric acid methyl ester 3 as a pale yellow powder, mp=143-144° C. Rf=0.3 (25:1 DCM/MeOH); LRMS (ES+) m/z 366.1 (C21H19NO5 +H requires 366.13); HPLC (300 nm, 47 min) 15.3 min.

Preparation of (2S, 3R)-3-Hydroxy-2-[4-(4-morpholin4-ylmethyl-phenylethynyl)-benzoylamino]-butyric acid methyl ester (4).

[0831]

139
140
	Reagent	MW	Eq.	g/ml	mmol
	Tolanylaldehyde (3)	365.38	1.0	0.822	g	2.25
	Morpholine	87.12	1.3	0.260	mL	2.97
	NaBH(OAc)3	211.94	1.4	0.670	g	3.16
	THF			15	ml

[0832] Sodium triacetoxyborohydride (0.670 g, 3.16 mmol) was added to a solution of benzaldehyde 3 (0.822 g, 2.25 mmol) and morpholine (260 μL, 2.97 mmol) in THF (15 mL) under N2 atmosphere and the reaction monitored by TLC (25:1 DCM/MeOH, Rf=0.2). After stirring 4 h, the reaction mixture was quenched with saturated NaHCO3 (150 mL), extracted with EtOAc (3×100 mL), dried over MgSO4, filtered and concentrated to give a yellow syrup. Purification by silica gel chromatography (35:1 DCM/MeOH) afforded 0.844 g (86% yield) of 4 as a sticky white foam.

Preparation of (2S, 3R)-N-(2-Hydroxy-1-hydroxycarbamoyl-propyl)-4-(4-morpholin-4-ylmethyl-phenylethynyl)-benzamide (5).

[0833]

141
142
	Reagent	MW	Eq.	g/ml	mmol
	Methyl ester (4)	436.50	1.0	0.829	g	1.90
	NH2OH—HCl	69.49	3.0	0.400	g	5.76
	NaOMe (25 wt%)	54.02	4.5	1.860	g	8.60
	MeOH			8	mL
	THF			3	mL

[0834] Sodium methoxide (25 wt % in MeOH, 1.860 g, 8.60 mmol) was added to a stirred solution of hydroxylamine hydrochloride (400 mg, 5.76 mmol) in anhydrous MeOH (5 mL) at 0° C. under N2 atmosphere. After stirring 20 min, a solution of methyl ester 4 (829 mg, 1.90 mmol) in 1:1 MeOH/THF (6 mL) was added and the reaction mixture stirred at 0° C. for 1 h and at room temperature for 4 h. The reaction was quenched with 1.0 M HCl (6 mL), concentrated by rotary evaporation to remove organic solvents, and diluted with DMSO (4 mL). Analytical RP-HPLC (C18 column, CH3CN gradient 5-35%, 0.1% TFA, UV analysis 300 nm, 16 min) indicated a purity of 85% for the crude product mixture. Purification by preparative RP-HPLC and lyophilization of the collected fractions gave 701 mg (81%) of 5 as a fluffy white solid. LRMS (ES+) m/z 438.1 (C24H27N3O5+H requires 438.20); RP-HPLC (300 nm, 16 min run) 8.7 min.

Resin Procedures for Synthesizing Tolanyl hydroxamates

Example 16

[0835] Synthesis of 4-[(4-{[(benzylamino)acetyl]amino}phenyl)ethynyl]-N-{(1S,2R)-2-hydroxy-1-[(hydroxyamino)carbonylipropyl}benzamide 143

[0836] 1. Coupling to Fmoc Hydroxylamine Resin

[0837] The resin was pre-swelled by adding DCM and shaking for 30 min. The resin was drained, 20% piperdine was added in DMF, the resin was shaken 1.25 hours, and finally drained and washed in 2×DMF and 2×DCM. After draining comnpletely, 20% piperdine in DMF was added to attain cleavage in 1.25 hours. The resin was washed 4×DMF, 4×DCM and drained completely. In a separate flask, the amino acid (Fmoc-Thr tBu-OH, or Fmoc-DAP Boc-OH, 4 eq) was mixed, HATU (4 eq), DMF (60 ml) and Hunig's (8 eq) base were added and stirred for 2-3 min. The mixture was added to the resin and shaken 20-24 hours. Subsequently, the resin was drained and run with a standard wash (1×DCM, 4×DMF and 4×DCM). The Fmoc was removed from the amino acid by adding 20% piperdine in DMF and shaken 1.25 hours, drained, and given the standard wash (1×DCM, 4×DMF and 4×DCM).

[0838] 2. Coupling of 4-iodobenzoic Acid to Amino Acid Resin

[0839] A mixture of 4-iodobenzoic acid (4 eq), HBTU (4 eq), DMF (60 ml) was shaken for several minutes. Hunig's base (8 eq) was subsequently added and the mixture was shaken further for 2-3 min. The pre-activated mixture was then added to the prepared Thr or DAP resin (Fmoc removed, 7.5 g, 5.775 mmol). The reaction is shaken 12-16 hours followed by the standard wash (1×DCM, 4×DMF and 4×DCM).

[0840] 3. Alkyne Coupling on Resin

[0841] To the 4-iodobenzoic resin (4 g, 3.08 mmol) was added 4-aminophenylacetylene (3 eq), Pd(PPh3)2Cl2 (0.04 eq), CuI (0.08 eq) and THF (purged with Argon). After mixing for 1 min., TEA (4.5 eq) was added and the reaction was shaken 12 hours at RT under argon.

[0842] 4. Aniline Coupling with Bromoacetyl Chloride on Resin

[0843] To aniline resin (4 g, 3.08 mmol) was added DCM (30 ml) lutidine (10 eq) and shaken for 1 min. Bromoacetyl chloride (8 eq) in DCM (5 ml) was added slowly. After the addition, the slurry was shaken for 1.5 to 1.75 hours. Subsequent draining and a wash with 2×DCM, 4×DMF and 4×DCM was then performed.

[0844] 5. Displacement with Amines on Resin

[0845] To the bromoacetyl resin (125 mg), was added NMP (1.5 ml) followed by amine (0.2 g or ml, ie excess) and the slurry was shaken for 12-16 hours at RT. To neutralize the salt, TEA was added. The imidazole was heated at 38° C. for 24 h (in the case of anilines, they were heated at 38° C. for 48 h). The reaction mixture was drained and washed 4×DMF and 4×DCM.

[0846] 6. Cleavage from Resin and Deprotection of Thr tBu and DAP Boc

[0847] The resin (125 mg) was soaked in TFA/water (80:20 v/v) (1.5 ml) at RT for 45 min. Upon cleavage the solution was collected and the resin was washed with more TFA/water mixture (0.75 ml). To the TFA/product solution was added acetonitrile/water solution (1:1 v/v, 10 ml) and pure water (2.5 ml). The-mixture was frozen in liquid nitrogen for 18 15 min and lyophilized. The dry residue was dissolved in the acetonitrile/water solution (1:1 v/v, 10 ml) again followed by addition of 1M aq. HCl (1.2 eq per basic nitrogen), frozen, and lyophilized to a powder.

Synthesis of 3′-Nitro-Tolan Threonine Hydroxamic Acid

Example 17

[0848] (1S,2R)-N-(2-hydroxy-1-hydroxycarbamoyl-propyl)-4-(3-nitro-phenylethynyl)-benzamide 144

Preparation of (1S,2R)-N-(2-tert-butoxy-1-hydroxycarbamoyl-propyl)-4-ethynyl-benzamide on Hydroxylamine 2-chlorotrityl Resin (3).

[0849]

Reagent	MW	Eq.	g/mL	mmol
Fmoc-threonine/resin (1)	0.70 mmol/g	1.0	0.522 g	0.365
4-Ethynylbenzoic acid (2)	146.14	3.0	0.160 g	1.10
DIC	126.20	4.9	0.28 mL	1.79
HOBt	135.13	3.0	0.148 g	1.10
DIEA	129.25	6.3	0.40 mL	2.30
DCM			1.0 mL
DMF			3.0 mL

[0850] The resin 1 (0.522 g, 0.365 mmol, 0.70 mmol) was swelled in DCM (5 mL) for 2 h and drained. The resin was treated with 20% piperidine in DMF (6 mL) for 1 hour, washed with DMF (4×6 mL) and DCM (4×6 mL) and drained completely. In a separate flask, 4-ethynylbenzoic acid 2 (0.160 g, 1.10 mmol), DIC (0.280 mL, 1.79 mmol), HOBt (0.148 g, 1.10 mmol) and DIEA (0.4 mL, 2.30 mmol) were dissolved in DCM (1 mL) and DMF (4 mL), stirred 15 min and added to the resin. After shaking for 36 h, the mixture was drained, washed with DMF (4×6 mL) and DCM (4×6 mL) and dried in vacuo to give 0.495 g of a yellow resin.

Preparation of (1S,2R)-N-(2-hydroxy-1-hydroxycarbamoyl-propyl)-4-(3-nitro-phenylethynyl)-benzamide (5).

[0851]

Reagent	MW	Eq.	g/mL	mmol
Alkyne on resin (3)	0.70 mmol/g	1.0	100 mg	0.070
1-Iodo-3-nitrobenzene (4)	249.01	5.0	87.1 mg	0.350
PdCl2(PPh3)2	701.89	0.2	10.0 mg	0.014
CuI	190.44	0.5	7.0 mg	0.036
Et3N	101.19	15	150 μL	1.10
DMF			1.5 mL

[0852] Resin 3 (100 mg, 0.070 mmol) was swelled in DCM (2 mL) for 1 h and drained. A solution of 1-iodo-3-nitrobenzene 4 (87.1 mg, 0.350 mmol) and Et3N (150 μL, 1.10 mmol) in DMF (1.5 mL) was purged with a stream of N2 bubbles for two minutes and added to the resin. After mixing for 5 min, PdCl2(PPh3)2 (10.0 mg, 0.014 mmol) and CuI (7.0 mg, 0.036 mmol) were added and the mixture shaken for 26 h. The resin was drained, washed with DMF (3×2 mL), DCM (3×2 mL) and cleaved with 10% TFA/DCM (1.5 mL) for 20 min. The solution was collected and the resin was rinsed with additional 10% TFA/DCM (1.0 mL). The cleavage fractions were combined, treated with neat TFA (2.0 mL), stirred for 1 h at rt and concentrated by rotary evaporation to give a crude brown residue. Purification by RP-HPLC (C18 column, CH3CN gradient 5-65%, 0.1% TFA, UV analysis 300 nm, 28 min) and lyophilization of the collected fractions afforded 6.0 mg (22% yield) of (1S,2R)-N-(2-hydroxy-1-hydroxycarbamoyl-propyl)-4-(3-nitro-phenylethynyl)-benzamide as a white foam. LRMS (ES+) m/z 384.2 (C19H17N3O6+H requires 384.15); RP-HPLC (300 nm, 28 min run) 15.2 min.

Synthesis of 4′-Trifluoromethoxy-Tolan Dap Hydroxamic Acid

Example 18

[0853] (1S)-N-(2-amino-1-hydroxycarbamoyl-ethyl)-4-(4-trifluoromethoxy-phenylethynyl)-benzamide (5) 145

[0854] Preparation of (1S)-N-(2-(Boc)-amino-1-hydroxycarbamoyl-ethyl)-4-ethynyl-benz-amide on Hydroxylamine 2-chlorotrityl Resin (3).

Reagent	MW	Eq.	g/mL	mmol
Fmoc-Dap/resin (1)	0.70 mmol/g	1.0	1.330 g	0.931
4-Ethynylbenzoic acid (2)	146.14	3.0	0.408 g	2.793
DIC	126.20	4.8	0.70 mL	4.470
HOBt	135.13	3.0	0.377 g	2.793
DIEA	129.25	6.2	1.0 mL	5.7
DCM			10.0 mL
DMF			2.0 mL

[0855] The resin 1 (1.330 g, 0.931 mmol, 0.70 mmol/g) was swelled in DCM (15 mL) for 2 h and drained. The resin was treated with 20% piperidine in DMF (20 mL) for 1 hour, washed with DMF (3×15 mL) and DCM (3×15 mL) and drained completely. In a separate flask, 4-ethynylbenzoic acid 2 (0.408 g, 2.793 mmol), DIC (0.70 mL, 4.470 mmol), HOBt (0.377 g, 2.793 mmol) and DIEA (1.0 mL, 5.7 mmol) were dissolved in DCM (10 mL) and DMF (2 mL), stirred 15 min and added to the resin. After shaking for 36 h, the mixture was drained, washed with DMF (3×15 mL) and DCM (3×15 mL) and dried in vacuo to give 1.290 g of a yellow resin.

[0856] Preparation of (1S)-N-(2-amino-1-hydroxycarbamoyl-ethyl)-4-(4-trifluoromethoxy-phenylethynyl)-benzamide (5).

Reagent	MW	Eq.	g/mL	mmol
Alkyne on resin (3)	0.70 mmol/g	1.0	120 mg	0.084
4-CF3O-iodobenzene (4)	287.99	4.0	96.8 mg	0.336
PdCl2(PPh3)2	701.89	0.3	18.0 mg	0.025
CuI	190.44	0.5	8.0 mg	0.042
Et3N	101.19	13	150 μL	1.10
DMF			2.0 mL

[0857] Resin 3 (120 mg, 0.084 mmol) was swelled in DCM (2 mL) for 1 h and drained. A solution of 4-(trifluoromethoxy)iodobenzene 4 (96.8 mg, 0.336 mmol) and Et3N (150 μL, 1.10 mmol) in DMF (2.0 mL) was purged with a stream of N2 bubbles for two minutes and added to the resin. After mixing for 5 min, PdCl2(PPh3)2 (18.0 mg, 0.025 mmol) and CuI (8.0 mg, 0.042 mmol) were added and the mixture shaken for 24 h. The resin was drained, washed with DMF (3×2 mL), DCM (3×2 mL) and cleaved with 10% TFA/DCM (2.0 mL) for 20 min. The solution was collected and the resin was rinsed with additional 10% TFA/DCM (1.0 mL). The cleavage fractions were combined, treated with neat TFA (3.0 mL), stirred for 1 h at rt and concentrated by rotary evaporation to give a crude brown residue. Purification by RP-HPLC (C18 column, CH3CN gradient 5-55%, 0.1% TFA, UV analysis 300 nm, 28 min) and lyophilization of the collected fractions afforded 9.0 mg (25% yield) of (1S)-N-(2-amino-1-hydroxycarbamoyl-ethyl)-4-(4-trifluoromethoxy-phenylethynyl)-benzamide as a white solid. LRMS (ES+) m/z 408.0 (C19H16F3N3O4+H requires 408.11); RP-HPLC (300 nm, 28 min run) 18.0 min.

Example 19

[0858] Synthesis of N-(1-(N-hydroxycarbamoyl)(1S,2R)-2-hydroxypropyl)[4-(4-phenylbuta-1,3-diynyl)phenyl]carboxamide

146
147
148
149
150
151
	Reagent	MW	EQ	g/ml	mmol
	Dibromovinylbenzoic acid (2)	320	1.0	5.76	g	18.0
	Ethynyl-benzene	102	1.4	2.57	g	25.2
	Pd2dba3	915	0.01	164	mg	0.18 (1% cat.)
	TMPP	352	0.04	253	mg	0.72 (4%)
	TEA	101	3.0	7.5	ml	54.0
	DMF			60	ml	degassed with argon

[0859] The 4-(2,2-Dibromo-vinyl)-benzoic acid methyl ester (2) was made by the method of Wang Shen and Le Wang in J.Org.Chem. 1999, 64, 8873-8879.

[0860] A solution of 4-(2,2-dibromo-vinyl)-benzoic acid methyl ester (2) (5.76 g, 18.0 mmol), ethynyl-benzene (2.57 g, 25.2 mmol), Pd2dba3 (164 mg, 0.18 mmol), tris(4-methoxyphenyl) phosphine (TMPP) (253 mg, 0.72 mmol) were dissolved in argon sparged (5 min.) DMF (60 ml). The reaction was sparged with argon for 1 min. TEA (7.5 ml, 54.0 mmol) was added to the stirred reaction mixture that was then heated under argon at 85° C. for 3.5 hours. The reaction was found complete by LCMS. The reaction was cooled to rt and diluted with EtOAc/hexane (1:1) (300 ml). The organic phase was washed with 1M HCl (2×50 ml), 1M NaOH (3×50 ml), water (2×50 ml), sat. brine (50 ml), dried with Na2SO4, filtered and concentrated under reduced pressure to obtain 5.25 g of crude product as an oil. The oil was treated with approximately 20 ml of a solution of 20% EtOAc/hexane that was heated to dissolve the residue. The walls of the flask were washed with the 20% EtOAc/hexane solution (5 ml) that upon cooling gave 1.45 g of pure product (31% yield) as a white solid. The balence of the crude reaction product was purified by flash chromatography using EtOAc (8%)/hexane as eluant. The pure fractions were evaporated and dried in vacuo to give addition product typically 25-30% addition yield.

[0861] 4-(4-Phenyl-buta-1,3-diynyl)-benzoic acid methyl ester (4) was made according to the method of Wang Shen and Sheela A. Thomas in Org.Lett. 2000, 2(18), 2857-2860.

Preparation of 4-(4-Phenyl-buta-1,3-diynyl)-benzoic acid (5)

[0862] A 3M aq. solution of NaOH (20 ml) was added to a stirred solution of methyl ester 4 (1.45 g, 5.6 mmol) in MeOH (100 ml) at rt. The reaction solution was heated to reflux for 45 min. until the reaction turned clear. All of the starting material was gone by TLC and HPLC. The reaction was cooled to rt and some MEOH (˜50 ml) was removed by evaporation under reduced pressure. Water (100 ml) was added to the mixture. Conc. HCl was added dropwise to the stirred solution until acidic by pH paper (pH2). The white precipitate that formed was collected by suction filtration. The solid was washed with water (3×20 ml) and hexane (2×20 ml) to give after drying 1.35 g of product acid 5 in 99% yield.

[0863] Subsequent conversion of compound 5 to compound 7 was performed according to the method described in Example 12 for the synthesis of N-(2-Hydroxy-1-hydroxycarbamoyl-propyl)-4-phenylethynyl-benzamide (compound 5). LCMS MH+363.13.

Example B

[0864] Synthesis of N-[(1S)-1-(aminomethyl)-2-(hydroxyamino)-2-oxoethyl]-4-[4-(4-aminophenyl)buta-1,3-diynyl]benzamide

[0865] Preparation of 2-{4-[4-(4-Amino-phenyl)-buta-1,3-diynyl]-benzoylamino}-3-tert-butoxycarbonylamino-propionic acid methyl ester (2).

152
153
	Reagent	MW	EQ	g/ml	mmol
	H-DAP(Boc)—OMe	254	1.05	5.12	g	20.1
	1,3-diynyl benzoic acid (1)	261.3	1.0	5.0	g	19.1
	HOBT	135.1	1.05	2.72	g	20.1
	EDC	191.71	1.05	3.85	g	20.1
	DIEA	129.25	3.0.	10.5	ml	60.3
	DMF			80	ml

[0866] DIEA (10.5 ml, 60.3 mmol) was added to a stirred solution of 4-[4-(4-Amino-phenyl)-buta-1,3-diynyl]-benzoic acid (1) (5.0 g, 19.1 mmol), HOBT (2.72 g, 20.1 mmol), EDC (3.85 g, 20.1 mmol) in DMF (80 ml). After 2 min., the H-DAP(Boc)-OMe was added in one portion. After 12 hours at rt, the reaction was found complete by LCMS. The reaction was diluted with EtOAc/hexane (4:1) (500 ml). The organic phase was washed with 1N NaOH (2×80 ml), water (2×80 ml), sat. brine (80 ml), dried with Na2SO4, filtered and concentrated under reduced pressure to give crude product. The residue was filtered through a filter plug of silica eluting with EtOAc/hexajie (4:1). The fractions with product were evaporated to give 8.02 g of product in 91% yield. Subsequent conversion of compound 2 to the final hydroxamic acid (for example, Example 892)was performed according to the method described in Example 12 for the synthesis of N-(2-Hydroxy-1-hydroxycarbamoyl-propyl)-4-phenylethynyl-benzamide (compound 5).

Synthesis of 4-(Buta-1,3-diynyl)-benzoic Acid (4) for making 1,3-diynyl analogues (such as Example 20 below)

[0867] 154

Preparation of 4-(4-trimethylsilanyl-buta-1,3-diynyl)-benzoic acid methyl ester (3).

[0868]

155
156
Reagent	MW	Eq.	g/ml	mmol
Methyl 4-iodobenzoate (2)	262.04	1.0	4.510	g	17.2
Trimethylsilylbutadiyne (1)	122.24	2.5	5.240	g	42.8
PdCl2(PPh3)2	701.89	0.04	0.483	g	0.690
CuI	190.44	0.08	0.262	g	1.37
Et3N	101.19	3.0	7.2	mL	52.0
CH3CN			50	mL

[0869] A solution of methyl 4-iodobenzoate 2 (4.510 g, 17.2 mmol), PdCl2(PPh3)2 (483 mg, 0.690 mmol), and CuI (262 mg, 1.37 mmol) in CH3CN (50 mL) was cooled to 0° C. under N2 atmosphere in the absence of light. Triethylamine (7.2 mL, 52.0 mmol) was added, followed by trimethylsilyl-1,3-butadiyne 1 (5.240 g, 42.8 mmol) and the reaction stirred 3 h at 0° C. and 30 h at ambient temperature. Removal of solvent by rotary evaporation afforded a crude black residue that was purified by silica gel chromatography (95:5 hexanes/EtOAc) to give 3.450 g (79% yield) of 4-(4-trimethylsilanyl-buta-1,3-diynyl)-benzoic acid methyl ester 3 as a brown solid, mp=67-68° C.

Preparation of 4-(buta-1,3-diynyl)-benzoic acid (4).

[0870]

157
	158
	Reagent	MW	Eq.	g/ml	mmol
	Methyl ester (3)	252.34	1.0	3.420	g	13.5
	KOH	56.11	4.9	3.700	g	65.9
	H2O			10	mL
	THF			26	mL

[0871] Potassium hydroxide (3.700 g, 65.9 mmol) was dissolved in H2O (10 mL) and added to a solution of 4-(4-trimethylsilanyl-buta-1,3-diynyl)-benzoic acid methyl ester 3 (3.420 g, 13.5 mmol) in THF (26 mL) in the absence of light. After stirring 16 h, the reaction was quenched with 1.0 M HCl (120 mL) and the resulting precipitate was filtered, washed with 1:1 hexanes/benzene (150 mL) and dried in vacuo to afford 2.100 g (91% yield, 98% pure) of 4-(buta-1,3-diynyl)-benzoic acid 4 as a brown solid, mp>230° C. Although diyne 4 was found to be unstable at room temperature it could be stored for several weeks at 0° C. with only small amounts of decomposition observed by TLC. Rf=0.2 (4:1 Hexanes/EtOAc); HPLC (300 nm, 28 min run) 16.0 min; LRMS (ES+) m/z 171.0 (C11H6O2+H requires 171.04).

Synthesis of a 3′-Nitrophenyl-Diacetylenic-Dap Hydroxamic Acid

Example 20

[0872] N-(1-(N-hydroxycarbamoyl)(1S)-2-aminoethyl){4-[4-(3-nitrophenyl)buta-1,3-diynyl]phenyl}carboxamide (6) 159

Preparation of Fmoc-Dap(Boc)-NHOH on hydroxylamine 2-chlorotrityl resin (2).

[0873]

160
Reagent	MW	Eq.	g/mL	mmol
Hydroxylamine resin (1)	0.77 mmol/g	1.0	3.288	g	2.53
Fmoc-Dap(Boc)-OH	426.47	3.0	3.175	g	7.44
HATU	380.25	3.0	2.829	g	7.44
DIEA	129.25	10.0	4.3	mL	24.7
DMF			35	mL

[0874] A suspension of N-Fmoc-hydroxylamine 2-chlorotrityl resin (3.288 g, 2.53 mmol, 0.77 mmol/g, Novabiochem) in DCM (40 mL) was shaken for 2 h and drained. The resin was treated with 20% piperidine in DMF (40 mL) for 1 hour, washed with DMF (2×40 mL), treated a second time with 20% piperidine in DMF (40 mL), washed with DMF (3×40 mL) and DCM (3×40 mL) and drained completely. In a separate flask, Fmoc-Dap(Boc)-OH (3.175 g, 7.44 mmol), HATU (2.829 g, 7.44 mmol) and DIEA (4.3 mL, 24.7 mmol) were dissolved in DMF (35 mL), stirred three minutes and added to the resin. After shaking for 48 h, the mixture was drained, washed with DMF (4×40 mL) and DCM (4×40 mL) and dried in vacuo to give 3.530 g of a yellow resin.

Preparation of (S)-N-(2-N-Fmoc-amino-1-hydroxycarbamoyl-ethyl)-4-buta-1,3-diynyl-benzamide on hydroxylamine 2-chlorotrityl resin (4).

[0875]

161
	162
Reagent	MW	Eq.	g/mL	mmol
Fmoc-Dap(Boc)/resin (2)	0.71 mmol/g	1.0	3.530	g	2.53
Butadiynyl benzoic acid (3)	170.16	2.5	1.076	g	6.32
EDCI	191.71	3.0	1.457	g	7.60
HOBt	135.13	3.0	1.048	g	7.75
DIEA	129.25	5.0	2.2	mL	12.6
DCM			25	mL
DMF			5	mL

[0876] The resin 2 (3.530 g, 2.53 mmol, 0.71 mmol/g) was swelled in DCM (40 mL) for 2 h and drained. The resin was treated with 20% piperidine in DMF (40 mL) for 1 hour, washed with DMF (4×40 mL) and DCM (4×40 mL) and drained completely. In a separate flask, 4-buta-1,3-diynyl-benzoic acid 3 (1.076 g, 6.32 mmol), EDCI (1.457 g, 7.60 mmol), HOBt (1.048 g, 7.75 mmol) and DIEA (2.2 mL, 12.6 mmol) were dissolved in DCM (25 mL) and DMF (5 mL), stirred 45 min and added to the resin. After shaking for 48 h, the mixture was drained, washed with DMF (4×40 mL) and DCM (4×40 mL) and dried in vacuo to give 3.35 g of a pale brown resin.

Preparation of (S)-N-(2-amino-1-hydroxycarbamoyl-ethyl)-4-[4-(3-nitro-phenyl)-buta-1,3-diynyl]-benzamide (6).

[0877]

163
	164
	Reagent	MW	Eq.	g/mL	mmol
	Diacetylene on resin (4)	0.77 mmol/g	1.0	176	mg	0.135
	1-Iodo-3-nitrobenzene (5)	249.01	3.5	118	mg	0.474
	PdCl2(PPh3)2	701.89	0.07	6.0	mg	0.009
	CuI	190.44	0.38	10.0	mg	0.052
	Et3N	101.19	10.6	200	μL	1.43
	DMF			3.0	mL

[0878] Resin 4 (176 mg, 0.135 mmol) was swelled in DCM (3 mL) for 1 h and drained. A solution of 1-iodo-3-nitrobenzene 5 (118 mg, 0.474 mmol) and Et3N (200 μL, 1.43 mmol) in DMF (3.0 mL) was purged with a stream of N2 bubbles for two minutes and added to the resin. After mixing for 5 min, PdCl2(PPh3)2 (6.0 mg, 0.009 mmol) and CuI (10.0 mg, 0.052 mmol) were added and the mixture shaken for 36 h. The resin was drained, washed with DMF (4×3 mL), DCM (4×3 mL) and cleaved with 10% TFA/DCM (2 mL) for 20 min. The solution was collected and the resin was rinsed with additional 10% TFA/DCM (2 mL). The cleavage fractions were combined, treated with neat TFA (4.0 mL), stirred for 1 h at rt and concentrated by rotary evaporation to give a crude brown residue. Purification by RP-HPLC (C18 column, CH3CN gradient 5-65%, 0.1% TFA, UV analysis 300 nm, 30 min) and lyophilization of the collected fractions afforded 12.0 mg (22%) of 470 as a white solid. LRMS (ES+) m/z 392.9 (C20H16N4O5+H requires 393.11); RP-HPLC (300 nm, 30 min run) 14.9 min.

Synthesis of 4′-Benzamide Diacetylene Dap Hydroxamic Acid

Example 21

[0879] N-((2S)-amino-1-hydroxycarbamoyl-ethyl)-4-{4-[4-(2-amino-ethylcarbamoyl)-phenyl]-buta-1,3-diynyl}-benzamide (3) 165

Preparation of N-((2S)-amino-1-hydroxycarbamoyl-ethyl)-4-{4-[4-(2-amino-ethylcarbamoyl)-phenyl]-buta-1,3-diynyl}-benzamide (3)

[0880]

Reagent	MW	Eq.	g/mL	mmol
Alkyne on resin (1)	0.77 mmol/g	1.0	145 mg	0.111
4-Ethynylbenzamide (2)	430.54	2.6	124 mg	0.288
PdCl2(PPh3)2	701.89	0.3	21 mg	0.030
CuI	190.44	1.0	22 mg	0.110
Et3N	101.19	6.5	100 μL	0.72
DMF			2.0 mL

[0881] Resin 1 (145 mg, 0.111 mmol) was swelled in DCM (2 mL) for 1 h and drained. A solution of 4-ethynylbenzamide 2 (124 mg, 0.288 mmol) and Et3N (100 μL, 0.72 mmol) in DMF (2.0 mL) was added and the resin agitated for 5 min. A mixture of PdCl2(PPh3)2 (21 mg, 0.030 mmol) and CuI (22 mg, 0.110 mmol) was added and the resin was agitated for 60 h. The resin was drained, washed with DMF (3×2 mL), DCM (3×2 mL) and cleaved with 10% TFA/DCM (1.5 mL) for 20 min. The solution was collected and the resin was rinsed with additional 10% TFA/DCM (1.0 mL). The cleavage fractions were combined, treated with neat TFA (2.0 mL), stirred for 1 h at rt and concentrated by rotary evaporation to give a crude brown residue. Purification by RP-HPLC (C18 column, CH3CN gradient 5-55%, 0.1% TFA, UV analysis 300 nm, 26 min) and lyophilization of the collected fractions afforded 2.6 mg (5% yield) of N-((2S)-amino-1-hydroxycarbamoyl-ethyl)-4-{4-[4-(2-amino-ethylcarbamoyl)-phenyl]-buta-1,3-diynyl}-benzamide. LRMS (ES+) m/z 434.0 (C23H23N5O4+H requires 434.19); RP-HPLC (300 nm, 26 min run) 15.3 min.

Synthesis of N-[4-Butadiynyl-benzoyll-Thr(tBu) on Resin (Continued to make Examples 22 and 23)

[0882] 166

[0883] Preparation of (2S, 3R)-2-N-Fmoc-amino-3-tert-butoxy-N-hydroxy-butyramide on hydroxylamine 2-chlorotrityl resin (2).

167
	168
Reagent	MW	Eq.	g/mL	mmol
Hydroxylamine resin (1)	0.77 mmol/g	1.0	3.188	g	2.45
Fmoc-Thr(tBu)-OH	397.50	3.0	2.927	g	7.36
HATU	380.25	3.0	2.798	g	7.36
DIEA	129.25	10.0	4.3	mL	24.6
DMF			40	mL

[0884] A suspension of N-Fmoc-hydroxylamine 2-chlorotrityl resin (3.188 g, 2.45 mmol, 0.77 mmol/g, Novabiochem) in DCM (40 mL) was shaken for 2 h and drained. The resin was treated with 20% piperidine in DMF (40 mL) for 1 hour, washed with DMF (2×40 mL), treated a second time with 20% piperidine in DMF (40 mL), washed with DMF (3×40 mL) and DCM (3×40 mL) and drained completely. In a separate flask, Fmoc-Thr(tBu)-OH (2.927 g, 7.36 mmol), HATU (2.798 g, 7.36 mmol) and DIEA (4.3 mL, 24.6 mmol) were dissolved in DMF (40 mL), stirred three minutes and added to the resin. After shaking for 24 h, the mixture was drained, washed with DMF (4×40 mL) and DCM (4×40 mL) and dried in vacuo to give 3.500 g of a yellow resin.

Preparation of 4-buta-1,3-diynyl-N-(2-tert-butoxy-1-hydroxycarbamoyl-propyl)-benzamide on hydroxylamine 2-chlorotrityl Resin (4).

[0885]

169
	170
	Reagent	MW	Eq.	g/mL	mmol
	Fmoc-threonine/resin (2)	0.77 mmol/g	1.0	2.030	g	1.56
	Butadiynyl benzoic acid (3)	170.16	2.3	0.617	g	3.63
	EDCI	191.71	2.8	0.834	g	4.35
	HOBt	135.13	2.8	0.588	g	4.35
	DIEA	129.25	3.7	1.0	mL	5.7
	DCM			15	mL
	DMF			4	mL

[0886] The resin 2 (2.030 g, 1.56 mmol, 0.77 mmol/g) was swelled in DCM (20 mL) for 2 h and drained. The resin was treated with 20% piperidine in DMF (20 mL) for 1 hour, washed with DMF (4×20 mL) and DCM (4×20 mL) and drained completely. In a separate flask, 4-buta-1,3-diynyl-benzoic acid 3 (0.617 g, 3.63 mmol), EDCI (0.834 g, 4.35 mmol), HOBt (0.588 g, 4.35 mmol) and DIEA (1.0 mL, 5.7 mmol) were dissolved in DCM (15 mL) and DMF (4 mL), stirred 45 min and added to the resin. After shaking for 36 h, the mixture was drained, washed with DMF (4×20 mL) and DCM (4×20 mL) and dried in vacuo to give 1.900 g of a pale brown resin.

Synthesis of Diacetylenic Threonine Hydroxamic Acids

Example 22

[0887] (2S,3R)-4-[4-(3-aminomethyl-phenyl)-buta-1,3-diynyl]-N-(2-hydroxy-1-hydroxycarbamoyl-propyl)-benzamide (3).

171
	172
	Reagent	MW	Eq.	g/mL	mmol
	Diacetylene on resin (1)	0.77 mmol/g	1.0	100	mg	0.077
	3-Iodobenzylamine HCl (2)	269.51	4.0	83.0	mg	0.308
	PdCl2(PPh3)2	701.89	0.2	11.0	mg	0.016
	CuI	190.44	0.5	7.0	mg	0.037
	Et3N	101.19	23	250	μL	1.80
	DMF			1.5	mL

[0888] Resin 1 (obtained from previous synthesis) (100 mg, 0.077 mmol) was swelled in DCM (2 mL) for 1 h and drained. A solution of 3-iodobenzylamine hydrochloride 2 (83.0 mg, 0.308 mmol) and Et3N (250 μL, 1.80 mmol) in DMF (1.5 mL) was purged with a stream of N2 bubbles for two minutes and added to the resin. After mixing for 5 min, PdCl2(PPh3)2 (11.0 mg, 0.016 mmol) and CuI (7.0 mg 0.037 mmol) were added and the mixture shaken for 36 h. The resin was drained, washed with DMF (4×2 mL), DCM (4×2 mL) and cleaved with 10% TFA/DCM (1.5 mL) for 20 min. The solution was collected and the resin was rinsed with additional 10% TFA/DCM (1.5 mL). The cleavage fractions were combined, treated with neat TFA (3.0 mL), stirred for 1 h at rt and concentrated by rotary evaporation to give a crude brown residue. Purification by RP-HPLC (C18 column, CH3CN gradient 5-65%, 0.1% TFA, UV analysis 300 nm, 28 min) and lyophilization of the collected fractions afforded 4.3 mg (14%) of (2S,3R)-4-[4-(3-aminomethyl-phenyl)-buta-1,3-diynyl]-N-(2-hydroxy-1-hydroxycarbamoyl-propyl)-benzamide as a white solid. LRMS (ES+) m/z 392.0 (C22H21N3O4+H requires 392.15); RP-HPLC (300 nm, 28 min run) 10.0 min.

Synthesis of Diacetylenic Benzylamine Analogues

Example 23

[0889] (1S, 2R)-N-2-bydroxy-1-hydroxycarbamoyl-propyl)-4-[4-(4-meorphoin-4-ylmethyl-phenyl)-buta-1,3-diynyl]-benzamide (4) 173

Preparation of Threonine Diacetylenic Benzaldehyde on Resin (3).

[0890]

174
	175
	Reagent	MW	Eq.	g/mL	mmol
	Diacetylene on resin (1)	0.77 mmol/g	1.0	1.00	g	0.770
	4-Iodobenzaldehyde	232.00	4.0	715	mg	3.081
	PdCl2(PPh3)2	701.89	0.07	40.0	mg	0.057
	CuI	190.44	0.13	19.0	mg	0.100
	Et3N	101.19	9.3	1.00	mL	7.17
	DMF			20.0	mL

[0891] Resin 1 (1.00 g, 0.77 mmol) was pre-swelled in DCM (25 mL) for 14 h and drained. A solution of 4-iodobenzaldehyde 2 (715 mg, 3.08 mmol) and Et3N (1.00 mL, 7.17 mmol) in DMF (20 mL) was purged with N2 for two minutes and added to the resin. After mixing for 5 min, PdCl2(PPh3)2 (40.0 mg, 0.057 mmol) and CuI (19.0 mg, 0.100 mmol) were added and the reaction shaken for 48 h. The resin was drained, washed with DMF (4×20 mL), DCM (4×20 mL) and dried in vacuo to give 1.100 g of a dark yellow resin.

Preparation of (1S, 2R)-N-2-hydroxy-1-hydroxycarbamoyl-propyl)-4-[4-(4-morpholin-4-ylmethyl-phenyl)-buta-1,3-diynyl]-benzamide (4).

[0892]

176
	177
	Reagent	MW	Eq.	mg/μl	mmol
	Benzaldehyde on resin (3)	0.77 mmol/g	1.0	188	mg	0.141
	Morpholine	87.12	6.0	75	μL	0.860
	NaCNBH3	62.84	4.5	40	mg	0.637
	Trimethyl orthoformate	106.12	6.5	100	μL	0.914
	Acetic acid	60.05	12.3	100	μL	1.750
	THF			3.0	mL
	MeOH			1.0	mL

[0893] A solution of morpholine (75 μL, 0.860 mmol) and trimethyl orthoformate (100 μL, 0.914 mmol) in THF (3.0 mL) was added to a Teflon-lined screw-capped vial containing the resin-bound diacetylenic benzaldehyde 3. The resin was agitated for 10 min, treated successively with acetic acid (100 μL, 1.75 mmol) and a solution of NaCNBH3 (40.0 mg, 0.637 nmmol) in MeOH (1.0 mL) and shaken for 44 h. The resin was filtered, washed with DMF (3×3 mL) and DCM (3×3 mL) and drained. Cleavage from the resin was achieved by treatment with 10% TFA/DCM (2.0 mL) and shaking 20 min. The solution was collected and the resin was rinsed with additional 10% TFA/DCM (2.0 mL). The cleavage fractions were combined, treated with neat TFA (3.0 mL), stirred for 1 h at rt and concentrated by rotary evaporation to give a crude yellow residue. Purification by RP-HPLC (C18 column, CH3CN gradient 5-35%, 0.1% TFA, UV analysis 300 nm, 18 min) and lyophilization of the collected fractions afforded 19.0 mg (29%) of 472 as a fluffy yellow solid. LRMS (ES+) m/z 462.0 (C26H27N3O5+H requires 462.10); HPLC (300 nm, 18 min run) 10.3 min.

Synthesis of 4′-Benzamide Diacetylene Threonine Hydroxamic Acid

Example 24

[0894] (1S,2R)-N-(2-hydroxy-1-hydroxycarbamoyl-propyl)-4-{4-[4-(2-amino-ethylcarbamoyl)-phenyl]-buta-1,3-diynyl}-benzamide (5) 178

Preparation of N-(2-trityl-amino-ethyl)-4-ethynyl-benzamide (3).

[0895]

Reagent	MW	Eq.	g/mL	mmol
4-Ethynylbenzoic acid (1)	146.14	1.0	0.292 g	2.00
N-Trityl ethylenediamine	302.41	1.3	0.810 g	2.67
EDCI	191.71	1.0	0.382 g	2.00
HOBt	135.13	3.0	0.270 g	2.00
DIEA	129.25	4.0	1.40 mL	8.00
DMF			10.0 mL

[0896] To a solution of 4-ethynylbenzoic acid 1 (292 mg, 2.00 mmol), EDCI (382 mg, 2.00 mmol), and HOBt (270 mg, 2.00 mmol) in DMF (10 mL) was added N-trityl ethylenediamine 2 (810 mg, 2.67 mmol) and DIEA (1.4 mL, 8.0 mmol). The reaction mixture was stirred 24 h, diluted with EtOAc (200 mL), washed with 0.5 M HCl (60 mL), saturated NaHCO3 (2×60 mL), H2O (4×60 mL), dried over MgSO4 and concentrated to give 836 mg (97% yield) of N-(2-trityl-amino-ethyl)-4-ethynyl-benzamide 3 as a white solid, mp 50-51° C. Rf=0.40 (1:1 Hexanes/EtOAc).

Preparation of (1S,2R)-N-(2-hydroxy-1-hydroxycarbamoyl-propyl)-4-{4-[4-(2-amino-ethylcarbamoyl)-phenyl]-buta-1,3-diynyl}-benzamide (5).

[0897]

Reagent	MW	Eq.	g/mL	mmol
Alkyne on resin (4)	0.77 mmol/g	1.00	150 mg	0.116
4-Ethynylbenzamide (3)	430.54	3.00	151 mg	0.350
PdCl2(PPh3)2	701.89	0.25	21 mg	0.030
CuI	190.44	1.25	28 mg	0.147
Et3N	101.19	9.50	150 μL	1.10
DMF			2.0 mL

[0898] Resin 4 (150 mg, 0.116 mmol) was swelled in DCM (2 mL) for 1 h and drained. A solution of 4-ethynylbenzamide 3 (151 mg, 0.350 mmol) and Et3N (150 μL, 1.10 mmol) in DMF (2.0 mL) was added and the resin agitated for 5 min. A mixture of PdCl2(PPh3)2 (21 mg, 0.030 mmol) and CuI (28 mg, 0.147 mmol) was added and the resin was agitated for 60 h. The resin was drained, washed with DMF (3×2 mL), DCM (3×2 mIL) and cleaved with 10% TFA/DCM (1.5 mL) for 20 min. The solution was collected and the resin was rinsed with additional 10% TFA/DCM (1.0 mL). The cleavage fractions were combined, treated with neat TFA (2.0 miL), stirred for 1 h at rt and concentrated by rotary evaporation to give a crude brown residue. Purification by RP-HPLC (C18 column, CH3CN gradient 5-65%, 0.1% TFA, UV analysis 300 nm, 26 min) and lyophilization of the collected fractions afforded 2.0 mg (4% yield) of (1S,2R)-N-(2-hydroxy-1-hydroxycarbamoyl-propyl)-4-{4-[4-(2-amino-ethylcarbamoyl)-phenyl]-buta-1,3-diynyl}-benzamide. LRMS (ES+) m/z 449.1 (C24H24N4O5 +H requires 449.18); RP-HPLC (300 nmn, 26 min run) 17.0 min.

Synthesis of 3′-Pyridine Diacetylene Threonine Hydroxamic Acid

Example 25

[0899] N-((2R)-hydroxy-(1S)-hydroxycarbamoyl-propyl)-4-(4-pyridin-3-yl-buta-1,3-diynyl)-benzamide (3) 179

[0900] Preparation of N-((2R)-hydroxy-(1S)-hydroxycarbamoyl-propyl)-4-(4-pyridin-3-yl-buta-1,3-diynyl)-benzamide

Reagent	MW	Eq.	g/mL	mmol
Alkyne on resin (1)	0.77 mmol/g	1.0	142 mg	0.109
3-Ethynylpyridine (2)	103.12	3.4	38 mg	0.368
PdCl2(PPh3)2	701.89	0.3	22 mg	0.031
CuI	190.44	1.2	25 mg	0.131
Et3N	101.19	13	200 μL	1.40
DMF			2.0 mL

[0901] Resin 1 (142 mg, 0.109 mmol) was swelled in DCM (2 mL) for 1 h and drained. A solution of 3-ethynylpyridine 2 (38 mg, 0.368 mmol) and Et3N (200 μL, 1.4 mmol) in DMF (2 mL) was added and the resin agitated for 5 min. A mixture of PdCl2(PPh3)2 (22 mg, 0.031 mmol) and CuI (25 mg, 0.131 mmol) was added and the resin was agitated for 72 h. The resin was drained, washed with DMF (3×2 mL), DCM (3×2 mL) and cleaved with 10% TFA/DCM (1.5 mL) for 20 min. The solution was collected and the resin was rinsed with additional 10% TFA/DCM (1.0 mL). The cleavage fractions were combined, treated with neat TFA (2.0 mL), stirred for 1 h at rt and concentrated by rotary evaporation to give a crude brown residue. Purification by RP-HPLC (C18 column, CH3CN gradient 5-65%, 0.1% TFA, UV analysis 300 nm, 24 min) and lyophilization of the collected fractions afforded 4.4 mg (11% yield) of N-((2R)-hydroxy-(1S)-hydroxycarbamoyl-propyl)-4-(4-pyridin-3-yl-buta-1,3-diynyl)-benzamide. LRMS (ES+) m/z 364.0 (C20H17N3O4+H requires 364.13); RP-HPLC (300 nm, 24 min run) 11.2 min.

