NOVEL COMPOUND HAVING CANCER METASTASIS INHIBITORY ACTIVITY, PREPARATION METHOD THEREFOR, AND PHARMACEUTICAL COMPOSITION FOR INHIBITING CANCER METASTASIS AND INVASION OR TREATING COLORECTAL CANCER, COMPRISING COMPOUND

Abstract

The present invention provides a novel compound that increases KAI1 promoter activity, a pharmaceutically acceptable salt thereof, and a composition for inhibiting cancer metastasis and invasion or treating colorectal cancer containing the same.

Description

TECHNICAL FIELD

The present invention provides a novel compound having cancer metastasis inhibitory activity, and a composition for inhibiting cancer metastasis and invasion or treating colorectal cancer containing the same.

BACKGROUND ART

The number of cancer (malignant neoplasm) deaths in Korea in 2002 was 62,887, which accounts for 25.5% (29.6% of male deaths, and 20.5% of female deaths) of the total number of deaths (246,515) in Korea in 2002, and cancer is the first leading cause of death in Korea. This means that about 131 people per 100,000 people in Korea die from cancer (2002 Statistics Korea). From the viewpoint of cancer treatment, one of the biggest reasons that the mortality rate of cancer patients cannot be reduced is that the invasion and metastasis of cancer cells cannot be suppressed in the process of malignancy. Recent studies have merely elucidated the molecular mechanism of the cancer metastasis process by identifying cancer metastasis-related genes (e.g., Twist, KAI1, etc.). Therefore, drugs or treatment methods capable of effectively inhibiting or preventing cancer metastasis using these cancer metastasis-related genes have not yet been reported. In the case of the United States, recent statistical analysis results show that the five-year survival rate for metastatic cancer has not improved for the past 20-30 years.

In this regard, KAI1 (Kangai 1) was initially identified as a metastatic suppressor in prostate carcinoma. The KAI1 protein is located on human chromosome 11p11 and belongs to the transmembrane 4 superfamily (TM4SF). KAI1 can regulate signal transduction from cell to cell and from cell to extracellular matrix (ECM), and may be involved in several basic biological processes such as fusion, migration, adhesion, mutation and invasion. Reduced or deleted expression of KAI1 has been demonstrated to be associated with metastasis and prognosis of various carcinomas, including laryngeal, prostate, breast, lung, gastric, colorectal and hepatocellular carcinomas.

Currently, as a method of treating cancer, surgery, chemotherapy, radiation therapy, etc. are used for cancer detected at an early stage, but the side effects thereof are also emerging as a big problem, and at the time when primary tumors are detected, metastases thereof are found in most cases. In addition, in the case of terminal cancer or metastatic cancer, there is no special treatment, and thus the patient dies within a limited period of time. Accordingly, to develop a new approach for cancer treatment, studies have been conducted to develop carcinogenic inhibitors and cancer treatment agents, which have few side effects and are highly effective in inhibiting or reducing metastasis of cancer, from natural products with relatively low toxicity.

DISCLOSURE

Technical Problem

Under this background, the present inventors have made extensive research efforts to discover novel small molecule compounds capable of inhibiting cancer metastasis, particularly colorectal cancer metastasis, and as a result, have found that novel compounds according to the present invention may exhibit excellent cancer metastasis inhibitory activity by efficiently increasing the activity of the KAI1 promoter gene, thereby completing the present invention.

Technical Solution

To achieve the above, one embodiment of the present invention provides a compound represented by the following Formula 1 or a pharmaceutically acceptable salt thereof:

wherein

X is C or N;

L is C1 to C4 alkylene or a bond;

R₁ is hydrogen, halogen, substituted or unsubstituted C1-C4 alkyl, substituted or unsubstituted C1-C4 alkoxy, di(C1-C4 alkyl)amino, mono(C1-C4 alkyl)amino, amino, or substituted or unsubstituted 5- to 12-membered heterocycle,

wherein the substituent of the substituted alkyl may be: amino unsubstituted or substituted with one or two substituents selected from the group consisting of C1-C6 alkyl, C2-C6 alkenyl, C2-C6 alkynyl, C6-C9 aryl, benzyl, hydroxy-C1-C6 alkyl and C3-C8 cycloalkyl; or a 5- to 12-membered heterocycle or heteroaryl unsubstituted or substituted with one or two substituents selected from the group consisting of C1-C4 alkyl, C1-C4 alkoxycarbonyl, C6-C9 aryl unsubstituted or substituted with one or two substituents selected from the group consisting of C1-C4 alkyl, C1-C4 alkoxy, halogen and nitro, and 5- to 10-membered heterocycles or heteroaryls;

R₂ is

R₃ is at least one selected from the group consisting of hydrogen, halogen, substituted or unsubstituted C1-C6 alkyl, substituted or unsubstituted C2-C6 alkenyl, substituted or unsubstituted C3-C8 cycloalkyl, substituted or unsubstituted C1-C6 alkoxy, substituted or unsubstituted 5- to 9-membered heteroaryl, substituted or unsubstituted C6-C10 aryl, substituted or unsubstituted C6-C10 aryloxy, substituted or unsubstituted 5- to 9-membered heterocyclyl, substituted or unsubstituted 5- to 9-membered heterocyclyloxy, nitro,

and —O—CH₂—C(O)—NH—R₅;

R₄ hydrogen; halogen; C1-C6 alkyl unsubstituted or substituted with C1-C4 alkoxy, phenoxy or phenyl, wherein the phenyl may be unsubstituted or substituted with halogen; C2-C6 alkenyl; amino; di(C1-C4 alkyl)amino; C6-C9 aryl unsubstituted or substituted with at least one selected from the group consisting of halogen, C1-C4 alkoxy, C1-C4 alkyl unsubstituted or substituted with at least one halogen, nitro, C1-C4 alkylcarbonyloxy, and —SO₂; C3-C8 cycloalkyl; or 5- to 9-membered heterocyclyl;

R₅ is at least one (one or two) selected from the group consisting of hydrogen, halogen, hydroxy, substituted or unsubstituted C1-C4 alkyl, nitro, and C6-C10 aryloxy; and

n is an integer ranging from 0 to 2, preferably an integer ranging from 0 to 1.

Preferably, the substituent of the substituted C1-C6 alkyl, substituted C2-C6 alkenyl, substituted C3-C8 cycloalkyl, substituted C1-C6 alkoxy, substituted 5- to 9-membered heteroaryl, substituted C6-C10 aryl, substituted C6-C10 aryloxy, substituted 5- to 9-membered heterocyclyl, or substituted 5- to 9-membered heterocyclyloxy of R₃ may be at least one selected from the group consisting of C1-C4 alkoxy, C6-C9 aryl and C6-C9 aryloxy, and more preferably, may be at least one selected from the group consisting of phenyl, methoxy and phenoxy.

Advantageous Effects

The compound or pharmaceutically acceptable salt thereof according to the present invention may efficiently increase the activity of the KAI1 promoter gene by significantly increasing the activity of the KAI1 promoter, thereby exhibiting an excellent activity of inhibiting cancer metastasis and invasion or treating colorectal cancer. Thus, it is useful as an inhibitor of cancer metastasis and invasion and as a cancer therapeutic agent.

BEST MODE

Hereinafter, the present invention will be described in more detail.

The definition of each substituent used herein will be described in detail. Unless otherwise specified, each substituent has the following definition.

In the present specification, examples of “halogen” include fluoro, chloro, bromo and iodo.

As used herein, the term “alkyl” refers to a linear or branched aliphatic saturated hydrocarbon group, preferably an alkyl having 1 to 6 carbon atoms, more preferably an alkyl having 1 to 4 carbon atoms. Examples of such alkyl include methyl, ethyl, propyl, isopropyl, butyl, isobutyl, sec-butyl, tert-butyl, pentyl, isopentyl, neopentyl, 1-ethylpropyl, hexyl, isohexyl, 1,1-dimethylbutyl, 2,2-dimethylbutyl, 3,3-dimethylbutyl, and 2-ethylbutyl.