Example 26

[0902] Synthesis of N-(1-(N-hydroxycarbamoyl)(1S,2R)-2-hydroxy propyl){4-[4-(6-morpholin4-yl(3-pyridyl))buta-1,3-diynyl]phenyl}carboxamide (5)

180
181
182
	183
	Reagent	MW	EQ	g/ml	mmol
	Dibromovinylbenzoic acid (1)	320	1.0	9.6	g	30.0
	2-Chloro-5-ethynyl-pyridine	138	1.3	5.43	g	39.0
	Pd2dba3	915	0.01	274	mg	0.3 (1% cat.)
	TMPP	352	0.04	422	mg	1.2 (4%)
	TEA	101	3.0	12.5	ml	90.0
	DMF			90	ml	degassed with argon

Preparation of 4-[4-(6Chloro-pyridin-3-yl)-buta-1,3-diynyl]-benzoic acid methyl ester

[0903] 184

[0904] 4-[4-(6-Chloro-pyridin-3-yl)-buta-1,3-diynyl]-benzoic acid was made according to the method of Wang Shen and Sheela A. Thomas in Org.Lett. 2000, 2(18), 2857-2860.

[0905] A solution of 4-(2,2-dibromo-vinyl)-benzoic acid methyl ester (1) (9.6 g, 30.0 mmol), ethynyl-pyridine (2) (5.43 g, 39.0 mmol), Pd2dba3 (274 mg, 0.3 mmol), tris(4-methoxyphenyl) phosphine (TMPP) (422 mg, 1.2 mmol) were dissolved in argon sparged (5 min.) DMF (60 ml). The reaction was sparged with argon for 1 min. TEA (12.5 ml, 90.0 mmol) was added to the stirred reaction mixture that was then heated under argon at 85° C. for 3 hours. The reaction was found complete by LCMS. The reaction was cooled to rt and diluted with EtOAc/hexane (1:1) (500 ml). The organic phase was washed with 1 M NaOH (2×80 ml), water (2×80 ml), sat. brine (80 ml), dried with Na2SO4, filtered concentrated under reduced pressure to give crude product. The residue was filtered through a filter plug of silica eluting with EtOAc/hexane (1:1). The fractions with product were evaporated to give 9.06 g of product in good purity (˜96% pure). The material was taken on without further purification.

Preparation of 4-[4-(6-Chloro-pyridin-3-yl)-buta-1,3-diynyl]-benzoic Acid (3)

[0906] A 6M aq. solution of NaOH (15 ml) was added to a stirred solution of 4-[4-(6-Chloro-pyridin-3-yl)-buta-1,3-diynyl]-benzoic acid methyl ester. (9.06 g, 30 mmol) in MeOH (350 ml) at rt. The reaction solution was heated to reflux for 3 hours. The reaction stayed a mixture and did not turn clear. HPLC and LCMS indicated that the reaction was forming side products. The reaction was cooled to rt and some MeOH (˜200 ml) was removed by evaporation under reduced pressure. Water (400 ml) was added to the mixture. Conc. HCl was added dropwise to the stirred solution until acidic by pH paper (pH2). The yellow precipitate that formed was collected by suction filtration. The solid was washed with water (3×20 ml) and hexane (2×20 ml) to give the crude product. HPLC indicated that there was approximately 40% product in the mixture. The crude reaction product was purified by flash chromatography using EtOAc (8-10%)/hexane as eluant. The pure fractions were evaporated and dried in vacuo to give 4.2 g of product 3 in 50% yield.

Preparation of [4-[4-(6-chloro-pyridin-3-yl)-buta-1,3-diynyl]-benzoyl]-HN-Thr(OtBu)-hydroxamic acid trityl resin (4)

[0907] 185

4-[4-(6-Chloro-pyridin-3-yl)-buta-1,3-diynyl]-beiizoic acid (3) was coupled to a tert-butyl protected threonine pre-loaded on hydroxylamine 2-chlorotrityl resin following the same procedure as used for Example 26. The coupling employed DIC and HOBT. [N-Fmoc-hydroxylamine 2-chlorotrityl resin was purchased from Novabiochem cat.# 01-64-0165.]

Preparation of N-(2-Hydroxy-1-hydroxycarbamoyl-propyl)-4-[4-(6-morpholin-4-yl-pyridin-3-yl)-buta-1,3-diynyl]-benzamide (5)

[0908] 186

[0909] A solution of morpholine (300 uL) in NMP (1 ml) was added to a vial containing the 2-cloropyridine resin (4) (150 mg, 0.12 mmol). The reaction mixture was purged with argon and heated to 85-90° C. for 24 hours. The resin was drained and washed with DMF and DCM alternately several times. The product was cleaved from the resin through treatment with a TFA/water solution (80:20) (1.5 ml) for 45 min. The resin was filtered and washed with fresh TFA/water solution (80:20) (0.5 ml). The combined TFA and organic fractions were diluted with CH3CN/water (1:1) (10 ml), water (2 ml) and lyophilized. The crude product was purified by prep. HPLC. The crude product was dissolved in DMSO (1 ml), passed through a Teflon syringe filter, and the clear filtrate was injected on a preparative HPLC. The purification used a 20×50 mm Ultro 120 C18 column running a 22 ml/min 2% gradient (AcCN/water, 0.1% TFA) for 16 min. The purified fractions were lyophilized to dryness to give 2.2 mg of pure product as the TFA salt (˜32% yield).

Example 27

[0910] Synthesis of 4-[4-(4-Amino-phenyl)-buta-1,3-diynyl]-N-(2-hydroxy-1-hydroxycarbamoyl-propyl)-benzamide (4) 187

[0911] Preparation of 2- {4-[4-(4-Amino-phenyl)-buta-1,3-diynyl]-benzoylamino}-3-tert-butoxycarbonyloxy-butyric hydroxamic acid trityl resin (3).

188
189
190
Reagent	MW	EQ	g/ml	mmol
H-Thr(Boc)-NHO-Trt Resin (1)		1.0	5.8	g	4.47
1,3-diynyl benzoic acid (2)	261.3	1.4	1.64	g	6.25
HOBT	135.1	1.4	0.85	g	6.25
DIC	126.2	1.4	0.98	ml	6.25
DIEA	129.25	3.5	2.7	ml	15.6
DMF			50	ml

[0912] DIEA (2.7 ml, 15.6 mmol) was added to a stirred solution of 4-[4-(4-Amino-phenyl)-buta-1,3-diynyl]-benzoic acid (2) (1.64 g, 6.3 mmol), HOBT (0.85 g, 6.3 mmol), DIC (0.98 ml, 6.3 mmol) in DMF (50 ml). After 2 min., the Thr hydroxylamine resin (5.8 g, 4.5 mmol) was added in one portion. [N-Fmoc-hydroxylamine 2-chiorotrityl resin was purchased from Novabiochem cat.# 01-64-0165.] After 12 hours at rt, the reaction was found complete by LCMS. The resin was drained and washed with DMF and DCM alternately 3 times each. The product on resin 3 was used as is in subsequent reactions without further treatment.

Preparation of 4-]4-(4-Ainino-phenyl)-buta-1,3-diynyl]-N-(2-hydroxy-1-hydroxy carbamoyl-propyl)-benzamide (4)

[0913]

191
192
Reagent	MW	EQ	g/ml	mmol
1,3-diynyl benzoic Tbr Resin (3)		1.0	120	mg	0.09
TFA/water (80:20)			1.5	ml

[0914] The product (4) (120 mg, 0.09 mmol) was cleaved from the resin through treatment with a TFA/water solution (80:20) (1.5 ml) for 45 min. The resin was filtered and washed with fresh TFA/water solution (80:20) (0.5 ml). The combined TFA and organic fractions were diluted with CH3CN/water (1:1) (10 ml), water (2 ml) and lyophilized. The crude product was purified by prep. HPLC. The crude product was dissolved in DMSO (1 ml), passed through a Teflon syringe filter, and the clear filtrate was injected on a preparative HPLC. The purification used a 20×50 mm Ultro 120 C18 column running a 22 ml/min 2% gradient (AcCN/water, 0.1% TFA) for 16 min. The purified fractions were lyophilized to dryness to give 2.2 mg of pure product as the TFA salt. The product (4) was lyophilized again from CH3CN/water with 10 equivalents of HCl to remove most of the TFA to yield 2 mg of product as the HCl salt (˜53% yeild).

Example 28

[0915] Synthesis of 4-{4-[4-(2-Dimethylamino-acetylamino)-phenyl]-buta-1,3-diynyl}-N-(2-hydroxy-1-hydroxycarbamoyl-propyl)-benzamide (6) (Continued from Compound 3 of Example 27 Above) 193

Preparation of 2-{4-(4-[4-(2-Bromo-acetylamino)-phenyl]-buta-1,3-diynyl}-benzoylamino)-3-tert-butoxycarbonyloxy-butyric acid hydroxamate trityl resin (5).

[0916]

194
195
Reagent	MW	EQ	g/ml	mmol
Amino 1,3-diynyl benzoic Thr		1.0	0.75	g	0.578
Trt Resin (3)
Bromo-acetyl chloride	157.4	8.0	0.728	g	4.62
Lutidine	107	10.0	1.07	ml	9.24
DMF			6	ml

[0917] A solution of bromo-acetyl chloride (0.75 g, 0.58 mmol) in DCM (2 ml) was added to a mixture of 2- {4-[4-(4-Amino-phenyl)-buta-1,3-diynyl]-benzoylamino}-3-tert-butoxycarbonyloxy-butyric acid hydroxamate Trt Resin (3) (0.75 g, 0.58 mmol), lutidine (1.1 ml, 9.2 mmol) and DCM (4 ml) at rt with shaking. After shaking for 1.5 hours, the reaction was found complete by LCMS. The resin was drained and washed with DCM (2×10 ml), DMF (3×10 ml) and DCM (3×10 ml) again. The resin was drained and dried in vacuo. The product on resin 5 was used as is in subsequent reactions without further treatment.

Preparation of 4-{4-[4-(2-Dimethylamino-acetylamino)-phenyl]-buta-1,3-diynyl}-N-(2-hydroxy-1-hydroxycarbamoyl-propyl)-benzamide (6).

[0918]

196
197
Reagent	MW	EQ	g/ml	mmol
Bromo acetic Thr Trt Resin (5)		1.0	125	mg	0.093
Dimethyl amine	45.08		0.2	ml	excess
NMP			1.2	ml

[0919] A solution of dimethyl amine (0.2 ml) in NMP (1.2 ml) was added to bromo acetic Thr Trt Resin (5) (125 mg, 0.09 mmol) at rt with shaking. After shaking for 12 hours, the reaction was found complete by LCMS. The resin was drained and washed with DCM (2×10), DMF (3×10) and DCM (3×10) again. The product (6 ml) was cleaved from the resin through treatment with a TFA/water solution (80:20) (1.5 ml) for 45 min. The resin was filtered and washed with fresh TFA/water solution (80:20) (0.5 ml). The combined TFA and organic fractions were diluted with CH3CN/water (1:1) (10 ml), water (2 ml) and lyophilized. The crude product was purified by prep. HPLC. The crude product was dissolved in DMSO (1 ml), passed through a Teflon syringe filter, and the clear filtrate was injected on a preparative HPLC. The purification used a 20×50 mm Ultro 120 C18 column running a 22 ml/min 2% gradient (AcCN/water, 0.1% TFA) for 16 min. The purified fractions were lyophilized to dryness to give 2 mg of pure product as the TFA salt (˜37% yeild).

Example 29

[0920] Synthesis of 4-{4-[4-(2-Amino-4-methyl-pentanoylamino)-phenyl]-buta-1,3-diynyl}-N-(2-hydroxy-1-hydroxycarbamoyl-propyl)-benzamide (7) (Continued from Compound 3 of Example 27 Above)

198
199
Reagent	MW	EQ	g/ml	mmol
Amino 1,3-diynyl benzoic Thr Trt		1.0	125	mg	0.093
Resin (3)
Fmoc-L-leucine	353.42	4.0	0.135	g	0.384
HATU	380	4.0	0.146	g	0.384
DIEA	129.25	8.0	133	ul	0.768
DMF			1.5	ml

[0921] A solution of Fmoc-L-leucine (0.135 g, 0.38 mmol), HATU (0.146 g, 0.38 mmol) in DMF (1.5 ml) was made. After 2 min. of shaking, the activated acid was added to the amino 1,3-diynyl benzoic Thr Trt Resin (3) (125 mg, 0.09 mmol) at rt with shaking. After shaking for 36 hours, the reaction was drained and washed with DCM (2×4 ml), DMF (3×4 m1) and DCM (3×4 ml) again. The resin was treated with 20% piperizine in DMF (4 ml ) for 2 hours twice. The resin was drained and washed with DMF and DCM alternately several times. The product was cleaved from the resin through treatment with a TFA/water solution (80:20) (1.5 ml) for 45 min. The resin was filtered and washed with fresh TFA/water solution (80:20) (0.5 ml). The combined TFA and organic fractions were diluted with CH3CN/water (1:1) (10 ml), water (2 ml) and lyophilized. The crude product was purified by prep. HPLC. The crude product was dissolved in DMSO (1 ml), passed through a Teflon syringe filter, and the clear filtrate was injected on a preparative HPLC. The purification used a 20×50 mm Ultro 120 C18 column running a 22 ml/min 2% gradient (AcCN/water, 0.1% TFA) for 16 min. The purified fractions were lyophilized to dryness to give 1.7 mg of pure product (7) as the TFA salt (˜30% yield).

Examples 30-1307 of Table 1 were Synthesized According to the Synthetic Schemes Described Above.

Biological Protocols and Data

[0922] P. aeruginosa LpxC Inhibition Assay

[0923] The assay followed the general method of Hyland et al (Journal of Bacteriology 1997 179, 2029-2037: Cloning, expression and purification of UDP-3-O-acyl-GlcNAc deacetylase from Pseudomonas aeruginosa: a metalloamidase of the lipid A biosynthesis pathway) and the radiolabeling procedure is according to Kline et al. supra. Briefly, samples were incubated with 2 nM P. aeruginosa LpxC and 150 nM [3H-Ac]-UDP-3-O-(R-3-hydroxydecanoyl)-GlcNAc in a total volume of 50 uL for 90 min at room temperature. Reactions were carried out in 96-well polypropylene plates in 50 mM sodium phosphate buffer, pH 7.5, containing 1 mg/mL BSA. Reactions were stopped by the addition of 180 uL of a 3% suspension of activated charcoal powder in 100 mM sodium acetate, pH 7.5. Supernatants were clarified by centrifugation. A portion of the clarified supernatant, containing the enzymatically released [3H]-acetate, was transferred to opaque white 96-well plates containing scintillation fluid. The radioactivity was measured in a Perkin-Elmer/Wallac Trilux Microbeta counter. Control reactions to which 5 mM EDTA had been added were included with each run to determine nonspecific tritium release.

[0924] Bacterial Screens and Cultures

[0925] Bacterial isolates were cultivated from −70° C. frozen stocks by two consecutive overnight passages at 35° C. in ambient air on 5% blood agar (Remel, Lenexa, Kans.). Clinical isolates tested were from a collection composed of isolates collected during clinical trials and recent clinical isolates obtained from various geographically diverse hospitals in the US. Quality control and primary panel strains were from the American Type Culture Collection (ATCC; Rockville, Md.), with the exception of P. aeruginosa PAO200, a strain with a deletion of the mexABoprM genes that was received from Dr. H. Schweizer. This strain does not express the principal multidrug efflux pump and is hypersusceptible to many antibacterials. Strain Z61 (ATCC 35151) is also hypersusceptible to antibacterials. It is thought that the hypersusceptibility of this strain is the result of increased permeability of its outer membrane (Angus B L et al, Antimicrobial Agents and Chemotherapy 1982 21, 299-309: Outer membrane permeability in Pseudomonas aeruginosa: Comparison of a wild-type with an antibacterial-supersusceptible mutant).

[0926] Susceptibility Testing

[0927] Minimum Inhibitory Concentrations (MICs) were determined by the broth microdilution method in accordance with the National Committee for Clinical Laboratory Standards (NCCLS) guidelines. In brief, organism suspensions were are adjusted to a 0.5 McFarland standard to yield a final inoculum between 3×105 and 7×105 colony-forming units (CFU)/mL. Drug dilutions and inocula were made in sterile, cation adjusted Mueller-Hinton Broth (Remel). An inoculum volume of 100 μl was added to wells containing 100 μl of broth with 2-fold serial dilutions of drug. All inoculated microdilution trays were incubated in ambient air at 35° C. for 18-24 hours. Following incubation, the lowest concentration of the drug that prevented visible growth was recorded as the MIC. Performance of the assay was monitored by the use of laboratory quality-control strains against tobramycin, that has a defined MIC spectrum, in accordance with NCCLS guidelines.

Efficacy in Mouse Model of Systemic Pseudomonas aeruginosa Infection

[0928] Female Balbic mice were injected intraperitoneally with 0.5 ml of a bacterial suspension containing approximately 100 times the dose that would kill 50% of animals (LD50) of P. aeruginosa strain PAO1 or E. coli ATCC 25922. At one and five hours post infection, the test compound was injected intravenously in doses ranging from 5 mg/kg to 100 mg/kg, five mice per group. Mice were observed for 5 days, and the dose of compound resulting in survival of 50% of mice (ED50) was calculated.

Drug Combination (Synergy) Studies

[0929] I. Principle

[0930] Checkerboard experiments can be performed to assess potential interactions between primary drug of interest (#1) and other related antibacterials (#2). P. aeruginosa ATCC 27853, S. aureeus ATCC 29213 and other organisms can be used as challenge strains as well as selected clinical isolates. Broth microdilution format can be used to assess the activity of drug #1 and test compound alone and in combination. Two-fold dilutions of the two compounds to be tested (each bracketing the expected MIC value) are used. The fractional inhibitory concentration (FIC) was calculated as the MIC of compound #1 in combination with a second compound, divided by the MIC of compound #1 alone. A summation FIC (ΣFIC) was computed for each drug combination as the sum of the individual FICs of compound #1 and #2. Synergy was defined as an ΣFIC ≦0.5, indifference as an ΣFIC between 0.5 and 4, and antagonism as ΣFIC>4. The lowest ΣFIC was used for the final interpretation of drug conbination studies.

[0931] Interpretation of summation (ΣFIC)

[0932] a) Synergism, x≦0.5

[0933] b) Indifference, 0.5<x≦4

[0934] c) Antagonism, x>4

TABLE 2
Demonstration of Antibacterial activity of Select
Compounds from Table 1
Enzyme inhibitory activity
Compound
Example # IC50 (nM)
12        <100 nM
572       <100 nM
481       <100 nM
19        <100 nM
516       <100 nM
280       <100 nM
366       <100 nM
777       <100 nM
315       <100 nM
779       <100 nM
860       <100 nM
801       <100 nM
13        <100 nM

[0935]

TABLE 3
Antibacterial activity vs standard panel of organisms (MIC, μg/ml).
	Bacterial strain:
Compound	P. aeruginosa	E. coli	S. aureus	hyper-permeable	P. aeruginosa
Example #	27853	25922	29213	P. aerug. 35151	PAO200 mexAB
12	A	A	C	A	A
572	A	A	C	A	A
481	A	A	C	A	A
19	A	A	B	A	A
516	A	A	C	A	A
280	A	A	C	A	A
366	A	A	C	A	A
777	A	A	C	A	A
315	A	A	C	A	A
779	A	A	C	A	A
860	A	A	C	A	A
801	A	A	C	A	A
13	A	A	C	AA	A
MIC Key
MIC's of 6.25 ug/ml or less = A
MIC's of greater than 6.25 ug/ml to 50 ug/ml = B
MIC's of greater than 50 ug/ml = C

[0936]

TABLE 4
Antibacterial activity vs cystic fibrosis isolates of Pseudomonas aeruginosa (MIC,
μg/ml). Strains have the following phenotypes: 3198 and 3236,
sensitive to most antibacterials; 2196, resistant to ciprofloxacin;
3224, resistant to ceftazidime; 3317, resistant to aztreonam; 1145
and 3206, multi-drug resistant.
Strain number:	3198	3236	2196	3224	3232	3317	1145	3206
Phenotype:	Sensitive	Sensitive	Cipro R	Tobra R	Ceftaz. R	Aztr. R	MDR	MDR
LpxC inhibitors
12	A	A	B	A	A	A	A	A
481	A	A	A	A	A	A	A	A
19	A	A	A	A	A	A	A	A
516	A	A	A	A	A	A	A	A
280	A	A	B	A	A	A	A	A
366	A	A	A	A	A	A	A	A
777	A	A	A	A	A	A	A	A
315	A	A	A	A	A	A	A	A
779	A	A	A	A	A	A	A	A
801	A	A	A	A	A	A	A	A
13	A	A	A	A	A	A	A	A
Comparator
antibacterials
Tobramycin	2	0.5	2	64	1	2	8-32	64
Aztreonam	1	0.5	1	1	1	64	>128	>128
Ceftazidime	2	0.25	2	2	64	4	>128	>128
Cefepime	4	2	2	8	2	8	>128	32
Ciprofloxacin	1	0.06	>8	2	2	0.5	4	>8
MIC Key
MIC's of 6.25 ug/ml or less = A
MIC's of greater than 6.25 ug/ml to 50 ug/ml = B
MIC's of greater than 50 ug/ml = C

[0937]

TABLE 5
Antibacterial activity vs non-CF clinical isolates of P. aeruginosa and vs other gram-
negative pathogens. Set 1: non-fermenting organisms. P. aer.,
P. aeruginosa ; Acinet. calc., Acinetobacter calcoaceticus;
Alcal. xyl. , Alcaligenes xylosoxidans; B. cep., Burkholderia cepacia;
S. malt. , Stenotrophomonas maltophilia
	Species:
		P. aer.		P. aer
	P. aer 27853	PAO1	P. aer 12307	psa-6b	Acinet. calc.	Alcal. xyl	B. cepacia	S. malt.
LpxC inhibitors
12	A	A	A	A	A	A	B	A
481	A	A	A	A	C	C	B	C
19	A	A	A	A	A	B	B	B
516	A		A	A	C	C	C	C
280	A	A	A	A	C	B	B	B
366	A	A	A	B	C	A	B	B
777	A		A	B	A	B	A	C
315	A	A	A	A	C	B	A	A
779	A	A		A	C	A	A	B
801	A	A		A	B	C	B	C
13	A	A		A	C	A	A	B
Comparator
antibacterials
Tobramycin			8	2	2	64	64/>128	0.5
Aztreonam			16	32	32	32	64	>128/16
Ceftazidime			4	64	16	1	8/4	1
Cefepime			2	8	8	8	32/16	8/1
Meropenem			0.5	0.25	4	0.5	4	64
Pip/Tazo			4	>128	8	1	64	16
Ciprofloxacin					0.5	2	0.5	0.5
MIC Key
MIC's of 6.25 ug/ml or less = A
MIC's of greater than 6.25 ug/ml to 50 ug/ml = B
MIC's of greater than 50 ug/ml = C

[0938]

TABLE 6
Antibacterial activity vs non-CF clinical isolates of P. aeruginosa and vs other gram-
negative pathogens, continued. Set 2: enteric organisms. E. aer., Enterobacter aerogenes; E.
clo. , Enterobacter cloacae; E. coli, Escherichia coli; K. pneu., Klebsiella pneumoniae; K. oxy.,
Klebsiella oxytoca ; P. mir., Proteus mirabilis; S. marc., Serratia marcescens.
	Species:
	E. aer.	E. clo.	E. coli 1619	E. coli 2788	K. pneu.	K. oxy.	P. mir.	S. marc.
LpxC inhibitors
12	C	A	A	A	A	A	A	A
481	C	A	A	A	A	A	A	A
19	A	A	A	A	A	A	A	A
516	C	B	A	B	C	C	C	A
280	C	A	A	A	B	C	B	B
366	C	A	A	A	B	B	A	A
777	B	A	A	A	A	A	A	A
315	C	A	A	A	C	C	C	B
779	C	A	A	A	B	B	B	A
801	B	A	A	A	A	A	A	A
13	C	A	A	A	A	A	A	A
Comparator
antibacterials
Tobramycin	64	0.06	16/64	0.06/2	64	1	2	2
Aztreonam		<=0.13	128/64	<=0.13/0.25	2	0.5	<=0.13	<=0.13
Ceftazidime	32	0.25	>128	0.25/<=0.13	8	0.25	<=0.13	0.25
Cefepime		<=0.13	4/<=0.13	<=0.13	8	<=0.13	<=0.13	<=0.13
Meropenem	2	<=0.06	0.25/0.13	<=0.06	0.13	<=0.06	0.5	0.13
Pip/Tazo		2	>128	1	>128	2	0.25	1
Ciprofloxacin	>8	0.015	2	0.03	0.06	0.03	0.03	0.25
MIC Key
MIC's of 6.25 ug/ml or less = A
MIC's of greater than 6.25 ug/ml to 50 ug/ml = B
MIC's of greater than 50 ug/ml = C

[0939]

TABLE 7
Drug Combination (Synergy) Studies Result
Minimum Concentration (mg/ml) required
to inhibit grouth of E. coli 25922
		Erythromycin	LpxC inhibitor 925
	LpxC inhibitor 925 only	—	6.25
	Erythromycin only	128	—
	LpxC inhibitor 925	2	0.78
	+erythromycin

[0940] Each of the Example compounds of Table 1 was synthesized and assayed as described above. Many of the Example compounds 1-1307 displayed an IC50 value of less than 10 μM with respect to LpxC. Many of these compounds displayed an IC50 value of less than or equal to 1 μM or less than or equal to 0.1 μM. Many of these compounds exhibited IC50 values of less than or equal to 0.050 μM, less than or equal to 0.030 μM, less than or equal to 0.025 μM, or less than or equal to 0.010 μM.

[0941] It should be understood that the organic compounds according to the invention may exhibit the phenomenon of tautomerism. As the chemical structures within this specification can only represent one of the possible tautomeric forms, it should be understood that the invention encompasses any tautomeric form of the drawn structure.