As used herein, the term “heterocycle” refers to a non-aromatic ring containing, a ring constituent atom, a heteroatom selected from a nitrogen atom, a sulfur atom and an oxygen atom other than a carbon atom, and preferably includes a 5- to 12-membered non-aromatic ring containing 1 to 4 heteroatoms. Examples of this non-aromatic ring include tetrahydrothienyl, tetrahydrofuranyl, pyrrolinyl, pyrrolidinyl, imidazolinyl, imidazolidinyl, oxazolinyl, oxazolidinyl, pyrazolinyl, pyrazolidinyl, thiazolinyl, thiazolidinyl, tetrahydroisothiazolyl, tetrahydrooxazolyl, tetrahydroisoxazolyl, piperidinyl, piperazinyl, tetrahydropyridinyl, dihydropyridinyl, dihydrothiopyranyl, tetrahydropyrimidinyl, tetrahydropyridazinyl, dihydropyranyl, tetrahydropyranyl, tetrahydrothiopyranyl, morpholinyl, thiomorpholinyl, azepanyl, diazepanyl, and azepinyl.

As used herein, the term “heteroaryl” refers to an aromatic ring containing, as a ring constituent atom, a heteroatom selected from among a nitrogen atom, a sulfur atom and an oxygen atom other than a carbon atom, and preferably includes a 5- to 12-membered aromatic ring containing 1 to 4 hetero atoms. Examples of this aromatic ring include thienyl, furyl, pyrrolyl, imidazolyl, pyrazolyl, thiazolyl, isothiazolyl, oxazolyl, isoxazolyl, pyridyl, pyrazinyl, pyrimidinyl, pyridazinyl, 1,2,4-oxadiazolyl, 1,3,4-oxadiazolyl, 1,2,4-thiadiazolyl, 1,3,4-thiadiazolyl, triazolyl, tetrazolyl, indenyl, triazinyl, and dihydroisoquinolinyl.

In a preferred embodiment, in the compound of Formula 1,

X is C or N;

L is C1 to C4 alkylene or a bond;

R₁ is hydrogen, F, Cl, Br, substituted or unsubstituted C1-C4 alkyl, methoxy, N(CH₃)₂, NH(CH₃), amino, or a substituted or unsubstituted 5 to 12-membered heterocycle,

wherein the substituent of the substituted alkyl may be unsubstituted or substituted with dimethylamino, diethylamino, dipropylamino, dibutylamino, hydroxyethyl(ethyl)amino, ethyl(butyl)amino, dipentylamino, methyl(ethynyl)amino, ethyl(phenyl)amino, diallylamino, methyl(benzyl)amino, methyl(hydroxyethyl)amino, phenyl(methyl)amino, ethyl(phenyl)amino, butyl(hydroxyethyl)amino, butyl(methyl)amino, dicyclohexylamino, ethoxycarbonyl-piperazine, t-butoxycarbonyl-piperazine, fluorophenyl-piperidine, pyridinyl-piperazine, pyrimidinyl-piperazine, hydroxyethylpiperazine, methoxyphenyl-piperazine, nitrophenyl-piperazine, dimethylmorpholine, morpholine, methylpiperazine, dihydroxyisoquinoline, cyclohexyl(methyl)amino, isopropyl(methyl)amino, fluorophenyl-piperazine, or piperidinylpiperidine;

R₃ is at least one selected from the group consisting of hydrogen, F, Cl, Br, substituted or unsubstituted C1-C4 alkyl, substituted or unsubstituted C2-C4 alkenyl, substituted or unsubstituted C3-C8 cycloalkyl, substituted or unsubstituted C1-C4 alkoxy, substituted or unsubstituted 5- to 9-membered heteroaryl, substituted or unsubstituted C6-C10 aryl, substituted or unsubstituted C6-C10 aryloxy, substituted or unsubstituted 5- to 9-membered heterocyclyl, substituted or unsubstituted 5- to 9-membered heterocyclyloxy, nitro,

and —O—CH₂—C(O)—NH—R₅;

R₄ is hydrogen; F, Cl, Br; C1-C4 unsubstituted or substituted with methoxy, ethoxy, phenoxy or phenyl, wherein the phenyl may be unsubstituted or substituted with halogen; C2-C4 alkenyl; amino; di(C1-C4 alkyl)amino; C6-C9 aryl unsubstituted or substituted with at least one selected from the group consisting of halogen, C1-C3 alkoxy, C1-C4 alkyl unsubstituted or substituted with at least one halogen, nitro, C1-C3 alkylcarbonyloxy, and —SO₂; C3-C8 cycloalkyl; or 5- to 9-membered heterocyclyl;

R₅ is at least one (one or two) selected from the group consisting of hydrogen, halogen, hydroxy, substituted or unsubstituted C1-C4 alkyl, nitro, and C6-C10 aryloxy; and

n is an integer ranging from 0 to 2, preferably an integer ranging from 0 to 1.

Preferably, the substituent of the substituted C1-C4 alkyl, substituted C2-C4 alkenyl, substituted C3-C8 cycloalkyl, substituted C1-C4 alkoxy, substituted 5- to 9-membered heteroaryl, substituted C6-C10 aryl, substituted C6-C10 aryloxy, substituted 5- to 9-membered heterocyclyl, or substituted 5- to 9-membered heterocyclyloxy of R₃ may be at least one selected from the group consisting of C1-C4 alkoxy, C6-C9 aryl and C6-C9 aryloxy, and more preferably, may be at least one selected from the group consisting of phenyl, methoxy and phenoxy.

In a specific embodiment, examples of the compound include compounds 1 to 305 shown in Table 1 below.