TABLE 1
Example	Structure	Name	MH+
30	200	3,4-difluoro-N-{(1S,2R)-2-hydroxy-1- [(hydroxyamino)carbonyl]propyl}benzamide	275.2
31	201	(2S,3R)-N,3-dihydroxy-2-[(4- phenylbutanoyl)amino]butanamide	281.3
32	202	(2S,3R)-N,3-dihydroxy-2-({4-[4- (methyloxy)phenyl]butanoyl}amino)butanamide	311.3
33	203	N-{(1S,2R)-2-hydroxy-1- [(hydroxyamino)carbonyl]propyl}-5- phenylpentanamide	295.3
34	204	(2E,4E)-N-{(1S,2R)-2-hydroxy-1- [(hydroxyamino)carbonyl]propyl}-5- phenylpenta-2,4-dienamide	291.3
35	205	(2E)-N-{(1S,2R)-2-hydroxy-1- [(hydroxyamino)carbonyl]propyl}-3- phenylprop-2-enamide	265.3
36	206	(2S,3R)-3-hydroxy-2-({(2E)-3-[4- (methyloxy)phenyl]prop-2- enoyl}amino)butanoic acid	280.3
37	207	(3R)-3-amino-N-((1S,2R)-2-hydroxy-1- [(hydroxyamino)carbonyl]propyl}-5- phenylpentanamide	310.4
38	208	(2E)-3-(4-fluorophenyl)-N-{(1S,2R)-2- hydroxy-1- [(hydroxyamino)carbonyl]propyl}prop- 2-enamide	283.3
39	209	(2E)-3-(3-bromophenyl)-N-{(1S,2R)-2- hydroxy-1- [(hydroxyamino)carbonyl]propyl}prop- 2-enamide	344.2
40	210	N-{(1S,2R)-2-hydroxy-1- [(hydroxyamino)carbonyl]propyl}-4-{[(2- phenylethyl)amino]methyl}benzamide	372.4
41	211	N-{(1S,2R)-2-hydroxy-1- [(hydroxyamino)carbonyl]propyl}-4-{[(4- phenylbutyl)amino]methyl}benzamide	400.5
42	212	4-[(cyclopropylanimo)methyl]-N-{(1S,2R)- 2-hydroxy-1- [(hydroxyamino)carbonyl]propyl}benzamide	308.3
43	213	4-[(hexylamino)methyl]-N-{(1S,2R)-2- hydroxy-1-[(hydroxyamino) carbonyl]propyl}benzamide	352.4
44	214	N-{(1S,2R)-2-hydroxy-1- [(hydroxyamino)carbonyl]propyl}-4-{[(2- pyridin-2-ylethyl)amino]methyl}benzamide	373.4
45	215	N-{(1S,2R)-2-hydroxy-1- [(hydroxyamino)carbonyl]propyl}-4-(4- methylpiperazin-1-yl)benzamide	337.4
46	216	N-{(1S,2R)-2-hydroxy-1- [(hydroxyamino)carbonyl]propyl}-4- (piperidin-1-ylmethyl)benzamide	336.4
47	217	N-{(1S,2R)-2-hydroxy-1- [(hydroxyamino)carbonyl]propyl}-4- (morpholin-4-ylmethyl)benzamide	338.4
48	218	N-{(1S,2R)-2-hydroxy-1- [(hydroxyamino)carbonyl]propyl}-4- ({[3-(2-oxopyrrolidin-1- yl)propyl]amino}methyl)benzamide	393.5
49	219	N-{(1S,2R)-2-hydroxy-1- [(hydroxyamino)carbonyl]propyl}-4- {[(3-phenylpropyl) amino]methyl}benzamide	386.5
50	220	(2S,5R)-N-{(1S,2R)-2-hydroxy-1- [(hydroxyamino)carbonyl]propyl}-5- phenylpyrrolidine-2-carboxamide	308.3
51	221	(2R,5S)-N-{(1S,2R)-2-hydroxy-1- [(hydroxyamino)carbonyl]propyl}-5- phenylpyrrolidine-2-carboxamide	308.3
52	222	(2S,3R)-2-{[(3S)-3-amino-4- phenylbutanoyl]amino}-N,3- dihydroxybutanamide	296.3
53	223	(2S,3R)-2-{[(2S)-2-amino-4- phenylbutanoyl]amino}-N,3- dihydroxybutanamide	296.3
54	224	N-{(1S,2R)-2-hydroxy-1- [(hydroxyamino)carbonyl]propyl}-6-(2- pyrrolidin-1-ylethyl)pyridine-3- carboxamide	337.4
55	225	2-{[(4′-ethyl-1,1′-biphenyl-4- yl)carbonyl]amino}-3-hydroxy-3- methylbutanoic acid	342.4
56	226	2-{[4-(4-ethylphenyl)phenyl]carbonylamino}-3-hydroxy-4- methylpentanoic acid	356.4
57	227	{[(4′-ethyl-1,1′-biphenyl-4- yl)carbonyl]amino}(thien-2- yl)acetic acid	366.5
58	228	N-(2-{[(1,1-dimethylethyl)oxy]amino}-2-oxo- 1-thien-2-ylethyl)-4′-ethyl-1,1′-biphenyl-4- carboxamide	437.6
59	229	3-(dimethylamino)-2-{[(4′-ethyl-1,1′-biphenyl- 4-yl)carbonyl]amino}propanoic acid	341.4
60	230	4′-ethyl-N-{(1S)-1-[({(1S,2R)-2-hydroxy-1- [(hydroxyamino)carbonyl]propyl}amino) carbonyl]-3-methylbutyl}-1,1′- biphenyl-4-carboxamide	456.6
61	231	4′-ethyl-N-[(1S)-2-({(1S,2R)-2-hydroxy-1- [(hydroxyamino)carbonyl]propyl}amino)-2- oxo-1-(phenylmethyl)ethyl]-1,1′- biphenyl-4-carboxamide	490.6
62	232	(2S)-1-[(4′-ethyl-1,1′-biphenyl-4-yl)carbonyl]- N-{(1S,2R)-2-hydroxy-1- [(hydroxyamino)carbonyl]propyl}pyrrolidine- 2-carboxamide	440.5
63	233	4′-ethyl-N-[(1S)-2-({(1S,2R)-2-hydroxy-1- [(hydroxyamino)carbonyl]propyl}amino)-1- (1H-imidazol-4-ylmethyl)-2-oxoethyl]-1,1′- biphenyl-4-carboxamide	480.5
64	234	(3S)-2-[(4′-ethyl-1,1′-biphenyl-4-yl)carbonyl]- N-{(1S,2R)-2-hydroxy-1- [(hydroxyamino)carbonyl]propyl}-1,2,3,4- tetrahydroisoquinoline-3-carboxamide	502.6
65	235	(2S)-2-[(1,1′-biphenyl-4-ylacetyl)amino]-N- {(1S,2R)-2-hydroxy-1- [(hydroxyamino)carbonyl]propyl}-4- methylpentanamide	442.5
66	236	(2S,3R)-2-({(2S)-2-[(1,1′-biphenyl-4- ylacetyl)amino]-3-phenylpropanoyl}amino)- N,3-dihydroxybutanamide	476.5
67	237	(2S,3R)-2-{[(2S)-2-[(1,1′-biphenyl-4- ylacetyl)amino]-3-(4- hydroxyphenyl)propanoyl]amino}-N,3- dihydroxybutanamide	492.5
68	238	(2S)-1-(1,1′-biphenyl-4-ylacetyl)-N-{(1S,2R)- 2-hydroxy-1-[(hydroxyamino) carbonyl]propyl}pyrrolidine- 2-carboxamide	426.5
69	239	(2S,3R)-2-{[(2S)-2-[(1,1′-biphenyl-4- ylacetyl)amino]-3-(1H-imidazol-4- yl)propanoyl]amino}-N,3- dihydroxybutanamide	466.5
70	240	(2S)-2-[(1,1′-biphenyl-4-ylacetyl)amino]- N˜1˜-{(1S,2R)-2-hydroxy-1- [(hydroxyamino)carbonyl]propyl}pentanediamide	457.5
71	241	(3S)-3-[(1,1′-biphenyl-4-ylacetyl)amino]-4- ({(1S,2R)-2-hydroxy-1- [(hydroxyamino)carbonyl]propyl}amino)- 4-oxobutanoic acid	444.5
72	242	(2S,4R)-1-[(4′-ethyl-1,1′-biphenyl-4- yl)carbonyl]-4-hydroxy-N-{(1S,2R)- 2-hydroxy-1-[(hydroxyamino) carbonyl]propyl}pyrrolidine- 2-carboxamide	456.5
73	243	N-[(1S)-1-(aminomethyl)-2-({(1S,2R)-2- hydroxy-1-[(hydroxyamino) carbonyl]propyl}amino)-2- oxoethyl]-4′-ethyl-1,1′-biphenyl-4- carboxamide	429.5
74	244	4′-ethyl-N-{(1S)-1-[({(1S,2R)-2-hydroxy-1- [(hydroxyamino)carbonyl]propyl}amino)carbonyl]but-3-ynyl}-1,1′- biphenyl-4-carboxamide	438.5
75	245	(2S,3R)-2-({(2S)-2-[(1,1′-biphenyl-4- ylacetyl)amino]propanoyl}amino)-N,3- dihydroxybutanamide	400.4
76	246	(2S,4R)-1-(1,1′-biphenyl-4-ylacetyl)-4- hydroxy-N-{(1S,2R)-2-hydroxy-1- [(hydroxyamino)carbonyl]propyl}pyrrolidine-2-carboxamide	442.5
77	247	4′-ethyl-N-{(1R,2R)-2-hydroxy-1- [(hydroxy{[(2-hydroxyethyl) amino]carbonyl}amino)methyl]propyl}-1,1′-biphenyl-4-carboxamide	416.5
78	248	N-((2R,3R)-2-{[(4′-ethyl-1,1′-biphenyl-4- yl)carbonyl]amino}-3-hydroxybutyl)-N- hydroxymorpholine-4-carboxamide	442.5
79	249	N-((2R,3R)-2-{[(4′-ethyl-1,1′-biphenyl-4- yl)carbonyl]amino}-3-hydroxybutyl)-N- hydroxy-4-methylpiperazine-1-carboxamide	455.6
80	250	N-((1R,2R)-1- {[[(cyclopropylamino)carbonyl](hydroxy) amino]methyl}-2-hydroxypropyl)- 4′-ethyl-1,1′-biphenyl-4-carboxamide	412.5
81	251	4-ethyl-N-{(1R,2R)-2-hydroxy-1- [(hydroxy{[(pyridin-3- ylmethyl)amino]carbonyl}amino) methyl]propyl}-1,1′- biphenyl-4-carboxamide	463.5
82	252	4′-ethyl-N-{(1R,2R)-2-hydroxy-1- [(hydroxy{[(2-pyridin-2-ylethyl)amino]carbonyl}amino)methyl]propyl}1,1′-biphenyl-4-carboxamide	477.6
83	253	4-ethyl-N-{(1R,2R)-2-hydroxy-1- [(hydroxy{[(4-morpholin-4-ylphenyl) amino]carbonyl}amino)methyl]propyl}- 1,1′-biphenyl-4-carboxamide	533.6
84	254	N˜1˜-((2R,3R)-2-{[(4′-ethyl-1,1′-biphenyl-4- yl)carbonyl]amino}-3-hydroxybutyl)-N˜1˜- hydroxypiperidine-1,4-dicarboxamide	483.6
85	255	4′-ethyl-N-[2-(hydroxyamino)ethyl]-1,1- biphenyl-4-carboxamide	285.4
86	256	N-{2-[(aminocarbonyl)(hydroxy)amino]ethyl}- 4′-ethyl-1,1′-biphenyl-4-carboxamide	328.4
87	257	N-{2-[(aminocarbonothioyl) (hydroxy)amino]ethyl}- 4′-ethyl-1,1′-biphenyl-4-carboxamide	344.4
88	258	N-{2-[({[2-(dimethylamino) ethyl]amino}carbonyl)(hydroxy) amino]ethyl}4-ethyl-1,1′-biphenyl- 4-carboxamide	399.5
89	259	N-{2-[{[(2-cyanaethyl) amino]carbonyl}(hydroxy)amino]ethyl}4′-ethyl-1,1′- biphenyl-4-carboxamide	381.4
90	260	4′-ethyl-N-[2-(hydroxy{[(2- hydroxyethyl)amino]carbonyl}amino)ethyl]- 1,1′-biphenyl-4-carboxamide	372.4
91	261	N-(2-{[(4′-ethyl-1,1′-biphenyl-4- yl)carbonyl]amino}ethyl)-N- hydroxymorpholine-4-carboxamide	398.5
92	262	N-(2-{[(4′-ethyl-1,1′-biphenyl-4- yl)carbonyl]amino}ethyl)-N-hydroxy-4- methylpiperazine-1-carboxamide	411.5
93	263	N˜1˜-(2-{[(4′-ethyl-1,1′-biphenyl-4- yl)carbonyl]amino}ethyl)-N˜1˜- hydroxypiperidine-1,4-dicarboxamide	439.5
94	264	N-(2-{[(4′-ethyl-1,1′-biphenyl-4- yl)carbonyl]amino}ethyl)-N- hydroxypyrrolidine-1-carboxamide	382.5
95	265	N-{2-[[(cyclopropylamino) carbonyl](hydroxy)amino]ethyl}4-ethyl-1,1′-biphenyl-4-carboxamide	368.4
96	266	4′-ethyl-N-{2-[hydroxy({[2- (methyloxy)ethyl]amino}carbonyl) amino]ethyl}-1,1′- biphenyl-4-carboxamide	386.5
97	267	N-{2-[({[2-(acetylamino)ethyl]amino}carbonyl)(hydroxy) amino]ethyl}-4′-ethyl-1,1′- biphenyl-4-carboxamide	413.5
98	268	4′-ethyl-N-{2-[hydroxy({[3-(2- oxopyrrolidin-1-yl)propyl]amino}carbonyl)amino]ethyl}-1,1′- biphenyl-4-carboxamide	453.6
99	269	4′-ethyl-N-[2-(hydroxy{[(3- hydroxypropyl)amino]carbonyl}amino) ethyl]-1,1′-biphenyl-4-carboxamide	386.5
100	270	4′-ethyl-N-{2-[hydroxy({[3- (methyloxy)propyl]amino}carbonyl)amino]ethyl}-1,1′-biphenyl-4-carboxamide	400.5
101	271	N-(2-{[(4′-ethyl-1,1′-biphenyl-4- yl)carbonyl]amino}ethyl)-N-hydroxy-1,4′- bipiperidine-1′-carboxamide	479.6
102	272	4′-ethyl-N-[2-(hydroxy{[(2-pyridin-2- ylethyl)amino]carbonyl}amino)ethyl]- 1,1′-biphenyl-4-carboxamide	433.5
103	273	4′-ethyl-N-[2-(hydroxy{[(pyridin-3- ylmethyl)amino]carbonyl}amino)ethyl]-1,1′- biphenyl-4-carboxamide	419.5
104	274	4′-ethyl-N-[2-(hydroxy{[(4-morpholin-4- ylphenyl)amino]carbonyl}amino)ethyl]-1,1′- biphenyl-4-carboxamide	489.6
105	275	N-(2-{[(4′-ethyl-1,1′-biphenyl-4- yl)carbonyl]amino}ethyl)-N,3- dihydroxypiperidine-1-carboxamide	412.5
106	276	N-{2-[{[(3-aminocyclohexyl) amino]carbonyl}(hydroxy)amino]ethyl}-4′-ethyl-1,1′-biphenyl- 4-carboxamide	425.5
107	277	N-{2-[{[(2-aminoethyl)amino]carbonyl}(hydroxy)amino]ethyl}- 4′-ethyl-1,1′-biphenyl-4-carboxamide	371.4
108	278	N-{2-[{[(3-aminopropyl)amino]carbonyl}(hydroxy)amino]ethyl}-4′- ethyl-1,1′-biphenyl-4-carboxamide	385.5
109	279	1,1-dimethylethyl 3-({[(2-{[(4′-ethyl-1,1′- biphenyl-4-yl)carbonyl]amino}ethyl)(hydroxy)amino]carbonyl}amino)propylcarbaniate	485.6
110	280	4′-ethyl-N-{2-[({[(4- fluorophenyl)methyl]amino}carbonyl) (hydroxy)amino]ethyl}-1,1′- biphenyl-4-carboxamide	436.5
111	281	N-(2-{[(4′-ethyl-1,1′-biphenyl-4- yl)carbonyl]amino}ethyl)-N-hydroxy-3- [(trifluoroacetyl)amino]pyrrolidine-1- carboxamide	493.5
112	282	N-{2-[{[(4-aminothien-3- yl)amino]carbonyl}(hydroxy)amino]ethyl}- 4′-ethyl-1,1′-biphenyl-4-carboxamide	425.5
113	283	4′-ethyl-N-(2-{hydroxy[(piperidin-3- ylamino)carbonyl]amino}ethyl)-1,1′- biphenyl-4-carboxamide	411.5
114	284	4′-ethyl-N-(2-{hydroxy[(piperidin-4- ylamino)carbonyl]amino}ethyl)-1,1′- biphenyl-4-carboxamide	411.5
115	285	4′-ethyl-N-[2-(hydroxy{[(piperidin-2- ylmethyl)amino]carbonyl}amino)ethyl]- 1,1′-biphenyl-4-carboxamide	425.5
116	286	4′-ethyl-N-[2-(hydroxy{[(piperidin-3- ylmethyl)amino]carbonyl}amino)ethyl]- 1,1′-biphenyl-4-carboxamide	425.5
117	287	3-amino-N-(2-{[(4′-ethyl-1,1′-biphenyl-4- yl)carbonyl]amino}ethyl)-N- hydroxypyrrolidine-1-carboxamide	397.5
118	288	1,1-dimethylethyl 3-[({[(2-{[(4′-ethyl-1,1′- biphenyl-4-yl)carbonyl]amino}ethyl)(hydroxy)amino]carbonyl}amino)methyl]piperidine-1-carboxylate	525.7
119	289	1,1-dimethylethyl 1-{[(2-{[(4′-ethyl-1,1′- biphenyl-4-yl)carbonyl]amino}ethyl)(hydroxy)amino]carbonyl}pyrrolidin-3-ylcarbamate	497.6
120	290	4′-ethyl-N-[(1S,2R)-2-hydroxy-1-({[2- (hydroxyarnino)ethyl]amino}carbonyl)propyl]- 1,1′-biphenyl-4-carboxamide	386.5
121	291	N-{(1S,2R)-1-[({2- [(aminocarbonyl)(hydroxy)amino]ethyl}amino)carbonyl]-2-hydroxypropyl}-4′- ethyl-1,1′-biphenyl-4-carboxamide	429.5
122	292	N-{(1S,2R)-1-[({2-[(aminocarbonothioyl) (hydroxy)amino]ethyl}amino) carbonyl]-2-hydroxypropyl}-4′-ethyl-1,1′- biphenyl-4-carboxamide	445.6
123	293	4′-ethyl-N-[(1S,2R)-2-hydroxy-1-({[2- (hydroxy{[(2-hydroxyethyl)amino]carbonyl}amino)ethyl]amino}carbonyl) propyl]-1′-biphenyl-4- carboxamide	473.5
124	294	4′-ethyl-N-{(1S)-6-hydroxy-1-[(1R)-1- hydroxyethyl]-2,7-dioxo-11-oxa-3,6,8- triazadodec-1-yl}-1,1′-biphenyl-4- carboxamide	487.6
125	295	4′-ethyl-N-{(1S)-6-hydroxy-1-[(1R)-1- hydroxyethyl]-11-methyl-2,7-dioxo-3,6,8,11- tetraazadodec-1-yl}-1,1′-biphenyl-4- carboxamide	500.6
126	296	4′-ethyl-N-{(1S)-6-hydroxy-1-[(1R)-1- hydroxyethyl]-2,7,12-trioxo-3,6,8,11- tetraazatridec-1-yl}-1,1′-biphenyl-4- carboxamide	514.6
127	297	4′-ethyl-N-{(1S,2R)-2-hydroxy-1-[({2- [hydroxy({[3-(2-oxopyrrolidin-1-yl) propyl]amino}carbonyl)amino]ethyl}amino)carbonyl]propyl}-1,1′-biphenyl-4- carboxamide	554.7
128	298	N-{(1S,2R)-1-[({2-[{[(2- cyanoethyl)aminolcarbonyl}(hydroxy)amino]ethyl}amino)carbonyl]-2-hydroxypropyl}-4′- ethyl-1,1′-biphenyl-4-carboxamide	482.6
129	299	N-{(1S,2R)-1-[({2-[[(cyclopropylamino) carbonyl](hydroxy)amino]ethyl}amino)carbonyl]-2-hydroxypropyl}-4′- ethyl-1,1′-biphenyl-4-carboxamide	469.6
130	300	N-{2-[((2S,3R)-2-{[(4′-ethyl-1,1′-biphenyl-4- yl)carbonyl]amino}-3- hydroxybutanoyl)amino]ethyl}-N- hydroxypyrrolidine-1-carboxamide	483.6
131	301	N-{2-[((2S,3R)-2-{[(4′-ethyl-1,1′-biphenyl-4- yl)carbonyl]amino}-3- hydroxybutanoyl)amino]ethyl}-N- hydroxymorpholine-4-carboxamide	499.6
132	302	N-{2-[((2S,3R)-2-{[(4′-ethyl-1,1-biphenyl-4- yl)carbonyl]amino}-3- hydroxybutanoyl)amino]ethyl}-N-hydroxy- 4-methylpiperazine-1-carboxamide	512.6
133	303	4′-ethyl-N-[(1S,2R)-2-hydroxy-1-({[2- (hydroxy{[(pyridin-3-ylmethyl)amino]carbonyl}amino)ethyl]amino}carbonyl)propyl]-1,1′-biphenyl-4- carboxamide	520.6
134	304	4′-ethyl-N-[(1S,2R)-2-hydroxy-1-({[2- (hydroxy{[(2-pyridin-2-ylethyl) amino]carbonyl}amino)ethyl]amino}carbonyl)propyl]-1,1′-biphenyl-4- carboxamide	534.6
135	305	3-chloro-N-{(1S,2S)-2-hydroxy-1- [(hydroxyamino)carbonyl]propyl}-4- [(trifluoromethyl)oxy]benzamide	357.7
136	306	N-{(1S,2R)-2-hydroxy-1- [(hydroxyamino)carbonyl]propyl}-4-{[(3- nitrophenyl)methyl]oxy}benzamide	390.4
137	307	(4R)-2-(4-fluoro-3-prop-2-enylphenyl)-N- hydroxy-4,5-dihydro-1,3-oxazole-4- carboxamide	265.3
138	308	3-fluoro-N-{(1S,2R)-2-hydroxy-1- [(hydroxyamino)carbonyl]propyl}-4- (methyloxy)benzamide	287.3
139	309	4-(but-3-enyloxy)-N-{(1S,2R)-2-hydroxy-1- [(hydroxyamino)carbonyl]propyl}benzamide	309.3
140	310	3-bromo-5-fluoro-N-{(1S,2R)-2-hydroxy-1- [(hydroxyamino)carbonyl]propyl}-4-(prop-2- enyloxy)benzamide	392.2
141	311	4-fluoro-N-{(1S,2S)-2-hydroxy-1- [(hydroxyamino)carbonyl]propyl}-3-prop-2- enylbenzamide	297.3
142	312	N-{(1S,2R)-2-hydroxy-1- [(hydroxyamino)carbonyl]propyl}-4- (prop-2-enyloxy)-3-(trifluoromethyl) benzamide	363.3
143	313	N-{(1S,2R)-2-hydroxy-1- [(hydroxyamino)carbonyl]propyl}-4- (methyloxy)benzamide	269.3
144	314	N-{(1S,2R)-2-hydroxy-1- [(hydroxyamino)carbonyl]propyl}-3- (phenyloxy)benzamide	331.3
145	315	N-{(1S,2R)-2-hydroxy-1- [(hydroxyamino)carbonyl]propyl}-4- (methyloxy)-3- [(trifluoromethyl)oxy]benzamide	353.3
146	316	N-{(1S,2S)-2-hydroxy-1- [(hydroxyamino)carbonyl]propyl}-4- [(trifluoromethyl)oxy]benzamide	323.2
147	317	N-{(1S,2R)-2-hydroxy-1- [(hydroxyamino)carbonyl]propyl}-4- [(trifluoromethyl)oxy]benzamide	323.2
148	318	N-{(1S,2R)-2-hydroxy-1- [(hydroxyamino)carbonyl]propyl}-4- (trifluoromethyl)benzamide	307.2
149	319	3,4-difluoro-N-{(2R)-2-hydroxy-1- [(hydroxyamino)carbonyl]propyl}benzamide	275.2
150	320	N-{(1S,2S)-2-hydroxy-1- [(hydroxyamino)carbonyl]propyl}-4- (methyloxy)benzamide	269.3
151	321	N-{(1S,2R)-2-hydroxy-1- [(hydroxyamino)carbonyl]propyl}- 4′-propyl-1,1′-biphenyl-4- carboxamide	357.4
152	322	N-{(1S,2R)-2-hydroxy-1- [(hydroxyamino)carbonyl]propyl}- 4′-propyl-1,1′-biphenyl-4- carboxamide	357.4
153	323	N-{(1S,2R)-2-hydroxy-1- [(hydroxyamino)carbonyl]propyl}- 4-[trifluoro(methylidene)-lambda˜6˜- sulfanyl]benzamide	341.3
154	324	N-{(1S,2R)-2-hydroxy-1- [(hydroxyamino)carbonyl]propyl}benzamide	239.2
155	325	N-{(1S,2R)-2-hydroxy-1- [(hydroxyamino)carbonyl]propyl}- 1,1′-biphenyl-4-carboxamide	315.3
156	326	3-bromo-N-{(1S,2R)-2-hydroxy-1- [(hydroxyamino)carbonyl]propyl}-4- (methyloxy)benzamide	348.2
157	327	4-fluoro-N-{(1S,2R)-2-hydroxy-1- [(hydroxyamino)carbonyl]propyl}-3- (prop-2-enyloxy)benzamide	313.3
158	328	2,3,5,6-tetrafluoro-N-{(1S,2R)-2-hydroxy-1- [(hydroxyamino)carbonyl]propyl}-4-prop- 2-enylbenzamide	351.3
159	329	3-fluoro-N-{(1S,2R)-2-hydroxy-1- [(hydroxyamino)carbonyl]propyl}-5- (trifluoromethyl)benzamide	325.2
160	330	4-bromo-2-fluoro-N-{(1S,2R)-2-hydroxy-1- [(hydroxyamino)carbonyl]propyl}benzamide	336.1
161	331	N-{(1S,2R)-2-hydroxy-1- [(hydroxyamino)carbonyl]propyl}-4- (phenyloxy)benzamide	331.3
162	332	4-(dimethylamino)-N-{(1S,2R)-2-hydroxy-1- [(hydroxyamino)carbonyl]propyl}benzamide	282.3
163	333	2-[3-fluoro-4-(methyloxy)-5-prop-2- enylphenyl]-N-hydroxy-4,5-dihydro-1,3- oxazole-4-carboxamide	295.3
164	334	N-{(1S,2R)-2-hydroxy-1- [(hydroxyamino)carbonyl]propyl}-5- [3-(trifluoromethyl)phenyl]furan-2-carboxamide	373.3
165	335	4-{[(1E)-1,2-difluorobuta-1,3-dienyl]oxy}- N-{(1S,2R)-2-hydroxy-1- [(hydroxyamino)carbonyl]propyl}benzamide	343.3
166	336	N-{(1S,2R)-2-hydroxy-1- [(hydroxyamino)carbonyl]propyl}quinoline- 2-carboxamide	290.3
167	337	N-[2-(hydroxyamino)-1-(hydroxymethyl)-2- oxoethyl]-1,1′-biphenyl-4-carboxamide	301.3
168	338	N-{(1S,2S)-2-hydroxy-1- [(hydroxyamino)carbonyl]propyl}-1,1- biphenyl-4-carboxamide	315.3
169	339	N-{(1S,2R)-2-hydroxy-1- [(hydroxyamino)carbonyl]propyl}-2′- methyl-1,1′-biphenyl-4-carboxamide	329.4
170	340	N-{(1S,2S)-2-hydroxy-1- [(hydroxyamino)carbonyl]propyl}-4- (trifluoromethyl)benzamide	307.2
171	341	4-fluoro-N-{(1S,2R)-2-hydroxy-1- [(hydroxyamino)carbonyl]propyl}-3- (trifluoromethyl)benzamide	325.2
172	342	N-{(1S,2R)-2-hydroxy-1- [(hydroxyamino)carbonyl]propyl}-4-{[(3- nitrophenyl)oxy]methyl}benzamide	390.4
173	343	N-[(1R)-2-(hydroxyamino)-1- (mercaptomethyl)-2-oxoethyl]-4- [(trifluoromethyl)oxy]benzamide	325.3
174	344	N-{(1S,2R)-2-hydroxy-1- [(hydroxyamino)carbonyl]propyl}-1,3- benzodioxole-5-carboxamide	283.3
175	345	N-{(1S,2R)-2-hydroxy-1- [(hydroxyamino)carbonyl]propyl}-6- (trifluoromethyl)pyridine-3-carboxamide	308.2
176	346	N-{3-hydroxy-1- [(hydroxyamino)carbonyl]propyl}-4- [(trifluoromethyl)oxy]benzamide	323.2
177	347	N-{3-hydroxy-1- [(hydroxyamino)carbonyl]propyl}- 1,1′-biphenyl-4-carboxamide	315.3
178	348	N-{(1S,2R)-2-hydroxy-1- (hydroxyamino)carbonyl]propyl}-4- [hydroxy(phenyl)methyl]benzamide	345.4
179	349	N-{(1S,2R)-2-hydroxy-1- [(hydroxyamino)carbonyl]propyl}-4-[({4- [(trifluoromethyl)oxy]phenyl}oxy) methyl]benzamide	429.4
180	350	4-[({4-bromo-2-[(trifluoromethyl) oxy]phenyl}oxy)methyl]-N- {(1S,2R)-2-hydroxy-1- [(hydroxyamino)carbonyl]propyl}benzamide	508.3
181	351	N-{(1S,2R)-2-hydroxy-1- [(hydroxyamino)carbonyl]propyl}-3′- nitro-1,1′-biphenyl-4-carboxamide	360.3
182	352	4-bromo-N-{(1S,2R)-2-hydroxy-1- [(hydroxyamino)carbonyl]propyl}benzamide	318.1
183	353	N-{(1S,2R)-2-hydroxy-1- [(hydroxyamino)carbonyl]propyl}-4′- (methyloxy)-1,1′-biphenyl-4-carboxamide	345.4
184	354	N-{(1S,2R)-2-hydroxy-1- [(hydroxyamino)carbonyl]propyl}-4′- [(trifluoromethyl)oxy]-1,1′-biphenyl-4- carboxamide	399.3
185	355	4′-(ethyloxy)-N-{(1S,2R)-2-hydroxy-1- [(hydroxyamino)carbonyl]propyl}-1,1′- biphenyl-4-carboxamide	359.4
186	356	N-{(1S,2R)-2-hydroxy-1- [(hydroxyamino)carbonyl]propyl}-4-{5-[(Z)- (hydroxyimino)methyl]thien-2-yl}benzamide	364.4
187	357	3′-(ethyloxy)-N-{(1S,2R)-2-hydroxy-1- [(hydroxyamino)carbonyl]propyl}-1,1′- biphenyl-4-carboxamide	359.4
188	358	(2R,3R)-N,3-dihydroxy-1-({4- [(trifluoromethyl)oxy]phenyl}carbonyl) pyrrolidine-2-carboxamide	335.2
189	359	N-[2-(hydroxyamino)-1-(hydroxymethyl)-2- oxoethyl]-3-(1-methylethyl)-4- (methyloxy)benzamide	297.3
190	360	N-[2-(hydroxyamino)-1-(hydroxymethyl)-2- oxoethyl]-3-(1-methylethyl)-4-(prop-2- enyloxy)benzamide	323.4
191	361	N-[2-(hydroxyamino)-1-(hydroxymethyl)-2- oxoethyl]-4-(methyloxy)-3-propylbenzamide	297.3
192	362	N-{(1S,2R)-2-hydroxy-1- [(hydroxyamino)carbonyl]propyl}-4′- (methylthio)-1,1′-biphenyl-4-carboxamide	361.4
193	363	5-bromo-N-{(1S,2R)-2-hydroxy-1- [(hydroxyamino)carbonyl]propyl}thiophene-2-carboxamide	324.2
194	364	N-{(1S,2R)-2-hydroxy-1- [(hydroxyamino)carbonyl]propyl}-5-{4- [(trifluoromethyl)oxy]phenyl}thiophene- 2-carboxamide	405.4
195	365	N-{(1S,2R)-2-hydroxy-1- [(hydroxyamino)carbonyl]propyl}-1- benzofuran-2-carboxamide	279.3
196	366	N-{(1S,2R)-2-hydroxy-1- [(hydroxyamino)carbonyl]propyl}-5- phenylthiophene-2-carboxamide	321.4
197	367	4′-(dimethylamino)-N-{(1S,2R)-2-hydroxy-1- [(hydroxyamino)carbonyl]propyl}-1,1′- biphenyl-4-carboxamide	358.4
198	368	(2S,3R)-N,3-dihydroxy-2-[({2- [(trifluoromethyl)oxy]phenyl}acetyl) amino]butanamide	337.3
199	369	5-[4-(ethyloxy)phenyl]-N-{(1S,2R)-2- hydroxy-1-[(hydroxyamino)carbonyl]propyl}thiophene-2-carboxamide	365.4
200	370	5-[3-(ethyloxy)phenyl]-N-{(1S,2R)-2- hydroxy-1-[(hydroxyamino)carbonyl]propyl}thiophene-2-carboxamide	365.4
201	371	(4R)-N-hydroxy-2-{2′-[(trifluoromethyl)oxy]- 1,1′-biphenyl-4-yl}-4,5-dihydro-1,3- oxazole-4-carboxamide	367.3
202	372	N-{(1S,2R)-2-hydroxy-1- [(hydroxyamino)carbonyl]propyl}-4′- (hydroxymethyl)-1,1′-biphenyl-4- carboxamide	345.4
203	373	N-{(1S,2R)-2-hydroxy-1- [(hydroxyamino)carbonyl]propyl}-4- {5-[(4-methylpiperazin- 1-yl)methyl]thien-2- yl}benzamide	433.5
204	374	N-{(1S,2R)-2-hydroxy-1- [(hydroxyamino)carbonyl]propyl}-4-{[4- (methyloxy)phenyl]carbonyl}benzamide	373.4
205	375	N-{(1S,2R)-2-hydroxy-1- [(hydroxyamino)carbonyl]propyl}-4-[(E)- phenyldiazenyl]benzamide	343.4
206	376	(4R)-N-hydroxy-2-{4-(methyloxy)-3- [(trifluoromethyl)oxy]phenyl}-4,5- dihydro-1,3-oxazole-4-carboxamide	321.2
207	377	4′-ethyl-N-{(1S,2R)-2-hydroxy-1- [(hydroxyamino)carbonyl]propyl}-1,1′- biphenyl-4-carboxamide	343.4
208	378	N-{(1S,2R)-2-hydroxy-1- [(hydroxyamino)carbonyl]propyl}-4′- (trifluoromethyl)-1,1′-biphenyl-4- carboxamide	383.3
209	379	5-(4-ethylphenyl)-N-{(1S,2R)-2-hydroxy-1- [(hydroxyamino)carbonyl]propyl}thiophene- 2-carboxamide	349.4
210	380	N-{(1S,2R)-2-hydroxy-1- [(hydroxyamino)carbonyl]propyl}-5-[4- (methylthio)phenyl]thiophene-2-carboxamide	351.4
211	381	N-{(1S,2R)-2-hydroxy-1- [(hydroxyamino)carbonyl]propyl}-5-[4- (methylthio)phenyl]thiophene-2-carboxamide	367.5
212	382	N-{(1S,2R)-2-hydroxy-1- [(hydroxyamino)carbonyl]propyl}-5-(3- nitrophenyl)thiophene-2-carboxamide	366.4
213	383	N-{(1S,2R)-2-hydroxy-1- [(hydroxyamino)carbonyl]propyl}-4-oxo- 4H-chromene-2-carboxamide	307.3
214	384	N-[1-[(hydroxyamino)carbonyl]-1- (hydroxymethyl)-2-methylpropyl]-4- [(trifluoromethyl)oxy]benzamide	351.3
215	385	N-[2-hydroxy-3-(hydroxyamino)-3-oxopropyl]- 1,1′-biphenyl-4-carboxamide	301.3
216	386	N-{(1S,2R)-2-hydroxy-1- [(hydroxyamino)carbonyl]propyl}-4-[(E)-2- phenylethenyl]benzamide	341.4
217	387	N-{(1S,2R)-2-hydroxy-1- [(hydroxyamino)carbonyl]propyl}-9H- fluorene-2-carboxamide	327.4
218	388	4′-[({(1S,2R)-2-hydroxy-1- [(hydroxyamino)carbonyl]propyl}amino) carbonyl]-1,1′-biphenyl-4-carboxylic acid	359.3
219	389	N-[2-(hydroxyamino)-1-(hydroxymethyl)-2- oxoethyl]-4-(prop-2-enyloxy)-3- propylbenzamide	323.4
220	390	N-{(1S,2R)-2-hydroxy-1- [(hydroxyamino)carbonyl]propyl}-4- iodobenzamide	365.1
221	391	4′-hydroxy-N-{(1S,2R)-2-hydroxy-1- [(hydroxyamino)carbonyl]propyl}-1,1′- biphenyl-4-carboxamide	331.3
222	392	6-bromo-N-{(1S,2R)-2-hydroxy-1- [(hydroxyamino)carbonyl]propyl}pyridine-2- carboxamide	319.1
223	393	N-{(1S,2R)-2-hydroxy-1- [(hydroxyamino)carbonyl]propyl}-6- phenylpyridine-2-carboxamide	316.3
224	394	4′-butyl-N-{(1S,2R)-2-hydroxy-1- [(hydroxyamino)carbonyl]propyl}-1,1′- biphenyl-4-carboxamide	371.4
225	395	4′-(1,1-dimethylethyl)-N-{(1S,2R)-2-hydroxy- 1-[(hydroxyamino)carbonyl]propyl}-1,1′- biphenyl-4-carboxamide	371.4
226	396	N-{(1S,2R)-2-hydroxy-1- [(hydroxyamino)carbonyl]propyl}-5-[3- (methyloxy)phenyl]thiophene-2-carboxamide	351.4
227	397	4′-[({(1S,2R)-2-hydroxy-1- [(hydroxyamino)carbonyl]propyl}amino) carbonyl-1,1′-biphenyl-4-yl dihydrogen phosphate	411.3
228	398	N-ethyl-N′-{(1S,2R)-2-hydroxy-1- [(hydroxyamino)carbonyl]propyl}-1,1′- biphenyl-4,4′-dicarboxamide	386.4
229	399	N-[(1S,2R)-1-(hydrazmocarbonyl)-2- hydroxypropyl]-4′-propyl-1,1′-biphenyl-4- carboxamide	356.4
230	400	N-{(1S,2R)-2-hydroxy-1- [(methylamino)carbonyl]propyl}-4′- propyl-1,1′-biphenyl-4-carboxamide	355.4
231	401	N-[(1S,2R)-1-(hydrazinocarbonyl)-2- hydroxypropyl]-4-(methyloxy)benzamide	268.3
232	402	(2S,3R)-2-[(1,1′-biphcnyl-4-ylsulfonyl)amino]- N,3-dihydroxybutanamide	351.4
233	403	4-hydroxy-N-{(1S,2R)-2-hydroxy-1- [(hydroxyamino)carbonyl]propyl}benzamide	255.2
234	404	3′-cyano-N-{(1S,2R)-2-hydroxy-1- [(hydroxyamino)carbonyl]propyl}-1,1′- biphenyl-4-carboxamide	340.3
235	405	1-dimethylethyl ({4-[({(1S,2R)-2-hydroxy-1- [(hydroxyamino)carbonyl]propyl}amino) carbonyl]phenyl}oxy)acetate	369.4
236	406	(2S,3R)-2-[(1,1′-biphenyl-4- ylsulfonyl)(methyl)amino]-N,3- dihydroxybutanamide	365.4
237	407	N-{(1S,2R)-2-hydroxy-1- [(hydroxyamino)carbonyl]propyl}-3′-[(Z)- (hydroxyimino)methyl]-4′-(methyloxy)-1,1′- biphenyl-4-carboxamide	388.4
238	408	N-{(1S,2R)-2-hydroxy-1- [(hydroxyamino)carbonyl]propyl}-4- [(phenylcarbonyl)amino]benzamide	358.4
239	409	N-hydroxy-2-[3-(1-methylethyl)-4-(prop-2- enyloxy)phenyl]-4,5-dihydro-1,3-oxazole-4- carboxamide	305.3
240	410	4′-butyl-N-{(1S,2R)-2-hydroxy-1- [(methylamino)carbonyl]propyl}-1,1′- biphenyl-4-carboxamide	369.5
241	411	N-{(1S,2R)-2-hydroxy-1- [(hydroxyamino)carbonyl]propyl}-4-(5- methylpyridin-2-yl)benzamide	330.4
242	412	5-bromo-N-{(1S,2R)-2-hydroxy-1- [(hydroxyamino)carbonyl]propyl}pyridine- 3-carboxamide	319.1
243	413	N-{(1S,2R)-2-hydroxy-1- [(hydroxyamino)carbonyl]propyl}-4- pyridin-3-ylbenzamide	316.3
244	414	N-{(1R,2R)-2-hydroxy-1- [(hydroxyamino)carbonyl]propyl}-N′- {(1S,2R)-2-hydroxy-1- [(hydroxyamino)carbonyl]propyl}-1,1′- biphenyl-4,4′-dicarboxamide	475.5
245	415	(2S,3R)-N,3-dihydroxy-2-[({4-[(E)-2- phenylethenyl]phenyl}methyl) amino]butanamide	327.4
246	416	4-{[(4-bromophenyl)sulfonyl]amino}-N- {(1S,2R)-2-hydroxy-1- [(hydroxyamino)carbonyl]propyl}benzamide	473.3
247	417	1,1-dimethylethyl-4-({4-[({(1S,2R)- 2-hydroxy-1- [(hydroxyamino)carbonyl]propyl}amino) carbonyl]phenyl}amino)-4- oxobutylcarbamate	439.5
248	418	4-[(4-amniobutanoyl)amino]-N-{(1S,2R)- 2-hyroxy-1- [(hydroxyamino)carbonyl]propyl}benzamide	339.4
249	419	1,1-dimethylethyl {4′-[({(1S,2R)-2-hydroxy-1- [(hydroxyamino)carbonyl]propyl}amino) methyl]-1,1′-biphenyl-4-yl}methylcarbamate	430.5
250	420	N-{(1S,2R)-2-hydroxy-1- [(hydroxyamino)carbonyl]propyl}-4- pyrimidin-5-ylbenzamide	317.3
251	421	1,1-dimethylethyl 5-{4-[({(1S,2R)-2-hydroxy- 1-[(hydroxyamino)carbonyl]propyl}amino)carbonyl]phenyl}pyridine- 3-carboxylate	416.4
252	422	5-{4-[({(1S,2R)-2-hydroxy-1- [(hydroxyamino)carbonyl]propyl}amino) carbonyl]phenyl}pyridine-3- carboxylic acid	360.3
253	423	(4S)-N-hydroxy-2-{4-(methyloxy)-3- [(trifluoromethyl)oxy]phenyl}-4,5-dihydro- 1,3-oxazole-4-carboxamide	321.2
254	424	(2S,3R)-2-({[4′-(aminomethyl)-1,1′-biphenyl-4- yl]methyl}amino)-N,3-dihydroxybutanamide	330.4
255	425	(3S)-1-hydroxy-3-[(1R)-1-bydroxyethyl]- 4-({4-[(E)-2-phenylethenyl]phenyl}methyl)piperazine-2,6-dione	367.4
256	426	(2S,3R)-N,3-dihydroxy-2-({[4- (phenylethynyl)phenyl]methyl}amino) butanamide	325.4
257	427	N-(3-aminopropyl)-N′-{(1S,2R)-2-hydroxy-1- [(hydroxyamino)carbonyl]propyl}benzene-1,4-dicarboxamide	339.4
258	428	N-{(1S,2R)-2-hydroxy-1- [(hydroxyamino)carbonyl]propyl}-4- (propanoylamino)benzamide	310.3
259	429	1,1-dimethylethyl 3-[({4-[({(1S,2R)-2- hydroxy-1-[(hydroxyamino)carbonyl]propyl}amino)carbonyl]phenyl}carbonyl)amino]propylcarbamate	439.5
260	430	N-{(1S,2R)-2-hydroxy-1- [(hydroxyamino)carbonyl]propyl}-4′- (phenyloxy)-1,1′-biphenyl-4-carboxamide	407.4
261	431	N-[(1S,2R)-1-({[cyano(phenyl)methyl]amino}carbonyl)-2-hydroxypropyl]- 4′-hydroxy-1,1′-biphenyl-4- carboxamide	430.5
262	432	4′-{[2-(hydroxyamino)-2-oxoethyl]oxy}-N- {(1S,2R)-2-hydroxy-1- [(hydroxyamino)carbonyl]propyl}-1,1′- biphenyl-4-carboxamide	404.4
263	433	4-({[(1S,2R)-1- {[(cyanomethyl)amino]carbonyl}-2- (propanoyloxy)propyl]amino}carbonyl)-1,1′- biphenyl-4-yl propanoate	466.5
264	434	4′-({[(1S,2R)-1- {[(cyanomethyl)(propanoyl)amino]carbonyl}- 2-(propanoyloxy)propyl]amino}carbonyl)- 1,1′-biphenyl-4-yl propanoate	522.6
265	435	N-((1S,2R)-1- {[(cyanomethyl)amino]carbonyl}-2- hydroxypropyl)-4′-hydroxy-1,1′-biphenyl-4- carboxamide	354.4
266	436	(2S,3S)-2-[(1,1′-biphenyl-4-ylnethyl)amino]- N,3-dihydroxybutanamide	301.4
267	437	N-{2-hydroxy-1-[(hydroxyamino)carbonyl]-2- phenylethyl}-1,1′-biphenyl-4-carboxamide	377.4
268	438	(2S,3R)-2-[(diphenylacetyl)amino]-N,3- dihydroxybutanamide	329.4
269	439	N-{(1S,2R)-2-hydroxy-1- [(hydroxyamino)carbonyl]propyl}-6- [(phenylmethyl)thio]pyridine-3-carboxamide	362.4
270	440	N,3-dihydroxy-2-({[4- (phenyloxy)phenyl]methyl}amino)butanamide	317.4
271	441	N-{(1S,2R)-2-hydroxy-1- [(hydroxyamino)carbonyl]propyl}-2′- [(trifluoromethyl)oxy]-1,1′-biphenyl-4- carboxamide	399.3
272	442	(2R,3S)-2-[(1,1′-biphenyl-4-ylmethyl)amino]- N,3-dihydroxybutanamide	301.4
273	443	4-[({(1S,2R)-2-hydroxy-1- [(hydroxyamino)carbonyl]propyl}amino) carbonyl]benzoic acid	283.3
274	444	1,1-dimethylethyl 4-[({(1S,2R)-2-hydroxy-1- [(hydroxyamino)carbonyl]propyl}amino) carbonyl]benzoate	339.4
275	445	(4R)-4-{[(4′-ethyl-1,1′-biphenyl-4- yl)carbonyl]amino}-5-(hydroxyamino)-5- oxopentanoic acid	371.4
276	446	4′-ethyl-N-[(1R)-2-(hydroxyamino)-1- (hydroxymethyl)-2-oxoethyl]-1,1′-biphenyl- 4-carboxamide	329.4
277	447	4′-ethyl-N-[(1S)-2-(hydroxyamino)-1- (hydroxymethyl)-2-oxoethyl]-1,1′-biphenyl- 4-carboxamide	329.4
278	448	(2S)-1-[(4′-ethyl-1,1′-biphenyl-4-yl)carbonyl]- N,4-dihydroxypyrrolidine-2-carboxamide	355.4
279	449	4′-ethyl-N-{(1S)-1- [(hydroxyamino)carbonyl]but-3-ynyl}-1,1′- biphenyl-4-carboxamide	337.4
280	450	N-[(1S)-1-(aminomethyl)-2-(hydroxyamino)-2- oxoethyl]-4′-ethyl-1,1′-biphenyl-4- carboxamide	328.4
281	451	N-{(1S)-1-[(hydroxyamino)carbonyl]-2- methylpropyl}-1,1′-biphenyl-4-carboxamide	313.4
282	452	N-{(1S,2R)-2-hydroxy-1- [(hydroxyamino)carbonyl]propyl}-N-methyl- 1,1′-biphenyl-4-carboxamide	329.4
283	453	4-ethynyl-N-{(1S,2R)-2-hydroxy-1- [(hydroxyamino)carbonyl]propyl}benzamide	263.3
284	454	4-(1,3-benzodioxol-5-yl)-N-{(1S,2R)-2- hydroxy-1- [(hydroxyamino)carbonyl]propyl}benzamide	359.3
285	455	N-{(1R,2S)-2-hydroxy-1- [(hydroxyamino)carbonyl]propyl}-4′-propyl- 1,1′-biphenyl-4-carboxamide	357.4
286	456	2-({[3′-(ethyloxy)-1,1′-biphenyl-4- yl]methyl}amino)-N,3-dihydroxybutanamide	345.4
287	457	N-{(1S,2R)-2-hydroxy-1- [(hydroxyamino)carbonyl]propyl}-3′,4′- bis(methyloxy)-1,1′-biphenyl-4-carboxamide	375.4
288	458	3′-formyl-N-{(1S,2R)-2-hydroxy-1- [(hydroxyamino)carbonyl]propyl}-4′- (methyloxy)-1,1′-biphenyl-4-carboxamide	373.4
289	459	N-{(1S,2R)-2-hydroxy-1- [(hydroxyamino)carbonyl]propyl}-4-(4-{4- [({(1S,2R)-2-hydroxy-1-[(hydroxyamino) carbonyl]propyl}amino)carbonyl]phenyl}buta-1,3-diynyl)benzamide	523.5
290	460	(2S,3R)-2-({[4′-(ethyloxy)-1,1′-biphenyl-4- yl]methyl}amino)-N,3-dihydroxybutanamide	345.4
291	461	3′-chloro-N-{(1S,2R)-2-hydroxy-1- [(hydroxyamino)carbonyl]propyl}-4- (methyloxy)-1,1′-biphenyl-4-carboxamide	379.8
292	462	(1R,2R)-N-{(1S,2R)-2-hydroxy-1- [(hydroxyamino)carbonyl]propyl}-2- phenylcyclopropanecarboxamide	279.3
293	463	N-{(1S,2R)-2-hydroxy-1- [(hydroxyamino)carbonyl]propyl}-4-(1H- pyrrol-1-yl)benzamide	304.3
294	464	N-{(1S,2R)-2-hydroxy-1- [(hydroxyamino)carbonyl]propyl}-4- propylbenzamide	281.3
295	465	N-{(1S,2R)-2-hydroxy-1- [(hydroxyamino)carbonyl]propyl}-4- pentylbenzamide	309.4
296	466	N-{(1S,2R)-2-hydroxy-1- [(hydroxyamino)carbonyl]propyl}-4- octylbenzamide	351.5
297	467	(2E)-N-{(1S,2R)-2-hydroxy-1- [(hydroxyamino)carbonyl]propyl}-3-(4- methylphenyl)prop-2-enamide	279.3
298	468	(2E)-N-{(1S,2R)-2-hydroxy-1- [(hydroxyamino)carbonyl]propyl}-3-[4- (trifluoromethyl)phenyl]prop-2-enamide	333.3
299	469	(2E)-3-(1,1′-biphenyl-4-yl)-N-{(1S,2R)-2- hydroxy-1- [(hydroxyamino)carbonyl]propyl}prop-2- enamide	341.4
300	470	(2S,3R)-2-[(1,1′-biphenyl-4-ylacetyl)amino]- N,3-dihydroxybutanamide	329.4
301	471	(2S,3R)-2-{[(2S)-2-amino-3-(1,1′-biphenyl-4- yl)propanoyl]amino}-N,3- dihydroxybutanamide	358.4
302	472	(2S,3R)-2-{[(2R)-2-amino-3-(1,1′-biphenyl-4- yl)propanoyl]amino}-N,3- dihydroxybutanamide	358.4
303	473	(3S)-3-amino-N-{(1S,2R)-2-hydroxy-1- [(hydroxyamino)carbonyl]propyl}-5- phenylpentanamide	310.4
304	474	N-{(1S,2R)-2-hydroxy-1- [(hydroxyamino)carbonyl]propyl}-4- [(phenylamino)methyl]benzamide	344.4
305	475	N-{(1S,2R)-2-hydroxy-1- [(hydroxyamino)carbonyl]propyl}-4- {[(phenylmethyl)amino]methyl}benzamide	358.4
306	476	4′-ethyl-N-{(1S,2R)-2-hydroxy-1- [({(1S,2R)-2-hydroxy-1- [(hydroxyamino)carbonyl]propyl}amino) carbonyl]propyl}-1,1′- biphenyl-4-carboxamide	444.5
307	477	(2S,3R)-2-[(1,1-biphenyl-4-ylacetyl)amino]-3- hydroxy-N-{(1S,2R)-2-hydroxy-1- [(hydroxyamino)carbonyl]propyl}butanamide	430.5
308	478	4-(4-chlorophenyl)-N-{(1S,2R)-2-hydroxy-1- [(hydroxyamino)carbonyl]propyl}cyclohexane carboxamide	355.8
309	479	N-{(1S,2R)-2-hydroxy-1- [(hydroxyamino)carbonyl]propyl}-4-(1H- pyrazol-1-yl)benzamide	305.3
310	480	N-{(1S,2R)-2-hydroxy-1- [(hydroxyamino)carbonyl]propyl}-4- morpholin-4-ylbenzamide	324.3
311	481	N-{(1S,2R)-2-hydroxy-1- [(hydroxyamino)carbonyl]propyl}-4-(1,2,3- thiadiazol-4-yl)benzamide	323.3
312	482	N-{(1S,2R)-2-hydroxy-1- [(hydroxyamino)carbonyl]propyl}-4-[(4- methylpiperazin-1-yl)methyl]benzamide	351.4
313	483	N-{(1S,2R)-2-hydroxy-1- [(hydroxyamino)carbonyl]propyl}-4-(1H- imidazol-1-ylmethyl)benzamide	319.3
314	484	(2S,4S)-N-{(1S,2R)-2-hydroxy-1- [(hydroxyamino)carbonyl]propyl}-4- phenylpyrrolidine-2-carboxamide	308.3
315	485	4′-bromo-N-{(1S,2R)-2-hydroxy-1- [(hydroxyamino)carbonyl]propyl}-1,1′- biphenyl-4-carboxamide	394.2
316	486	4′-bromo-N-{(1S,2R)-2-hydroxy-1- [(hydroxyamino)carbonyl]propyl}-1,1′- biphenyl-4-carboxamide	394.2
317	487	4′-bromo-N-{(1S,2R)-2-hydroxy-1- [(hydroxyamino)carbonyl]propyl}-1,1′- biphenyl-4-carboxamide	394.2
318	488	(2R)-2-{[(4′-ethyl-1,1′-biphenyl-4- yl)carbonyl]amino}-N˜1˜- hydroxypentanediamide	370.4
319	489	(2S,3S)-1-[(4′-ethyl-1,1′-biphenyl-4- yl)carbonyl]-3-hydroxypyrrolidine-2- carboxylic acid	340.4
320	490	(2S,3S)-N-[(1,1-dimethylethyl)oxy]-1-[(4′-ethyl-1,1′-biphenyl-4-yl)carbonyl]-3- hydroxypyrrolidine-2-carboxamide	411.5
321	491	(2S,3S)-1-[(4′-ethyl-1,1′-biphenyl-4- yl)carbonyl]-N,3-dihydroxypyrrolidine-2- carboxamide	355.4
322	492	N-{(1S,2R)-2-hydroxy-1- [(hydroxyamino)carbonyl]propyl}-4- [(4-nitrophenyl)ethynyl]benzamide	384.4
323	493	N-{(1S,2R)-2-hydroxy-1- [(hydroxyamino)carbonyl]prapyl}-4- {[4-(1H-pyrrol-1-yl)phenyl]ethynyl}benzamide	404.4
324	494	N-{(1S,2R)-2-hydroxy-1- [(hydroxyamino)carbonyl]propyl}-4′- nitro-1,1′-biphenyl-4-carboxamide	360.3
325	495	(2S,3R)-N,3-dihydroxy-2-({[4′-(methyloxy)-3′- propyl-1,1′-biphenyl-4- yl]methyl}amino)butanamide	373.5
326	496	4′-cyano-N-{(1S,2R)-2-hydroxy-1- [(hydroxyamino)carbonyl]propyl}-1,1′- biphenyl-4-carboxamide	340.3
327	497	(2S,3R)-2-({[4-(ethyloxy)-4-(methyloxy)-1,1′- biphenyl-3-yl]methyl}amino)-N,3- dihydroxybutanamide	375.4
328	498	2′,5′-difluoro-N-{(1S,2R)-2-hydroxy-1- [(hydroxyamino)carbonyl]propyl}-1,1′- biphenyl-4-carboxamide	351.3
329	499	N-[(1S)-1-[(acetylamino)methyl]-2- (hydroxyamino)-2-oxoethyl]4-ethyl-1,1′- biphenyl-4-carboxamide	370.4
330	500	N-{(1S)-4-amino-1- [(hydroxyamino)carbonyl]butyl}4-ethyl-1,1′- biphenyl-4-carboxamide	356.4
331	501	4′-ethyl-N-[(1S)-2-(hydroxyamino)-1-(1H- imidazol-5-ylmethyl)-2-oxoethyl]-1,1′- biphenyl-4-carboxamide	379.4
332	502	(2S,3R)-2-{[1-(1,1′-biphenyl-4- yl)ethyl]amino}-N,3-dihydroxybutanamide	315.4
333	503	(2S,3R)-2-{[1-(1,1′-biphenyl-4- yl)propyl]amino}-N,3-dihydroxybutanamide	329.4
334	504	(2S,3R)-2-{[1-(4′-bromo-1,1′-biphenyl-4- yl)ethyl]amino}-N,3-dihydroxybutanamide	394.3
335	505	(2S,3R)-N,3-dihydroxy-2-{[1-(4′-methyl-1,1′- biphenyl-4-yl)ethyl]amino}butanamide	329.4
336	506	N-[(1S)-1-(aminomethyl)-2-(hydroxyamino)-2- oxoethyl]-1,1′-biphenyl-4-carboxamide	300.3
337	507	N-[(1S)-1-(aminomethyl)-2-(hydroxyamino)-2- oxoethyl]-4-(1H-pyrrol-1-yl)benzamide	289.3
338	508	N-[(1S)-1-(aminomethyl)-2-(hydroxyamino)-2- oxoethyl]-4-(4- chlorophenyl)cyclohexanecarboxamide	340.8
339	509	N-[(1S)-1-(aminomethyl)-2-(hydroxyamino)-2- oxoethyl]-4-pentylbenzamide	294.4
340	510	(2E)-N-[(1S)-1-(aminomethyl)-2- (hydroxyamino)-2-oxoethyl]-3-(1,1′-biphenyl- 4-yl)prop-2-enamide	326.4
341	511	(2S)-3-amino-2-{[(4′-ethyl-1,1′-biphenyl-4- yl)methyl]amino}-N-hydroxypropanamide	314.4
342	512	(2S)-3-amino-2-[(1,1′-biphenyl-4- ylmethyl)amino]-N-hydroxypropanamide	286.3
343	513	(2S)-3-amino-2-{[1-(4′-bromo-1,1′-biphenyl-4- yl)ethyl]amino}-N-hydroxypropanamide	379.3
344	514	(2S)-3-amino-N-hydroxy-2-{[1-(4′-methyl-1,1′- biphenyl-4-yl)ethyl]amino}propanamide	314.4
345	515	4′-ethyl-N-[(1S)-2-({(1S,2R)-2-hydroxy-1- [(hydroxyamino)carbonyl]propyl}amino)-1- (hydroxymethyl)-2-oxoethyl]-1,1′-biphenyl- 4-carboxamide	430.5
346	516	4′-ethyl-N-{(1S)-2-({(1S,2R)-2-hydroxy-1- [(hydroxyamino)carbonyl]propyl}amino)-1-[(4- hydroxyphenyl)methyl]-2-oxoethyl}-1,1′- biphenyl-4-carboxamide	506.6
347	517	(2S)-2-{[(4′-ethyl-1,1′-biphenyl-4- yl)carbonyl]amino}-N˜1˜-{(1S,2R)- 2-hydroxy-1-[(hydroxyamino)carbonyl]propyl}pentanediamide	471.5
348	518	(4S)-4-{[(4′-ethyl-1,1′-biphenyl-4- yl)carbonyl]amino}-5-({(1S,2R)-2-hydroxy-1- [(hydroxyamino)carbonyl]propyl}amino)- 5-oxopentanoic acid	472.5
349	519	(3S)-3-{[(4′-ethyl-1,1′-biphenyl-4- yl)carbonyl]amino}-4-({(1S,2R)-2-hydroxy-1- [(hydroxyamino)carbonyl]propyl}amino)-4- oxobutanoic acid	458.5
350	520	(3S)-2-(1,1′-biphenyl-4-ylacetyl)-N-{(1S,2R)- 2-hydroxy-1-[(hydroxyamino) carbonyl]propyl}-1,2,3,4- tetrahydroisoquinoline-3-carboxamide	488.6
351	521	4′-ethyl-N-[(1S)-2-({(1S,2R)-2-hydroxy-1- [(hydroxyamino)carbonyl]propyl}amino)-1- methyl-2-oxoethyl]-1,1′-biphenyl-4- carboxamide	414.5
352	522	(2S,3R)-2-({(2S)-3-amino-2-[(1,1′-biphenyl-4- ylacetyl)amino]propanoyl}amino)-N,3- dihydroxybutanamide	415.5
353	523	(2S)-2-[(1,1′-biphenyl-4-ylacetyl)amino]-N- {(1S,2R)-2-hydroxy-1- [(hydroxyamino)carbonyl]propyl}pent-4-ynamide	424.5
354	524	(2S,3R)-2-{[(2S)-2-amino-2-(1,1′-biphenyl-4- yl)ethanoyl]amino}-N,3-dihydroxybutanamide	344.4
355	525	(2S,3R)-2-{[(2R)-2-amino-2-(1,1′-biphenyl-4- yl)ethanoyl]amino}-N,3-dihydroxybutanamide	344.4
356	526	N-(3-aminopropyl)-4′-ethyl-N-[2- (hydroxyamino)-2-oxoethyl]-1,1′-biphenyl-4- carboxamide	356.4
357	527	N-(2-cyanoethyl)-4′-ethyl-N-[2- (hydroxyamino)-2-oxoethyl]-1,1′- biphenyl-4-carboxamide	352.4
358	528	N-[2-(acetylamino)ethyl]4-ethyl-N-[2- (hydroxyamino)-2-oxoethyl]-1,1′-biphenyl-4- carboxamide	384.4
359	529	4′-ethyl-N-[2-(hydroxyamino)-2-oxoethyl]-N- prop-2-ynyl-1,1′-biphenyl-4-carboxamide	337.4
360	530	4-cyano-N-{(1S,2R)-2-hydroxy-1- [(hydroxyamino)carbonyl]propyl}benzamide	264.3
361	531	N-[(1S)-1-(aminomethyl)-2-(hydroxyamino)- 2-oxoethyl]-4-cyanobenzamide	249.2
362	532	1,1-dimethylethyl (2S)-2-{[(4- ethynylphenyl)carbonyl]amino}-3- (hydroxyamino)-3-oxopropylcarbamate	348.4
363	533	1,1-dimethylethyl (2S)-3-(hydroxyamino)-3- oxo-2-[({4-[(E)-2-phenylethenyl]phenyl}methyl)amino]propylcarbamate	412.5
364	534	N-{(1R,2S)-2-hydroxy-1- [(hydroxyamino)carbonyl]propyl}-3′- (trifluoromethyl)-1,1′-biphenyl-4-carboxamide	383.3
365	535	(2S,3R)-2-[(1,1′-biphenyl-4-ylmethyl)amino]- 3-hydroxybutanoic acid	286.3
366	536	N-[(1S)-1-(aminomethyl)-2-(hydroxyamino)- 2-oxoethyl]-4-(phenylethynyl)benzamide	324.4
367	537	1,1-dimethylethyl (2S)-3-(hydroxyamino)- 3-oxo-2-({[4-(phenylethynyl) phenyl]carbonyl}amino)propyl carbamate	424.5
368	538	N-[(1S)-1-(aminomethyl)-2-(hydroxyamino)-2- oxoethyl]-4-ethynylbenzamide	248.3
369	539	N-[(1S)-1-(aminomethyl)-2-(hydroxyamino)-2- oxoethyl]-4-ethynylbenzamide	248.3
370	540	N-{(1S,2R)-2-hydroxy-1- [(hydroxyamino)carbonyl]propyl}-4- {[4-(methyloxy)phenyl]ethynyl}benzamide	369.4
371	541	(2S)-3-amino-N-hydroxy-2-[({4-[(E)-2- phenylethenyl]phenyl}methyl)amino]propanamide	312.4
372	542	1,1-dimethylethyl 2-{4′-[({(1S,2R)-2- hydroxy-1-[(hydroxyamino) carbonyl]propyl}amino)carbonyl]- 1,1′-biphenyl-4-yl}ethylcarbamate	458.5
373	543	(2S,3R)-N,3-dihydroxy-2-[({4′-[(2-pyrrolidin- 1-ylethyl)oxy]-1,1′-biphenyl-4- yl}methyl)amino]butanamide	414.5
374	544	1,1-dimethylethyl (1S)-4-({[(1,1- dimethylethyl)oxy]carbonyl}amino)-1- ({[4-({4-[({(1S,2R)-2-hydroxy-1- [(hydroxyamino)carbonyl]propyl}amino) carbonyl]phenyl}ethynyl)phenyl]amino}carbonyl)butylcarbamate	668.8
375	545	4-(4-chlorophenyl)-N-[(1S)-2-({(1S,2R)-2- hydroxy-1-[(hydroxyamino)carbonyl]propyl}amino)-1-methyl-2- oxoethyl]cyclohexanecarboxamide	426.9
376	546	4′-ethyl-N-[2-({(1S,2R)-2-hydroxy-1- [(hydroxyamino)carbonyl]propyl}amino)-2- oxoethyl]-1,1′-biphenyl-4-carboxamide	400.4
377	547	4′-ethyl-N-[3-({(1S,2R)-2-hydroxy-1- [(hydroxyamino)carbonyl]propyl}amino)-3- oxopropyl]-1,1′-biphenyl-4-carboxamide	414.5
378	548	4′-ethyl-N-[4-({(1S,2R)-2-hydroxy-1- [(hydroxyamino)carbonyl]propyl}amino)-4- oxobutyl]-1,1′-biphenyl-4-carboxamide	428.5
379	549	N-((1S)-2-{[(1S)-1-(aminomethyl)-2- (hydroxyamino)-2-oxoethyl]amino}-1-methyl- 2-oxoethyl)-4′-ethyl-1,1′-biphenyl-4- carboxamide	399.5
380	550	N-(2-{[(1S)-1-(aminomethyl)-2- (hydroxyamino)-2-oxoethyl]amino}-2- oxoethyl)-4′-ethyl-1,1′-biphenyl-4- carboxamide	385.4
381	551	N-(3-{[(1S)-1-(aminomethyl)-2- (hydroxyamino)-2-oxoethyl]amino}-3- oxopropyl)-4′-ethyl-1,1′-biphenyl-4- carboxamide	399.5
382	552	N-(4-{[(1S)-1-(aminomethyl)-2- (hydroxyamino)-2-oxoethyl]amino}-4- oxobutyl)-4′-ethyl-1,1′-biphenyl-4- carboxamide	413.5
383	553	4′-ethyl-N-[1-[(hydroxyamino)carbonyl]-2- (methyloxy)propyl]-1,1′-biphenyl-4- carboxamide	357.4
384	554	4-ethyl-N-[(1S,2R)-1- [(hydroxyamino)carbonyl]-2- (methyloxy)propyl]-1,1′-biphenyl-4- carboxamide	357.4
385	555	N-[1-[(dimethylamino)methyl]-2- (hydroxyamino)-2-oxoethyl]-4′-ethyl-1,1′- biphenyl-4-carboxamide	356.4
386	556	N-{(1S)-3-cyano-1- [(hydroxyamino)carbonyl]propyl}-4′-ethyl- 1,1′-biphenyl-4-carboxamide	352.4
387	557	N-{(1S)-5-amino-1- [(hydroxyamino)carbonyl]pentyl}-4′-ethyl- 1,1′-biphenyl-4-carboxamide	370.5
388	558	N-{(1S)-3-amino-1- [(hydroxyamino)carbonyl]propyl}-4′-ethyl- 1,1′-biphenyl-4-carboxamide	342.4
389	559	4′-ethyl-N-hydroxy-1,1′-biphenyl-4- carboxamide	242.3
390	560	4′-ethyl-N-{2-hydroxy-1- [(hydroxyamino)carbonyl]-2-methylpropyl}- 1,1′-biphenyl-4-carboxamide	357.4
391	561	N-[(2S)-2-{[(4′-ethyl-1,1′-biphenyl-4- yl)carbonyl]amino}-3-(hydroxyamino)-3- oxopropyl]morpholine-4-carboxamide	441.5
392	562	N-[(1S)-1-{[(aminocarbonyl)amino]methyl}-2- (hydroxyamino)-2-oxoethyl]-4′-ethyl-1,1′- biphenyl-4-carboxamide	371.4
393	563	N-[(1S)-1- ({[amino(imino)methyl]amino}methyl)-2- (hydroxyamino)-2-oxoethyl]-4′-ethyl-1,1′- biphenyl-4-carboxamide	370.4
394	564	N-[(2S)-2-amino-3-(hydroxyamino)-3- oxopropyl]-4′-ethyl-1,1′-biphenyl-4- carboxamide	328.4
395	565	1-[(4′-ethyl-1,1′-biphenyl-4-yl)carbonyl]-N- hydroxypiperazine-2-carboxamide	354.4
396	566	N-[(2S)-2-amino-3-(hydroxyamino)-3- oxopropyl]-4-(phenylethynyl)benzamide	324.4
397	567	N-hydroxy-1-{[4-(phenylethynyl) phenyl]carbonyl}piperazine-2- carboxamide	350.4
398	568	N-{(1S,2R)-2-hydroxy-1- [(hydroxyamino)carbonyl]propyl}-4-[(4- pentylphenyl)ethynyl]benzamide	409.5
399	569	N-{(1S,2R)-2-hydroxy-1- [(hydroxyamino)carbonyl]propyl}-4-{[3- (methyloxy)phenyl]ethynyl}benzamide	369.4
400	570	4-[(3-fluoro-4-methylphenyl)ethynyl]-N- {(1S,2R)-2-hydxoxy-1- [(hydroxyamino)carbonyl]propyl}benzamide	371.4
401	571	4-[(2,4-difluorophenyl)ethynyl]-N-{(1S,2R)- 2-hydroxy-1- [(hydroxyamino)carbonyl]propyl}benzamide	375.3
402	572	methyl (2E)-3-(ethylamino)-2-({[4- (phenylethynyl)phenyl]carbonyl}amino)but-2-enoate	363.4
403	573	1,1-dimethylethyl 4-{[(2S)-3-(hydroxyamino)- 3-oxo-2-({[4-(phenylethynyl)phenyl]carbonyl}amino)propyl]amino}- 4-oxobutylcarbamate	509.6
404	574	N-(1-(N-hydroxycarbamoyl)-2-hydroxy-3- methylbutyl)[4-(4- ethylphenyl)phenyl]carboxamide	371.4
405	575	N-((1R,2R)-1-{[(aminocarbonyl) (hydroxy)amino]methyl}-2- hydroxypropyl)-4′-ethyl-1,1′- biphenyl-4-carboxamide	372.4
406	576	4′-ethyl-N-((1R,2R)-1- {[formyl(hydroxy)amino]methyl}-2- hydroxypropyl)-1,1′-biphenyl-4-carboxamide	357.4
407	577	N-{(1S,2R)-2-hydroxy-1- [(hydroxyamino)carbonyl]propyl}-4-{[4- (trifluoromethyl)phenyl]ethynyl}benzamide	407.4
408	578	1,1-dimethylethyl 2-{[(2S)-3-(hydroxyamino)- 3-oxo-2-({[4-(phenylethynyl)phenyl]carbonyl}amino)propyl]amino}-2-oxoethylcarbamate	481.5
409	579	N-[(1S)-1-{[(aminoacetyl)amino]methyl}-2- (hydroxyamino)-2-oxoethyl]-4- (phenylethynyl)benzamide	381.4
410	580	N-[(1S)-1-{[(4-aminobutanoyl)amino]methyl}- 2-(hydroxyamino)-2-oxoethyl]-4- (phenylethynyl)benzamide	409.5
411	581	N-{(1S,2R)-2-hydroxy-1- [(hydroxyamino)carbonyl]propyl}-4-pent-1- ynylbenzamide	305.3
412	582	N-{(1S,2R)-2-[(1,1-dimethylethyl)oxy]-1- [(hydroxyamino)carbonyl]propyl}-4′-propyl- 1,1′-biphenyl-4-carboxamide	413.5
413	583	1,1-dimethylethyl (1S)-4-({[(1,1- dimethylethyl)oxy]carbonyl}amino)-1- {[(2-55 4′-[({(1S,2R)-2-hydroxy-1- [(hydroxyamino)carbonyl]propyl}amino) carbonyl]-1,1′-biphenyl-4- yl}ethyl)amino]carbonyl}butylcarbamate	672.8
414	584	4′-(2-aminoethyl)-N-{(1S,2R)-2-hydroxy-1- [(hydroxyamino)carbonyl]propyl}-1,1′- biphenyl-4-carboxamide	358.4
415	585	4′-(2-{[(2S)-2,5-diaminopentanoyl]amino}ethyl)-N-{(1S,2R)-2-hydroxy-1- [(hydroxyamino)carbonyl]propyl}- 1,1′-biphenyl-4-carboxamide	472.6
416	586	4-(cyclohex-1-en-1-ylethynyl)-N-{(1S,2R)-2- hydroxy-1- [(hydroxyamino)carbonyl]propyl}benzamide	343.4
417	587	4-(3,3-dimethylbut-1-ynyl)-N-{(1S,2R)-2- hydroxy-1-[(hydroxyamino) carbonyl]propyl}benzamide	319.4
418	588	N-{(1S)-1-{[(aminoacetyl)amino]methyl}-2- [(2-{[(2S)-3-(hydroxyamino)-3-oxo-2-({[4- (phenylethynyl)phenyl]carbonyl}amino) propyl]amino}-2-oxoethyl)amino]-2- oxoethyl}-4-(phenylethynyl)benzamide	728.8
419	589	4-[(4-{[(2S)-2,5-diaminopentanoyl]amino}phenyl)ethynyl]-N- {(1S,2R)-2-hydroxy-1- [(hydroxyamino)carbonyl]propyl}benzamide	468.5
420	590	4′-(2-aminoethyl)-N-{(1E)-1- [(hydroxyamino)carbonyl]prop-1-enyl}- 1,1′-biphenyl-4-carboxamide	340.4
421	591	2′,4′-difluoro-N-{(1S,2R)-2-hydroxy-1- [(hydroxyamino)carbonyl]propyl}-1,1′- biphenyl-4-carboxamide	351.3
422	592	N-[(1E)-1-formylprop-1-enyl]-4′-propyl-1,1- biphenyl-4-carboxamide	308.4
423	593	N-hydroxy-4-(pyridin-3-ylethynyl)benzamide	239.2
424	594	4-(3-hydroxy-3,5-dimethylhex-1-ynyl)-N- {(1S,2R)-2-hydroxy-1- [(hydroxyamino)carbonyl]propyl}benzamide	363.4
425	595	4′-ethyl-N-{(1R,2R)-2-hydroxy-1- [(hydroxyamino)methyl]propyl}-1,1′- biphenyl-4-carboxamide	329.4
426	596	4′-ethyl-N-{(1R,2R)-1- [(hydroxyamino)methyl]-2- [(phenylmethyl)oxy]propyl}-1,1′- biphenyl-4-carboxamide	419.5
427	597	4′-ethyl-N-[(5R,6R)-3-hydroxy-6-methyl-2- oxo-1,3-oxazman-5-yl]-1,1′-biphenyl-4- carboxamide	355.4
428	598	N-((1R,2R)-1 {[({[2-(dimethylamino) ethyl]amino}carbonyl)(hydroxy) amino]methyl}-2-hydroxypropyl)-4′- ethyl-1,1′-biphenyl-4-carboxamide	443.6
429	599	N-((1R,2R)-1-{[{[(2-cyanoethyl)amino]carbonyl}(hydroxy)amino]methyl}- 2-hydroxypropyl)-4′-ethyl-1,1′- biphenyl-4-carboxamide	425.5
430	600	4′-ethyl-N-((1R,2R)-2-hydroxy-1- {[hydroxy({[3-(2-oxopyrrolidin- 1-yl)propyl]amino}carbonyl)amino]methyl}propyl)-1,1′-biphenyl-4-carboxamide	497.6
431	601	(1R,2R)-3-[({[2-(dimethylamino)ethyl]amino}carbonyl)(hydroxy)amino]-2- {[(4′-ethyl-1,1′-biphenyl-4- yl)carbonyl]amino}-1-methylpropyl 2- (dimethylamino)ethylcarbamate	557.7
432	602	(1R,2R)-3-[{[(2-cyanoethyl)amino]carbonyl}(hydroxy)amino]-2- {[(4′-ethyl-1,1′-biphenyl-4- yl)carbonyl]amino}-1-methylpropyl 2- cyanoethylcarbamate	521.6
433	603	N-{(1E)-1-[(E)-(hydroxylmino)methyl]prop-1- enyl}-4′-propyl-1,1′-biphenyl-4-carboxamide	323.4
434	604	N-{(1S,2R)-2-hydroxy-1-(hydroxyamino) carbonyl]propyl}-4-(pyridin-3- ylethynyl)benzamide	340.3
435	605	N-{(1S,2R)-2-hydroxy-1- [(hydroxyamino)carbonyl]propyl}-4-[3- (methylamino)prop-1-ynyl]benzamide	306.3
436	606	N-[(1S)-1-[(dimethylamino)methyl]-2- (hydroxyamino)-2-oxoethyl]-4′-ethyl-1,1′- biphenyl-4-carboxamide	356.4
437	607	N-[1-(N-hydroxycarbamoylmethyl)(1R,2R)- 2-hydroxypropyl][4-(4- ethylphenyl)phenyl]carboxamide	357.4
438	608	N-[(1S)-1-[(diethylamino)methyl]-2- (hydroxyamino)-2-oxoethyl]-4′-ethyl-1,1′- biphenyl-4-carboxamide	384.5
439	609	4-[(3-aminophenyl)ethynyl]-N-{(1S,2R)-2- hydroxy-1- [(hydroxyamino)carbonyl]propyl}benzamide	354.4
440	610	4-[3-(dimethylamino)prop-1-ynyl]-N- {(1S,2R)-2-hydroxy-1- [(hydroxyamino)carbonyl]propyl}benzamide	320.4
441	611	4-[3-(dimethylamino)prop-1-ynyl]-N-{(1S,2R)- 2-hydroxy-1- [(hydroxyamino)carbonyl]propyl}benzamide	320.4
442	612	4-({4-[(aminoacetyl)amino]phenyl}ethynyl)-N- {(1S,2R)-2-hydroxy-1- [(hydroxyamino)carbonyl]propyl}benzamide	411.4
443	613	3′-fluoro-N-{(1S,2R)-2-hydroxy-1- [(hydroxyamino)carbonyl]-4′-methyl- 1,1′-biphenyl-4-carboxamide	347.4
444	614	N-[(1S)-1-formyl-2-methylpropyl]-1,1′- biphenyl-4-carboxamide	282.4
445	615	N-{(1S)-1-[(E)-(hydroxylmino)methyl]-2- methylpropyl}-1,1′-biphenyl-4-carboxamide	297.4
446	616	N-((1E)-1-{(E)-[(aminocarbonyl) hydrazono]methyl}prop-1- enyl)-4′-propyl-1,1′-biphenyl-4-carboxamide	365.4
447	617	4-[(4-aminophenyl)ethynyl]-N-{(1S,2R)-2- hydroxy-1-[(hydroxyamino) carbonyl]propyl}benzamide	354.4
448	618	4-{[3-(aminomethyl)phenyl]ethynyl}-N- {(1S,2R)-2-hydroxy-1- [(hydroxyamino)carbonyl]propyl}benzamide	368.4
449	619	N-(2-aminoethyl)-3-({4-[({(1S,2R)-2- hydroxy-1-[(hydroxyamino) carbonyl]propyl}amino)carbonyl]phenyl}ethynyl)benzamide	425.5
450	620	N-((1S)-1-{(1E)-[(aminocarbonyl) hydrazono]methyl}-2- methylpropyl)-1,1′-biphenyl-4-carboxamide	339.4
451	621	N-{(1S,2R)-2-hydroxy-1- [(hydroxyamino)carbonyl]propyl}-4-{[3- (propanoylamino)phenyl]ethynyl}benzamide	410.4
452	622	N-{(1S,2R)-2-hydroxy-1- [(hydroxyamino)carbonyl]propyl}-4-{[3- (morpholin-4- ylmethyl)phenyl]ethynyl}benzamide	438.5
453	623	4-[(3-{[(2-aminoethyl)amino]methyl}phenyl) ethynyl]-N- {(1S,2R)-2-hydroxy-1- [(hydroxyamino)carbonyl]propyl}benzamide	411.5
454	624	N-[(1R)-2-(hydroxyamino)-1-(hydroxymethyl)- 2-oxoethyl]-4′-propyl-1,1′-biphenyl-4- carboxamide	343.4
455	625	N-[1-(N-hydroxycarbamoylmethyl)(1R,2R)-2- hydroxypropyl][4-(2- phenylethynyl)phenyl]carboxamide	353.4
456	626	4′-ethyl-N-[(1R,2R)-1- [(hydroxyamino)carbonyl]-2- (methyloxy)propyl]-1,1′-biphenyl-4- carboxamide	357.4
457	627	4′-ethyl-N-[(1S)-1-[(ethylamino)methyl]-2- (hydroxyaxnmo)-2-oxoethyl]-1,1′- biphenyl-4-carboxamide	356.4
458	628	4′-ethyl-N-[(1S)-2-(hydroxyamino)-2-oxo-1- ({[(2S)-pyrrolidin-2-ylmethyl]amino}methyl)ethyl]-1,1′-biphenyl-4- carboxamide	411.5
459	629	N-[(1S)-1-[(ethylamino)methyl]-2- (hydroxyamino)-2-oxoethyl]-4- (phenylethynyl)benzamide	352.4
460	630	N-[(1S)-2-(hydroxyamino)-2-oxo-1-({[(2S)- pyrrolidin-2-ylmethyl]amino}methyl) ethyl]-4-(phenylethynyl)benzamide	407.5
461	631	4′-ethyl-N-((1S)-2-(hydroxyamino)-1-{[(1- methylethyl)amino]methyl}-2-oxoethyl)-1,1′- biphenyl-4-carboxamide	370.5
462	632	4′-ethyl-N-[(1S)-2-(hydroxyamino)-1-({[2- (methylamino)ethyl]amino}methyl)-2- oxoethyl]-1,1′-biphenyl-4-carboxamide	385.5
463	633	4′-ethyl-N-((1S)-2-(hydroxyamino)-1-{[(1- methylpiperidin-4-yl)amino]methyl}-2- oxoethyl)-1,1′-biphenyl-4-carboxamide	425.5
464	634	N-((1S)-2-(hydroxyamino)-1-{[(1- methylethyl)amino]methyl}-2-oxoethyl)-4- (phenylethynyl)benzamide	366.4
465	635	N-[(1S)-2-(hydroxyamino)-1-({[2- (methylamino)ethyl]amino}methyl)-2- oxoethyl]-4-(phenylethynyl)benzamide	381.4
466	636	N-((1S)-2-(hydroxyamino)-1-{[(1- methylpiperidin-4-yl)amino]methyl}-2- oxoethyl)-4-(phenylethynyl)benzamide	421.5
467	637	N-[(1S)-1-{[(2-aminoethyl)amino]methyl}-2- (hydroxyamino)-2-oxoethyl]-4- (phenylethynyl)benzamide	367.4
468	638	N-[(1S)-1-{[bis(2-aminoethyl)amino]methyl}- 2-(hydroxyamino)-2-oxoethyl]-4- (phenylethynyl)benzamide	410.5
469	639	N-{(1S,2R)-2-hydroxy-1- [(hydroxyamino)carbonyl]propyl}-4-({4- [(morpholin-4- ylacetyl)amino]phenyl}ethynyl)benzamide	481.5
470	640	N-{(1S,2R)-2-hydroxy-1- [(hydroxyamino)carbonyl]propyl}-4-{[4- (propanoylamino)phenyl]ethynyl}benzamide	410.4
471	641	N-{(1S,2R)-2-hydroxy-1- [(hydroxyamino)carbonyl]propyl}-4-({4- [(trifluoromethyl)oxy]phenyl}ethynyl)benzamide	423.4
472	642	1,1-dimethylethyl (2S)-3-(hydroxyamino)-3- oxo-2-{[(4-{[3-(propanoylamino) phenyl]ethynyl}phenyl)carbonyl]amino}propylcarbamate	495.5
473	643	1,1-dimethylethyl (2S)-3-(hydroxyamino)-3- oxo-2-([(4-pent-1-ynylphenyl) carbonyl]amino}propylcarbamate	390.4
474	644	N-[(1S)-1-(aminomethyl)-2-(hydroxyamino)- 2-oxoethyl]-4-{[3- (propanoylamino)phenyl]ethynyl}benzamide	395.4
475	645	N-[(1S)-1-(aminomethyl)-2-(hydroxyamino)- 2-oxoethyl]-4-pent-1-ynylbenzamide	290.3
476	646	4-(phenyloxy)benzaldehyde thiosemicarbazone	272.3
477	647	4-(phenyloxy)benzaldehyde semicarbazone	256.3
478	648	4 {[3-(trifluoromethyl)phenyl]oxy}benzaldehyde thiosemicarbazone	340.3
479	649	4-[(3,4-difluorophenyl)ethynyl]-N- {(1S,2R)-2-hydroxy-1- [(hydroxyamino)carbonyl]propyl}benzamide	375.5
480	650	4-[(2,4-dioxo-1,2,3,4-tetrahydropyrimidin-5- yl)ethynyl]-N-{(1S,2R)-2-hydroxy-1- [(hydroxyamino)carbonyl]propyl}benzamide	373.3
481	651	N-[(1S)-1-(aminomethyl)-2-(hydroxyamino)- 2-oxoethyl]-4-(4-phenylbuta-1,3- diynyl)benzamide	348.4
482	652	N-[(1S)-1-(aminomethyl)-2-(hydroxyamino)- 2-oxoethyl]-4′-propyl-1,1′-biphenyl-4- carboxamide	342.4
483	653	N-[(1S)-1-(aminomethyl)-2-(hydroxyamino)- 2-oxoethyl]-1,1′:4′,1″-terphenyl-4-carboxamide	376.4
484	654	N-{(1S,2R)-2-hydroxy-1- [(hydroxyamino)carbonyl]propyl}-1,1′:4′,1″- terphenyl-4-carboxamide	391.4
485	655	1,1-dimethylethyl (2S)-2-[({4-[(4-{({[(1,1- dimethylethyl)oxy]carbonyl}amino)acetyl]amino}phenyl)ethynyl]phenyl}carbonyl) amino]-3-(hydroxyamino)- 3-oxopropylcarbamate	596.6
486	656	N-[(1S,2R)-1-(hydrazinocarbonyl)-2- hydroxypropyl]-4-(phenylethynyl) benzamide	338.4
487	657	2-[(2S,3R)-3-hydroxy-2-({[4- (phenylethynyl)phenyl]carbonyl}amino) butanoyl]hydrazinecarboxamide	381.4
488	658	N-{(1S,2R)-2-hydroxy-1- [(hydroxyamino)carbonyl]propyl}-4-[(2- methylphenyl)ethynyl]benzamide	353.4
489	659	N-{(1S,2R)-2-hydroxy-1- [(hydroxyamino)carbonyl]propyl}-4-[(3- hydroxyphenyl)ethynyl]benzamide	355.4
490	660	4-({3-[(aminoacetyl)amino]phenyl}ethynyl)- N-{(1S,2R)-2-hydroxy-1- [(hydroxyamino)carbonyl]propyl}benzamide	411.4
491	661	4-{[4-({[(cyanomethyl)amino]acetyl}amino)phenyl]ethynyl}-N-{(1S,2R)- 2-hydroxy-1-[(hydroxyamino) carbonyl]propyl}benzamide	450.5
492	662	4′-ethyl-N-{(1S)-2-(hydroxyamino)-2-oxo-1- [(tetrahydro-2H-pyran-4- ylamino)methyl]ethyl}-1,1′-biphenyl-4- carboxamide	412.5
493	663	N-{(1S)-2-(hydroxyamino)-2-oxo-1- [(tetrahydro-2H-pyran-4- ylamino)methyl]ethyl}-4- (phenylethynyl)benzamide	408.5
494	664	4-[(4-chlorophenyl)ethynyl]-N-{(1S,2R)- 2-hydroxy-1- [(hydroxyamino)carbonyl]propyl}benzamide	373.8
495	665	N-{(1S,2R)-2-hydroxy-1- [(hydroxyamino)carbonyl]propyl}-4-[(4- methylphenyl)ethynyl]benzamide	353.4
496	666	4-[(2-fluorophenyl)ethynyl]-N-{(1S,2R)- 2-hydroxy-1- [(hydroxyamino)carbonyl]propyl}benzamide	357.4
497	667	4-[(3-fluorophenyl)ethynyl]-N-{(1S,2R)- 2-hydroxy-1- [(hydroxyamino)carbonyl]propyl}benzamide	357.4
498	668	4-[(4-fluorophenyl)ethynyl]-N-{(1S,2R)- 2-hydroxy-1- [(hydroxyamino)carbonyl]propyl}benzamide	357.4
499	669	4-[(4-{[(cyclopropylamino)acetyl]amino}phenyl)ethynyl]-N- {(1S,2R)-2-hydroxy-1- [(hydroxyamino)carbonyl]propyl}benzamide	451.5
500	670	4-({4-[({[2-(dimethylamino)ethyl]amino}acetyl)amino]phenyl}ethynyl)-N-{(1S,2R)-2-hydroxy-1- [(hydroxyamino)carbonyl]propyl}benzamide	482.6
501	671	4-({4-[({[2-(acetylamino)ethyl]amino}acetyl)amino]phenyl}ethynyl)-N-{(1S,2R)-2-hydroxy-1- [(hydroxyamino)carbonyl]propyl}benzamide	496.5
502	672	N-{(1S,2R)-2-hydroxy-1- [(hydroxyamino)carbonyl]propyl}-4- ({4-[({[3-(2-oxopyrrolidin-1- yl)propyl]amino}acetyl)amino]phenyl}ethynyl)benzamide	536.6
503	673	N-{(1S,2R)-2-hydroxy-1- [(hydroxyamino)carbonyl]propyl}-4- {[4-({[(pyridin-3-ylmethyl) amino]acetyl}amino)phenyl]ethynyl}benzamide	502.5
504	674	N-{(1S,2R)-2-hydroxy-1- [(hydroxyamino)carbonyl]propyl}-4- {[4-({[(2-pyridin-2-ylethyl) amino]acetyl}amino)phenyl]ethynyl}benzamide	516.6
505	675	N-{(1S,2R)-2-hydroxy-1- [(hydroxyamino)carbonyl]propyl}-4- [(4-{[(4-methylpiperazin-1- yl)acetyl]amino}phenyl)ethynyl]benzamide	494.6
506	676	4-({4-[(1,4′-bipiperidin-1′- ylacetyl)amino]phenyl}ethynyl)-N- {(1S,2R)-2-hydroxy-1- [(hydroxyamino)carbonyl]propyl}benzamide	562.7
507	677	1-(2-{[4-({4-[({(1S,2R)-2-hydroxy-1- [(hydroxyamino)carbonyl]propyl}amino) carbonyl]phenyl}ethynyl)phenyl]amino}-2-oxoethyl)piperidine- 4-carboxamide	522.6
508	678	N-{(1S,2R)-2-hydroxy-1- [(hydroxyamino)carbonyl]propyl}-4- [(4-{[(piperidin-3-ylamino) acetyl]amino}phenyl)ethynyl]benzamide	494.6
509	679	N-{(1S,2R)-2-hydroxy-1- [(hydroxyamino)carbonyl]propyl}-4- [(4-{[(piperidin-4-ylamino) acetyl]amino}phenyl)ethynyl]benzamide	494.6
510	680	N-{(1S,2R)-2-hydroxy-1- [(hydroxyamino)carbonyl]propyl}-4- {[4-({[(piperidin-2- ylmethyl)amino]acetyl}amino) phenyl]ethynyl}benzamide	508.6
511	681	N-{(1S,2R)-2-hydroxy-1- [(hydroxyamino)carbonyl]propyl}-4- {[4-({[(piperidin-3- ylmethyl)amino]acetyl}amino) phenyl]ethynyl}benzamide	508.6
512	682	4-[(4-{[(3-aminopyrrolidin-1- yl)acetyl]amino}phenyl)ethynyl]- N-{(1S,2R)-2-hydroxy-1- [(hydroxyamino)carbonyl]propyl}benzamide	480.5
513	683	4-({4-[(azepan-1-ylacetyl) amino]phenyl}ethynyl)-N- {(1S,2R)-2-hydroxy-1- [(hydroxyamino)carbonyl]propyl}benzamide	493.6
514	684	N-{(1S,2R)-2-hydroxy-1-[(hydroxyamino) carbonyl]propyl}-4-{[4-({[(4- morpholin-4-ylphenyl)amino]acetyl}amino)phenyl]ethynyl}benzamide	572.6
515	685	N-[(1S)-1-(aminomethyl)-2-(hydroxyamino)- 2-oxoethyl]-4-{[4-({[(2-hydroxyethyl) amino]acetyl}amino)phenyl]ethynyl}benzamide	440.5
516	686	N-[(1S)-1-(aminomethyl)-2-(hydroxyamino)- 2-oxoethyl]-4-[(4-{[(cyclopropylamino) acetyl]amino}phenyl)ethynyl]benzamide	436.5
517	687	N-[(1S)-1-(aminomethyl)-2-(hydroxyamino)- 2-oxoethyl]-4-({4-[({[3-(2- oxopyrrolidin-1-yl)propyl]amino}acetyl)amino]phenyl}ethynyl) benzamide	521.6
518	688	N-[(1S)-1-(aminomethyl)-2-(hydroxyamino)- 2-oxoethyl]-4-[(4-{[(4- methylpiperazin-1-yl) acetyl]amino}phenyl)ethynyl]benzamide	479.6
519	689	N-[(1S)-1-(aminomethyl)-2-(hydroxyamino)- 2-oxoethyl]-4-{[4-({[(pyridin-3- ylmethyl)amino]acetyl}amino) phenyl]ethynyl}benzamide	487.5
520	690	N-[(1S)-1-(aminomethyl)-2-(hydroxyamino)- 2-oxoethyl]-4-({4-[(piperidin-1- ylacetyl)amino]phenyl}ethynyl)benzamide	464.5
521	691	4-{[4-({[(2-hydroxyethyl)amino]acetyl}amino)phenyl]ethynyl}- N-{(1S,2R)-2-hydroxy-1- [(hydroxyamino)caxbonyl]propyl}benzamide	455.5
522	692	N-{(1S,2R)-2-hydroxy-1- [(hydroxyamino)carbonyl]propyl}-4- ({4-[({[2-(methyloxy)ethyl]amino}acetyl)amino]phenyl}ethynyl)benzamide	469.5
523	693	N-{(1S,2R)-2-hydroxy-1- [(hydroxyamino)carbonyl]propyl}-4- ({4-[({methyl[2- (methyloxy)ethyl]amino}acetyl) amino]phenyl}ethynyl)benzamide	483.5
524	694	4-{[4-({[[2-(dimethylamino)ethyl](methyl)amino]acetyl}amino) phenyl]ethynyl}-N-{(1S,2R)-2-hydroxy- 1-[(hydroxyamino)carbonyl]propyl}benzamide	496.6
525	695	4-{[4-({[(3R)-3-(dimethylamino) pyrrolidin-1-yl]acetyl}amino) phenyl]ethynyl}-N-{(1S,2R)- 2-hydroxy-1- [(hydroxyamino)carbonyl]propyl}benzamide	508.6
526	696	4-{[4-({[(3S)-3-(dimethylamino) pyrrolidin-1-yl]acetyl}amino) phenyl]ethynyl}-N-{(1S,2R)- 2-hydroxy-1- [(hydroxyamino)carbonyl]propyl}benzamide	508.6
527	697	4-{[4-({[(3R)-3-(acetylamino) pyrrolidin-1-yl]acetyl}amino)phenyl]ethynyl}-N-{(1S,2R)-2- hydroxy-1-[(hydroxyamino) carbonyl]propyl}benzamide	522.6
528	698	4-{[4-({[(3S)-3-(acetylamino) pyrrolidin-1-yl]acetyl}amino)phenyl]ethynyl}-N-{(1S,2R)-2- hydroxy-1-[(hydroxyamino) carbonyl]propyl}benzamide	522.6
529	699	4-{[4-({[(3R)-1-(azabicyclo [2.2.2]oct-3-ylamino]acetyl}amino) phenyl]ethynyl}-N-{(1S,2R)-2- hydroxy-1-[(hydroxyamino) carbonyl]propyl}benzamide	520.6
530	700	4-{[4-({[(3S)-1-azabicyclo[2.2.2]oct-3-ylamino]acetyl}amino)phenyl]ethynyl}-N-{(1S,2R)-2-hydroxy-1- [(hydroxyamino)carbonyl]propyl}benzamide	520.6
531	701	N-{(1S,2R)-2-hydroxy-1- [(hydroxyamino)carbonyl]propyl}-4-({4- [({[(2R)-pyrrolidin-2- ylmethyl]amino}acetyl)amino]phenyl}ethynyl)benzamide	494.6
532	702	N-{(1S,2R)-2-hydroxy-1- [(hydroxyamino)carbonyl]propyl}-4-({4- [({[(2S)-pyrralidin-2- ylmethyl]amino}acetyl)amino]phenyl}ethynyl)benzamide	494.6