TABLE 1
Compound				Quanti-	DMSO
No.	Code	Structure	MW	ty (mg)	(ul)
1	DKC25a01		273.72	1.1 mg	402
2	DKC25a02		283.33	0.9 mg	318
3	DKC25a03		257.26	1.3 mg	505
4	DKC25a04		257.26	1.5 mg	583
5	DKC25a05		229.24	1.3 mg	567
6	DKC25a06		273.72	1.4 mg	511
7	DKC25a07		273.72	1.2 mg	438
8	DKC25a08		203.24	1.2 mg	590
9	DKC25a09		267.33	1.0 mg	374
10	DKC25a10		189.21	1.2 mg	634
11	DKC25a11		253.30	0.8 mg	316
12	DKC25a12		269.30	1.5 mg	557
13	DKC25a13		253.30	1.2 mg	474
14	DKC25a14		191.23	1.4 mg	732
15	DKC25a15		245.32	0.8 mg	326
16	DKC25a16		203.24	1.7 mg	836
17	DKC25a17		217.27	1.7 mg	782
18	DKC25a18		245.30	1.4 mg	571
19	DKC25a19		233.31	1.0 mg	429
20	DKC25a20		219.28	1.0 mg	456
21	DKC25a21		320.32	1.3 mg	406
22	DKC25a22		275.25	0.9 mg	327
23	DKC25a23		207.23	1.2 mg	579
24	DKC25a24		219.28	1.2 mg	547
25	DKC25a25		213.25	0.9 mg	422
26	DKC25a26		293.31	1.3 mg	443
27	DKC25a27		289.35	1.1 mg	380
28	DKC25a28		289.35	1.7 mg	588
29	DKC25a29		375.27	1.1 mg	293
30	DKC25a30		307.27	1.4 mg	456
31	DKC25a31		307.27	1.4 mg	456
32	DKC25a32		307.27	1.1 mg	358
33	DKC25a33		291.71	1.2 mg	411
34	DKC25a34		284.27	1.0 mg	352
35	DKC25a35		275.25	1.5 mg	545
36	DKC25a36		308.16	0.9 mg	292
37	DKC25a37		308.16	1.5 mg	487
38	DKC25a38		323.27	1.4 mg	433
39	DKC25a39		323.27	1.7 mg	526
40	DKC25a40		267.33	1.4 mg	524
41	DKC25a41		323.27	1.4 mg	433
42	DKC25a42		299.33	1.4 mg	468
43	DKC25a43		315.37	1.4 mg	444
44	DKC25b01		291.71	1.3 mg	446
45	DKC25b02		291.71	1.0 mg	343
46	DKC25b03		263.68	1.1 mg	417
47	DKC25b04		308.16	0.9 mg	292
48	DKC25b05		237.68	1.0 mg	421
49	DKC25b06		301.77	1.5 mg	497
50	DKC25b07		223.66	1.7 mg	760
51	DKC25b08		287.74	1.5 mg	521
52	DKC25b09		303.74	1.4 mg	461
53	DKC25b10		287.74	1.2 mg	417
54	DKC25b11		225.67	1.3 mg	576
55	DKC25b12		279.76	0.9 mg	322
56	DKC25b13		237.68	0.9 mg	379
57	DKC25b14		251.71	1.0 mg	397
58	DKC25b15		279.74	1.5 mg	536
59	DKC25b16		317.77	1.0 mg	315
60	DKC25b17		267.75	12. mg	448
61	DKC25b18		253.73	1.1 mg	434
62	DKC25b19		303.74	1.0 mg	329
63	DKC25b20		354.76	1.0 mg	282
61	DKC25b21		309.70	1.6 mg	517
65	DKC25b22		241.67	1.0 mg	414
66	DKC25b23		253.73	1.2 mg	473
67	DKC25b24		327.75	1.4 mg	427
68	DKC25b25		323.79	1.1 mg	340
69	DKC25b26		344.21	1.7 mg	494
73	DKC25b27		323.79	1.6 mg	494/
71	DKC25b28		339.79	1.6 mg	471
72	DKC25b29		409.71	1.7 mg	415
73	DKC25b30		341.71	1.5 mg	439
74	DKC25b31		341.71	1.1 mg	322
75	DKC25b32		341.71	1.2 mg	351
76	DKC25b33		326.15	1.5 mg	460
77	DKC25b34		317.71	1.7 mg	533
78	DKC25b35		309.70	0.8 mg	258
79	DKC25b36		342.60	1.2 mg	350
80	DKC25b37		342.60	1.5 mg	438
81	DKC25b38		357.71	1.1 mg	308
82	DKC25b39		357.71	1.5 mg	419
83	DKC25b40		301.77	1.0 mg	331
84	DKC25b41		357.71	1.5 mg	419
85	DKC25b42		333.77	0.8 mg	240