533	703	4-{[4-({[(3-aminocyclohexyl)amino]acetyl}amino)phenyl]ethynyl}-N- {(1S,2R)-2-hydroxy-1- [(hydroxyamino)carbonyl]propyl}benzamide	508.6
534	704	N-{(1S,2R)-2-hydroxy-1- [(hydroxyamino)carbonyl]propyl}-4- [(4-{[(3-hydroxypipendin-1- yl)acetyl]amino}phenyl)ethynyl]benzamide	495.5
535	705	N-{(1S,2R)-2-hydroxy-1- [(hydroxyamino)carbonyl]propyl}-4- {[4-({[(3-morpholin-4- ylpropyl)amino]acetyl}amino) phenyl]ethynyl}benzamide	538.6
536	706	N-{(1S,2R)-2-hydroxy-1- [(hydroxyamino)carbonyl]propyl}-4- {[4-({[(2-methylpropyl)amino]acetyl}amino)phenyl]ethynyl}benzamide	467.5
537	707	4-[(4-{[(ethylamino)acetyl]amino}phenyl)ethynyl]N- {(1S,2R)-2-hydroxy-1- [(hydroxyamino)carbonyl]propyl}benzamide	439.5
538	708	N-{(1S,2R)-2-hydroxy-1- [(hydroxyamino)carbonyl]propyl}-4-({4- [(piperidin-1-ylacetyl) amino]phenyl}ethynyl)benzamide	479.5
539	709	N-{(1S,2R)-2-hydroxy-1- [(hydroxyamino)carbonyl]propyl}-4- {[4-({[(3-hydroxypropyl)amino]acetyl}amino)phenyl]ethynyl}benzamide	469.5
540	710	N-{(1S,2R)-2-hydroxy-1- [(hydroxyamino)carbonyl]propyl}-4- ({4-[({[3-(methyloxy)propyl]amino}acetyl)amino]phenyl}ethynyl)benzamide	483.5
541	711	4-{[4-({[(2-cyanoethyl)amino]acetyl}amino)phenyl]ethynyl}-N- {(1S,2R)-2-hydroxy-1- [(hydroxyamino)carbonyl]propyl}benzamide	464.5
542	712	N-{(1S,2R)-2-hydroxy-1- [(hydroxyamino)carbonyl]propyl}-4- {[4-({[(2-pyrrolidin-1-ylethyl)amino]acetyl}amino)phenyl]ethynyl}benzamide	508.6
543	713	N-{(1S,2R)-2-hydroxy-1- [(hydroxyamino)carbonyl]propyl}-4- [(4-{[(2-methyl-1H-imidazol-1- yl)acetyl]amino}phenyl)ethynyl]benzamide	476.5
544	714	N-[(1S)-1-(aminomethyl)-2-(hydroxyamino)- 2-oxoethyl]-4-[(4- {[(methylamino)acetyl]amino}phenyl) ethynyl]benzamide	410.4
545	715	N-[(1S)-1-(aminomethyl)-2-(hydroxyamino)- 2-oxoethyl]-4-{[4-({[(2-methylpropyl) amino]acetyl}amino)phenyl]ethynyl}benzamide	452.5
546	716	N-[(1S)-1-(aminomethyl)-2-(hydroxyamino)- 2-oxoethyl]-4-({4-[({[2-(methyloxy) ethyl]amino}acetyl)amino]phenyl}ethynyl)benzamide	454.5
547	717	N-[(1S)-1-(aminomethyl)-2-(hydroxyamino)- 2-oxoethyl]-4-({4-[({methyl[2- (methyloxy)ethyl]amino}acetyl) amino)phenyl}ethynyl)benzamide	468.5
548	718	N-[(1S)-1-(aminomethyl)-2-(hydroxyamino)- 2-oxoethyl]-4-{[4-({[(3- hydroxypropyl)amino]acetyl}amino) phenyl]ethynyl}benzamide	454.5
549	719	N-[(1S)-1-(aminomethyl)-2-(hydroxyamino)- 2-oxoethyl]-4-({4-[({[3- (methyloxy)propyl]amino}acetyl) amino]phenyl}ethynyl)benzamide	468.5
550	720	N-[(1S)-1-(aminomethyl)-2-(hydroxyamino)- 2-oxoethyl]-4-({4-[({[2- (dimethylamino)ethyl]amino}acetyl) amino]phenyl}ethynyl)benzamide	467.5
551	721	N-[(1S)-1-(aminomethyl)-2-(hydroxyamino)- 2-oxoethyl]-4-{[4-({[[2- (dimethylamino)ethyl](methyl)amino]acetyl}amino)phenyl]ethynyl}benzamide	481.6
552	722	4-({4-[({[2-(acetylamino)ethyl]amino}acetyl)amino]phenyl}ethynyl)-N- [(1S)-1-(aminomethyl)-2- (hydroxyamino)-2-oxoethyl]benzamide	481.5
553	723	N-[(1S)-1-(aminomethyl)-2-(hydroxyamino)- 2-oxoethyl]-4-{[4-({[(2- cyanoethyl)amino]acetyl}amino) phenyl]ethynyl}benzamide	449.5
554	724	N-[(1S)-1-(aminomethyl)-2-(hydroxyamino)- 2-oxoethyl]-4-{[4-({[(2- pyrrolidin-1-ylethyl)amino]acetyl}amino)phenyl]ethynyl}benzamide	493.6
555	725	N-[(1S)-1-(aminomethyl)-2-(hydroxyamino)- 2-oxoethyl]-4-({4-[({[4- (dimethylamino)butyl]amino}acetyl) amino]phenyl}ethynyl) benzamide	495.6
556	726	N-[(1S)-1-(aminomethyl)-2-(hydroxyamino)- 2-oxoethyl]-4-({4-[(morpholin-4- ylacetyl)amino]phenyl}ethynyl)benzamide	466.5
557	727	N-[(1S)-1-(aminomethyl)-2-(hydroxyamino)- 2-oxaethyl]-4-({4-[(azepan-1- ylacetyl)amino]phenyl}ethynyl)benzamide	478.6
558	728	N-[(1S)-1-(aminomethyl)-2-(hydroxyamino)- 2-oxoethyl]-4-({4-[(pyrrolidin-1- ylacetyl)amino]phenyl}ethynyl)benzamide	450.5
559	729	1-{2-[(4-{[4-({[(1S)-1-(aminomethyl)-2- (hydroxyamino)-2-oxoethyl]amino}carbonyl)phenyl]ethynyl}phenyl) amino]-2-axoethyl}piperidine-4- carboxamide	507.6
560	730	4-{[4-({[(3R)-3-(acetylamino)pyrrolidin-1- yl]acetyl}amino)phenyl]ethynyl}-N-[(1S)-1- (aminomethyl)-2-(hydroxyamino)-2- oxaethyl]benzamide	507.6
561	731	N-[(1S)-1-(aminomethyl)-2-(hydroxyamino)- 2-oxoethyl]-4-{[4-({[(3R)-3- (dimethylamino)pyrrolidin-1- yl]acetyl}amino)phenyl]ethynyl}benzamide	493.6
562	732	N-[(1S)-1-(aminomethyl)-2-(hydroxyamino)- 2-oxoethyl]-4-[(4-{[(3-aminopyrrolidin-1- yl)acetyl]amino}phenyl)ethynyl]benzamide	465.5
563	733	N-[(1S)-1-(aminomethyl)-2-(hydroxyamino)- 2-oxoethyl]-4-[(4-{[(piperidin-3- ylamino)acetyl]amino}phenyl) ethynyl]benzamide	479.6
564	734	N-[(1S)-1-(aminomethyl)-2-(hydroxyamino)- 2-oxoethyl]-4-[(4-{[(piperidin- 4-ylamino)acetyl]amino}phenyl) ethynyl]benzamide	479.6
565	735	N-[(1S)-1-(aminomethyl)-2-(hydroxyamino)- 2-oxoethyl]-4-{[4-({[(piperidin- 2-ylmethyl)amino]acetyl}amino) phenyl]ethynyl}benzamide	493.6
566	736	N-[(1S)-1-(aminomethyl)-2-(hydroxyamino)- 2-oxoethyl]-4-{[4-({[(piperidin- 3-ylmethyl)amino]acetyl}amino) phenyl]ethynyl}benzamide	493.6
567	737	N-[(1S)-1-(aminomethyl)-2-(hydroxyamino)- 2-oxoethyl]-4-{[4-({[(pyridin-2- ylmethyl)amino]acetyl}amino) phenyl]ethynyl}benzamide	487.5
568	738	N-[(1S)-1-(aminomethyl)-2-(hydroxyamino)- 2-oxoethyl]-4-{[4-({[(pyridin-4- ylmethyl)amino]acetyl}amino) phenyl]ethynyl}benzamide	487.5
569	739	N-[(1S)-1-(aminomethyl)-2-(hydroxyamino)- 2-oxoethyl]-4-{[4-({[(2-pyridin-2- ylethyl)amino]acetyl}amino) phenyl]ethynyl}benzamide	501.6
570	740	N-[(1S)-1-(aminomethyl)-2-(hydroxyamino)- 2-oxoethyl]-4-{[4-({[(2-pyridin-3- ylethyl)amino]acetyl}amino) phenyl]ethynyl}benzamide	501.6
571	741	N-[(1S)-1-(aminomethyl)-2-(hydroxyamino)- 2-oxoethyl]-4-{[4-({[(2-pyridin-4- ylethyl)amino]acetyl}amino) phenyl]ethynyl}benzamide	501.6
572	742	N-[(1S)-1-(aminomethyl)-2-(hydroxyamino)- 2-oxoethyl]-4-[(4-{[(phenylamino) acetyl]amino}phenyl)ethynyl]benzamide	472.5
573	743	N-[(1S)-1-(aminomethyl)-2-(hydroxyamino)- 2-oxoethyl]-4-{[4-({[(phenylmethyl) amino]acetyl}amino)phenyl]ethynyl}benzamide	486.5
574	744	N-[(1S)-1-(aminomethyl)-2-(hydroxyamino)- 2-oxoethyl]-4-{[4-({[(2- phenylethyl)amino]acetyl}amino) phenyl]ethynyl}benzamide	500.6
575	745	N-[(1S)-1-(aminomethyl)-2-(hydroxyamino)- 2-oxoethyl]-4-({4-[(1H-imidazol-1- ylacetyl)amino]phenyl}ethynyl)benzamide	447.5
576	746	N-{(1S,2R)-2-hydroxy-1- [(hydroxyamino)carbonyl]propyl}-4- ({4-[(1H-imidazol-1-ylacetyl) amino]phenyl}ethynyl)benzamide	462.5
577	747	N-{(1S,2R)-2-hydroxy-1- [(hydroxyamino)carbonyl]propyl}-4- [(4-{[(phenylamino)acetyl]amino}phenyl)ethynyl]benzamide	487.5
578	748	N-{(1S,2R)-2-hydroxy-1- [(hydroxyamino)carbonyl]propyl}-4- {[4-({[(2-phenylethyl)amino]acetyl}amino)phenyl]ethynyl}benzamide	515.6
579	749	N-{(1S,2R)-2-hydroxy-1- [(hydroxyamino)carbonyl]propyl}-4- {[4-({[(3-phenylpropyl)amino]acetyl}amino)phenyl]ethnyl}benzamide	529.6
580	750	4-[(3-{[(aminoacetyl)amino]methyl }phenyl)ethynyl]-N-{(1S,2R)-2- hydroxy-1-[(hydroxyamino) carbonyl]propyl}benzamide	425.5
581	751	4-[(2-aminopyrimidin-5-yl)ethynyl]-N- {(1S,2R)-2-hydroxy-1- [(hydroxyamino)carbonyl]propyl}benzamide	356.4
582	752	4-[(4-acetylphenyl)ethynyl]-N-{(1S,2R)-2- hydroxy-1- [(hydroxyamino)carbonyl]propyl}benzamide	381.4
583	753	N-{(1S,2R)-2-hydroxy-1-[(hydroxyamino) carbonyl]propyl}-4-[(4-{[({2-[4- (phenylmethyl)piperazin-1-yl]ethyl}amino)acet-yl]amino}phenyl)ethynyl]benzamide	613.7
584	754	4-{[4-({[(aminoacetyl)amino]acetyl}amino)phenyl]ethynyl}- N-{(1S,2R)-2-hydroxy-1- [(hydroxyamino)carbonyl]propyl}benzamide	468.5
585	755	4-{[4-({[4-(2-hydroxyethyl)piperazin-1- yl]acetyl}amino)phenyl]ethynyl}-N- {(1S,2R)-2-hydroxy-1- [(hydroxyamino)carbonyl]propyl}benzamide	524.6
586	756	N-{(1S,2R)-2-hydroxy-1- [(hydroxyamino)carbonyl]propyl}-4-({4- [({(3R)-3-[(trifluoroacetyl)amino]pyrrolidin-1- yl}acetyl)amino]phenyl}ethynyl)benzamide	576.5
587	757	N-{(1S,2R)-2-hydroxy-1- [(hydroxyamino)carbonyl]propyl}-4-[(4- {[(methylamino)acetyl]amino}phenyl) ethynyl]benzamide	425.5
588	758	N-{(1S,2R)-2-hydroxy-1- [(hydroxyamino)carbonyl]propyl}-4-({4- [(piperazin-1-ylacetyl)amino]phenyl}ethynyl)benzamide	480.5
589	759	N-{(1S,2R)-2-hydroxy-1- [(hydroxyamino)carbonyl]propyl}-4-{[4- ({[(pyridin-2-ylmethyl)amino]acetyl}amino)phenyl]ethynyl}benzamide	502.5
590	760	N-{(1S,2R)-2-hydroxy-1- [(hydroxyamino)carbonyl]propyl}-4-{[4- ({[(pyridin-4-ylmethyl)amino]acetyl}amino)phenyl]ethynyl}benzamide	502.5
591	761	N-{(1S,2R)-2-hydroxy-1- [(hydroxyamino)carbonyl]propyl}-4-{[4- ({[(2-pyridin-3-ylethyl)amino]acetyl}amino)phenyl]ethynyl}benzamide	516.6
592	762	N-{(1S,2R)-2-hydroxy-1- [(hydroxyamino)carbonyl]propyl}-4-{[4- ({[(2-pyridin-4-ylethyl)amino]acetyl}amino)phenyl]ethynyl}benzamide	516.6
593	763	4-({4-[({[(2-fluorophenyl)methyl]amino}acetyl)amino]phenyl}ethynyl)-N-{(1S,2R)-2-hydroxy-1- [(hydroxyamino)carbonyl]propyl}benzamide	519.5
594	764	4-({4-[({[(2-chlorophenyl)methyl]amino}acetyl)amino]phenyl}ethynyl)-N-{(1S,2R)-2-hydroxy-1- [(hydroxyamino)carbonyl]propyl}benzamide	536.0
595	765	N-{(1S,2R)-2-hydroxy-1- [(hydroxyamino)carbonyl]propyl}-4- [(4-{[({[2-(methyloxy)phenyl]methyl}amino)acetyl]amino}phenyl) ethynyl]benzamide	531.6
596	766	4-({4-[({[(3-fluorophenyl)methyl]amino }acetyl)amino]phenyl}ethynyl)-N- {(1S,2R)-2-hydroxy-1-[(hydroxyamino) carbonyl]propyl}benzamide	519.5
597	767	4-({4-[({[(3-chlorophenyl)methyl]amino }acetyl)amino]phenyl}ethynyl)-N- {(1S,2R)-2-hydroxy-1-[(hydroxyamino) carbonyl]propyl}benzamide	536.0
598	768	N-{(1S,2R)-2-hydroxy-1-[(hydroxyamino) carbonyl]propyl}-4-[(4-{[({[3- (methyloxy)phenyl]methyl}amino) acetyl]amino}phenyl) ethynyl]benzamide	531.6
599	769	N-{(1S,2R)-2-hydroxy-1-[(hydroxyamino) carbonyl]propyl}-4-({4-[({[(3- methylphenyl)methyl]amino}acetyl) amino]phenyl}ethynyl)benzamide	515.6
600	770	N-{(1S,2R)-2-hydroxy-1-[(hydroxyamino) carbonyl]propyl}-4-[(4-{[({[3- (trifluoromethyl)phenyl]methyl}amino)acetyl]amino}phenyl) ethynyl]benzamide	569.5
601	771	N-{(1S,2R)-2-hydroxy-1-[(hydroxyamino) carbonyl]propyl}-4-([4-({[({3- [(trifluoromethyl)oxy]phenyl}methyl)amino]acetyl}amino) phenyl]ethynyl}benzamide	585.5
602	772	4-({4-[({[(4-fluorophenyl)methyl]amino}acetyl)′amino]phenyl}ethynyl)-N-{(1S,2R)-2-hydroxy- 1-[(hydroxyamino)carbonyl]propyl}benzamide	519.5
603	773	N-{(1S,2R)-2-hydroxy-1- [(hydroxyamino)carbonyl]propyl}-4- ({4-[({[(4-methylphenyl)methyl]amino}acetyl)amino]phenyl}ethynyl)benzamide	515.6
604	774	4-[(4-{[({[4-(dimethylamino)phenyl]methyl}amino)acetyl]amino}phenyl) ethynyl]-N-{(1S,2R)-2-hydroxy-1- [(hydroxyamino)carbonyl]propyl}benzamide	544.6
605	775	N-{(1S,2R)-2-hydroxy-1- [(hydroxyamino)carbonyl]propyl}-4- [(4-{[({[4-(trifluoromethyl) phenyl]methyl}amino)acetyl]amino}phenyl)ethynyl]benzamide	569.5
606	776	4-[(4-{[({[4-fluoro-2- (trifluoromethyl)phenyl]methyl}amino) acetyl]amino}phenyl)ethynyl]-N- {(1S,2R)-2-hydroxy-1- [(hydroxyamino)carbonyl]propyl}benzamide	587.5
607	777	4-({4-[({[(2,4-difluorophenyl) methyl]amino}acetyl)amino]phenyl}ethynyl)-N-{(1S,2R)-2-hydroxy-1- [(hydroxyamino)carbonyl]propyl}benzamide	537.5
608	778	4-({4-[({[(2,4-dichlorophenyl) methyl]amino}acetyl)amino]phenyl}ethynyl)-N-{(1S,2R)-2-hydroxy-1- [(hydroxyamino)carbonyl]propyl}benzamide	570.4
609	779	4-{[4-({[(2-fluorophenyl)amino]acetyl}amino)phenyl]ethynyl}- N-{(1S,2R)-2-hydroxy-1- [(hydroxyamino)carbonyl]propyl}benzamide	505.5
610	780	4-{[4-({[(4-fluorophenyl)amino]acetyl}amino)phenyl]ethynyl}- N-{(1S,2R)-2-hydroxy-1- [(hydroxyamino)carbonyl]propyl}benzamide	505.5
611	781	4-({4-[({[(3,5-difluorophenyl)methyl]amino}acetyl)amino]phenyl}ethynyl) -N-{(1S,2R)-2-hydroxy-1- [(hydroxyamino)carbonyl]propyl}benzamide	537.5
612	782	4-{[4-({[(4-bromophenyl)amino]acetyl}amino)phenyl]ethnyl}- N-{(1S,2R)-2-hydroxy-1- [(hydroxyamino)carbonyl]propyl}benzamide	566.4
613	783	4-({4-[({[4-(dimethylamino)phenyl]amino}acetyl)amino[phenyl}ethynyl)-N-{(1S,2R)-2-hydroxy-1- [(hydroxyamino)carbonyl]propyl}benzamide	530.6
614	784	N-[(1S)-1-(aminomethyl)-2-(hydroxyamino)- 2-oxoethyl]-4-[(4-{[(2S)-2- aminopropanoyl]amino}phenyl) ethynyl]benzamide	410.4
615	785	N-[(1S)-1-(aminomethyl)-2-(hydroxyamino)- 2-oxoethyl]-4-[(4-{[(2R)-2- aminopropanoyl]amino}phenyl) ethynyl]benzamide	410.4
616	786	N-[(1S)-1-(aminomethyl)-2-(hydroxyamino)- 2-oxoethyl]-4-[(4-{[(2S)-2- amino-4-methylpentanoyl]amino}phenyl)ethynyl]benzamide	452.5
617	787	4-[(4-{[(2S,3R)-2-amino-3- hydroxybutanoyl]amino}phenyl)ethynyl- N-[(1S)-1-(aminomethyl)-2- (hydroxyamino)-2-oxoethyl]benzamide	440.5
618	788	4-[(4-{[(2S)-2-amino-4- cyanobutanoyl]amino}phenyl)ethynyl]-N- [(1S)-1-(aminomethyl)-2-(hydroxyamino)- 2-oxoethyl]benzamide	449.5
619	789	N-[(1S)-1-(aminomethyl)-2-(hydroxyamino)- 2-diaminopropanoyl]amino}phenyl) ethynyl]benzamide	425.5
620	790	(2S)-N-(4-{[4-({[(1S)-1-(aminomethyl)-2- (hydroxyamino)-2-oxoethyl]amino}carbonyl)phenyl]ethynyl}phenyl) pyrrolidine-2-carboxamide	436.5
621	791	(2S)-N-(4-{[4-({[(1S)-1-(aminomethyl)-2- (hydroxyamino)-2-oxoethyl]amino}carbonyl)phenyl]ethynyl}phenyl) pipendine-2-carboxamide	450.5
622	792	N-(4-{[4-({[(1S)-1-(aminomethyl)-2- (hydroxyamino)-2-oxoethyl]amino}carbonyl)phenyl]ethynyl}phenyl) piperidine-3-carboxamide	450.5
623	793	4-[(4-{[(2S)-2-amino-3-(1H-imidazol-4- yl)propanoyl]amino}phenyl)ethynyl]- N-[(1S)-1-(aminomethyl)-2- (hydroxyamino)-2-oxoethyl]benzamide	476.5
624	794	N-[(1S)-1-(aminomethyl)-2-(hydroxyamino)- 2-oxoethyl]-4-[(4- methylphenyl)ethynyl]benzamide	338.4
625	795	N-[(1S)-1-(aminomethyl)-2-(hydroxyamino)- 2-oxoethyl]-4-[(2- fluorophenyl)ethynyl]benzamide	342.3
626	796	N-[(1S)-1-(aminomethyl)-2-(hydroxyamino)- 2-oxoethyl]-4-[(3- fluorophenyl)ethynyl]benzamide	342.3
627	797	N-[(1S)-1-(aminomethyl)-2-(hydroxyamino)- 2-oxoethyl]-4-[(4- fluorophenyl)ethynyl]benzamide	342.3
628	798	N-[(1S)-1-(aminomethyl)-2-(hydroxyamino)- 2-oxoethyl]-4-[(4- chlorophenyl)ethynyl]benzamide	358.8
629	799	4-[(4-{[(2S)-2-amino-4- methylpentanoyl]amino}phenyl)ethynyl]- N-{(1S,2R)-2-hydroxy-1- [(hydroxyamino)carbonyl]propyl}benzamide	467.5
630	800	4-[(4-{[(2S)-2-amino-4- cyanobutanoyl]amino}phenyl)ethynyl]-N- {(1S,2R)-2-hydroxy-1- [(hydroxyamino)carbonyl]propyl}benzamide	464.5
631	801	4-[(4-{[(2S)-2,3-diaminopropanoyl]amino}phenyl)ethynyl]-N- {(1S,2R)-2-hydroxy-1- [(hydroxyamino)carbonyl]propyl}benzamide	440.5
632	802	N-[4-({4-[({(1S,2R)-2-hydroxy-1- [(hydroxyamino)carbonyl]propyl}amino) carbonyl]phenyl}ethynyl)phenyl]piperidine-3-carboxamide	465.5
633	803	N-{(1S,2R)-2-hydroxy-1- [(hydroxyamino)carbonyl]propyl}-4-({3- [(morpholin-4- ylacetyl)amino]phenyl}ethynyl)benzamide	481.5
634	804	N-{(1S,2R)-2-hydroxy-1- [(hydroxyamino)carbonyl]propyl}-4- (pyrazin-2-ylethynyl)benzamide	341.3
635	805	N-{(1S,2R)-2-hydroxy-1- [(hydroxyamino)carbonyl]propyl}-4- ({4-[({[3-(1H-imidazol-1- yl)propyl]amino}acetyl)amino]phenyl}ethynyl)benzamide	519.6
636	806	N-((1S)-2-(hydroxyamino)-1-{[({[3-(1H- imidazol-1-yl)propyl]amino}acetyl)amino]methyl}-2- oxoethyl)-4-(phenylethynyl)benzamide	489.5
637	807	4-({4-[({(1S,2R)-2-hydroxy-1- [(hydroxyamino)carbonyl]propyl}amino) carbonyl]phenyl}ethynyl)benzoic acid	383.4
638	808	N-(2-{[4-({4-[({(1S,2R)-2-hydroxy-1- [(hydroxyamino)carbonyl]propyl}amino) carbonyl]phenyl}ethynyl)phenyl]amino}- 2-oxoethyl)-1,3-benzodioxole-4- carboxamide	559.5
639	809	4-({4-[((2R)-2-{[(2R)-2,5- diaminopentanoyl]amino}-4- phenylbutanoyl)amino]phenyl}ethynyl)- N-{(1S,2R)-2-hydroxy-1- [(hydroxyamino)carbonyl]propyl}benzamide	629.7
640	810	4-[(4-{[(2R)-2-amino-4- phenylbutanoyl]amino}phenyl)ethynyl]-N- {(1S,2R)-2-hydroxy-1- [(hydroxyamino)carbonyl]propyl}benzamide	515.6
641	811	4-[(4-{[(2S)-2-amino-3- phenylpropanoyl]amino}phenyl)ethynyl]-N- {(1S,2R)-2-hydroxy-1- [(hydroxyamino)carbonyl]propyl}benzamide	501.6
642	812	4-{[4-({[(2-aminoethyl)amino]acetyl}amino)phenyl]ethynyl}-N- {(1S,2R)-2-hydroxy-1- [(hydroxyamino)carbonyl]propyl}benzamide	454.5
643	813	N-{(1S)-2-(hydroxyamino)-1-[({[methyl(1- methylpiperidin-4-yl)amino]acetyl}amino)methyl]-2-oxoethyl}-4- (phenylethynyl)benzamide	492.6
644	814	4-[(4-{[(cyclobutylamino)acetyl]amino}phenyl)ethynyl]-N-{(1S,2R)- 2-hydroxy-1- [(hydroxyamino)carbonyl]propyl}benzamide	465.5
645	815	4-[(4-{[(cyclopentylamino)acetyl]amino}phenyl)ethynyl]-N-{(1S,2R)- 2-hydroxy-1- [(hydroxyamino)carbonyl]propyl}benzamide	479.5
646	816	4-[(4-{[(cyclohexylamino)acetyl]amino}phenyl)ethynyl]-N-{(1S,2R)-2-hydroxy-1- [(hydroxyamino)carbonyl]propyl}benzamide	493.6
647	817	4-[(4-{[(cycloheptylamino)acetyl]amino}phenyl)ethynyl]-N- {(1S,2R)-2-hydroxy-1- [(hydroxyamino)carbonyl]propyl}benzamide	507.6
648	818	4-[(4-{[(cyclooctylamino)acetyl]amino}phenyl)ethynyl]-N- {(1S,2R)-2-hydroxy-1- [(hydroxyamino)carbonyl]propyl}benzamide	521.6
649	819	N-{(1S,2R)-2-hydroxy-1- [(hydroxyamino)carbonyl]propyl}-4-[(4- {[(propylamino)acetyl]amino}phenyl) ethynyl]benzamide	453.5
650	820	4-[(4-{[(hexylamino)acetyl]amino}phenyl)ethynyl]-N-{(1S,2R)-2- hydroxy-1-[(hydroxyamino)carbonyl]propyl}benzamide	495.6
651	821	N-{(1S,2R)-2-hydroxy-1- [(hydroxyamino)carbonyl]propyl}-4- {[4-({[(1-methylethyl)amino]acetyl}amino)phenyl]ethynyl}benzamide	453.5
652	822	4-{[4-({[(1,1-dimethylethyl)amino]acetyl}amino)phenyl]ethynyl}-N- {(1S,2R)-2-hydroxy-1-[(hydroxyamino) carbonyl]propyl}benzamide	467.5
653	823	4-{[4-({[ethyl(methyl)amino]acetyl}amino)phenyl]ethnyl}-N-{(1S,2R)- 2-hydroxy-1-[(hydroxyamino) carbonyl]propyl}benzamide	453.5
654	824	4-[(4-{[(diethylamino)acetyl]amino}phenyl)ethynyl]-N-{(1S,2R)-2- hydroxy-1-[(hydroxyamino) carbonyl]propyl}benzamide	467.5
655	825	4-{[4-({[(1,1-dimethylethyl)(methyl) amino]acetyl}amino)phenyl]ethynyl}-N-{(1S,2R)-2-hydroxy-1- [(hydroxyamino)carbonyl]propyl}benzamide	481.6
656	826	4-{[4-({[cyclohexyl(methyl) amino]acetyl}amino)phenyl]ethynyl}-N-{(1S,2R)-2-hydroxy-1- [(hydroxyamino)carbonyl]propyl}benzamide	507.6
657	827	4-{[4-({[bis(1-methylethyl)amino]acetyl}amino)phenyl]ethynyl}- N-{(1S,2R)-2-hydroxy-1- [(hydroxyamino)carbonyl]propyl}benzamide	495.6
658	828	4-{[4-({[(cyclohexylmethyl)amino]acetyl}amino)phenyl]ethynyl}- N-{(1S,2R)-2-hydroxy-1- [(hydroxyamino)carbonyl]propyl}benzamide	507.6
659	829	4-{[4-({[(2,3-dimethylcyclohexyl)amino]acetyl}amino)phenyl]ethynyl}- N-{(1S,2R)-2-hydroxy-1- [(hydroxyamino)carbonyl]propyl}benzamide	521.6
660	830	4-{[4-({[(1R,2R,4S)-bicyclo[2.2.1]hept-2- ylamino]acetyl}amino)phenyl]ethynyl}- N-{(1S,2R)-2-hydroxy-1- [(hydroxyamino)carbonyl]propyl}benzamide	505.6
661	831	4-[(4-{[({[(1S,2R,5S)-6,6- dimethylbicyclo[3.1.1]hept-2-yl]methyl}amino)acetyl]amino}phenyl) ethynyl]-N-{(1S,2R)-2-hydroxy-1- [(hydroxyamino)carbonyl]propyl}benzamide	547.7
662	832	N-{(1S,2R)-2-hydroxy-1- [(hydroxyamino)carbonyl]propyl}-4- {[4-({[4-(trifluoromethyl)piperidin- 1-yl]acetyl}amino) phenyl]ethynyl}benzamide	547.5
663	833	N-[(1S)-1-(aminomethyl)-2- (hydroxyamino)-2-oxoethyl]-4-({4- [({[(2-fluorophenyl)methyl]amino}acetyl)amino]phenyl}ethynyl)benzamide	504.5
664	834	N-[(1S)-1-(aminomethyl)-2- (hydroxyamino)-2-oxoethyl]-4-({4- [({[(2-chlorophenyl)methyl]amino}acetyl)amino]phenyl}ethynyl)benzamide	521.0
665	835	N-[(1S)-1-(aminomethyl)-2- (hydroxyamino)-2-oxoethyl]-4-({4- [({[(2-methylphenyl)methyl]amino}acetyl)amino]phenyl}ethynyl)benzamide	500.6
666	836	N-[(1S)-1-(aminomethyl)-2- (hydroxyamino)-2-oxoethyl]-4-[(4- {[({[2-(methyloxy)phenyl]methyl}amino)acetyl]amino}phenyl)ethynyl]benzamide	516.6
667	837	N-[(1S)-1-(aminomethyl)-2- (hydroxyamino)-2-oxoethyl]-4-[(4- {[({[2-(trifluoromethyl)phenyl]methyl}amino)acetyl]amino}phenyl)ethynyl]benzamide	554.5
668	838	N-[(1S)-1-(aminomethyl)-2- (hydroxyamino)-2-oxoethyl]-4-{[4- ({[({2-[(trifluoromethyl)oxy]phenyl}methyl)amino]acetyl}amino) phenyl]ethynyl}benzamide	570.5
669	839	N-[(1S)-1-(aminomethyl)-2- (hydroxyamino)-2-oxoethyl]-4-({4- [({[(3-fluorophenyl)methyl]amino}acetyl)amino]phenyl}ethynyl)benzamide	504.5
670	840	N-[(1S)-1-(aminomethyl)-2- (hydroxyamino)-2-oxoethyl]-4-({4- [({[(3-chlorophenyl)methyl]amino}acetyl)amino]phenyl}ethynyl)benzamide	521.0
671	841	N-[(1S)-1-(aminomethyl)-2- (hydroxyamino)-2-oxoethyl]-4-({4- [({[(3-methylphenyl)methyl]amino}acetyl)amino]phenyl}ethynyl)benzamide	500.6
672	842	N-[(1S)-1-(aminomethyl)-2- (hydroxyamino)-2-oxoethyl]-4-[(4- {[({[3-(methyloxy)phenyl]methyl}amino)acetyl]amino}phenyl)ethynyl]benzamide	516.6
673	843	N-[(1S)-1-(aminomethyl)-2- (hydroxyamino)-2-oxoethyl]-4-[(4- {[({[3-(trifluoromethyl)phenyl]methyl}amino)acetyl]amino}phenyl)ethynyl]benzamide	554.5
674	844	N-[(1S)-1-(aminomethyl)-2- (hydroxyamino)-2-oxoethyl]-4-{[4- ({[({3-[(trifluoromethyl)oxy]phenyl}methyl)amino]acetyl}amino)phenyl]ethynyl}benzamide	570.5
675	845	N-[(1S)-1-(aminomethyl)-2- (hydroxyamino)-2-oxoethyl]-4-({4- [({[(4-fluorophenyl)methyl]amino}acetyl)amino]phenyl}ethynyl)benzamide	504.5
676	846	N-[(1S)-1-(aminomethyl)-2- (hydroxyamino)-2-oxoethyl]-4-({4- [({[(4-chlorophenyl)methyl]amino}acetyl)amino]phenyl}ethynyl)benzamide	521.0
677	847	N-[(1S)-1-(aminomethyl)-2- (hydroxyamino)-2-oxoethyl]-4-({4- [({[(4-methylphenyl)methyl]amino}acetyl)amino]phenyl}ethynyl)benzamide	500.6
678	848	N-[(1S)-1-(aminomethyl)-2- (hydroxyamino)-2-oxoethyl]-4-[(4- {[({[4-(methyloxy)phenyl]methyl}amino)acetyl]amino}phenyl) ethynyl]benzamide	516.6
679	849	N-[(1S)-1-(aminomethyl)-2- (hydroxyamino)-2-oxoethyl]-4-[(4- {[({[4-(trifluoromethyl)phenyl]methyl}amino)acetyl]amino}phenyl)ethynyl]benzamide	554.5
680	850	N-[(1S)-1-(aminomethyl)-2- (hydroxyamino)-2-oxoethyl]-4-[(4- {[({[4-(1,1-dimethylethyl) phenyl]methyl}amino)acctyl]amino}phenyl)ethynyl]benzamide	542.6
681	851	N-{(1S)-1-(aminomethyl)-2- (hydroxyamino)-2-oxoethyl]-4-({4-[({[(1R)-1- phenylethyl]amino}acetyl)amino]phenyl}ethyl)benzamide	500.6
682	852	N-[(1S)-1-(aminomethyl)-2- (hydroxyamino)-2-oxoethyl]-4-({4- [({[(1S)-1-phenylethyl]amino}acetyl)amino]phenyl}ethynyl) benzamide	500.6
683	853	N-[(1S)-1-(aminomethyl)-2- (hydroxyamino)-2-oxoethyl]-4-{[4- ({[(cyclahexylmethyl)amino]acetyl}amino)phenyl]ethynyl}benzamide	492.6
684	854	N-[(1S)-1-(aminomethyl)-2- (hydroxyamino)-2-oxoethyl]-4-[(4- {[(cyclobutylamino)acetyl]amino}phenyl)ethynyl]benzamide	450.5
685	855	N-[(1S)-1-(aminomethyl)-2- (hydroxyamino)-2-oxoethyl]-4-[(4- {[(cyclopentylamino)acetyl]amino}phenyl)ethynyl]benzamide	464.5
686	856	N-[(1S)-1-(aminomethyl)-2- (hydroxyamino)-2-oxoethyl]-4-[(4- {[(cyclohexylamino)acetyl]amino}phenyl)ethynyl]benzamide	478.6
687	857	N-[(1S)-1-(aminomethyl)-2- (hydroxyamino)-2-oxoethyl]-4-[(4- {[(cycloheptylamino)acetyl]amino}phenyl)ethynyl]benzamide	492.6
688	858	N-[(1S)-1-(aminomethyl)-2- (hydroxyamino)-2-oxoethyl]-4-[(4- {[(cyclooctylamino)acetyl]amino}phenyl)ethynyl]benzamide	506.6
689	859	N-[(1S)-1-(aminomethyl)-2- (hydroxyamino)-2-oxoethyl[-4-[(4- {[(ethylamino)acetyl]amino}phenyl)ethynyl]benzamide	424.5
690	860	N-[(1S)-1-(aminomethyl)-2- (hydroxyamino)-2-oxoethyl]-4-[(4- {[(propylamino)acetyl]amino}phenyl)ethynyl]benzamide	438.5
691	861	N-[(1S)-1-(aminomethyl)-2- (hydroxyamino)-2-oxoethyl]-4-[(4- {[(butylamino)acetyl]amino}phenyl) ethynyl]benzamide	452.5
692	862	N-[(1S)-1-(aminomethyl)-2- (hydroxyamino)-2-oxoethyl]-4-[(4- {[(hexylamino)acetyl]amino}phenyl) ethynyl]benzamide	480.6
693	863	N-[(1S)-1-(aminomethyl)-2- (hydroxyamino)-2-oxoethyl]-4-{[4-({[(1- methylethyl)amino]acetyl}amino)phenyl]ethynyl}benzamide	438.5
694	864	N-[(1S)-1-(aminomethyl)-2- (hydroxyamino)-2-oxoethyl]-4-{[4- ({[(1,1-dimethylethyl)amino]acetyl}amino)phenyl]ethynyl}benzamide	452.5
695	865	N-[(1S)-1-(aminomethyl)-2- (hydroxyamino)-2-oxoethyl]-4-{[4- ({[ethyl(methyl)amino]acetyl}amino) phenyl]ethynyl}benzamide	438.5
696	866	N-[(1S)-1-(aminomethyl)-2- (hydroxyamino)-2-oxoethyl]-4-[(4- {[(diethylamino)acetyl]amino}phenyl) ethynyl]benzamide	452.5
697	867	N-[(1S)-1-(aminomethyl)-2- (hydroxyamino)-2-oxoethyl]-4-{[4- ({[(1,1-dimethylethyl)(methyl) amino]acetyl}amino)phenyl]ethynyl}benzamide	466.6
698	868	N-[(1S)-1-(aminomethyl)-2- (hydroxyamino)-2-oxoethyl]-4-{[4- ({[cyclohexyl(methyl)amino]acetyl}amino)phenyl]ethynyl}benzamide	492.6
699	869	N-[(1S)-1-(aminomethyl)-2- (hydroxyamino)-2-oxoethyl]-4-({4-[({[2-(2- fluorophenyl)ethyl]amino}acetyl)amino]phenyl}ethynyl)benzamide	518.6
700	870	N-[(1S)-1-(aminomethyl)-2- (hydroxyamino)-2-oxoethyl]-4-({4-[({[2-(3- fluorophenyl)ethyl]amino}acetyl)amino]phenyl}ethynyl)benzamide	518.6
701	871	N-[(1S)-1-(aminomethyl)-2- (hydroxyamino)-2-oxoethyl]-4-({4-[({[2-(4- fluorophenyl)ethyl]amino}acetyl)amino]phenyl}ethynyl)benzamide	518.6
702	872	N-[(1S)-1-(aminomethyl)-2- (hydroxyamino)-2-oxoethyl]-4-({4-[({[(1S,2R)- 2-phenylcyclopropyl]amino}acetyl) amino]phenyl}ethynyl) benzamide	512.6
703	873	N-[(1S)-1-(aminomethyl)-2- (hydroxyamino)-2-oxoethyl]-4-({4-[({[(2,4- difluorophenyl)methyl]amino}acetyl) amino]phenyl}ethynyl)benzamide	522.5
704	874	N-[(1S)-1-(aminomethyl)-2- (hydroxyamino)-2-oxoethyl]-4-({4-[({[(2,4- dichlorophenyl)methyl]amino}acetyl) amino]phenyl}ethynyl)benzamide	555.4
705	875	N-[(1S)-1-(aminomethyl)-2- (hydroxyamino)-2-oxoethyl]-4-[(4- {[({[4-fluoro-2-(trifluoromethyl) phenyl]methyl}amino)acetyl]amino}phenyl)ethynyl]benzamide	572.5
706	876	N-[(1S)-1-(aminomethyl)-2- (hydroxyamino)-2-oxoethyl]-4-({4-[({[(2,5- difluorophenyl)methyl]amino}acetyl) amino]phenyl}ethynyl)benzamide	522.5
707	877	N-[(1S)-1-(aminomethyl)-2- (hydroxyamino)-2-oxoethyl]-4-({4-[({[(3,4- difluorophenyl)methyl]amino}acetyl) amino]phenyl}ethynyl)benzamide	522.5
708	878	N-[(1S)-1-(aminomethyl)-2- (hydroxyamino)-2-oxoethyl]-4-({4-[({[(3,4- dichlorophenyl)methyl]amino}acetyl) amino]phenyl}ethynyl)benzamide	555.4
709	879	N-[(1S)-1-(aminomethyl)-2- (hydroxyamino)-2-oxoethyl]-4-({4-[({[(3,4- dimethylphenyl)methyl]amino}acetyl) amino]phenyl}ethynyl)benzamide	514.6
710	880	N-[(1S)-1-(aminomethyl)-2- (hydroxyamino)-2-oxoethyl]-4-({4-[({[(3,5- difluorophenyl)methyl]amino}acetyl) amino]phenyl}ethynyl)benzamide	522.5
711	881	N-[(1S)-1-(aminomethyl)-2- (hydroxyamino)-2-oxoethyl]-4-({4-[({[(3,5- dichlorophenyl)methyl]amino}acetyl) amino]phenyl}ethynyl)benzamide	555.4
712	882	N-[(1S)-1-(aminomethyl)-2- (hydroxyamino)-2-oxoethyl]-4-[(4-{[({[3,5- bis(trifluoromethyl)phenyl]methyl}amino)acetyl]amino}phenyl)ethynyl]benzamide	622.5
713	883	N-[(1S)-1-(aminomethyl)-2- (hydroxyamino)-2-oxoethyl]-4-({4-[({[(4- nitrophenyl)methyl]amino}acetyl) amino]phenyl}ethynyl)benzamide	531.5
714	884	N-[(1S)-1-(aminomethyl)-2- (hydroxyamino)-2-oxoethyl]-4-[(4-{[(pyridin-2- ylamino)acetyl]amino}phenyl)ethynyl]benzamide	473.5
715	885	N-[(1S)-1-(aminomethyl)-2- (hydroxyamino)-2-oxoethyl]-4-[(4-{[(pyridin-3- ylamino)acetyl]amino}phenyl)ethynyl]benzamide	473.5
716	886	N-[(1S)-1-(aminomethyl)-2- (hydroxyamino)-2-oxoethyl]-4-{[4-({[(2- fluorophenyl)amino]acetyl}amino) phenyl]ethynyl}benzamide	490.5
717	887	N-[(1S)-1-(aminomethyl)-2- (hydroxyamino)-2-oxoethyl]-4-{[4-({[(3- fluorophenyl)amino]acetyl}amino) phenyl]ethynyl}benzamide	490.5
718	888	N-[(1S)-1-(aminomethyl)-2- (hydroxyamino)-2-oxoethyl]-4-{[4-({[(4- fluorophenyl)amino]acetyl}amino) phenyl]ethynyl}benzamide	490.5
719	889	N-[(1S)-1-(aminomethyl)-2- (hydroxyamino)-2-oxoethyl]-4-[(4-{[(pyridin-4- ylamino)acetyl]amino}phenyl) ethynyl]benzamide	473.5
720	890	N-[(1S)-1-(aminomethyl)-2- (hydroxyamino)-2-oxoethyl]-4-{[4- ({[(2,2,2-trifluoroethyl)amino]acetyl}amino)phenyl]ethnyl}benzamide	478.4
721	891	N-{(1S,2R).2-hydroxy-1- [(hydroxyamino)carbonyl]propyl}-4- [(4-{[(pyridin-2-ylamino)acetyl]amino}phenyl)ethynyl]benzamide	488.5
722	892	N-{(1S,2R)-2-hydroxy-1- [(hydroxyamino)carbonyl]propyl}-4-[(4- {[(pyridin-3-ylamino)acetyl]amino}phenyl)ethynyl]benzamide	488.5
723	893	N-{(1S,2R)-2-hydroxy-1- [(hydroxyamino)carbonyl]propyl}-4-[(4- {[(pyridin-4-ylamino)acetyl]amino}phenyl)ethynyl]benzamide	488.5
724	894	N-{(1S,2R)-2-hydroxy-1- [(hydroxyamino)carbonyl]propyl}-4-[(4- {[(4-phenylpiperazin-1- yl)acetyl]amino}phenyl) ethynyl]benzamide	556.6
725	895	4-{[4-({[4-(4-fluorophenyl) piperazin-1-yl]acetyl}amino) phenyl]ethynyl}-N-{(1S,2R)-2- hydroxy-1-[(hydroxyamino) carbonyl]propyl}benzamide	574.6
726	896	4-{[4-({[(1-acetylpiperidin-4- yl)(cyclopropyl)amino]acetyl}amino) phenyl]ethynyl}-N-{(1S,2R)-2- hydroxy-1-[(hydroxyamino) carbonyl]propyl}benzamide	576.7
727	897	4-[(4-{[(butylamino)acetyl]amino}phenyl)ethynyl]-N- {(1S,2R)-2-hydroxy-1- [(hydroxyamino)carbonyl]propyl}benzamide	467.5
728	898	N-{(1S,2R)-2-hydroxy-1- [(hydroxyamino)carbonyl]propyl}-4-({4- [({[(1R)-1-phenylethyl]amino}acetyl)amino]phenyl}ethyl)benzamide	515.6
729	899	N-{(1S,2R)-2-hydroxy-1- [(hydroxyamino)carbonyl]propyl}-4-({4- [({[(1S)-1-phenylethyl]amino}acetyl)amino]phenyl}ethyl)benzamide	515.6
730	900	4-{[4-({[cyclopropyl(methyl) amino]acetyl}amina)phenyl]ethynyl}-N-{(1S,2R)-2- hydroxy-1-[(hydroxyamino) carbonyl]propyl}benzamide	465.5
731	901	N-{(1S,2R)-2-hydroxy-1- [(hydroxyamino)carbonyl]propyl}-4-([4- ({[methyl(phenyhnethyl)amino]acetyl}amino)phenyl]ethynyl}benzamide	515.6
732	902	N-[(1S)-1-(aminomethyl)-2- (hydroxyamino)-2-oxoethyl]-4- {[4-({[cyclopropyl(methyl) amino]acetyl}amino)phenyl]ethynyl}benzamide	450.5
733	903	4-[(4-{[(2S)-2-aminopropanoyl]amino}phenyl)ethynyl]-N-{(1S,2R)-2- hydroxy-1-[(hydroxyamino) carbonyl]propyl}benzamide	425.5
734	904	4-[(4-{[(2R)-2-aminopropanoyl]amino}phenyl)ethynyl]-N-{(1S,2R)-2- hydroxy-1-[(hydroxyamino) carbonyl]propyl}benzamide	425.5
735	905	4-[(4-{[(2S)-2-amino-3- methylbutanoyl]amino}phenyl) ethynyl]-N-{(1S,2R)- 2-hydroxy-1-[(hydroxyamino) carbonyl]propyl}benzamide	453.5
736	906	4-[(4-{[(2S,3R)-2-amino-3- hydroxybutanoyl]amino}phenyl) ethynyl]-N-{(1S,2R)-2- hydroxy-1-[(hydroxyamino) carbonyl]propyl}benzamide	455.5
737	907	(2S)-N-[4-({4-[({(1S,2R)-2- hydroxy-1-[(hydroxyamino) carbonyl]propyl}amino) carbonyl]phenyl}ethynyl)phenyl]pyrrolidine-2-carboxamide	451.5
738	908	4-[(4-{[(2S)-2-amino-3-(1H- imidazol-4-yl)propanoyl]amino}phenyl)ethynyl]-N-{(1S,2R)-2- hydroxy-1-[(hydroxyamino)carbonyl]propyl}benzamide	491.5
739	909	N-{(1S,2R)-2-hydroxy-1- [(hydroxyamino)carbonyl]propyl}-4- [(4-{[(methyloxy)acetyl]amino}phenyl)ethynyl]benzamide	426.4