86	DKC25b43		349.81	1.0 mg	286
87	DKC25b44		308.16	1.0 mg	325
88	DKC25c01		316.79	1.4 mg	442
81	DKC25b38		357.71	1.1 mg	308
82	DKC25b39		357.71	1.5 mg	419
83	DKC25b40		301.77	1.6 mg	331
84	DKC25b41		357.71	1.5 mg	419
85	DKC25b42		333.77	0.8 mg	240
86	DKC25b43		369.81	1.0 mg	286
87	DKC25b44		303.16	1.0 mg	325
88	DKC25c01		316.79	1.6 mg	442
96	DKC25c09		296.37	0.9 mg	304
97	DKC25c10		312.37	0.8 mg	256
98	DKC25c11		296.37	1.4 mg	472
99	DLC25c12		234.30	1.0 mg	427
100	DKC25c13		246.31	0.9 mg	365
101	DKC25c14		288.37	1.0 mg	347
102	DKC25c15		276.38	1.4 mg	507
103	DKC25c16		262.35	1.1 mg	419
104	DKC25c17		312.37	1.0 mg	320
105	DKC25c18		318.32	1.0 mg	314
106	DKC25c19		250.30	1.5 mg	599
107	DKC25c20		336.38	1.1 mg	327
108	DKC25c21		352.83	1.2 mg	340
109	DKC25c22		318.39	0.9 mg	283
110	DKC25c23		332.42	0.9 mg	271
111	DKC25c24		348.42	1.9 mg	545
112	DKC25c25		350.34	1.3 mg	371
113	DKC25c26		350.34	1.0 mg	285
114	DKC25c27		350.34	1.4 mg	400
115	DKC25c28		334.78	1.0 mg	299
116	DKC25c29		318.32	1.2 mg	377
117	DKC25c30		351.23	0.8 mg	228
118	DKC25c31		351.23	1.3 mg	370
119	DKC25c32		366.34	1.0 mg	273
120	DKC25c33		310.40	1.0 mg	322
121	DKC25c34		342.40	1.1 mg	321
122	DKC25d01		303.74	1.2 mg	395
123	DKC25d02		233.27	0.8 mg	343
124	DKC25d03		221.26	1.4 mg	633
125	DKC25d04		233.27	1.7 mg	729
126	DKC25d05		247.29	1.2 mg	485
127	DKC25d06		275.32	1.4 mg	508
128	DKC25d07		249.31	1.5 mg	602
129	DKC25d08		305.35	1.3 mg	426
130	DKC25e01		274.70	1.0 mg	364
131	DKC25e02		284.32	0.9 mg	317
132	DKC25e03		258.25	1.0 mg	387
133	DKC25e04		258.25	0.8 mg	310
134	DKC25e05		204.23	1.1 mg	539
135	DKC25e06		254.29	1.1 mg	433
136	DKC25e07		192.22	1.0 mg	520
137	DKC25f01		342.37	1.13 mg	380
138	DKC25f02		358.82	1.4 mg	390
139	DKC25f03		288.35	0.9 mg	312
140	DKC25f04		354.41	0.7 mg	198
141	DKC25f05		338.41	1.0 mg	295
142	DKC25f06		376.34	0.5 mg	133
143	DKC25f07		288.35	0.8 mg	277
144	DKC25f08		302.37	0.9 mg	298
145	DKC25f09		304.39	0.8 mg	263
146	DKC25f10		378.42	0.9 mg	238
147	DKC25f11		394.87	1.0 mg	253
148	DKC25f12		360.43	0.8 mg	222
149	DKC25f13		374.46	1.5 mg	401
150	DKC25f14		390.45	1.1 mg	282
151	DKC25g01		476.15	1.4 mg	294
152	DKC25g02		486.22	1.1 mg	226
153	DKC25g03		460.18	1.2 mg	261
154	DKC25g04		460.18	1.4 mg	304
155	DKC25g05		432.17	0.9 mg	208
156	DKC25g06		476.15	0.9 mg	189
157	DMC25g07		476.15	1.0 mg	210
158	DKC25g08		406.19	1.4 mg	345
159	DKC25g09		470.10	0.9 mg	191
160	DKC25g10		392.00	1.0 mg	255
161	DKC25g11		456.20	0.9 mg	197
162	DKC25g12		472.20	1.0 mg	212
163	DKC25g13		456.20	1.0 mg	219
164	DKC25g14		394.00	1.1 mg	279
165	DKC25g15		448.24	0.9 mg	201
166	DKC25g16		406.19	1.4 mg	345
167	DKC25g17		420.20	1.2 mg	286
168	DKC25g18		448.15	1.3 mg	290