[0942]

Example	Structure	Name	MH+
740	910	4-[(4-{[(2S)-2-amino-3- methylbutanoyl]amino}phenyl)ethynyl]-N- [(1S)-1-(aminomethyl)-2-(hydroxyamino)-2- oxoethyl]benzamide	438.5
741	911	N-[(1S)-1-(aminomethyl)-2-(hydroxyamino)-2- oxoethyl]-4-{[4-({[(3- phenylpropyl)amino]acetyl}amino)phenyl]ethnyl}benzamide	514.6
742	912	N-{(1S,2R)-2-hydroxy-1- [(hydroxyamino)carbonyl]propyl}-4-(thien-2- ylethynyl)benzamide	345.4
743	913	4-({4-[((2S)-2-{[(2S)-2,5- diaminopentanoyl]amino}-3- phenylpropanoyl)amino]phenyl}ethynyl)-N-{(1S,2R)-2- hydroxy-1-[(hydroxyamino) carbonyl]propyl}benzamide	615.7
744	914	3,4-dihydroxy-N-[(2S)-3-(hydroxyamino)-3- oxo-2-({[4-(phenylethynyl) phenyl]carbonyl}amino)propyl]benzamide	460.5
745	915	1,1-dimethylethyl 3-[(2-{[(2S)-3- (hydroxyamino)-3-oxo-2-({[4- (phenylethynyl)phenyl]carbonyl}amino)propyl]amino}-2- oxoethyl)amino]propylcarbamate	538.6
746	916	N-[(1S)-2-(hydroxyamino)-1-({[(4- methylpiperazin-1-yl)acetyl]amino}methyl)-2-oxoethyl]-4- (phenylethynyl)benzamide	464.5
747	917	4-{[4-({2-[(2-aminoethyl)amino]-2- oxoethyl}oxy)phenyl]ethynyl}-N- {(1S,2R)-2-hydroxy-1- [(hydroxyammo)carbonyl]propyl}benzamide	455.5
748	918	N-[(1S)-1-(aminomethyl)-2-(hydroxyamino)-2- oxoethyl]-4-{[3- (aminomethyl)phenyl]ethynyl}benzamide	353.4
749	919	1,1-dimethylethyl (2S)-3-(hydroxyamino)-2- [({4-[(4-{[2-(hydroxyamino)-2- oxoethyl]oxy}phenyl)ethynyl]phenyl}carbonyl)amino]-3- oxopropylcarbamate	513.5
750	920	N-[(1S)-1-(aminomethyl)-2-(hydroxyamino)-2- oxoethyl]-4-[(4-{[2-(hydroxyamino)-2- oxoethyl]oxy}phenyl)ethynyl]benzamide	413.4
751	921	3,4-dihydroxy-N-(2-{[4-({4-[({(1S,2R)-2- hydroxy-1-[(hydroxyamino) carbonyl]propyl}amino)carbonyl]phenyl}ethynyl)phenyl]amino}-2- oxoethyl)benzamide	547.5
752	922	4-({4-[({[(2S)-2,5- diaminopentanoyl]amino}acetyl) amino]phenyl}ethynyl)-N- {(1S,2R)-2-hydroxy-1- [(hydroxyamino)carbonyl]propyl}benzamide	525.6
753	923	4-[(4-{[(2-aminoethyl)amino]carbonyl}phenyl)ethynyl]-N- {(1S,2R)-2-hydroxy-1- [(hydroxyamino)carbonyl]propyl}benzamide	425.5
754	924	N-[(1S)-1-[({[(3-aminopropyl) amino]acetyl}amino)methyl]-2- (hydroxyamino)-2-oxoethyl]-4- (phenylethynyl)benzamide	438.5
755	925	3-({4-[({(1S,2R)-2-hydroxy-1- [(hydroxyamino)carbanyl]propyl}amino) carbonyl]phenyl}ethynyl) benzoic acid	383.4
756	926	4-{[4-({[(3-aminopropyl)amino]acetyl}amino)phenyl]ethynyl}-N- {(1S,2R)-2-hydroxy-1- [(hydroxyamino)carbonyl]propyl}benzamide	468.5
757	927	N-[(1S)-1-(aminomethyl)-2-(hydroxyamino)-2- oxoethyl]-4-(pyrazin-2-ylethynyl)benzamide	326.3
758	928	4-({3-[(4-aminobutanoyl)amino]phenyl}ethynyl)-N-[(1S)-1- (aminomethyl)-2-(hydroxyamino)-2- oxoethyl]benzamide	424.5
759	929	N-[(1S)-1-(aminomethyl)-2- (hydroxyamino)-2-oxoethyl]-4- [(4-{[(2S)-2,5-diaminopentanoyl]amino}phenyl)ethynyl]benzamide	453.5
760	930	4-({2-[(aminoacetyl)amino]phenyl}ethynyl)- N-[(1S)-1-(aminomethyl)-2- (hydroxyamino)-2-oxoethyl]benzamide	396.4
761	931	N-[(1S)-1-(aminomethyl)-2-(hydroxyamino)-2- oxoethyl]-4-({4-[2-(ethylamino)-2- oxoethyl]phenyl}ethynyl)benzamide	409.5
762	932	4-({4-[(aminoacetyl)amino]-3- methylphenyl}ethynyl)-N-[(1S)-1- (animomethyl)-2-(hydroxyamino)-2- oxoethyl]benzamide	410.4
763	933	4-({4-[(aminoacetyl)amino]phenyl}ethynyl)-N-[(1S)-1-(aminomethyl)- 2-(hydroxyamino)-2- oxoethyl]-3-fluorobenzamide	414.4
764	934	N-[(1S)-1-(aminomethyl)-2- (hydroxyamino)-2-oxoethyl]-4-{[4- ({[(cyanomethyl)amino]acetyl}amino) phenyl]ethynyl}benzamide	435.5
765	935	[4-({4-[({(1S,2R)-2-hydroxy-1- [(hydroxyamino)carbonyl]propyl}amino)carbonyl]phenyl}ethynyl) phenyl]acetic acid	397.4
766	936	4-amino-2-({[4-({4-[({(1S,2R)-2-hydroxy-1- [(hydraxyan-nno)carbonyl]propyl}amino) carbonyl]phenyl}ethynyl)phenyl]carbonyl}amino)-4- oxobutanoic acid
767	937	4-amino-2-[({[4-({4-[({(1S,2R)-2-hydroxy-1- [(hydroxyamino)carbonyl]propyl}amino)carbonyl]phenyl}ethynyl)phenyl]oxy}acetyl)amino]- 4-oxobutanoic acid	527.5
768	938	N-((1S)-2-(hydroxyamino)-1-{[(morpholin-4- ylacetyl)amino]methyl}-2-oxoethyl)-4- (phenylethynyl)benzamide	451.5
769	939	N-[(1S)-1-[({[2,3-dihydroxypropyl) thio]acetyl}amino)methyl]-2- (hydroxyamino)-2-oxoethyl]-4- (phenylethynyl)benzamide	472.5
770	940	methyl (2S)-3-amino-2-({[4- (phenylethynyl)phenyl]carbonyl}amino) propanoate	323.4
771	941	N-{(1S)-2-(hydroxyamino)-2-oxo-1-[({[(2- phenylethyl)amino]acetyl}amino) methyl]ethyl}-4- (phenylethynyl)benzamide	485.6
772	942	4-[(4-{2-{(2-aminoethyl)amino]-2- oxoethyl}phenyl)ethynyl]-N-{(1S,2R)- 2-hydroxy-1- [(hydroxyamino)carbonyl]propyl}benzamide	439.5
773	943	4-[(4-{[(6-aminohexyl)amino]carbonyl}phenyl)ethynyl]- N-{(1S,2R)-2-hydroxy-1- [(hydroxyamino)carbonyl]propyl}benzamide	481.6
774	944	4-[4-(4-{[(ethylamino)acetyl]amino}phenyl)buta-1,3-diynyl]-N- {(1S,2R)-2-hydroxy-1- [(hydroxyamino)carbonyl]propyl}benzamide	463.5
775	945	4-[4-(4-{[(cyclopropylamino) acetyl]amino}phenyl)buta-1,3- diynyl]-N-{(1S,2R)-2-hydroxy-1- [(hydroxyamino)carbonyl]propyl}benzamide	475.5
776	946	N-{(1S,2R)-2-hydroxy-1- [(hydroxyamino)carbonyl]propyl}-4-(4-{4- [(piperidin-1-ylacetyl)amino]phenyl}buta- 1,3-diynyl)benzamide	503.6
777	947	N-{(1S,2R)-2-hydroxy-1- [(hydroxyamino)carbonyl]propyl}-4-[4-(4- {[(phenylamino)acetyl]amino}phenyl)buta-1,3-diynyl]benzamide	511.5
778	948	N-{(1S,2R)-2-hydroxy-1- [(hydroxyamino)carbonyl]propyl}-4-{4-[4- ({[(phenylmethyl)amino]acetyl}amino) phenyl]buta-1,3-diynyl}benzamide	525.6
779	949	N-{(1S,2R)-2-amino-1- [(hydroxyamino)carbonyl]propyl}4′- ethyl-1,1′-biphenyl-4-carboxamide	342.4
780	950	4-[(4-{[(dimethylamino)acetyl amino}phenyl)ethynl]-N-{(1S,2R)- 2-hydroxy-1- [(hydroxyamino)carbonyl]propyl}benzamide	439.5
781	951	N-{(1S,2R)-2-hydroxy-1- [(hydroxyamino)carbonyl]propyl}-4- ({4-[(pyrrolidin-1- ylacetyl)amino]phenyl}ethynyl)benzamide	465.5
782	952	N-{(1S,2R)-2-hydroxy-1- [(hydroxyamino)carbonyl]propyl}-4- [(4-{[(pentylamino)acetyl]amino}phenyl)ethynyl]benzamide	481.6
783	953	N-{(1S,2R)-2-hydroxy-1- [(hydroxyamino)carbonyl]propyl}-4- {[4-({[(thien-2-ylmethyl) amino]acetyl}amino)phenyl]ethynyl}benzamide	507.6
784	954	4-{[4-({[(1H-benzimidazol-2- ylmethyl)amino]acetyl}amino)phenyl]ethynyl}-N- {(1S,2R)-2-hydroxy-1- [(hydroxyamino)carbonyl]propyl}benzamide	541.6
785	955	4-{[4-({[(1-benzothien-3- ylmethyl)amino]acetyl}amino) phenyl]ethynyl}-N-{(1S,2R)- 2-hydroxy-1- [(hydroxyamino)carbonyl]propyl}benzamide	557.6
786	956	4-(4-{4-[({[(2-fluorophenyl)methyl]amino}acetyl)amino]phenyl}buta- 1,3-diynyl)-N-{(1S,2R)-2-hydroxy-1- [(hydroxyamino)carbonyl]propyl}benzamide	543.6
787	957	4-(4-{4-[({[(3-fluorophenyl)methyl]amino}acctyl)amino]phenyl}buta- 1,3-diynyl)-N-{(1S,2R)-2-hydroxy-1- [(hydroxyamino)carbonyl]propyl}benzamide	543.6
788	958	4-(4-{4-[({[(4-fluorophenyl)methyl]amino}acetyl)amino]phenyl}buta- 1,3-diynyl)-N-{(1S,2R)-2-hydroxy-1- [(hydroxyamino)carbonyl]propyl}benzamide	543.6
789	959	N-{(1S,2R)-2-hydroxy-1- [(hydroxyamino)carbonyl]propyl}-4- (4-{4-[({[(2-methylphenyl)methyl]amino}acetyl)amino]phenyl}buta-1,3-diynyl)benzamide	539.6
790	960	N-{(1S,2R)-2-hydroxy-1- [(hydroxyamino)carbonyl]propyl}-4- (4-{4-[({[(3-methylphenyl)methyl]amino}acetyl)amino]phenyl}buta-1,3-diynyl)benzamide	539.6
791	961	N-{(1S,2R)-2-hydroxy-1- [(hydroxyamino)carbonyl]propyl}-4- (4-{4-[({[(4-methylphenyl)methyl]amino}acetyl)amino]phenyl}buta-1,3-diynyl)benzamide	539.6
792	962	N-{(1S,2R)-2-hydroxy-1- [(hydroxyamino)carbonyl]propyl}-4- {4-[4-({[(pyridin-2- ylmethyl)amino]acetyl}amino) phenyl]buta-1,3-diynyl}benzamide	526.6
793	963	N-{(1S,2R)-2-hydroxy-1- [(hydroxyamino)carbonyl]propyl}-4- {4-[4-({[(pyridin-3- ylmethyl)amino]acetyl}amino) phenyl]buta-1,3-diynyl}benzamide	526.6
794	964	N-{(1S,2R)-2-hydroxy-1- [(hydroxyamino)carbonyl]propyl}-4- {4-[4-({[(pyridin-4- ylmethyl)amino]acetyl}amino) phenyl]buta-1,3-diynyl}benzamide	526.6
795	965	N-{(1S,2R)-2-hydroxy-1- [(hydroxyamino)carbonyl]propyl}-4- [4-(4-{[{([2-(methyloxy) phenyl]methyl}amino)acetyl]amino}phenyl)buta-1,3- diynyl]benzamide	555.6
796	966	N-{(1S,2R)-2-hydroxy-1- [(hydroxyamino)carbonyl]propyl}-4- [4-(4-{[({[3-(methyloxy)phenyl]methyl}amino)acetyl]amino}phenyl)buta-1,3-diynyl]benzamide	555.6
797	967	N-{(1S,2R)-2-hydroxy-1- [(hydroxyamino)carbonyl]propyl}-4- [4-(4-{[({[4-(methyloxy)phenyl]methyl}amino)acetyl]amino}phenyl)buta-1,3-diynyl]benzamide	555.6
798	968	4-{4-[4-({[(2-fluorophenyl)amino]acetyl}amino)phenyl]buta-1,3- diynyl}-N-{(1S,2R)-2-hydroxy-1- [(hydroxyamino)carbonyl]propyl}benzamide	529.5
799	969	4-{4-[4-({[(3-fluorophenyl)amino]acetyl}amino)phenyl]buta-1,3- diynyl}-N-{(1S,2R)-2-hydroxy-1- [(hydroxyamino)carbonyl]propyl}benzamide	529.5
800	970	4-{4-[4-({[(4-fluorophenyl)amino]acetyl}amino)phenyl]buta-1,3- diynyl}-N-{(1S,2R)-2-hydroxy-1- [(hydroxyamino)carbonyl]propyl}benzamide	529.5
801	971	N-{(1S,2R)-2-hydroxy-1- [(hydroxyamino)carbonyl]propyl}-4-[4-(4- {[(pyridin-2-ylamino)acetyl]amino}phenyl)buta-1,3- diynyl]benzamide	512.5
802	972	N-{(1S,2R)-2-hydroxy-1- [(hydroxyamino)carbonyl]propyl}-4-[4-(4- {[(pyridin-3-ylamino)acetyl]amino}phenyl)buta-1,3- diynyl]benzamide	512.5
803	973	N-{(1S,2R)-2-hydroxy-1- [(hydroxyamino)carbonyl]propyl}-4-[4-(4- {[(pyridin-4-ylamino)acetyl]amino}phenyl)buta-1,3- diynyl]benzamide	512.5
804	974	4-[4-(4-{[(cyclobutylamino)acetyl]amino}phenyl)buta-1,3-diynyl]- N-{(1S,2R)-2-hydroxy-1- [(hydroxyamino)carbonyl]propyl}benzamide	489.5
805	975	4-[4-(4-{[(cyclopentylamino)acetyl]amino}phenyl)buta-1,3-diynyl]- N-{(1S,2R)-2-hydroxy-1- [(hydroxyamino)carbonyl]propyl}benzamide	503.6
806	976	4-[4-(4-{[(cyclohexylamino)acetyl]amino}phenyl)buta-1,3-diynyl]- N-{(1S,2R)-2-hydroxy-1- [(hydroxyamino)carbonyl]propyl}benzamide	517.6
807	977	4-[4-(4-{[(cycloheptylamino)acetyl]amino}phenyl)buta-1,3-diynyl]- N-{(1S,2R)-2-hydroxy-1- [(hydroxyamino)carbonyl]propyl}benzamide	531.6
808	978	N-{(1S,2R)-2-hydroxy-1- [(hydroxyamino)carbonyl]propyl}-4-[4-(4- {[(methylamino)acetyl]amino}phenyl buta-1,3-diynyl]benzamide	449.5
809	979	N-{(1S,2R)-2-hydroxy-1- [(hydroxyamino)carbonyl]propyl}-4-[4-(4- {[(propylamino)acetyl]amino}phenyl) buta-1,3-diynyl]benzamide	477.5
810	980	4-[4-(4-{[(butylamino)acetyl]amino}phenyl)buta-1,3- diynyl]-N-{(1S,2R)-2-hydroxy-1- [(hydroxyamino)carbonyl]propyl}benzamide	491.6
811	981	N-{(1S,2R)-2-hydroxy-1- [(hydroxyamino)carbonyl]propyl}-4-[4-(4- {[(pentylamino)acetyl]amino}phenyl) buta-1,3-diynyl]benzamide	505.6
812	982	4-[4-(4-{[(hexylamino)acetyl]amino}phenyl)buta-1,3-diynyl]-N- {(1S,2R)-2-hydroxy-1- [(hydroxyamino)carbonyl]propyl}benzamide	519.6
813	983	4-{4-[4-({[ethyl(methyl)amino]acetyl}amino)phenyl]buta- 1,3-diynyl}-N-{(1S,2R)-2-hydroxy-1- [(hydroxyamino)carbonyl]propyl}benzamide	477.5
814	984	N-{(1S,2R)-2-hydroxy-1- [(hydroxyamino)carbonyl]propyl}-4- {4-[4-({[(1-methylethyl)amino]acetyl}amino)phenyl]buta- 1,3-diynyl}benzamide	477.5
815	985	N-{(1S,2R)-2-hydroxy-1- [(hydroxyamino)carbonyl]propyl}-4- {4-[4-({[(2-methylpropyl)amino]acetyl}amino)phenyl]buta- 1,3-diynyl}benzamide	491.6
816	986	N-{(1S,2R)-2-hydroxy-1- [(hydroxyamino)carbonyl]propyl}-4- {4-[4-({[(2,2,2-trifluoroethyl)amino]acetyl}amino)phenyl]buta-1,3- diynyl}benzamide	517.5
817	987	4-{4-[4-({[(2-hydroxyethyl)amino]acetyl}amino)phenyl]buta-1,3- diynyl}-N-{(1S,2R)-2-hydroxy-1- [(hydroxyamino)carbonyl]propyl}benzamide	479.5
818	988	N-{(1S,2R)-2-hydroxy-1- [(hydroxyamino)carbonyl]propyl}-4-(4-{4- [({[2-(methyloxy)ethyl]amino}acetyl)amino]phenyl}buta-1,3- diynyl)benzamide	493.5
819	989	4-(4-{4-[({[2-(dimethylamino) ethyl]amino}acetyl)amino]phenyl}buta-1,3-diynyl)-N-{(1S,2R)- 2-hydroxy-1-[(hydroxyamino) carbonyl]propyl}benzamide	506.6
820	990	4-{4-[4-({[(2-cyanoethyl)amino]acetyl}amino)phenyl]buta- 1,3-diynyl}-N-{(1S,2R)-2-hydroxy-1- [(hydroxyamino)carbonyl]propyl}benzamide	488.5
821	991	N-{(1S,2R)-2-hydroxy-1- [(hydroxyamino)carbonyl]propyl}-4-(4- {4-[(pyrrolidin-1-ylacetyl) amino]phenyl}buta-1,3- diynyl)benzamide	489.5
822	992	4-(4-{4-[(azepan-1-ylacetyl) amino]phenyl}buta-1,3-diynyl)-N- {(1S,2R)-2-hydroxy-1- [(hydroxyamino)carbonyl]propyl}benzamide	517.6
823	993	N-{(1S,2R)-2-hydroxy-1- [(hydroxyamino)carbonyl]propyl}-4- [4-(4-{[(4-methylpiperazin-1- yl)acetyl]amino}phenyl)buta-1,3- diynyl]benzamide	518.6
824	994	N-{(1S,2R)-2-hydroxy-1- [(hydroxyamino)carbonyl]propyl}-4- (4-{4-[(morpholin-4-ylacetyl) amino]phenyl}buta-1,3- diynyl)benzamide	505.5
825	995	4-{4-[4-({[cyclohexyl(methyl)amino]acetyl}amino)phenyl]buta-1,3- diynyl}-N-{(1S,2R)-2-hydroxy-1- [(hydroxyamino)carbonyl]propyl}benzamide	531.6
826	996	N-{(1S,2R)-2-hydroxy-1- [(hydroxyamino)carbonyl]propyl}-4- (4-{4-[({[(1R)-1-phenylethyl]amino}acetyl)amino]phenyl}buta-1,3-diynyl)benzamide	539.6
827	997	N-{(1S,2R)-2-hydroxy-1- [(hydroxyamino)carbonyl]propyl}-4- (4-{4-[({[(1S)-1-phenylethyl]amino}acetyl)amino]phenyl}buta-1,3-diynyl)benzamide	539.6
828	998	N-{(1S,2R)-2-hydroxy-1- [(hydroxyamino)carbonyl]propyl}-4- {4-[4-({[(2-phenylethyl)amino]acetyl}amino)phenyl]buta-1,3-diynyl}benzamide	539.6
829	999	N-{(1S,2R)-2-hydroxy-1- [(hydroxyamino)carbonyl]propyl}-4- (4-{4-[(1H-imidazol-1-ylacetyl) amino]phenyl}buta- 1,3-diynyl)benzamide	486.5
830	1000	4-{4-[4-({[(1R,2R,4S)-bicyclo[2.2.1]hept-2- ylamino]acetyl}amino)phenyl]buta-1,3- diynyl}-N-{(1S,2R)-2-hydroxy-1- [(hydroxyamino)carbonyl]propyl}benzamide	529.6
831	1001	4-{4-[4-({[(cyclohexylmethyl) amino]acetyl}amino)phenyl]buta- 1,3-diynyl}-N-{(1S,2R)-2-hydroxy-1- [(hydroxyamino)carbonyl]propyl}benzamide	531.6
832	1002	N-[(1S)-1-(aminomethyl)-2-(hydroxyamino)- 2-oxoethyl]-4′-ethyl-2-fluoro-1,1′- biphenyl-4-carboxamide	346.4
833	1003	4-({4-[(aminoacetyl)amino]phenyl}ethynyl)-N-{(1S,2R)-2-hydroxy-1- [(hydroxyamino)carbonyl]propyl}-3- (methyloxy)benzamide	441.5
834	1004	4′-ethyl-N-{(1S,2R)-2-hydroxy-1- [(hydroxyamino)carbonyl]propyl}-2- (methyloxy)-1,1′-biphenyl-4-carboxamide	373.4
835	1005	N-{(1S,2R)-2-hydroxy-1- [(hydroxyamino)carbonyl]propyl}-3- (methyloxy)-4-(phenylethynyl)benzamide	369.4
836	1006	4-[(4-ethylphenyl)ethynyl]-N-{(1S,2R)-2- hydroxy-1- [(hydroxyamino)carbonyl]propyl}benzamide	367.4
837	1007	N-{(1S,2R)-2-hydroxy-1- [(hydroxyamino)carbonyl]propyl}-4-[(4- hydroxyphenyl)ethynyl]benzamide	355.4
838	1008	2-[(2-{[(2S)-3-(hydroxyamino)-3-oxo-2-({[4- (phenylethynyl)phenyl]carbonyl}amino) propyl]amino}-2-oxoethyl)thio]prapanoic acid	470.5
839	1009	4-amino-2-[(2-{[(2S)-3-(hydroxyamino)- 3-oxo-2-({[4-(phenylethynyl) phenyl]carbonyl}amino)propyl]amino}-2-oxoethyl)amino]-4- oxobutanoic acid	496.5
840	1010	1,1-dimethylethyl 4-amino-2-[(2-{[(2S)-3- (hydroxyamino)-3-oxo-2-({[4- (phenylethynyl)phenyl]carbonyl}amino)propyl]amino}-2-oxoethyl) amino]-4-oxobutanoate	552.6
841	1011	2,6-dihydroxy-N-[(2S)-3-(hydroxyamino)- 3-oxo-2-({[4-(phenylethynyl) phenyl]carbonyl}amino)propyl]pyridine-4-carboxamide	461.4
842	1012	N-[(1S)-1-(aminomethyl)-2-(hydroxyamino)- 2-oxoethyl]-4-[(4- aminophenyl)ethynyl]benzamide	339.4
843	1013	N-[(1S)-1-(aminomethyl)-2-(hydroxyamino)- 2-oxoethyl]-4-[(4- ethylphenyl)ethynyl]benzamide	352.4
844	1014	N-[(1S)-1-(aminomethyl)-2-(hydroxyamino)- 2-oxoethyl]-4-[(4-ethylphenyl)ethynyl]- 3-fluorobenzamide	370.4
845	1015	N-[(1S)-1-(aminomethyl)-2-(hydroxyamino)- 2-oxoethyl]-4-({4-[(3- aminopropanoyl)amino]phenyl}ethynyl)benzamide	410.4
846	1016	N-[(1S)-1-(aminomethyl)-2-(hydroxyamino)- 2-oxoethyl]-4-[(4- [(dimethylamino)acetyl]amino}phenyl) ethynl]benzamide	424.5
847	1017	4({4[(4-aminobutanoyl)amino]phenyl}ethynyl)-N-[(1S)- 1-(aminomethyl)-2-(hydroxyamino)-2- oxoethyl]benzamide	424.5
848	1018	N-{(1S)-2-(hydroxyamino)-1-[({[2- (methyloxy)phenyl]methyl}amino) methyl]-2-oxoethyl}-4-(phenylethynyl) benzamide	444.5
849	1019	N-[(1S)-1-[(diprop-2-enylamino)methyl]- 2-(hydroxyamino)-2-oxoethyl]-4- (phenylethynyl)benzamide	404.5
850	1020	N-[(1S)-2-(hydroxyamino)-1-({[({[2- (methoxy)phenyl]methyl}amino) acetyl]amino}methyl)-2- oxoethyl]-4-(phenylethynyl)benzamide	501.6
851	1021	N-((1S)-2-(hydroxyamino)-1-{[({[2- (methyloxy)phenyl]thio}acetyl)amino]methyl}-2-oxoethyl)-4- (phenylethynyl)benzamide	504.6
852	1022	(2S,3R)-3-amino-2-({[4-(phenylethynyl) phenyl]carbonyl}amino)butanoic acid	323.4
853	1023	N-[(1S)-1-(aminomethyl)-2-(hydroxyamino)- 2-oxoethyl]-4-[4-(4- {[(dimethylamino)acetyl]amino}phenyl)buta-1,3- diynyl]benzamide	448.5
854	1024	N-[(1S)-1-(aminomethyl)-2-(hydroxyamino)- 2-oxoethyl]-4-[4-(4- {[(ethylamino)acetyl]amino}phenyl)buta-1,3- diynyl]benzamide	448.5
855	1025	N-[(1S)-1-(aminomethyl)-2-(hydroxyamino)- 2-oxoethyl]-4-[4-(4- {[(cyclopropylamino)acetyl]amino}phenyl)buta-1,3-diynyl]benzamide	460.5
856	1026	N-[(1S)-1-(aminomethyl)-2-(hydroxyamino)- 2-oxoethyl]-4-(4-{4-[(piperidin-1- ylacetyl)amino]phenyl}buta-1,3- diynyl)benzamide	488.6
857	1027	N-[(1S)-1-(aminomethyl)-2-(hydroxyamino)- 2-oxoethyl]-4-[4-(4- {[(phenylamino)acetyl]amino}phenyl) buta-1,3-diynyl]benzamide	496.5
858	1028	N-[(1S)-1-(aminomethyl)-2-(hydroxyamino)- 2-oxoethyl]-4-{4-[4- ({[(phenylmethyl)amino]acetyl}amino)phenyl]buta-1,3- diynyl}benzamide	510.6
859	1029	N-[(1S)-1-(aminomethyl)-2-(hydroxyamino)- 2-oxoethyl]-4-[4-(4- aminophenyl)buta-1,3- diynyl]benzamide	363.4
860	1030	N-{(1S,2R)-2-hydroxy-1- [(hydroxyamino)carbonyl]propyl}-4- [(4-{[(pyrazin-2-ylamino) acetyl]amino}phenyl)ethynyl]benzamide	489.5
861	1031	N-{(1S,2R)-2-hydroxy-1- [(hydroxyamino)carbonyl]propyl}-4- [(4-{[(4-phenylpiperidin-1- yl)acetyl]amino}phenyl) ethynyl]benzamide	555.6
862	1032	4-{[4-({[4-(2-fluorophenyl) piperazin-1-yl]acetyl}amino) phenyl]ethynyl}-N- {(1S,2R)-2-hydroxy-1- [(hydroxyamino)carbonyl]propyl}benzamide	574.6
863	1033	4-{[4-({[(1S,4R)-bicyclo[2.2.1]hept-2- ylamino]acetyl}amino)phenyl]ethynyl}-N- {(1S,2R)-2-hydroxy-1- [(hydroxyamino)carbonyl]propyl}benzamide	505.6
864	1034	N-{(1S,2R)-2-hydroxy-1- [(hydroxyamino)carbonyl]propyl}-4-({4- [({[(1S,2S,3S,5R)-2,6,6- trimethylbicyclo[3.1.1]hept-3- yl]amino}acetyl)amino]phenyl}ethynyl)benzamide	547.7
865	1035	N-{(1S,2R)-2-hydroxy-1- [(hydroxyamino)carbonyl]propyl}-4-([4- ({[(tricyclo[3.3.1.1˜3,7˜]dec-1- ylmethyl)amino]acetyl}amino) phenyl]ethynyl}benzamide	559.7
866	1036	N-{(1S,2R)-2-hydroxy-1- [(hydroxyamino)carbonyl]propyl}-4-{[4-({[(4- methylcyclohexyl)amino]acetyl}amino) phenyl]ethynyl}benzamide	507.6
867	1037	N-{(1S,2R)-2-hydroxy-1- [(hydroxyamino)carbonyl]propyl}-4-([4- ({[(2,2,2-trifluoroethyl)amino]acetyl}amino)phenyl]ethnyl}benzamide	493.5
868	1038	4-({4-[({[2-(2-fluorophenyl)ethyl]amino}acetyl)amino]phenyl}ethynyl)-N-{(1S,2R)-2-hydroxy-1- [(hydroxyamino)carbonyl]propyl}benzamide	533.6
869	1039	4-({4-[({[2-(3-fluorophenyl)ethyl]amino}acetyl)amino]phenyl}ethynyl)-N-{(1S,2R)-2-hydroxy-1- [(hydroxyamino)carbonyl]propyl}benzamide	533.6
870	1040	4-({4-[({[2-(4-fluorophenyl)ethyl]amino}acetyl)amino]phenyl}ethynyl)-N-{(1S,2R)-2-hydroxy-1- [(hydroxyamino)carbonyl]propyl}benzamide	533.6
871	1041	N-{(1S,2R)-2-hydroxy-1- [(hydroxyamino)carbonyl]propyl}-4-({4- [({[(1S,2R)-2-phenylcyclopropyl]amino}acetyl)amino]phenyl}ethynyl)benzamide	527.6
872	1042	N-{(1S,2R)-2-hydroxy-1- [(hydroxyamino)carbonyl]propyl}-4-({4-[({[(2- methylphenyl)methyl]amino}acetyl) amino]phenyl}ethynyl)benzamide	515.6
873	1043	N-{(1S,2R)-2-hydroxy-1- [(hydroxyamino)carbonyl]propyl}-4-[(4-{[({[2- (trifluoromethyl)phenyl]methyl}amino) acetyl]amino}phenyl)ethynyl]benzamide	569.5
874	1044	N-{(1S,2R)-2-hydroxy-1- [(hydroxyamino)carbonyl]propyl}-4-{[4- ({[({2-[(trifluoromethyl)oxy]phenyl}methyl)amino]acetyl}amino)phenyl]ethynyl}benzamide	585.5
875	1045	4-({4-[({[(4-chlorophenyl)methyl]amino}acetyl)amino]phenyl}ethynyl)-N-{(1S,2R)-2-hydroxy-1- [(hydroxyamino)carbonyl]propyl}benzamide	536.0
876	1046	N-{(1S,2R)-2-hydroxy-1- [(hydroxyamino)carbonyl]propyl}-4-[(4- {[({[4-(methyloxy)phenyl]methyl}amino)acetyl]amino}phenyl)ethynyl]benzamide	531.6
877	1047	4-[(4-{[({[4-(1,1-dimethylethyl)phenyl]methyl}amino)acetyl]amino}phenyl)ethynyl]-N-{(1S,2R)-2-hydroxy-1- [(hydroxyamino)carbonyl]propyl}benzamide	557.7
878	1048	N-{(1S,2R)-2-hydroxy-1- [(hydroxyamino)carbonyl]propyl}- 4-({4-[({[(4-nitrophenyl)methyl]amino}acetyl)amino]phenyl}ethynyl)benzamide	546.5
879	1049	N-{(1S,2R)-2-hydroxy-1- [(hydroxyamino)carbonyl]propyl}-4-{[4- ({[({4-[(trifluoromethyl)oxy]phenyl}methyl)amino]acetyl}amino)phenyl]ethynyl}benzamide	585.5
880	1050	N-{(1S,2R)-2-hydroxy-1- [(hydroxyamino)carbonyl]propyl}-4-[(4- {[({[4-(methylthio)phenyl]methyl}amino)acetyl]amino}phenyl) ethynyl]benzamide	547.6
881	1051	N-{(1S,2R)-2-hydroxy-1- [(hydroxyamino)carbonyl]propyl}-4-{[4- ({[({4-[(trifluoromethyl)thio]phenyl}methyl)amino]acetyl}amino)phenyl]ethynyl}benzamide	601.6
882	1052	N-{(1S,2R)-2-hydroxy-1- [(hydroxyamino)carbonyl]propyl}-4-[(4- {[({[4-(methylsulfonyl)phenyl]methyl}amino)acetyl]amino}phenyl)ethynyl]benzamide	579.6
883	1053	4-({4-[({[(2,5-difluorophenyl)methyl]amino}acetyl)amino]phenyl}ethynyl)-N-{(1S,2R)-2-hydroxy-1- [(hydroxyamino)carbonyl]propyl}benzamide	537.5
884	1054	4-({4-[({[(2,6-difluorophenyl)methyl]amino}acetyl)amino]phenyl}ethynyl)-N-{(1S,2R)-2-hydroxy-1- [(hydroxyamino)carbonyl]propyl}benzamide	537.5
885	1055	4-({4-[({[(3,4-difluorophenyl)methyl]amino}acetyl)amino]phenyl}ethynyl)-N-{(1S,2R)-2-hydroxy-1- [(hydroxyamino)carbonyl]propyl}benzamide	537.5
886	1056	4-({4-[({[(3,4-dichlorophenyl)methyl]amino}acetyl)amino]phenyl}ethynyl)-N-{(1S,2R)-2-hydroxy-1- [(hydroxyamino)carbonyl]propyl}benzamide	570.4
887	1057	4-({4-[({[(3,4-dimethylphenyl)methyl]amino}acetyl)amino]phenyl}ethynyl)-N-{(1S,2R)-2-hydroxy-1- [(hydroxyamino)carbonyl]propyl}benzamide	529.6
888	1058	4-({4-[({[(3,5-dichlorophenyl)methyl]amino}acetyl)amino]phenyl}ethynyl)-N-{(1S,2R)-2-hydroxy-1- [(hydroxyamino)carbonyl]propyl}benzamide	570.4
889	1059	4-[(4-{[({[3,5-bis(trifluoromethyl)phenyl]methyl}amino)acetyl]amino}phenyl)ethynyl]-N-{(1S,2R)-2- hydroxy-1- [(hydroxyamino)carbonyl]propyl}benzamide	637.5
890	1060	N-{(1S,2R)-2-hydroxy-1- [(hydroxyamino)carbonyl]propyl}-4-({4- [({[(2,3,4-trifluorophenyl)methyl]amino}acetyl)amino]phenyl}ethynyl)benzamide	555.5
891	1061	N-{(1S,2R)-2-hydroxy-1- [(hydroxyamino)carbonyl]propyl}-4-({4- [({[(2,4,5-trifluorophenyl)methyl]amino}acetyl)amino]phenyl}ethynyl)benzamide	555.5
892	1062	N-{(1S,2R)-2-hydroxy-1- [(hydroxyamino)carbonyl]propyl}-4-({4- [({[(3,4,5-trifluorophenyl)methyl]amino}acetyl)amino]phenyl}ethynyl)benzamide	555.5
893	1063	N-[(1S)-1-(aminomethyl)-2-(hydroxyamino)-2- oxoethyl]-4-[(4-{[(pentylamino) acetyl]amino}phenyl)ethynyl]benzamide	466.6
894	1064	N-[(1S)-1-(aminomethyl)-2-(hydroxyamino)-2- oxoethyl]-4-{[4-({[(thien-2- ylmethyl)amino]acetyl}amino)phenyl]ethynyl}benzamide	492.6
895	1065	N-[(1S)-1-(aminomethyl)-2-(hydroxyamino)-2- oxoethyl]-4-[(4-{[(4-phenylpiperidin-1- yl)acetyl]amino}phenyl)ethynyl]benzamide	540.6
896	1066	N-[(1S)-1-(aminomethyl)-2-(hydroxyamino)-2- oxoethyl]-4-[(4-{[(4-phenylpiperazin-1- yl)acetyl]amino}phenyl)ethynyl]benzamide	541.6
897	1067	N-[(1S)-1-(aminomethyl)-2-(hydroxyamino)-2- oxoethyl]-4-{[(4-({[4-(2- fluorophenyl)piperazin-1- yl]acetyl}amino)phenyl]ethynyl}benzamide	559.6
898	1068	N-[(1S)-1-(aminomethyl)-2-(hydroxyamino)-2- oxoethyl]-4-{[4-({[4-(4- fluorophenyl)piperazin-1- yl]acetyl}amino)phenyl]ethynyl}benzamide	559.6
899	1069	4-{[4-({[(1-acetylpiperidin-4- yl)(cyclopropyl)amino]acetyl}amino)phenyl]ethynyl}-N- [(1S)-1-(aminomethyl)-2- (hydroxyamino)-2-oxoethyl]benzamide	561.7
900	1070	N-[(1S)-1-(aminomethyl)-2-(hydroxyamino)-2- oxoethyl]-4-{[4-({[(2,3- dimethylcyclohexyl)amino]acetyl}amino) phenyl]ethynyl}benzamide	506.6
901	1071	N-[(1S)-1-(aminomethyl)-2-(hydroxyamino)-2- oxoethyl]-4-{[4-({[(1R,2R,4S)- bicyclo[2.2.1]hept-2- ylamino]acetyl}amino)phenyl]ethynyl}benzamide	490.6
902	1072	N-[(1S)-1-(aminomethyl)-2-(hydroxyamino)-2- oxoethyl]-4-[(4-{[({[(1S,2R,5S)-6,6- dimethylbicyclo[3.1.1]hept-2- yl]methyl}amino)acetyl]amino}phenyl)ethynyl]benzamide	532.7
903	1073	N-[(1S)-1-(aminomethyl)-2-(hydroxyamino)-2- oxoethyl]-4-{[4-({[(1S,4R)-bicyclo[2.2.1]hept-2-ylamino]acetyl}amino) phenyl]ethynyl}benzamide	490.6
904	1074	N-[(1S)-1-(aminomethyl)-2-(hydroxyamino)-2- oxoethyl]-4-({4-[({[(1S,2S,3S,5R)-2,6,6- trimethylbicyclo[3.1.1]hept-3- yl]amino}acetyl)amino]phenyl}ethynyl)benzamide	532.7
905	1075	N-[(1S)-1-(aminomethyl)-2-(hydroxyamino)-2- oxoethyl]-4-{[4-({[(tricyclo[3.3.1.1˜3,7˜]dec-1-ylmethyl)amino]acetyl}amino)phenyl]ethynyl}benzamide	544.7
906	1076	N-[(1S)-1-(aminomethyl)-2-(hydroxyamino)-2- oxoethyl]-4-({4-[({[(2,6- difluorophenyl)methyl]amino}acetyl)amino]phenyl}ethynyl) benzamide	522.5
907	1077	N-[(1S)-1-(aminomethyl)-2-(hydroxyamino)-2- oxoethyl]-4-[(4-{[({[4- (methylthio)phenyl]methyl}amino) acetyl]amino}phenyl)ethynyl]benzamide	532.6
908	1078	N-[(1S)-1-(aminomethyl)-2-(hydroxyamino)-2- oxoethyl]-4-[(4-{[({[4- (methylsulfonyl)phenyl]methyl}amino)acetyl]amino}phenyl)ethynyl]benzamide	564.6
909	1079	N-[(1S)-1-(aminomethyl)-2-(hydroxyamino)-2- oxoethyl]-4-{[4-({[({4- [(trifluoromethyl)thio]phenyl}methyl) amino]acetyl}amino)phenyl]ethynyl}benzamide	586.6
910	1080	N-[(1S)-1-(aminomethyl)-2-(hydroxyamino)-2- oxoethyl]-4-{[4-({[({4- [(trifluoromethyl)oxy]phenyl}methyl) amino]acetyl}amino)phenyl]ethynyl}benzamide	570.5
911	1081	N-[(1S)-1-(aminomethyl)-2-(hydroxyamino)-2- oxoethyl]-4-({4-[({[(2,4,5- trifluorophenyl)methyl]amino}acetyl) amino]phenyl}ethynyl)benzamide	540.5
912	1082	N-[(1S)-1-(aminomethyl)-2-(hydroxyamino)-2- oxoethyl]-4-({4-[({[(2,3,4- trifluorophenyl)methyl]amino}acetyl) amino]phenyl}ethynyl)benzamide	540.5
913	1083	N-[(1S)-1-(aminomethyl)-2-(hydroxyamino)-2- oxoethyl]-4-({4-[({[(3,4,5- trifluorophenyl)methyl]amino}acetyl) amino]phenyl}ethynyl)benzamide	540.5
914	1084	N-[(1S)-1-(aminomethyl)-2-(hydroxyamino)-2- oxoethyl]-4-(4-{4-[(pyrrolidin-1- ylacetyl)amino]phenyl}buta-1,3- diynyl)benzamide	474.5
915	1085	N-[(1S)-1-(aminomethyl)-2-(hydroxyamino)-2- oxoethyl]-4-(4-{4-[(azepan-1- ylacetyl)amino]phenyl}buta-1,3- diynyl)benzamide	502.6
916	1086	N-[(1S)-1-(aminomethyl)-2-(hydroxyamino)-2- oxoethyl]-4-(4-{4-[(piperazin-1- ylacetyl)amino]phenyl}buta-1,3- diynyl)benzamide	489.5
917	1087	N-[(1S)-1-(aminomethyl)-2-(hydroxyamino)-2- oxoethyl]-4-[4-(4-{[(4-methylpiperazin-1- yl)acetyl]amino}phenyl)buta-1,3- diynyl]benzamide	503.6
918	1088	N-[(1S)-1-(aminomethyl)-2-(hydroxyamino)-2- oxoethyl]-4-(4-{4-[(morpholin-4- ylacetyl)amino]phenyl}buta-1,3- diynyl)benzamide	490.5
919	1089	N-[(1S)-1-(aminomethyl)-2-(hydroxyamino)-2- oxoethyl]-4-{4-[4- ({[cyclohexyl(methyl)amino]acetyl}amino) phenyl]buta-1,3-diynyl}benzamide	516.6
920	1090	N-[(1S)-1-(aminomethyl)-2-(hydroxyamino)-2- oxoethyl]-4-(4-{4-[({[(2- fluorophenyl)methyl]amino}acetyl) amino]phenyl}buta-1,3- diynyl)benzamide	528.6
921	1091	N-[(1S)-1-(aminomethyl)-2-(hydroxyamino)-2- oxoethyl]-4-(4-{4-[({[(3- fluorophenyl)methyl]amino}acetyl) amino]phenyl}buta-1,3- diynyl)benzamide	528.6
922	1092	N-[(1S)-1-(aminomethyl)-2-(hydroxyamino)-2- oxoethyl]-4-(4-{4-[({[(4- fluorophenyl)methyl]amino}acetyl) amino]phenyl}buta-1,3- diynyl)benzamide	528.6
923	1093	N-[(1S)-1-(aminomethyl)-2-(hydroxyamino)-2- oxoethyl]-4-(4-{4-[({[(2- methylphenyl)methyl]amino}acetyl) amino]phenyl}buta-1,3- diynyl)benzamide	524.6
924	1094	N-[(1S)-1-(aminomethyl)-2-(hydroxyamino)-2- oxoethyl]-4-(4-{4-[({[(3- methylphenyl)methyl]amino}acetyl) amino]phenyl}buta-1,3- diynyl)benzamide	524.6
925	1095	N-[(1S)-1-(aminomethyl)-2-(hydroxyamino)-2- oxoethyl]-4-(4-{4-[({[(4- methylphenyl)methyl]amino}acetyl) amino]phenyl}buta-1,3- diynyl)benzamide	524.6
926	1096	N-[(1S)-1-(aminomethyl)-2-(hydroxyamino)-2- oxoethyl]-4-{4-[4-({[(pyridin-2- ylmethyl)amino]acetyl}amino) phenyl]buta-1,3-diynyl}benzamide	511.6
927	1097	N-[(1S)-1-(aminomethyl)-2-(hydroxyamino)-2- oxoethyl]-4-{4-[4-({[(pyridin-3- ylmethyl)amino]acetyl}amino) phenyl]buta-1,3-diynyl}benzamide	511.6
928	1098	N-[(1S)-1-(aminomethyl)-2-(hydroxyamino)-2- oxoethyl]-4-{4-[4-({[(pyridin-4- ylmethyl)amino]acetyl}amino) phenyl]buta-1,3-diynyl}benzamide	511.6
929	1099	N-[(1S)-1-(aminomethyl)-2-(hydroxyamino)-2- oxoethyl]-4-[4-(4-{[({[2- (methyloxy)phenyl]methyl}amino) acetyl]amino}phenyl) buta-1,3-diynyl]benzamide	540.6
930	1100	N-[(1S)-1-(aminomethyl)-2-(hydroxyamino)-2- oxoethyl]-4-[4-(4-{[({[3- (methyloxy)phenyl]methyl}amino) acetyl]amino}phenyl)buta- 1,3-diynyl]benzamide	540.6
931	1101	N-[(1S)-1-(aminomethyl)-2-(hydroxyamino)-2- oxoethyl]-4-[4-(4-{[{[4- (methyloxy)phenyl]methyl}amino) acetyl]amino}phenyl)buta- 1,3-diynyl]benzamide	540.6
932	1102	N-[(1S)-1-(aminomethyl)-2-(hydroxyamino)-2- oxoethyl]-4-{4-[4-({[(2- fluorophenyl)amino]acetyl}amino) phenyl]buta-1,3-diynyl}benzamide	514.5
933	1103	N-[(1S)-1-(aminomethyl)-2-(hydroxyamino)-2- oxoethyl]-4-{4-[4-({[(3- fluorophenyl)amino]acetyl}amino) phenyl]buta-1,3-diynyl}benzamide	514.5
934	1104	N-[(1S)-1-(aminomethyl)-2-(hydroxyamino)-2- oxoethyl]-4-{4-[4-({[(4- fluorophenyl)amino]acetyl}amino) phenyl]buta-1,3-diynyl}benzamide	514.5
935	1105	N-[(1S)-1-(aminomethyl)-2-(hydroxyamino)-2- oxoethyl]-4-[4-(4-{[(pyridin-2- ylamino)acetyl]amino}phenyl)buta-1,3- diynyl]benzamide	497.5
936	1106	N-[(1S)-1-(aminomethyl)-2-(hydroxyamino)-2- oxoethyl]-4-[4-(4-{[(pyridin-3- ylamino)acetyl]amino}phenyl)buta-1,3- diynyl]benzamide	497.5
937	1107	N-[(1S)-1-(aminomethyl)-2-(hydroxyamino)-2- oxoethyl]-4-[4-(4-{[(pyridin-4- ylamino)acetyl]amino}phenyl)buta-1,3- diynyl]benzamide	497.5
938	1108	N-[(1S)-1-(aminomethyl)-2-(hydroxyamino)-2- oxoethyl]-4-[4-(4-{[(cyclobutylamino) acetyl]amino}phenyl)buta-1,3- diynyl]benzamide	474.5
939	1109	N-[(1S)-1-(aminomethyl)-2-(hydroxyamino)-2- oxoethyl]-4-[4-(4-{[(cyclopentylamino) acetyl]amino}phenyl)buta-1,3- diynyl]benzamide	488.6
940	1110	N-[(1S)-1-(aminomethyl)-2-(hydroxyamino)-2- oxoethyl]-4-[4-(4-{[(cyclohexylamino) acetyl]amino}phenyl)buta- 1,3-diynyl]benzamide	502.6
941	1111	N-[(1S)-1-(aminomethyl)-2-(hydroxyamino)-2- oxoethyl[-4-[4-(4-{[(cycloheptylamino) acetyl]amino}phenyl)buta- 1,3-diynyl]benzamide	516.6
942	1112	N-[(1S)-1-(aminomethyl)-2-(hydroxyamino)-2- oxoethyl]-4-[4-(4-{[(methylamino) acetyl]amino}phenyl)buta-1,3- diynyl]benzamide	434.5
943	1113	N-[(1S)-1-(aminomethyl)-2-(hydroxyamino)-2- oxoethyl]-4-[4-(4-{[(propylamino) acetyl]amino}phenyl)buta-1,3- diynyl]benzamide	462.5
944	1114	N-[(1S)-1-(aminomethyl)-2-(hydroxyamino)-2- oxoethyl]-4-[4-(4-{[(butylamino) acetyl]amino}phenyl)buta-1,3- diynyl]benzamide	476.5
945	1115	N-[(1S)-1-(aminomethyl)-2-(hydroxyamino)-2- oxoethyl]-4-[4-(4-{[(pentylamino) acetyl]amino}phenyl)buta-1,3- diynyl]benzamide	490.6
946	1116	N-[(1S)-1-(aminomethyl)-2-(hydroxyamino)-2- oxoethyl]-4-[4-(4-{[(hexylamino) acetyl]amino}phenyl)buta-1,3- diynyl]benzamide	504.6
947	1117	N-[(1S)-1-(aminomethyl)-2-(hydroxyamino)-2- oxoethyl]-4-{4-[4-({[ethyl (methyl)amino]acetyl}amino)phenyl]buta-1,3-diynyl}benzamide	462.5
948	1118	N-[(1S)-1-(aminomethyl)-2-(hydroxyamino)-2- oxoethyl]-4-{4-[4-({[(1- methylethyl)amino]acetyl}amino) phenyl]buta-1,3-diynyl}benzamide	462.5
949	1119	N-[(1S)-1-(aminomethyl)-2-(hydroxyamino)-2- oxoethyl]-4-{4-[4-({[(2- methylpropyl)amino]acetyl}amino) phenyl]buta-1,3-diynyl}benzamide	476.5
950	1120	N-[(1S)-1-(aminomethyl)-2-(hydroxyamino)-2- oxoethyl]-4-{4-[4-({[(2- hydroxyethyl)amino]acetyl}amino) phenyl]buta-1,3-diynyl}benzamide	464.5
951	1121	N-[(1S)-1-(aminomethyl)-2-(hydroxyamino)-2- oxoethyl]-4-(4-{4-[({[2- (methyloxy)ethyl]amino}acetyl)amino]phenyl}buta-1,3-diynyl)benzamide	478.5
952	1122	N-[(1S)-1-(aminomethyl)-2-(hydroxyamino)-2- oxoethyl]-4-(4-{4-[({[2- (dimethylamino)ethyl]amino}acetyl) amino]phenyl}buta-1,3- diynyl)benzamide	491.6
953	1123	N-[(1S)-1-(aminomethyl)-2-(hydroxyamino)-2- oxoethyl]-4-{4-[4-({[(2- cyanoethyl)amino]acetyl}amino) phenyl]buta-1,3-diynyl}benzamide	473.5
954	1124	N-[(1S)-1-(aminomethyl)-2-(hydroxyamino)-2- oxoethyl]-4-{4-[4-({[(thien-2- ylmethyl)amino]acetyl}amino) phenyl]buta-1,3-diynyl}benzamide	516.6
955	1125	N-[(1S)-1-(aminomethyl)-2-(hydroxyamino)-2- oxoethyl]-4-(4-{4-[({[(1R)-1- phenylethyl]amino}acetyl)amino]phenyl}buta-1,3-diynyl)benzamide	524.6
956	1126	N-[(1S)-1-(aminomethyl)-2-(hydroxyamino)-2- oxoethyl]-4-(4-{4-[({[(1S)-1- phenylethyl]amino}acetyl)amino]phenyl}buta-1,3-diynyl)benzamide	524.6
957	1127	N-[(1S)-1-(aminomethyl)-2-(hydroxyamino)-2- oxoethyl]-4-{4-[4-({[(2- phenylethyl)amino]acetyl}amino) phenyl]buta-1,3-diynyl}benzamide	524.6
958	1128	N-[(1S)-1-(aminomethyl)-2-(hydroxyamino)-2- oxoethyl]-4-(4-{4-[(1H-imidazol-1- ylacetyl)amino]phenyl}buta-1,3- diynyl)benzamide	471.5
959	1129	N-[(1S)-1-(aminomethyl)-2-(hydroxyamino)-2- oxoethyl]-4-{4-[4-({[(1R,2R,4S)- bicyclo[2.2.1]hept-2- ylamino]acetyl}amino)phenyl]buta-1,3- diynyl}benzamide	514.6
960	1130	N-[(1S)-1-(aminomethyl)-2-(hydroxyamino)-2- oxoethyl]-4-{4-[4- ({[(cyclohexyhnethyl)amino]acetyl}amino) phenyl]buta-1,3-diynyl}benzamide	516.6
961	1131	N-{(1S,2R)-2-hydroxy-1- [(hydroxyamino)carbonyl]propyl}-4-[(6- pipendin-1-ylpyridin-3-yl)ethynyl]benzamide	423.5
962	1132	N-{(1S,2R)-2-hydroxy-1- [(hydroxyamino)carbonyl]propyl}-4-{[6-(4- methylpiperazin-1-yl)pyridin-3- yl]ethynyl}benzamide	438.5
963	1133	N-{(1S,2R)-2-hydroxy-1- [(hydroxyamino)carbonyl]propyl}-4-[(6- piperazin-1-ylpyridin-3- yl)ethynyl]benzamide	424.5
964	1134	4-[(6-azepan-1-ylpyridin-3-yl)ethynyl]-N- {(1S,2R)-2-hydroxy-1- [(hydroxyamino)carbonyl]propyl}benzamide	437.5
965	1135	4-{[6-(cyclobutylamino)pyridin-3- yl]ethynyl}-N-{(1S,2R)- 2-hydroxy-1- [(hydroxyamino)carbonyl]propyl}benzamide	409.5
966	1136	4-{[6-(cyclohexylamino)pyridin-3- yl]ethynyl}-N-{(1S,2R)- 2-hydroxy-1- [(hydroxyamino)carbonyl]propyl}benzamide	437.5
967	1137	4-{[6-(butylamino)pyridin-3- yl]ethynyl}-N-{(1S,2R)- 2-hydroxy-1- [(hydroxyamino)carbonyl]propyl}benzamide	411.5
968	1138	4-({6-[(2-hydroxyethyl)amino]pyridin-3- yl}ethynyl)-N-{(1S,2R)-2-hydroxy-1- [(hydroxyamino)carbonyl]propyl}benzamide	399.4
969	1139	4-[(6-{[2-(dimethylamino)ethyl]amino}pyridin-3-yl)ethynyl]- N-{(1S,2R)-2-hydroxy-1- [(hydroxyamino)carbonyl]propyl}benzamide	426.5
970	1140	N-{(1S,2R)-2-hydroxy-1- [(hydroxyamino)carbonyl]propyl}-4-({6- [(phenylmethyl)amino]pyridin-3- yl}ethynyl)benzamide	445.5
971	1141	4-[(6-{[(4-fluorophenyl)methyl]amino}pyridin-3-yl)ethynyl]-N- {(1S,2R)-2-hydroxy-1- [(hydroxyamino)carbonyl]propyl}benzamide	463.5
972	1142	N-{(1S,2R)-2-hydroxy-1- [(hydroxyamino)carbonyl]propyl}-4-{[6- (pyridin-4-ylamino)pyridin-3- yl]ethynyl}benzamide	432.4
973	1143	4-[(6-chloropyridin-3-yl)ethynyl]-N- {(1S,2R)-2-hydroxy-1- [(hydroxyamino)carbonyl]propyl}benzamide	374.8
974	1144	1,1-dimethylethyl (2S)-2-[({4-[(4- ethylphenyl)ethynyl]phenyl}carbonyl) amino]-3-(hydroxyamino)-3- oxopropylcarbamate	452.5
975	1145	N-[(1S)-1-(aminomethyl)-2-(hydroxyamino)-2- oxoethyl]-4-{4-[4-({[(1S)-1- (aminomethyl)-2-(hydroxyamino)-2- oxoethyl]amino}carbonyl)phenyl]buta-1,3-diynyl}benzamide	493.5
976	1146	N-{(1S,2R)-2-hydroxy-1- [(hydroxyamino)carbonyl]propyl}-4-{[4- (morpholin-4- ylmethyl)phenyl]ethynyl}benzamide	438.5
977	1147	4-[(4-{[(2-aminoethyl)amino]methyl}phenyl)ethynyl]-N- {(1S,2R)-2-hydroxy-1- [(hydroxyamino)carbonyl]propyl}benzamide	411.5
978	1148	4-({4-[((2S)-2-amino-5- {[amino(imino)methyl]amino}pentanoyl)amino]phenyl}ethynyl)- N-[(1S)-1-(aminomethyl)-2- (hydroxyamino)-2-oxoethyl]benzamide	495.6
979	1149	(2S)-6-amino-2-({[4-({4-[({(1S,2R)- 2-hydroxy-1-[(hydroxyamino) carbonyl]propyl}amino)carbonyl]phenyl}ethynyl)phenyl]carbonyl}amino)hexanoic acid	511.5
980	1150	(2S)-6-amino-2-({[4-({4-[({(1S,2R)- hydroxy-1-[(hydroxyamino) carbonyl]propyl}amino)carbonyl]phenyl}ethynyl)phenyl]acetyl}amino)hexanoic acid	525.6
981	1151	5-{[(2S)-3-(hydroxyamino)-3-oxo-2-({[4- (phenylethynyl)phenyl]carbonyl}amino)propyl]amino}- 5-oxopentanoic acid	438.4
982	1152	N-(2-aminoethyl)-N′-[(2S)-3- (hydroxyamino)-3-oxo-2-({[4- (phenylethynyl)phenyl]carbonyl}amino) propyl]pentanediamide	480.5
983	1153	N-[(1S)-1-[(2,6-dioxopiperidin-1-yl)methyl]-2- (hydroxyamino)-2-oxoethyl]-4- (phenylethynyl)benzamide	420.4
984	1154	N,N′-bis[(2S)-3-(hydroxyamino)-3-oxo- 2-({[4-(phenylethynyl)phenyl]carbonyl}amino)propyl]pentanediamide	743.8
985	1155	N-((1S)-2-(hydroxyamino)-2-axo-1- {[({[(1S)-1-phenylethyl]amino}acetyl)amino]methyl}ethyl)- 4-(phenylethynyl)benzamide	485.6
986	1156	N-{(1S)-2-hydroxy-1- [(hydroxyamino)carbonyl]-2-methylpropyl}- 4-(phenylethynyl)benzamide	353.4
987	1157	N-[(1S)-1-(aminomethyl)-2-(hydroxyamino)- 2-oxoethyl]-4-[(6-piperidin-1- ylpyridin-3-yl)ethynyl]benzamide	408.5
988	1158	N-[(1S)-1-(aminomethyl)-2-(hydroxyamino)- 2-oxoethyl]-4-[(6-morpholin-4- ylpyridin-3-yl)ethynyl]benzamide	410.4
989	1159	N-[(1S)-1-(aminomethyl)-2-(hydroxyamino)- 2-oxoethyl]-4-{[6-(4- methylpiperazin-1-yl)pyridin- 3-yl]ethynyl}benzamide	423.5
990	1160	N-[(1S)-1-(aminomethyl)-2-(hydroxyamino)- 2-oxoethyl]-4-[(6-piperazin-1- ylpyridin-3-yl)ethynyl]benzamide	409.5
991	1161	N-[(1S)-1-(aminomethyl)-2-(hydroxyamino)- 2-oxoethyl]-4-[(6-azepan-1- ylpyridin-3-yl)ethynyl]benzamide	422.5
992	1162	N-[(1S)-1-(aminomethyl)-2-(hydroxyamino)- 2-oxoethyl]-4-{[6-(cyclobutylamino) pyridin-3-yl]ethynyl}benzamide	394.4
993	1163	N-[(1S)-1-(aminomethyl)-2-(hydroxyamino)- 2-oxoethyl]-4-{[6-(cyclohexylamino) pyridin-3-yl]ethynyl}benzamide	422.5
994	1164	N-[(1S)-1-(aminomethyl)-2-(hydroxyamino)- 2-oxoethyl]-4-{[6-(butylamino) pyridin-3-yl]ethynyl}benzamide	396.5
995	1165	N-[(1S)-1-(aminomethyl)-2-(hydroxyamino)- 2-oxoethyl]-4-[(6-{[2- (methyloxy)ethyl]amino}pyridin-3- yl)ethynyl]benzamide	398.4
996	1166	N-{(1S,2R)-2-hydroxy-1- [(hydroxyamino)carbonyl]propyl}-4-{[4- (piperidin-1-ylmethyl) phenyl]ethynyl}benzamide	436.5
997	1167	4-[(4-{[(2S)-2-amino-3-(4- aminophenyl)propanoyl]amino}phenyl)ethynyl]-N-{(1S,2R)- 2-hydroxy-1-[(hydroxyamino) carbonyl]propyl}benzamide	516.6
998	1168	4-((2S)-2-amino-3-{[4-({4-[({(1S,2R)-2- hydroxy-1-[(hydroxyamino) carbonyl]propyl}amino)carbonyl]phenyl}ethynyl)phenyl]amino}-3- oxopropyl)benzoic acid	545.6
999	1169		573.6
1000	1170	N-{(1S,2R)-2-hydroxy-1- [(hydroxyamino)carbonyl]propyl}-4- ({4-[({[1-(hydroxymethyl)-2- methylpropyl]amino}acetyl)amino]phenyl}ethynyl)benzamide	497.6
1001	1171	4-[4-(3-aminophenyl)buta-1,3-diynyl]-N- {(1S,2R)-2-hydroxy-1- [(hydroxyamino)carbonyl]propyl}benzamide	378.4
1002	1172	4-[4-(3-{[(2-aminoethyl)amino]methyl}phenyl)buta-1,3- diynyl]-N-{(1S,2R)-2-hydroxy-1- [(hydroxyamino)carbonyl]propyl}benzamide	435.5
1003	1173	5-[(4-{[4-({[(1S)-1-(aminomethyl)-2- (hydroxyamino)-2-oxoethyl]amino}carbonyl)phenyl]ethynyl}phenyl)amino]-5- oxopentanoic acid	453.5
1004	1174	N-(2-aminoethyl)-3-{4-[4-({[(1S)-1- (aminomethyl)-2-(hydroxyamino)-2- oxoethyl]amino}carbonyl)phenyl]buta- 1,3-diynyl}benzamide	434.5
1005	1175	N-[(1S)-1-(aminomethyl)-2-(hydroxyamino)-2- oxoethyl]-4-{4-[3-(aminomethyl) phenyl]buta-1,3-diynyl}benzamide	377.4
1006	1176	N-[(1S)-1-(aminomethyl)-2-(hydroxyamino)-2- oxoethyl]-4-{4-[3- (trifluoromethyl)phenyl]buta-1,3- diynyl}benzamide	416.4
1007	1177	N-[(1S)-1-(aminomethyl)-2-(hydroxyamino)-2- oxoethyl]-4-buta-1,3-diynylbenzamide	272.3
1008	1178	N-[(1S)-1-(aminomethyl)-2-(hydroxyamino)-2- oxoethyl]-4-[4-(2-methylphenyl)buta- 1,3-diynyl]benzamide	362.4
1009	1179	4-(4-{4-[(3-aminopropanoyl)amino]phenyl}buta-1,3-diynyl)-N- {(1S,2R)-2-hydroxy-1- [(hydroxyamino)carbonyl]propyl}benzamide	449.5
1010	1180	4-[4-(3-{[(aminoacetyl)amino]methyl}phenyl)buta-1,3- diynyl]-N-{(1S,2R)-2-hydroxy-1- [(hydroxyamino)carbonyl]propyl}benzamide	449.5
1011	1181	4-(4-{3-[(aminoacetyl)amino]phenyl}buta- 1,3-diynyl)-N-{(1S,2R)-2-hydroxy-1- [(hydroxyamino)carbonyl]propyl}benzamide	435.4
1012	1182	4-[4-(4-{[(2S)-2-aminopropanoyl]amino}phenyl)buta-1,3- diynyl]-N-{(1S,2R)-2-hydroxy-1- [(hydroxyamino)carbonyl]propyl}benzamide	449.5
1013	1183	4-(4-{4-[(aminoacetyl)amino]phenyl}buta- 1,3-diynyl)-N-[(1S)-1-(aminomethyl)-2- (hydroxyamino)-2-oxoethyl]benzamide	420.4
1014	1184	4-[4-(3-{[(aminoacetyl)amino]methyl}phenyl)buta-1,3- diynyl]-N-[(1S)-1-(aminomethyl)-2- (hydroxyamino)-2-oxoethyl]benzamide	434.5
1015	1185	N-[(1S)-1-(aminomethyl)-2-(hydroxyamino)- 2-oxoethyl]-4-(4-{4-[(3- aminopropanoyl)amino]phenyl}buta-1,3- diynyl)benzamide	434.5
1016	1186	4-(4-{3-[(aminoacetyl)amino]phenyl}buta- 1,3-diynyl)-N-[(1S)-1-(aminomethyl)-2- (hydroxyamino)-2-oxoethyl]benzamide	420.4
1017	1187	4-[(4-{[(2S)-2-amino-3-(4- hydroxyphenyl)propanoyl]amino}phenyl)ethynyl]-N-{(1S,2R)- 2-hydroxy-1-[(hydroxyamino) carbonyl]propyl}benzamide	517.6
1018	1188	4-(4-{4-[(aminoacetyl)amino]phenyl}buta-1,3-diynyl)-N-{(1S,2R)-2- hydroxy-1- [(hydroxyamino)carbonyl]propyl}benzamide	435.4
1019	1189	N-[(1S)-1-(aminomethyl)-2-(hydroxyamino)- 2-oxoethyl]-4-({4- [(butylamino)methyl]phenyl}ethynyl) benzamide	409.5
1020	1190	N-[(1S)-1-(aminomethyl)-2-(hydroxyamino)- 2-oxoethyl]-4-{[4-(piperidin-1- ylmethyl)phenyl]ethynyl}benzamide	421.5
1021	1191	N-[(1S)-1-(aminomethyl)-2-(hydroxyamino)- 2-oxoethyl]-4-[(4- formylphenyl)ethynyl]benzamide	352.4
1022	1192	N-{(1S,2R)-2-hydroxy-1- [(hydroxyamino)carbonyl]propyl}-4-({4- [(methylsulfonyl)amino]phenyl}ethynyl) benzamide	432.5
1023	1193	N-[(1S)-1-(aminomethyl)-2-(hydroxyamino)- 2-oxoethyl]-4-({4- [(methylsulfonyl)amino]phenyl}ethynyl) benzamide	417.5
1024	1194	N-[(1S)-1-(aminomethyl)-2-(hydroxyamino)- 2-oxoethyl]-4-({4- [(phenylsulfonyl)amino]phenyl}ethynyl) benzamide	479.5
1025	1195	N-[(1S)-1-(aminomethyl)-2-(hydroxyamino)- 2-oxoethyl]-4-(4-{4- [(phenylsulfonyl)amino]phenyl}buta-1,3- diynyl)benzamide	503.5
1026	1196	N-[(1S)-1-(aminomethyl)-2-(hydroxyamino)- 2-oxoethyl]-4-{[4-(morpholin-4- ylmethyl)phenyl]ethynyl}benzamide	423.5
1027	1197	N-[(1S)-1-(aminomethyl)-2-(hydroxyamino)- 2-oxoethyl]-4-({4-[(4-methylpiperazin-1- yl)methyl]phenyl}ethynyl)benzamide	436.5
1028	1198	N-[(1S)-1-(aminomethyl)-2-(hydroxyamino)- 2-oxoethyl]-4-[(4-{[(2- hydroxyethyl)amino]methyl}phenyl) ethynyl]benzamide	397.4
1029	1199	N-[(1S)-1-(aminomethyl)-2-(hydroxyamino)- 2-oxoethyl]-4-{[4-({[2- (methylaxy)ethyl]amino}methyl)phenyl]ethynyl}benzamide	411.5
1030	1200	N-[(1S)-1-(aminomethyl)-2-(hydroxyamino)- 2-oxoethyl]-4-({4-[(cyclohexylamino) methyl]phenyl}ethynyl)benzamide	435.5
1031	1201	N-[(1S)-1-(aminomethyl)-2-(hydroxyamino)- 2-oxoethyl]-4-[(4- {[(phenylmethyl)amino]methyl}phenyl)ethynyl]benzamide	443.5
1032	1202	N-[(1S)-1-(aminomethyl)-2-(hydroxyamino)- 2-oxoethyl]-4-[(6-chloropyridin-3- yl)ethynyl]benzamide	359.8
1033	1203	N-{(1S,2R)-2-hydroxy-1- [(hydroxyamino)carbonyl]propyl}-4-(4- {4-[({[6-(methyloxy)pyridin-3- yl]amino}acetyl)amino]phenyl}buta-1,3-diynyl)benzamide	542.6
1034	1204	4-{4-[4-({[(6-chloropyridin-3- yl)amino]acetyl}amino)phenyl]buta-1,3- diynyl}-N-{(1S,2R)-2-hydroxy-1- [(hydroxyamino)carbonyl]propyl}benzamide	547.0
1035	1205	N-{(1S,2R)-2-hydroxy-1- [(hydroxyamino)carbonyl]propyl}-4-{[4- (pyrrolidin-1- ylmethyl)phenyl]ethynyl}benzamide	422.5
1036	1206	4-({4-[(ethylamino)methyl]phenyl}ethynyl)-N-{(1S,2R)-2-hydroxy-1- [(hydroxyamino)carbonyl]propyl}benzamide	396.5
1037	1207	4-({4-[(dimethylamino)methyl]phenyl}ethynyl)- N-{(1S,2R)-2-hydroxy-1- [(hydroxyamino)carbonyl]propyl}benzamide	396.5
1038	1208	N-{(1S,2R)-2-hydroxy-1- [(hydroxyamino)carbonyl]propyl}-4- ({4-[(4-methylpiperazin-1- yl)methyl]phenyl}ethynyl)benzamide	451.5
1039	1209	N-{(1S,2R)-2-hydroxy-1- [(hydroxyamino)carbonyl]propyl}-4- {[4-({[3-(1H-imidazol-1-yl) propyl]amino}methyl)phenyl]ethynyl}benzamide	476.5
1040	1210	N-[(1S)-1-(aminomethyl)-2-(hydroxyamino)- 2-oxoethyl]-4-(4-thien-2-ylbuta- 1,3-diynyl)benzamide	354.4
1041	1211	N,N,N-triethyl-2-{[4-(4-{4-[({(1S,2R)-2- hydroxy-1-[(hydroxyamino) carbonyl]propyl}amino)carbonyl]phenyl}buta-1,3-diynyl)phenyl]amino}-2- oxoethanaminium	520.6
1042	1212	4-[4-(2-aminophenyl)buta-1,3-diynyl]-N- {(1S,2R)-2-hydroxy-1- [(hydroxyamino)carbonyl]propyl}benzamide	378.4
1043	1213	4-[4-(3-{[(2-aminoethyl)amino]methyl}phenyl)buta-1,3- diynyl]-N-[(1S)-1-(aminomethyl)-2- (hydroxyamino)-2-oxoethyl]benzamide	420.5
1044	1214	4-buta-1,3-diynyl-N-{(1S,2R)-2-hydroxy-1- [(hydroxyamino)carbonyl]propyl}benzamide	287.3
1045	1215	4-[4-(4-{[(2S)-2-amino-4- methylpentanoyl]amino}phenyl)buta-1,3- diynyl]-N-{(1S,2R)-2-hydroxy-1- [(hydroxyamino)carbonyl]propyl}benzamide	491.6
1046	1216	(2S)-4-[4-(4-{4-[({(1S,2R)-2-hydroxy-1- [(hydroxyamino)caxbonyl]propyl}amino) carbonyl]phenyl}buta-1,3-diynyl) phenyl]pyrrolidine-2-carboxamide	475.5
1047	1217	(2S)-N-[4-(4-{4-[({(1S,2R)-2-hydroxy-1- [(hydroxyamino)carbonyl]propyl}amino) carbonyl]phenyl}buta-1,3-diynyl) phenyl]piperidine-2-carboxamide	489.5
1048	1218	4-[4-(4-{[(2S)-2,3-diaminopropanoyl]amino}phenyl)buta-1,3- diynyl]-N-{(1S,2R)-2-hydroxy-1- [(hydroxyamino)carbonyl]propyl}benzamide	464.5
1049	1219	4-[4-(4-{[(2S)-2-amino-3-(1H-imidazol-nl 4-yl)propanoyl]amino}phenyl)buta- 1,3-diynyl]-N-{(1S,2R)-2- hydroxy-1- [(hydroxyamino)carbonyl]propyl}benzamide	515.5
1050	1220	N-[1-[(hydroxyamino)carbonyl]-2- (propylamino)propyl]-4-[(4- {[(propylamino)acetyl]amino}phenyl)ethynyl]benzamide	494.6
1051	1221	4-[(4-{[(cyclobutylamino)acetyl]amino}phenyl)ethynyl]-N- {2-(cyclobutylamino)-1- [(hydroxyamino)carbonyl]propyl}benzamide	518.6
1052	1222	N-{(1S,2R)-2-amino-1- [(hydroxyamino)carbonyl]propyl}-4-[(4- {[(cyclopropylamino)acetyl]amino}phenyl)ethynyl]benzamide	450.5
1053	1223	1-[(1R,2S)-2-[({4-[(4- {[(cyclopropylamino)acetyl]amino}phenyl)ethynyl]phenyl}carbonyl) amino]-3-(hydroxyamino)-1- methyl-3-oxopropyl]triaza-1,2- dien-2-ium	477.5
1054	1224	N-{(1S,2R)-2-amino-1- [(hydroxyamino)carbonyl]propyl}-4- ({4-[({[(4-fluorophenyl)methyl]amino}acetyl)amino]phenyl}ethynyl)benzamide	518.6
1055	1225	N-{(1S,2R)-2-amino-1- [(hydroxyamino)carbonyl]propyl}-4-({4- [({[(3-fluorophenyl)methyl]amino}acetyl)amino]phenyl}ethynyl)benzamide	518.6
1056	1226	N-{(1S,2R)-2-amino-1- [(hydroxyamino)carbonyl]propyl}-4-[(4- {[(propylamino)acetyl]amino}phenyl) ethynyl]benzamide	452.5
1057	1227	N-{(1S,2R)-2-amino-1- [(hydroxyamino)carbonyl]propyl}-4-{[4- ({[(phenylmethyl)amino]acetyl}amino) phenyl]ethynyl}benzamide	500.6
1058	1228	1-((1R,2S)-3-(hydroxyamino)-1-methyl- 3-oxo-2-{[(4-{[4-({[(phenylmethyl) amino]acetyl}amino)phenyl]ethynyl}phenyl)carbonyl]amino}propyl)triaza-1,2-dien-2-ium	527.6
1059	1229	N-{(1S,2R)-2-amino-1-[(hydroxyamino) carbonyl]propyl}-4-[(4- {[(cyclobutylamino)acetyl]amino}phenyl)ethynyl]benzamide	464.5
1060	1230	1-[(1R,2S)-2-[({4-[(4- {[(cyclobutylamino)acetyl]amino}phenyl) ethynyl]phenyl}carbonyl)amino]-3- (hydroxyamino)-1-methyl-3-oxopropyl]triaza-1,2-dien-2-ium	491.5
1061	1231	4-[(4-ethylphenyl)ethynyl]-N-{(1S)-1- [(hydroxyamino)carbonyl]-2- methylpropyl}benzamide	365.4
1062	1232	4-(4-{4-(ethylamino)methyl]phenyl}buta-1,3- diynyl)-N-{(1S,2R)-2-hydroxy-1- [(hydroxyamino)carbonyl]propyl}benzamide	420.5
1063	1233	N-[(1S)-1-(aminomethyl)-2-(hydroxyamino)- 2-oxoethyl]-4-[4-(3-aminophenyl)buta- 1,3-diynyl]benzamide	363.4
1064	1234	4-(4-{3-[(4-aminobutanoyl)amino]phenyl}buta-1,3-diynyl)-N- {(1S,2R)-2-hydroxy-1- [(hydroxyamino)carbonyl]propyl}benzamide	463.5
1065	1235	N-{(1S,2R)-2-hydroxy-1- [(hydroxyamino)carbonyl]propyl}-4-[4-(3- hydroxyphenyl)buta-1,3-diynyl]benzamide	379.4
1066	1236	4-(4-{2-[(aminoacetyl)amino]phenyl}buta-1,3- diynyl)-N-{(1S,2R)-2-hydroxy-1- [(hydroxyamino)carbonyl]propyl}benzamide	435.4
1067	1237	N-[(1S)-1-(aminomethyl)-2-(hydroxyamino)-2- oxoethyl]-4-{4-[2,4-bis(methyloxy) pyrimidin-5-yl]buta- 1,3-diynyl}benzamide	410.4
1068	1238	(2S)-6-amino-2-{[(4-{4-[4-({[(1S)-1- (aminomethyl)-2-(hydroxyamino)-2- oxoethyl]amino}carbonyl)phenyl]buta-1,3- diynyl}phenyl)carbonyl]amino}hexanoic acid	520.6
1069	1239	N-[(1S)-1-(aminomethyl)-2-(hydroxyamino)- 2-oxoethyl]-4-[4-(2-aminophenyl)buta-1,3- diynyl]benzamide	363.4
1070	1240	4-[4-(4-{2-[(2-aminoethyl)amino]-2- oxoethyl}phenyl)buta-1,3-diynyl]-N- [(1S)-1-(aminomethyl)-2- (hydroxyamino)-2-oxoethyl]benzamide	448.5
1071	1241	N-[(1S)-1-(aminomethyl)-2-(hydroxyamino)- 2-oxoethyl]-4-[4-(2-aminopyrimidin-5- yl)buta-1,3-diynyl]benzamide	365.4
1072	1242	4-(4-{3-[(4-aminobutanoyl)amino]phenyl}buta-1,3-diynyl)-N-[(1S)- 1-(aminomethyl)-2-(hydroxyamino)- 2-oxoethyl]benzamide	448.5
1073	1243	4-(4-{2-[(aminoacetyl)amino]phenyl}buta- 1,3-diynyl)-N-[(1S)-1-(aminomethyl)-2- (hydroxyamino)-2-oxoethyl]benzamide	420.4
1074	1244	4-[4-(4-{2-[(2-aminoethyl)amino]-2- oxoethyl}phenyl)buta-1,3-diynyl]-N- {(1S,2R)-2-hydroxy-1- [(hydroxyamino)caxbonyl]propyl}benzamide	463.5
1075	1245	4-[4-(4-{[(2,3-dihydroxypropyl)amino]methyl}phenyl)buta-1,3-diynyl]-N- {(1S,2R)-2-hydroxy-1- [(hydroxyamino)carbonyl]propyl}benzamide	466.5
1076	1246	N-{(1S,2R)-2-hydroxy-1- [(hydroxyamino)carbonyl]propyl}-4-(4- {4-[({[2-(methyloxy)phenyl]methyl}amino)methyl]phenyl}buta-1,3-diynyl)benzamide	512.6
1077	1247	N-{(1S,2R)-2-hydroxy-1- [(hydroxyamino)carbonyl]propyl}-4-(4- {4-[(pyridin-2-ylamino)methyl]phenyl}buta-1,3-diynyl)benzamide	469.5
1078	1248	4-[4-(4-{[(2-aminoethyl)amino]methyl}phenyl)buta-1,3-diynyl]-N- {(1S,2R)-2-hydroxy-1- [(hydroxyamino)carbonyl]propyl}benzamide	435.5
1079	1249	4-[(4-ethylphenyl)ethynyl]-N-[(1R)-1- [(ethylthio)methyl]-2- (hydroxyamino)-2-oxoethyl]benzamide	397.5
1080	1250	4-[(4-{[(2S)-2-aminopropanoyl]amino}phenyl)ethynyl]-N- [(1R)-1-[(ethylthio)methyl]-2- (hydroxyamino)-2-oxoethyl]benzamide	455.5
1081	1251	N-[(1S)-1-(aminomethyl)-2-(hydroxyamino)-2- oxoethyl]-4-[4-(3-chlorophenyl)buta- 1,3-diynyl]benzamide	382.8
1082	1252	N-[(1S)-1-(aminomethyl)-2-(hydroxyamino)-2- oxoethyl]-4-{4-[3-(methyloxy)phenyl]buta- 1,3-diynyl}benzamide	378.4
1083	1253	N-{(1S,2R)-2-hydroxy-1- [(hydroxyamino)carbonyl]propyl}-4- (4-{4-[(methylsulfonyl)amino]phenyl}buta-1,3-diynyl) benzamide	456.5
1084	1254	N-{(1S,2R)-2-hydroxy-1- [(hydroxyamino)carbonyl]propyl}-4- (4-{3-[(methylsulfonyl)amino]phenyl}buta-1,3-diynyl) benzamide	456.5
1085	1255	N-[(1S)-1-(aminomethyl)-2-(hydroxyamino)-2- oxoethyl]-4-(4-pyrazin-2-ylbuta-1,3- diynyl)benzamide	350.3
1086	1256	N-{(1S,2R)-2-hydroxy-1- [(hydroxyamino)carbonyl]propyl}-4-[4-(3- nitrophenyl)buta-1,3-diynyl]benzamide	408.4
1087	1257	N-{(1S,2R)-2-hydroxy-1- [(hydroxyamino)carbonyl]propyl}-4-[(3- {[(methylsulfonyl)amino]methyl}phenyl)ethynyl]benzamide	446.5
1088	1258	4-[(2-formylphenyl)ethynyl]-N-{(1S,2R)-2- hydroxy-1- [(hydroxyamino)carbonyl]propyl}benzamide	367.4
1089	1259	N-{(1R,2R)-2-hydroxy-1- [(hydroxyamino)carbonyl]propyl}-4-{(3- {[(methylsulfonyl)amino]methyl}phenyl)ethynyl]benzamide	446.5
1090	1260	4-({2-[(aminoacetyl)amino]phenyl}ethynyl)- N-{(1S,2R)-2-hydroxy-1- [(hydroxyamino)carbonyl]propyl}benzamide	411.4
1091	1261	N-{(1S)-2-hydroxy-1- [(hydroxyamino)carbonyl]propyl}-4-{4-[3- (morpholin-4-ylmethyl)phenyl]buta-1,3- diynyl}benzamide	462.5
1092	1262	N-[(1S)-1-(aminomethyl)-2-(hydroxyamino)- 2-oxoethyl]-4-({4- [(methylamino)methyl]phenyl}ethynyl)benzamide	367.4
1093	1263	N-[(1S)-1-(aminomethyl)-2-(hydroxyamino)- 2-oxoethyl]-4-({4- [(ethylamino)methyl]phenyl}ethynyl)benzamide	381.4
1094	1264	N-[(1S)-1-(aminomethyl)-2-(hydroxyamino)- 2-oxoethyl]-4-({4- [(propylamino)methyl]phenyl}ethynyl)benzamide	395.5
1095	1265	N-[(1S)-1-(aminomethyl)-2-(hydroxyamino)- 2-oxoethyl]-4-({4- [(pentylamino)methyl]phenyl}ethynyl)benzamide	423.5
1096	1266	N-[(1S)-1-(aminomethyl)-2-(hydroxyamino)- 2-oxoethyl]-4-({4- [(hexylamino)methyl]phenyl}ethynyl)benzamide	437.6
1097	1267	N-[(1S)-1-(aminomethyl)-2-(hydroxyamino)- 2-oxoethyl]-4-[(4-{[(1- methylethyl)amino]methyl}phenyl) ethynyl]benzamide	395.5
1098	1268	N-[(1S)-1-(aminomethyl)-2-(hydroxyamino)- 2-oxoethyl]-4-[(4-{[(2- methylpropyl)amino]methyl}phenyl) ethynyl]benzamide	409.5
1099	1269	N-[(1S)-1-(aminomethyl)-2-(hydroxyamino)- 2-oxoethyl]-4-[(4-{[(1,1- dimethylethyl)amino]methyl}phenyl) ethynyl]benzamide	409.5
1100	1270	N-[(1S)-1-(aminomethyl)-2-(hydroxyamino)- 2-oxoethyl]-4-({4- [(dimethylamino)methyl]phenyl}ethynyl)benzamide	381.4
1101	1271	N-[(1S)-1-(aminomethyl)-2-(hydroxyamino)- 2-oxoethyl]-4-[(4-{[ethyl(methyl) amino]methyl}phenyl)ethynyl]benzamide	395.5
1102	1272	N-[(1S)-1-(aminomethyl)-2-(hydroxyamino)- 2-oxoethyl]-4-{[4-({[2- (dimethylamino)ethyl]amino}methyl)phenyl]ethynyl}benzamide	424.5
1103	1273	N-[(1S)-1-(aminomethyl)-2-(hydroxyamino)- 2-oxoethyl]-4-{[4-({[4- (dimethylamino)butyl]amino}methyl)phenyl]ethynyl}benzamide	452.6
1104	1274	N-[(1S)-1-(aminomethyl)-2-(hydroxyamino)- 2-oxoethyl]-4-[(4-{[(2- cyanoethyl)amino]methyl}phenyl) ethynyl]benzamide	406.5
1105	1275	4-{[4-({[2-(acetylamino)ethyl]amino}methyl)phenyl]ethynyl}- N-[(1S)-1-(aminomethyl)-2- (hydroxyamino)-2-oxoethyl]benzamide	438.5
1106	1276	4-[(4-{[(2-aminoethyl)amino]methyl}phenyl)ethynyl]-N- [(1S)-1-(aminomethyl)-2- (hydroxyamino)-2-oxoethyl]benzamide	396.5
1107	1277	N-[(1S)-1-(aminomethyl)-2-(hydroxyamino)- 2-oxoethyl]-4-[(4-{[(3- hydroxypropyl)amino]methyl}phenyl) ethynyl]benzamide	411.5
1108	1278	N-[(1S)-1-(aminomethyl)-2-(hydroxyamino)- 2-oxoethyl]-4-{[4-({[3- (methyloxy)propyl]amino}methyl) phenyl]ethynyl}benzamide	425.5
1109	1279	N-[(1S)-1-(aminomethyl)-2-(hydroxyamino)- 2-oxoethyl]-4-{[4-({methyl[2- (methylaxy)ethyl]amino}methyl) phenyl]ethynyl}benzamide	425.5
1110	1280	N-[(1S)-1-(aminomethyl)-2-(hydroxyamino)- 2-oxoethyl]-4-{[4-({[3-(2- oxopyrrolidin-1-yl)propyl]amino}methyl)phenyl]ethynyl}benzamide	478.6
1111	1281	N-[(1S)-1-(aminomethyl)-2-(hydroxyamino)- 2-oxoethyl]-4-[(4-{[(3-morpholin-4- ylpropyl)amino]methyl}phenyl) ethynyl]benzamide	480.6
1112	1282	N-[(1S)-1-(aminomethyl)-2-(hydroxyamino)- 2-oxoethyl]-4-({4- [(cyclopropylamino)methyl]phenyl}ethynyl)benzamide	393.5
1113	1283	N-[(1S)-1-(aminomethyl)-2-(hydroxyamino)- 2-oxoethyl]-4-({4- [(cyclobutylamino)methyl]phenyl}ethynyl)benzamide	407.5
1114	1284	N-[(1S)-1-(aminomethyl)-2-(hydroxyamino)- 2-oxoethyl]-4-({4- [(cyclopentylamino)methyl]phenyl}ethynyl)benzamide	421.5
1115	1285	N-[(1S)-1-(aminomethyl)-2-(hydroxyamino)- 2-oxoethyl]-4-({4- (cycloheptylamino)methyl]phenyl}ethynyl)benzamide	449.6
1116	1286	N-[(1S)-1-(aminomethyl)-2-(hydroxyamino)- 2-oxoethyl]-4-({4- [(cyclooctylamino)methyl]phenyl}ethynyl)benzamide	463.6
1117	1287	N-[(1S)-1-(aminomethyl)-2-(hydroxyamino)- 2-oxoethyl]-4-{[4-(pyrrolidin-1- ylmethyl)phenyl]ethynyl}benzamide	407.5
1118	1288	N-[(1S)-1-(aminomethyl)-2-(hydroxyamino)- 2-oxoethyl]-4-{[4-(azepan-1- ylmethyl)phenyl]ethynyl}benzamide	435.5
1119	1289	N-[(1S)-1-(aminomethyl)-2-(hydroxyamino)- 2-oxoethyl]-4-[(4-{[(3R)-3- (dimethylamino)pyrrolidin-1- yl]methyl}phenyl)ethynyl]benzamide	450.6
1120	1290	N-[(1S)-1-(aminomethyl)-2-(hydroxyamino)- 2-oxoethyl]-4-[(4-{[(3S)-3- (dimethylamino)pyrrolidin-1- yl]methyl}phenyl)ethynyl]benzanude	450.6
1121	1291	4-[(4-{[(3R)-3-(acetylamino)pyrrohdin-1- yl]methyl}phenyl)ethynyl]-N-[(1S)-1- (aminomethyl)-2-(hydroxyamino)-2- oxoethyl]benzamide	464.5
1122	1292	4-[(4-{[(3S)-3-(acetylamino)pyrrolidin-1- yl]methyl}phenyl)ethynyl]-N-[(1S)-1- (aminomethyl)-2-(hydroxyamino)-2- oxoethyl]benzamide	464.5
1123	1293	N-[(1S)-1-(aminomethyl)-2-(hydroxyamino)- 2-oxoethyl]-4-{[4-(1,4′-bipiperidin-1′- ylmethyl)phenyl]ethynyl}benzamide	504.6
1124	1294	N-[(1S)-1-(aminomethyl)-2-(hydroxyamino)- 2-oxoethyl]-4-[(4- {[(cyclohexylmethyl)amino]methyl}phenyl)ethynyl]benzamide	449.6
1125	1295	N-[(1S)-1-(aminomethyl)-2-(hydroxyamino)- 2-oxoethyl]-4-[(4- [cyclohexyl(methyl)amino]methyl}phenyl)ethynyl]benzamide	449.6
1126	1296	N-[(1S)-1-(aminomethyl)-2-(hydroxyamino)- 2-oxoethyl]-4-{[4-({[(1R)-1- phenylethyl]amino}methyl)phenyl]ethynyl}benzamide	457.5
1127	1297	N-[(1S)-1-(aminomethyl)-2-(hydroxyamino)- 2-oxoethyl]-4-{[4-({[(1S)-1- phenylethyl]amino}methyl)phenyl]ethynyl}benzamide	457.5
1128	1298	N-[(1S)-1-(aminomethyl)-2-(hydroxyamino)- 2-oxoethyl]-4-[(4-{[(thien-2- ylmethyl)amino]methyl}phenyl) ethynyl]benzamide	449.5
1129	1299	N-[(1S)-1-(aminomethyl)-2-(hydroxyamino)- 2-oxoethyl]-4-[(4-{[(2- phenylethyl)amino]methyl}phenyl) ethynyl]benzamide	457.5
1130	1300	N-[(1S)-1-(aminomethyl)-2-(hydroxyamino)- 2-oxoethyl]-4-({4-[(piperidin-3- ylamino)methyl]phenyl}ethynyl) benzamide	436.5
1131	1301	N-[(1S)-1-(aminomethyl)-2-(hydroxyamino)- 2-oxoethyl]-4-({4-[(piperidin-4- ylamino)methyl]phenyl}ethynyl) benzamide	436.5
1132	1302	N-[(1S)-1-(aminomethyl)-2-(hydroxyamino)- 2-oxoethyl]-4-[(4-{[(piperidin- 2-ylmethyl)amino]methyl}phenyl) ethynyl]benzamide	450.6
1133	1303	N-[(1S)-1-(aminomethyl)-2-(hydroxyamino)- 2-oxoethyl]-4-[(4-{[(piperidin-3- ylmethyl)amino]methyl}phenyl) ethynyl]benzamide	450.6
1134	1304	N-[(1S)-1-(aminomethyl)-2-(hydroxyamino)- 2-oxoethyl]-4-{[4-({[(2R)- pyrrolidin-2-ylmethyl]amino}methyl)phenyl]ethynyl}benzamide	436.5
1135	1305	N-[(1S)-1-(aminomethyl)-2-(hydroxyamino)- 2-oxoethyl]-4-{[4-({[(2S)- pyrrolidin-2-ylmethyl]amino}methyl)phenyl]ethynyl}benzamide	436.5
1136	1306	N-[(1S)-1-(aminomethyl)-2-(hydroxyamino)- 2-oxoethyl]-4-({4-[(pyrrolidin-3- ylamino)methyl]phenyl}ethynyl) benzamide	422.5
1137	1307	N-[(1S)-1-(aminomethyl)-2-(hydroxyamino)- 2-oxoethyl]-4-{[4-({[(2- fluorophenyl)methyl]amino}methyl) phenyl]ethynyl}benzamide	461.5
1138	1308	N-[(1S)-1-(aminomethyl)-2-(hydroxyamino)- 2-oxoethyl]-4-{[4-({[(3- fluorophenyl)methyl]amino}methyl) phenyl]ethynyl}benzamide	461.5
1139	1309	N-[(1S)-1-(aminomethyl)-2-(hydroxyamino)- 2-oxoethyl]-4-{[4-({[(4- fluorophenyl)methyl]amino}methyl) phenyl]ethynyl}benzamide	461.5
1140	1310	N-[(1S)-1-(aminomethyl)-2-(hydroxyamino)- 2-oxoethyl]-4-{[4-({[(2- methylphenyl)methyl]amino}methyl) phenyl]ethynyl}benzamide	457.5
1141	1311	N-[(1S)-1-(aminomethyl)-2-(hydroxyamino)- 2-oxoethyl]-4-{[4-({[(3- methylphenyl)methyl]amino}methyl) phenyl]ethynyl}benzamide	457.5
1142	1312	N-[(1S)-1-(aminomethyl)-2-(hydroxyamino)- 2-oxoethyl]-4-{[4-({[(4- methylphenyl)methyl]amino}methyl) phenyl]ethynyl}benzamide	457.5
1143	1313	N-[(1S)-1-(aminomethyl)-2-(hydroxyamino)- 2-oxoethyl]-4-({4-[({[2- (methyloxy)phenyl]methyl}amino) methyl]phenyl}ethynyl)benzamide	473.5
1144	1314	N-[(1S)-1-(aminomethyl)-2-(hydroxyamino)- 2-oxoethyl]-4-({4-[({[3- (methyloxy)phenyl]methyl}amino) methyl]phenyl}ethynyl)benzamide	473.5
1145	1315	N-[(1S)-1-(aminomethyl)-2-(hydroxyamino)- 2-oxoethyl]-4-({4-[({[4- (methyloxy)phenyl]methyl}amino) methyl]phenyl}ethynyl)benzamide	473.5
1146	1316	N-[(1S)-1-(aminomethyl)-2-(hydroxyamino)- 2-oxoethyl]-4-({4-[(phenylamino) methyl]phenyl}ethynyl)benzamide	429.5
1147	1317	N-[(1S)-1-(aminomethyl)-2-(hydroxyamino)- 2-oxoethyl]-4-[(4-{[(pyridin-3- ylmethyl)amino]methyl}phenyl) ethynyl]benzamide	444.5
1148	1318	N-[(1S)-1-(aminomethyl)-2-(hydroxyamino)- 2-oxoethyl]-4-({4-[(4-phenylpiperidin- 1-yl)methyl]phenyl}ethynyl)benzamide	497.6
1149	1319	N-[(1S)-1-(aminomethyl)-2-(hydroxyamino)- 2-oxoethyl]-4-({4-[(4-phenylpiperazin- 1-yl)methyl]phenyl}ethynyl)benzamide	498.6
1150	1320	N-[(1S)-1-(aminomethyl)-2-(hydroxyamino)- 2-oxoethyl]-4-[(4-{[(1R,2R,4S)- bicyclo[2.2.1]hept-2-ylamino]methyl}phenyl)ethynyl]benzamide	447.5
1151	1321	N-[(1S)-1-(aminomethyl)-2-(hydroxyamino)- 2-oxoethyl]-4-({4-{({[(1S,2R,5S)-6,6- dimethylbicyclo[3.1.1]hept-2- yl]methyl}amino)methyl]phenyl}ethynyl)benzamide	489.6
1152	1322	N-[(1S)-1-(aminomethyl)-2-(hydroxyamino)- 2-oxoethyl]-4-[(4-{[(1S,4R)-bicyclo[2.2.1]hept-2-ylamino]methyl}phenyl) ethynyl]benzamide	447.5
1153	1323	N-[(1S)-1-(aminomethyl)-2-(hydroxyamino)- 2-oxoethyl]-4-{[4-({[(1S,2S,3S,5R)-2,6,6- trimethylbicyclo[3.1.1]hept-3- yl]amino}methyl)phenyl]ethynyl}benzamide	489.6
1154	1324	1-((1R,2S)-3-(hydroxyamino)-1-methyl-3- oxo-2-{[(4-{[4-({[(pyridin-4- ylmethyl)amino]acetyl}amino) phenyl]ethynyl}phenyl)carbonyl]amino}propyl)triaza-1,2-dien-2-ium	528.6
1155	1325	1-((1R,2S)-3-(hydroxyamino)-1-methyl-3- oxo-2-{[(4-{[4-({[(pyridin-3- ylmethyl)amino]acetyl}amino) phenyl]ethynyl}phenyl)carbonyl]amino}propyl)triaza-1,2-dien-2-ium	528.6
1156	1326	N-{(1S,2R)-2-amino-1- [(hydroxyamino)carbonyl]propyl}-4-([4- ({[(pyridin-4-ylmethyl)amino]acetyl}amino)phenyl]ethynyl}benzamide	501.6
1157	1327	N-{(1S,2R)-2-amino-1- [(hydroxyamino)carbonyl]propyl}-4-{[4- ({[(pyridin-3-ylmethyl)amino]acetyl}amino)phenyl]ethynyl}benzamide	501.6
1158	1328	N-[1-[(hydroxyamino)carbonyl]-2- (methylamino)propyl]-4-{[4- ({[(phenylmethyl)amino]acetyl}amino) phenyl]ethynyl}benzamide	514.6
1159	1329	4-[(4-{[(cyclobutylamino)acetyl]amino}phenyl)ethynyl]-N-[1- [(hydroxyamino)carbonyl]-2- (methylamino)propyl]benzamide	478.6
1160	1330	4-[(4-{[(2S)-2-aminopropanoyl]amino}phenyl)ethynyl]-N-[(1R)-1- {[ethyl(hydroxy)-lambda˜4˜- sulfanyl]methyl}-2-(hydroxyamino)-2- oxoethyl]benzamide	473.6
1161	1331	4-[(4-ethylphenyl)ethynyl]-N- hydroxybenzamide	266.3
1162	1332	N-[(1S)-1-(aminomethyl)-2-(hydroxyamino)- 2-oxoethyl]-4-[4-(2,4-difluorophenyl)buta- 1,3-diynyl]benzamide	384.4
1163	1333	N-[(1S)-1-(aminomethyl)-2-(hydroxyamino)- 2-oxoethyl]-4-[(2- aminophenyl)ethynyl]benzamide	339.4
1164	1334	N-[(1S)-1-(aminomethyl)-2-(hydroxyamino)- 2-oxoethyl]-4-[4-(3- {[(methylsulfonyl)amino]methyl}phenyl) buta-1,3-diynyl]benzamide	455.5
1165	1335	N-[(1S)-1-(aminomethyl)-2-(hydroxyamino)- 2-oxoethyl]-4-[4-(3- {[(methylsulfonyl)amnio]methyl}phenyl) buta-1,3-diynyl]benzamide	455.5
1166	1336	N-[(1S)-1-(aminomethyl)-2-(hydroxyamino)- 2-oxoethyl]-4-({3- [(methylsulfonyl)amino]phenyl}ethynyl)benzamide	417.5
1167	1337	4-[(4-{[(2S)-2-aminopropanoyl]amino}phenyl)ethynyl]-N- hydroxybenzamide	324.4
1168	1338	4-[(2-{[(2-aminoethyl)amino]methyl}phenyl)ethynyl]-N- {(1S,2R)-2-hydroxy-1- [(hydroxyamino)carbonyl]propyl}benzamide	411.5
1169	1339	N-{(1R,2R)-2-amino-1- [(hydroxyamino)carbonyl]propyl}-4- (phenylethynyl)benzamide	338.4
1170	1340	N-{(1S,2R)-2-amino-1- [(hydroxyamino)carbonyl]propyl}-4- [4-(4-aminophenyl)buta-1,3- diynyl]benzamide	377.4
1171	1341	N-[(1S)-1-(aminomethyl)-2-(hydroxyamino)- 2-oxoethyl]-4-[4-(3-hydroxyphenyl)buta- 1,3-diynyl]benzamide	364.4
1172	1342	N-[(1S)-1-(aminomethyl)-2-(hydroxyamino)- 2-oxoethyl]-4-{4-[3-(morpholin-4- ylmethyl)phenyl]buta-1,3-diynyl}benzamide	447.5
1173	1343	N-{(1S,2R)-2-hydroxy-1- [(hydroxyamino)carbonyl]propyl}-4- ({4-[({[2-(methyloxy)phenyl]methyl}amino)methyl]phenyl}ethynyl)benzamide	488.6
1174	1344	4-[(4-{[(2,3-dihydroxypropyl)amino]methyl}phenyl)ethynyl]-N- {(1S,2R)-2-hydroxy-1- [(hydroxyamino)carbonyl]propyl}benzamide	442.5
1175	1345	4-({2-[(dimethylamino)methyl]phenyl}ethynyl)-N-{(1S,2R)- 2-hydroxy-1- [(hydroxyamino)carbonyl]propyl}benzamide	396.5
1176	1346	N-{(1S,2R)-2-hydroxy-1- [(hydroxyamino)carbonyl]propyl}-4-({4- [(methylamino)methyl]phenyl}ethynyl)benzamide	382.4
1177	1347	N-{(1S,2R)-2-hydroxy-1- [(hydroxyamino)carbonyl]propyl}-4-({4- [(propylamino)methyl]phenyl}ethynyl)benzamide	410.5
1178	1348	4-({4-[(butylamino)methyl]phenyl}ethynyl)-N- {(1S,2R)-2-hydroxy-1- [(hydroxyamino)carbonyl]propyl}benzamide	424.5
1179	1349	N-{(1S,2R)-2-hydroxy-1- [(hydroxyamino)carbonyl]propyl}-4-({4- [(pentylamino)methyl)phenyl}ethynyl)benzamide	438.5
1180	1350	4-({4-[(hexylamino)methyl]phenyl}ethynyl)-N- {(1S,2R)-2-hydroxy-1- [(hydroxyamino)carbonyl]propyl}benzamide	452.6
1181	1351	N-{(1S,2R)-2-hydroxy-1- [(hydroxyamino)carbonyl]propyl}-4- [(4-{[(1-[(hydroxyamino) carbonyl]propyl}-4-[(4-{[(1- methylethyl)amino]methyl}phenyl) ethynyl]benzamide	410.5
1182	1352	N-{(1S,2R)-2-hydroxy-1- [(hydroxyamino)carbonyl]propyl}-4- [(4-{[(2-methylpropyl) amino]methyl}phenyl)ethynyl]benzamide	424.5
1183	1353	4-[(4-{[(1.1-dimethylethyl)amino]methyl}phenyl)ethynyl]-N- {(1S,2R)-2-hydroxy-1- [(hydroxyamino)carbonyl]propyl}benzamide	424.5
1184	1354	4-[(4-{[ethyl(methyl)amino]methyl}phenyl)ethynyl]-N- {(1S,2R)-2-hydroxy-1- [(hydroxyamino)carbonyl]propyl}benzamide	410.5
1185	1355	4-{[4-({[(2-(dimethylamino)ethyl]amino}methyl)phenyl]ethynyl}- N-{(1S,2R)-2-hydroxy-1- [(hydroxyamino)carbonyl]propyl}benzamide	439.5
1186	1356	4-{[4-({[4-(dimethylamino)butyl]amino}methyl)phenyl]ethynyl}- N-{(1S,2R)-2-hydroxy-1- [(hydroxyamino)carbonyl]propyl}benzamide	467.6
1187	1357	4-[(4-{[(2-hydroxyethyl)amino]methyl}phenyl)ethynyl]- N-{(1S,2R)-2-hydroxy-1- [(hydroxyamino)carbonyl]propyl}benzamide	412.5
1188	1358	N-{(1S,2R)-2-hydroxy-1- [(hydroxyamino)carbonyl]propyl}-4-[(4- {[(3-hydroxypropyl)amino]methyl}phenyl)ethynyl]benzamide	426.5
1189	1359	N-{(1S,2R)-2-hydroxy-1- [(hydroxyamino)carbonyl]propyl}-4-{[4- ({methyl[2-(methyloxy)ethyl]amino}methyl)phenyl]ethynyl}benzamide	440.5
1190	1360	N-{(1S,2R)-2-hydroxy-1- [(hydroxyamino)carbonyl]propyl}-4-{[4-({[2- (methyloxy)ethyl]axmno}methyl) phenyl]ethynyl}benzamide	426.5
1191	1361	N-{(1S,2R)-2-hydroxy-1- [(hydroxyamino)carbonyl]propyl}-4-{[4-({[3- (methyloxy)propyl]amino}methyl) phenyl]ethynyl}benzamide	440.5
1192	1362	4-[(4-{[(2-cyanoethyl)amino]methyl}phenyl)ethynyl]-N- {(1S,2R)-2-hydroxy-1- [(hydroxyamino)carbonyl]propyl}benzamide	421.5
1193	1363	4-{[4-({[2-(acetylamino)ethyl]amino}methyl)phenyl]ethynyl}- N-{(1S,2R)-2-hydroxy-1- [(hydroxyamino)carbonyl]propyl}benzamide	453.5
1194	1364	N-{(1S,2R)-2-hydroxy-1- [(hydroxyamino)carbonyl]propyl}-4- {[4-({[3-(2-oxopyrrolidin-1- yl)propyl]amino}methyl) phenyl]ethynyl}benzamide	493.6
1195	1365	N-{(1S,2R)-2-hydroxy-1- [(hydroxyamino)carbonyl]propyl}-4- [(4-{[(3-morpholin-4- ylpropyl)amino]methyl}phenyl) ethynyl]benzamide	495.6
1196	1366	4-({4-[(cyclopropylamino)methyl]phenyl}ethynyl)-N-{(1S,2R)-2- hydroxy-1-[(hydroxyamino) carbonyl]propyl}benzamide	408.5
1197	1367	4-({4-[(cyclobutylamino)methyl]phenyl}ethynyl)-N- {(1S,2R)-2-hydroxy-1- [(hydroxyamino)carbonyl]propyl}benzamide	422.5
1198	1368	4-({4-[(cyclopentylamino)methyl]phenyl}ethynyl)-N- {(1S,2R)-2-hydroxy-1- [(hydroxyamino)carbonyl]propyl}benzamide	436.5
1199	1369	4-({4-[(cyclohexylamino)methyl]phenyl}ethynyl)-N- {(1S,2R)-2-hydroxy-1- [(hydroxyamino)carbonyl]propyl}benzamide	450.5
1200	1370	4-({4-[(cycloheptylamino)methyl]phenyl}ethynyl)-N- {(1S,2R)-2-hydroxy-1- [(hydroxyamino)carbonyl]propyl}benzamide	464.6
1201	1371	4-({4-[(cyclooctylamino)methyl]phenyl}ethynyl)-N- {(1S,2R)-2-hydroxy-1- [(hydroxyamino)carbonyl]propyl}benzamide	478.6
1202	1372	4-{[4-(azepan-1-ylmethyl)phenyl]ethynyl}- N-{(1S,2R)-2-hydroxy-1- [(hydroxyamino)carbonyl]propyl}benzamide	450.5
1203	1373	4-[(4-{[(3R)-3-(dimethylamino)pyrrolidin-1- yl]methyl}phenyl)ethynyl]-N-{(1S,2R)-2- hydroxy-1- [(hydroxyamino)carbonyl]propyl}benzamide	465.6
1204	1374	4-[(4-{[(3S)-3-(dimethylamino)pyrrolidin-1- yl]methyl}phenyl)ethynyl]-N-{(1S,2R)-2- hydroxy-1- [(hydroxyamino)carbonyl]propyl}benzamide	465.6
1205	1375	4-[(4-{[(3R)-3-(acetylamino)pyrrolidin-1- yl]methyl}phenyl)ethynyl]-N-{(1S,2R)-2- hydroxy-1- [(hydroxyamino)carbonyl]propyl}benzamide	479.5
1206	1376	4-[(4-{[(3S)-3-(acetylamino)pyrrolidin-1- yl]methyl}phenyl)ethynyl]-N-{(1S,2R)-2- hydroxy-1- [(hydroxyamino)carbonyl]propyl}benzamide	479.5
1207	1377	4-{[4-(1,4′-bipiperidin-1′- ylmethyl)phenyl]ethynyl}-N-{(1S,2R)-2- hydroxy-1- [(hydroxyamino)carbonyl]propyl}benzamide	519.7
1208	1378	4-[(4-{[(cyclohexylmethyl)amino]methyl}phenyl)ethynyl]-N- {(1S,2R)-2-hydroxy-1- [(hydroxyamino)carbonyl]propyl}benzamide	464.6
1209	1379	N-{(1S,2R)-2-hydroxy-1- [(hydroxyamino)carbonyl]propyl}-4-({4-[(4- phenylpiperazin-1- yl)methyl]phenyl}ethynyl)benzamide	513.6
1210	1380	N-{(1S,2R)-2-hydroxy-1- [(hydroxyamino)carbonyl]propyl}-4- [(4-{[(2-phenylethyl)amino]methyl}phenyl)ethynyl]benzamide	472.6
1211	1381	N-{(1S,2R)-2-hydroxy-1- [(hydroxyamino)carbonyl]propyl}-4- {[4-({[(1R)-1-phenylethyl]amino}methyl)phenyl]ethynyl}benzamide	472.6
1212	1382	N-{(1S,2R)-2-hydroxy-1- [(hydroxyamino)carbonyl]propyl}-4- {[4-({[(1S)-1-phenylethyl]amino}methyl)phenyl]ethynyl}benzamide	472.6
1213	1383	N-{(1S,2R)-2-hydroxy-1- [(hydroxyamino)carbonyl]propyl}-4- [(4-{[(thien-2-ylmethyl)amino]methyl}phenyl)ethynyl]benzamide	464.6
1214	1384	N-{(1S,2R)-2-hydroxy-1- [(hydroxyamino)carbonyl]propyl}-4- ({4-[(piperidin-3-ylamino) methyl]phenyl}ethynyl)benzamide	451.5
1215	1385	N-{(1S,2R)-2-hydroxy-1- [(hydroxyamino)carbonyl]propyl}-4- ({4-[(piperidin-4-ylamino) methyl]phenyl}ethynyl)benzamide	451.5
1216	1386	N-{(1S,2R)-2-hydroxy-1- [(hydroxyamino)carbonyl]propyl}-4- [(4-{[(piperidin-2-ylmethyl)amino]methyl}phenyl)ethynyl]benzamide	465.6
1217	1387	N-{(1S,2R)-2-hydroxy-1- [(hydroxyamino)carbonyl]propyl}-4- [(4-{[(piperidin-3-ylmethyl)amino]methyl}phenyl)ethynyl]benzamide	465.6
1218	1388	N-{(1S,2R)-2-hydroxy-1- [(hydroxyamino)carbonyl]propyl}-4- {[4-({[(2R)-pyrrolidin-2- ylmethyl]amino}methyl)phenyl]ethynyl}benzamide	451.5
1219	1389	N-{(1S,2R)-2-hydroxy-1- [(hydroxyamino)carbonyl]propyl}-4- {[4-({[(2S)-pyrrolidin-2- ylmethyl]amino}methyl)phenyl]ethynyl}benzamide	451.5
1220	1390	N-{(1S,2R)-2-hydroxy-1- [(hydroxyamino)carbonyl]propyl}-4- ({4-[(pyrrolidin-3- ylamino)methyl]phenyl}ethynyl) benzamide	437.5
1221	1391	4-{[4-({[(2-fluorophenyl)methyl]amino}methyl)phenyl]ethynyl}-N-{(1S,2R)- 2-hydroxy-1- [(hydroxyamino)carbonyl]propyl}benzamide	476.5
1222	1392	4-{[4-({[(3-fluorophenyl)methyl]amino}methyl)phenyl]ethynyl}-N-{(1S,2R)- 2-hydroxy-1-[(hydroxyamino) carbanyl]propyl}benzamide	476.5
1223	1393	4-{[4-({[(4-fluorophenyl)methyl]amino}methyl)phenyl]ethynyl}-N-{(1S,2R)- 2-hydroxy-1-[(hydroxyamino) carbonyl]propyl}benzamide	476.5
1224	1394	N-{(1S,2R)-2-hydroxy-1- [(hydroxyamino)carbonyl]propyl}-4- {[4-({[(2-methylphenyl)methyl]amino}methyl)phenyl]ethynyl}benzamide	472.6
1225	1395	N-{(1S,2R)-2-hydroxy-1- [(hydroxyamino)carbonyl]propyl}-4- {[4-({[(3-methylphenyl)methyl]amino}methyl)phenyl]ethynyl}benzamide	472.6
1226	1396	N-{(1S,2R)-2-hydroxy-1- [(hydroxyamino)carbonyl]propyl}-4- {[4-({[(4-methylphenyl)methyl]amino}methyl)phenyl]ethynyl}benzamide	472.6
1227	1397	N-{(1S,2R)-2-hydroxy-1- [(hydroxyamino)carbonyl]propyl}-4- [(4-{[(phenylmethyl)amino]methyl}phenyl)ethynyl]benzamide	458.5
1228	1398	N-{(1S,2R)-2-hydroxy-1- [(hydroxyamino)carbonyl]propyl}-4- ({4-[(phenylamino)methyl]phenyl}ethynyl)benzamide	444.5
1229	1399	N-{(1S,2R)-2-hydroxy-1- [(hydroxyamino)carbonyl]propyl}-4- [(4-{[(pyridin-3-ylmethyl) amino]methyl}phenyl)ethynyl]benzamide	459.5
1230	1400	4-[(4-{[(1R,2R,4S)-bicyclo[2.2.1]hept-2- ylamino]methyl}phenyl)ethynyl]-N- {(1S,2R)-2-hydroxy-1- [(hydroxyamino)carbonyl]propyl}benzamide	462.6
1231	1401	(3R)-N-hydroxy-3-({[4- (phenylethynyl)phenyl]carbonyl}amino) piperidine-3-carboxamide	364.4
1232	1402	4-({[4-(phenylethynyl)phenyl]carbonyl}amino)piperidine-4- carboxylic acid	349.4
1233	1403	N-{(1S)-2-(hydroxyamino)-2-oxo-1-[(2S)- pyrrolidin-2-ylmethyl]ethyl}-4- (phenylethynyl)benzamide	378.4
1234	1404	(3R)-3-{[(4-ethyl-1,1′-biphenyl-4- yl)carbonyl]amino}-N- hydroxypiperidine-3-carboxamide	368.4
1235	1405	1,1-dimethylethyl 3-(4-{4-[({(1S,2R)-2- hydroxy-1-[(hydroxyamino) carbonyl]propyl}amino)carbonyl]phenyl}buta-1,3-diynyl) phenylcarbamate	478.5
1236	1406	4-[4-(3-amino-4-methylphenyl)buta-1,3- diynyl]-N-{(1S,2R)-2-hydroxy-1- [(hydroxyamino)carbonyl]propyl}benzamide	392.4
1237	1407	N-[(1S)-1-(aminomethyl)-2-(hydroxyamino)-2- oxoethyl]-4-[4-(3-amino-4-methylphenyl) buta-1,3-diynyl]benzamide	377.4
1238	1408	4-(4-{4-[(aminoacetyl)amino]-3- methylphenyl}buta-1,3-diynyl)-N-[(1S)-1- (aminomethyl)-2-(hydroxyamino)-2- oxoethyl]benzamide	434.5
1239	1409	N-{(1S,2R)-2-amino-1- [(hydroxyamino)carbonyl]propyl}-4-(2- phenylethenyl)benzamide	340.4
1240	1410	N-[(2R)-2-amino-3-(hydroxyamino)-3- oxopropyl]-4′-ethyl-1,1′-biphenyl-4- carboxamide	328.4
1241	1411	N-[(2R)-2-amino-3-(hydroxyamino)-3- oxopropyl]-4-(phenylethynyl) benzamide	324.4
1242	1412	N-[(2R)-2-amino-3-(hydroxyamino)-3- oxopropyl]-4-(4- chlorophenyl)cyclohexanecarboxamide	340.8
1243	1413	N-[(2S)-2-amino-3-(hydroxyamino)-3- oxopropyl]-4-(4- chlorophenyl)cyclohexanecarboxamide	340.8
1244	1414	N-[(1S)-1-(aminomethyl)-2-(hydroxyamino)- 2-oxoethyl]-4-[2-(4- methylphenyl)ethyl]benzamide	342.4
1245	1415	N-[(1S)-1-(aminomethyl)-2-(hydroxyamino)- 2-oxoethyl]-4-[4-(4- aminophenyl)butyl]benzamide	371.4
1246	1416	N-{(1S,2R)-2-hydroxy-1- [(hydroxyamino)carbonyl]propyl}-4-{[4- ({[methyl(pyridin-2- ylmethyl)amino]acetyl}amino) phenyl]ethynyl}benzamide	516.6
1247	1417	4-{[4-({[[(2-fluorophenyl)methyl](methyl) amino]acetyl}amino)phenyl]ethynyl}-N-{(1S,2R)-2-hydroxy-1- [(hydroxyamino)carbonyl]propyl}benzamide	533.6
1248	1418	4-{[4-({[[(3-fluorophenyl)methyl](methyl) amino]acetyl}amino)phenyl]ethynyl}-N-{(1S,2R)-2-hydroxy-1- [(hydroxyamino)carbonyl]propyl}benzamide	533.6
1249	1419	4-{[4-({[[(4-fluorophenyl)methyl](methyl) amino]acetyl}amino)phenyl]ethynyl}-N-{(1S,2R)-2-hydroxy-1- [(hydroxyamino)carbonyl]propyl}benzamide	533.6
1250	1420	N-[(1S)-1-(aminomethyl)-2-(hydroxyamino)-2- oxoethyl]-4-{[4-({[[(2- fluorophenyl)methyl](methyl)amino]acetyl}amino)phenyl]ethynyl}benzamide	518.6
1251	1421	N-[(1S)-1-(aminomethyl)-2-(hydroxyamino)-2- oxoethyl]-4-{[4-({[[(3- fluorophenyl)methyl](methyl)amino]acetyl}amino)phenyl]ethynyl}benzamide	518.6
1252	1422	N-[(1S)-1-(aminomethyl)-2-(hydroxyamino)-2- oxoethyl]-4-{[4-({[[(3- fluorophenyl)methyl](methyl)amino]acetyl}amino)phenyl]ethynyl}benzamide	518.6
1253	1423	N-[(1S)-1-(aminomethyl)-2-(hydroxyamino)-2- oxoethyl]-4-({4-[({methyl[(2- methylphenyl)methyl]amino}acetyl) amino]phenyl}ethynyl)benzamide	514.6
1254	1424	N-[(1S)-1-(aminomethyl)-2-(hydroxyamino)-2- oxoethyl]-4-({4-[({methyl[(4- methylphenyl)methyl]amino}acetyl) amino]phenyl}ethynyl)benzamide	514.6
1255	1425	N-[(1S)-1-(aminomethyl)-2-(hydroxyamino)-2- oxoethyl]-4-{[4- ({[methyl(phenylmethyl)amino]acetyl}amino)phenyl]ethynyl}benzamide	500.6
1256	1426	N-{(1S,2R)-2-hydroxy-1- [(hydroxyamino)carbonyl]propyl}-4-{[4- ({[methyl(propyl)amino]acetyl}amino)phenyl]ethynyl}benzamide	467.5
1257	1427	4-{[4-({[butyl(methyl)amino]acetyl}amino)phenyl]ethynyl}- N-{(1S,2R)-2-hydroxy-1- [(hydroxyamino)carbonyl]propyl}benzamide	481.6
1258	1428	N-{(1S,2R)-2-hydroxy-1- [(hydroxyamino)carbonyl]propyl}-4-{[4- {[methyl(pentyl)amino]acetyl}amino)phenyl]ethynyl}benzamide	495.6
1259	1429	4-{[4-({[hexyl(methyl) amino]acetyl}amino)phenyl]ethynyl}-N-{(1S,2R)-2-hydroxy-1- [(hydroxyamino)carbonyl]propyl}benzamide	509.6
1260	1430	N-{(1S,2R)-2-hydroxy-1- [(hydroxyamino)carbonyl]propyl}-4-{[4- ({[methyl(1-methylethyl)amino]acetyl}amino)phenyl]ethynyl}benzamide	467.5
1261	1431	N-{(1S,2R)-2-hydroxy-1- [(hydroxyamino)carbonyl]propyl}-4-{[4- ({[methyl(2-methylpropyl)amino]acetyl}amino)phenyl]ethynyl}benzamide	481.6
1262	1432	N-{(1S,2R)-2-hydroxy-1- [(hydroxyamino)carbonyl]propyl}-4-({4- [({methyl[(2-methylphenyl)methyl]amino}acetyl)amino]phenyl}ethynyl)benzamide	529.6
1263	1433	N-{(1S,2R)-2-hydroxy-1- [(hydroxyamino)carbonyl]propyl}-4-({4- [({methyl[(4-methylphenyl)methyl]amino}acetyl)amino]phenyl}ethynyl)benzamide	529.6
1264	1434	N-[(1S)-1-(aminomethyl)-2-(hydroxyamino)-2- oxoethyl]-4-{[4-({[methyl(propyl) amino]acetyl}amino)phenyl]ethynyl}benzamide	452.5
1265	1435	N-[(1S)-1-(aminomethyl)-2-(hydroxyamino)-2- oxoethyl]-4-{[4-({[butyl(methyl) amino]acetyl}amino)phenyl]ethynyl}benzamide	466.6
1266	1436	N-[(1S)-1-(aminomethyl)-2-(hydroxyamino)-2- oxoethyl]-4-{[4-({[methyl(pentyl) amino]acetyl}amino)phenyl]ethynyl}benzamide	480.6
1267	1437	N-[(1S)-1-(aminomethyl)-2-(hydroxyamino)-2- oxoethyl]-4-{[4-({[hexyl(methyl) amino]acetyl}amino)phenyl]ethynyl}benzamide	494.6
1268	1438	N-[(1S)-1-(aminomethyl)-2-(hydroxyamino)-2- oxoethyl]-4-{[4-({[methyl(1- methylethyl)amino]acetyl}amino) phenyl]ethynyl}benzamide	452.5
1269	1439	N-[(1S)-1-(aminomethyl)-2-(hydroxyamino)-2- oxoethyl]-4-{[4-({[methyl(2- methylpropyl)amino]acetyl}amino) phenyl]ethynyl}benzamide	466.6
1270	1440	N-[(1S)-1-(aminomethyl)-2-(hydroxyamino)-2- oxoethyl]-4-{[4-({[methyl(pyridin-2- ylmethyl)amino]acetyl}amino) phenyl]ethynyl}benzamide	501.6
1271	1441	4-{[4-({[(3,4-dihydroxyphenyl) methyl]amino}methyl)phenyl]ethynyl}-N-{(1S,2R)-2-hydroxy-1- [(hydroxyamino)carbonyl]propyl}benzamide	490.5
1272	1442	4-({2-[(aminoacetyl)amino]phenyl}ethynyl)-N- {(1S,2S)-2-hydroxy-1- [(hydroxyamino)carbonyl]propyl}benzamide	411.4
1273	1443	4-[(4-{[(2S)-2-aminopropanoyl]amino}phenyl)ethynyl]-N- {(1S,2S)-2-hydroxy-1- [(hydroxyamino)carbonyl]propyl}benzamide	425.5
1274	1444	N-[(1S)-1-(aminomethyl)-2-(hydroxyamino)- 2-oxoethyl]-4-{[4- (diethylamino)phenyl]ethynyl}benzamide	395.5
1275	1445	N-[(1S)-1-(aminomethyl)-2-(hydroxyamino)-2- oxoethyl]-4-{4-[4-(ethylamino)phenyl]buta-1,3-diynyl}benzamide	391.4
1276	1446	N-[(1S)-1-(aminomethyl)-2-(hydroxyamino)-2- oxoethyl]-4-[(4-{[(2-amino-2- oxoethyl)amino]methyl}phenyl) ethynyl]benzamide	410.4
1277	1447	N-[(1S)-1-(aminomethyl)-2-(hydroxyamino)-2- oxoethyl]-4-{[4-({[1-(hydroxymethyl)-2- methylpropyl]amino}methyl)phenyl]ethynyl}benzamide	439.5
1278	1448	N-[(1S)-1-(aminomethyl)-2-(hydroxyamino)-2- oxoethyl]-4-({4-[(pyridin-2- ylamino)methyl]phenyl}ethynyl) benzamide	430.5
1279	1449	N-[(1S)-1-(aminomethyl)-2-(hydroxyamino)-2- oxoethyl]-4-{4-[3-(ethylamino)phenyl]buta-1,3-diynyl}benzamide	391.4
1280	1450	N-[(1S)-1-(aminomethyl)-2-(hydroxyamino)-2- oxoethyl]-4-{[3- (ethylamino)phenyl]ethynyl}benzamide	367.4
1281	1451	N-[(1S)-1-(aminomethyl)-2-(hydroxyamino)-2- oxoethyl]-4-{[4- (hydroxymethyl)phenyl]ethynyl}benzamide	354.4
1282	1452	N-[(1S)-1-(aminomethyl)-2-(hydroxyamino)-2- oxoethyl]-4-{[3- (diethylamino)phenyl]ethynyl}benzamide	395.5
1283	1453	N-{(1S,2S)-2-hydroxy-1- [(hydroxyamino)carbonyl]propyl}-4-{[4- (morpholin-4- ylmethyl)phenyl]ethynyl}benzamide	438.5
1284	1454	4-({4-[(dimethylamino)methyl]phenyl}ethynyl)-N-{(1S,25)-2- hydroxy-1-[(hydroxyamino)carbonyl]propyl}benzamide	396.5
1285	1455	4-[(4-aminophenyl)ethynyl]-N-{(1S,2S)-2- hydroxy-1- [(hydroxyamino)carbonyl]propyl}benzamide	354.4
1286	1456	4-[4-(4-aminophenyl)buta-1,3-diynyl]-N- {(1S,2S)-2-hydroxy-1- [(hydroxyamino)carbonyl]propyl}benzamide	378.4
1287	1457	1,1-dimethylethyl 4-(4-{4-[({(1S,2R)-2- hydroxy-1- [(hydroxyamino)carbonyl]propyl}amino) carbonyl]phenyl}buta-1,3- diynyl)phenylcarbamate	478.5
1288	1458	N-[(1S)-1-(aminomethyl)-2-(hydroxyamino)-2- oxoethyl]-4-{4-[4-({[1-(hydroxymethyl)-2- methylpropyl]amino}methyl)phenyl]buta-1,3-diynyl}benzamide	463.5
1289	1459	N-[(1S)-1-(aminomethyl)-2-(hydroxyamino)-2- oxoethyl]-4-[4-(4-hydroxyphenyl)buta-1,3- diynyl]benzamide	364.4
1290	1460	4-[(2,4-difluorophenyl)ethynyl]-N-{(1S,2S)-2- hydroxy-1- [(hydroxyamino)carbonyl]propyl}benzamide	375.3
1291	1461	N-[(1S)-1-(aminomethyl)-2-(hydroxyamino)-2- oxoethyl]-4-{4-[4-(morpholin-4- ylmethyl)phenyl]buta-1,3-diynyl}benzamide	447.5
1292	1462	N-[(1S)-1-(aminomethyl)-2-(hydroxyamino)-2- oxoethyl]-4-{4-[4- (hydroxymethyl)phenyl]buta-1,3- diynyl}benzamide	378.4
1293	1463	4-({3-[(2-aminoethyl)amino]phenyl}ethynyl)- N-{(1S,2R)-2-hydroxy-1- [(hydroxyamino)carbonyl]propyl}benzamide	397.4
1294	1464	N-[(1S)-1-(aminomethyl)-2-(hydroxyamino)-2- oxoethyl]-4-{[4- (trifluoromethyl)phenyl]ethynyl}benzamide	392.3
1295	1465	(2S,3R)-3-hydroxy-2-({[4- (phenylethynyl)phenyl]carbonyl}amino)butanoic acid	324.3
1296	1466	N-{(1S,2R)-1-{[(2- aminoethyl)amino]carbonyl}-2- hydroxypropyl)-4-(phenylethynyl)benzamide	366.4
1297	1467	1,1-dimethylethyl (2S)-3-(hydroxyamino)-3- oxo-2-({[4-(4-phenylbuta-1,3- diynyl)phenyl]carbonyl}amino) propylcarbamate	448.5
1298	1468	N-{(1S,2R)-2-hydroxy-1- [(hydroxyamino)carbonyl]propyl}-4-(4-{4-[(3- morpholin-4-ylpropyl)amino]phenyl}buta-1,3-diynyl)benzamide	505.6
1299	1469	N-[(1S,2R)-2-hydroxy-1-({[2- (methylthio)phenyl]amino}carbonyl) propyl]-4-(phenylethynyl)benzamide	445.6
1300	1470	N-{(1S,2R)-2-hydroxy-1-[(pyridin-2- ylamino)carbonyl]propyl}-4- (phenylethynyl)benzamide	400.4
1301	1471	N-((1S)-1-(aminomethyl)-2-{[(1,1- dimethylethyl)oxy]amino}-2-oxoethyl)-4-(4- phenylbuta-1,3-diynyl)benzamide	404.5
1302	1472	N-{(1S,2S)-2-hydroxy-1- [(hydroxyamino)carbonyl]propyl}-4-(4- phenylbuta-1,3-diynyl)benzamide	363.4
1303	1473	(2S,3R)-N,3-dihydroxy-2-({[4-(4-phenylbuta- 1,3-diynyl)phenyl]methyl}amino)butanamide	349.4
1304	1474	1,1-dimethylethyl (2S)-3-(hydroxyamino)-3- oxo-2-({[4-(4-phenylbuta-1,3- diynyl)phenyl]methyl}amino) propylcarbamate	434.5
1305	1475	(2S)-3-amino-N-hydroxy-2-({[4-(4- phenylbuta-1,3-diynyl)phenyl]methyl}amino)propanamide	334.4
1306	1476	N-[(1S)-2-(hydroxyamino)-1-(hydroxymethyl)- 2-oxoethyl]-4- [(trifluoromethyl)oxy]benzamide	309.2
1307	1477	N-{2-hydroxy-1-[(hydroxyamino)carbonyl]-2- phenylethyl}-4- [(trifluoromethyl)oxy]benzamide	385.3

Claims

1. A compound according to the formula I:

2. A compound of claim 1, wherein wherein E is absent or selected from the group consisting of (1) H, (2) substituted or unsubstituted C1-C6-alkyl, (3) substituted or unsubstituted aryl, (4) substituted or unsubstituted heterocyclyl, and (5) substituted or unsubstituted heteroaryl; L is absent or selected from the group consisting of (1) —(CH2)j—NR3L—(CH2)k—, (2) —C(R1L, R2L)j—NR3L—C(R1L, R2L)k—, (3) —C(R1L, R2L)j—O—C(R1L, R2L)k—, (4) —(CH2)j—NR3L—C(R1L, R2L)k—CONH—(CH2)k—, (5) —CO—C(R1L, R2L)—NHCO—, (6) —CONH—, and (7) —NHCO—, wherein R1L, R2L, R3L are independently selected from the group consisting of (a) H, (b) substituted or unsubstituted C1-C6-alkyl, (c) C1-C6-alkyl substituted with aryl, (d) C1-C6-alkyl substituted with heterocyclyl, (e) C1-C6-alkyl substituted with heteroaryl, or R1L and R3L, together with the atoms to which they are attached can form a substituted or unsubstituted heterocyclic ring, having from 5 to 8 ring atoms, wherein 1-2 ring atoms of the heterocyclic ring system are selected from N, O and S; j is an integer of 0-4; k is an integer of 0-4; D is absent or selected from the group consisting of (1) substituted or unsubstituted C3-C8-cycloalkyl, (2) substituted or unsubstituted aryl, (3) substituted or unsubstituted heterocyclyl, (4) substituted or unsubstituted heteroaryl, and G is absent or selected from the group consisting of (1) —C(═O)—, (2) —NHC(═O)—, (3) —C(═O)NH—, (4) —(CH2)iNHCH2C(═O)NH—, (5) —C≡C—, and (6) —C≡C—C≡C—, wherein i is an interger of 0-4; Y is selected from the group consisting of (1) substituted or unsubstituted C3-C8-cycloalkyl, (2) substituted or unsubstituted aryl, (3) substituted or unsubstituted heterocyclyl, and (4) substituted or unsubstituted heteroaryl; X is selected from the group consisting of (1) —(C═O)—, (2) —C1-C6-alkyl-(C═O)—, (3) —C2-C6-alkenyl-(C═O)—, (4) —C2-C6-alkynyl-(C═O)—, and (5) —CH2—; or when B is absent, X and A, together with the atoms to which they are attached can form a heterocyclic ring, having from 5 to 8 ring atoms, wherein 1-2 ring atoms of the heterocyclic ring system are selected from N, O and S; B is absent or 1481wherein R1b and R2b are independently selected from the group consisting of (a) H (b)) substituted or unsubstituted C1-C6-alkyl, (c) substituted or unsubstituted C2-C6-alkenyl, (d) substituted or unsubstituted C2-C6-alkenyl, (e) substituted or unsubstituted aryl, (f) substituted or unsubstituted heterocyclyl, (g) substituted or unsubstituted heteroaryl, (h) C1-C6-alkyl substituted with aryl, (i) C1-C6-alkyl substituted with heterocyclyl, and (j) C1-C6-alkyl substituted with heteroaryl, or R1b and R2b, together with the atoms to which they are attached can form a substituted or unsubstituted heterocyclic ring, having from 5 to 8 ring atoms, wherein 1-2 ring atoms of the heterocyclic ring system are selected from N, O and S; q is an integer of 0-2; R3 is H or substituted or-unsubstituted C1-C6-alkyl, or R3 and A, together with the atoms to which they are attached can form a substituted or unsubstituted 3-10 membered cycloalkyl or a heterocyclic ring system, wherein the heterocyclic ring system may have from 3 to 10 ring atoms, with 1 to 2 rings being in the ring system and contain from 1-4 heteroatoms selected from N, O and S; R4 is H or substituted or unsubstituted C1-C6-alkyl, or R4 and A, together with the atoms to which they are attached can form a substituted or unsubstituted heterocyclic ring, having from 5 to 8 ring atoms, wherein 1-2 ring atoms of the heterocyclic ring system are selected from N, O and S; A is selected from the group consisting of (1) H, (2) —(CH2)rC(R1a, R2a)(CH2)sOR3a, (3) —(CH2)rC(R1a, R2a)N(R4a, R5a), (4) —(CH2)rC(R1a, R2a)N(R4a)COR3a, (5) —(CH2)rC(R1a, R2a)NHCON(R4a, R5a), (6) —(CH2)rC(R1a, R2a)NHC(═NH)N(R4a, R5a), (7) —CH(R1a, R2a), (8) —C≡CH, (9) —(CH2)rC(R1a, R2a)CN, and (10) —(CH2)rC(R1a, R2a)CO2R3a, wherein R1a, R2a, R2a, R4a, and R5a, are independently selected from the group consisting of (a) H, (b) substituted or unsubstituted C1-C6-alkyl, (c) C1-C6-alkyl substituted with aryl, (d) C1-C6-alkyl substituted with heterocyclyl, and (e) C1-C6-alkyl substituted with heteroaryl, or R4a and R5a, together with the N atom to which they are attached can form a substituted or unsubstituted heterocyclic ring, having from 5 to 8 ring atoms, wherein 1-2 ring atoms of the heterocyclic ring system are selected from N, O and S; r is an integer of 0-4; Q is absent or selected from the group consisting of (1) —C(═O)N(R1, R2), (2) —NHC(═O)N(R1, R2), (3) —N(OH)C(═O)N(R1, R2), (4) —CH(OH)C(═O)N(R1, R2), (5) —CH[N(R2q, R3q)]C(═O)N(R1, R2), and (6) —CHR1qC(═O)N(R1, R2), R1 is selected from the group consisting of (1) H, (2) OH, (3) OC1-6-alkyl, (4) N(R2q, R3q), and (5) substituted or unsubstituted C1-6-alkyl; R2 is selected from the group consisting of (1) H, (2) substituted or unsubstituted C1-C6-alkyl, (3) substituted or unsubstituted aryl, (4) substituted or unsubstituted heterocyclyl, (5) substituted or unsubstituted heteroaryl, (6) C1-C6-alkyl substituted with aryl, (7) C1-C6-alkyl substituted with heterocyclyl, and (8) C1-C6-alkyl substituted with heteroaryl, or R1 and R2, together with the N atom to which they are attached can form a substituted or unsubstituted heterocyclic ring, having from 3 to 10 ring atoms, wherein 1-4 ring atoms of the heterocyclic ring system are selected from N, O and S, R1q, R2q, and R3q are selected from H or C1-C6 alkyl, wherein B is absent, or E, L, G, and B are absent, or E, L, and G are absent, or E, L, and B are absent, or E, L, D, G, and B are absent.

3. A compound of claim 1, having the formula II:

4. A compound of claim I, having the formular III:

5. A compound of claim 1, having the formula IV:

6. A compound of claim 1, having the formula V:

7. A compound of claim 1, having the formula VI:

8. A compound of claim 1, having the formula VII:

9. A compound of claim 1, having the formula VIII:

10. A compound of claim 1, having the formula IX:

11. A compound of claim 1, having the formula X:

12. A compound of claim 1, having the formula XI:

13. A compound of claim 1, having the formula XII:

14. A compound of claim 1, having the formula XIII:

15. A compound of claim 1, having the formula XIV:

16. A compound of claim 1, having the formula XV:

17. A compound of claim 1, having the formula XVI:

18. A compound of claim 1, having the formula XVII:

19. A pharmaceutical composition comprising a compound from one of claims 1-18 and a pharmaceutically acceptable excipient.

20. A pharmaceutical composition comprising a compound from one of claims 1-18, a second agent, and a pharmaceutically acceptable excipient.

21. A method of treating a patient comprising administering to a patient in need thereof, an effective amount of a compound from one of claims 1-18.

22. A method of treating a patient comprising administering to a patient in need thereof, an effective amount of a compound from one of claims 1-18 and an effective amount of a second agent.

23. A method of treating an infection comprising administering to a patient in need thereof, an effective amount of a compound from one of claims 1-18.

24. A method of treating an infection comprising administering to a patient in need thereof, an effective amount of a compound from one of claims 1-18 and an effective amount of a second agent.