169	DKC25g19		486.20	1.4 mg	288
170	DKC25g20		436.24	1.2 mg	275
171	DKC25g21		451.21	1.0 mg	222
172	DKC25g22		522.22	1.2 mg	230
173	DKC25g23		572.20	1.4 mg	245
174	DKC25g24		470.22	1.4 mg	298
175	DKC25g25		541.11	1.1 mg	203
176	DKC25g26		519.00	1.2 mg	231
177	DKC25g27		478.00	0.9 mg	188
178	DKC25g28		410.00	1.1 mg	268
179	DKC25g29		422.22	1.3 mg	308
180	DKC25g30		409.20	0.9 mg	220
181	DKC25g31		520.10	0.9 mg	173
182	DKC25g32		380.17	1.0 mg	263
183	DKC25g33		416.14	1.4 mg	336
184	DKC25g34		496.15	1.2 mg	242
185	DKC25g35		492.17	1.1 mg	224
186	DKC25g36		512.12	1.2 mg	234
187	DKC25g37		478.16	1.2 mg	251
188	DKC25g38		492.17	0.8 mg	163
189	DKC25g39		408.17	1.4 mg	343
190	DKC25g40		578.16	1.4 mg	242
191	DKC25g41		510.18	1.4 mg	274
192	DKC25g42		510.18	1.1 mg	216
193	DKC25g43		510.18	1.4 mg	274
194	DKC25g44		494.14	1.0 mg	202
195	DKC25g45		487.17	1.4 mg	287
196	DKC25g46		478.17	1.4 mg	293
197	DKC25g47		510.11	1.3 mg	255
198	DKC25g48		510.11	1.3 mg	255
199	DKC25g49		526.17	1.4 mg	266
200	DKC25g50		526.17	1.4 mg	266
201	DKC25h01		388.14	1.2 mg	309
202	DKC25h02		402.16	1.4 mg	348
203	DKC25h03		352.14	0.9 mg	256
204	DKC25h04		402.16	1.0 mg	249
205	DKC25h05		420.15	0.8 mg	190
206	DKC25h06		432.17	0.8 mg	185
207	DKC25h07		436.14	1.4 mg	321
208	DKC25h08		389.14	0.8 mg	206
209	DKC25h09		418.15	1.4 mg	335
210	DKC25h10		430.19	1.4 mg	325
211	DKC25h11		451.12	1.4 mg	310
212	DKC25h12		446.15	1.4 mg	314
213	DKC25h13		430.19	1.4 mg	325
214	DKC25h14		480.17	1.4 mg	292
215	DKC25h15		462.16	1.4 mg	303
216	DKC25h16		448.16	1.5 mg	335
217	DKC25h17		432.43	1.4 mg	324
218	DKC25h18		446.15	1.4 mg	314
219	DKC25h19		428.17	0.9 mg	210
220	DKC25h20		446.18	1.0 mg	224
221	DKC25h21		480.17	1.3 mg	271
222	DKC25h22		474.12	0.8 mg	169
223	DKC25h23		404.14	0.9 mg	223
224	DKC25h24		422.10	1.2 mg	284
225	DKC25h25		466.05	0.9 mg	193
226	DKC25h26		354.16	1.0 mg	282
227	DKC25h27		428.17	1.4 mg	327
228	DKC25h28		354.16	1.0 mg	282
229	DKC25h29		382.19	0.8 mg	209
230	DKC25h30		394.19	1.4 mg	355
231	DKC25i01		296.37	1.9 mg	641
232	DKC25i02		384.48	2.4 mg	624
233	DKC25i03		324.42	1.6 mg	493
234	DKC25i04		430.52	1.4 mg	325
235	DKC25i05		415.50	1.8 mg	433
236	DKC25i06		443.55	2.5 mg	564
237	DKC25i07		419.57	2.0 mg	477
238	DKC25i08		458.52	1.1 mg	240
239	DKC25i09		372.47	2.2 mg	591
240	DKC25i10		414.51	1.2 mg	289
241	DKC25i11		348.45	1.8 mg	517
242	DKC25i12		372.47	1.9 mg	510
243	DKC25i13		326.40	1.7 mg	521
244	DKC25i14		368.48	2.0 mg	543
245	DKC25i15		437.54	2.3 mg	526
246	DKC25i16		338.45	1.3 mg	384
247	DKC25i17		324.42	1.7 mg	524
248	DKC25i18		352.48	1.5 mg	426
249	DKC25i19		352.48	1.0 mg	284
250	DKC25i20		408.59	1.6 mg	392
251	DKC25i21		306.37	1.1 mg	359
252	DKC25i22		338.41	1.6 mg	473
253	DKC25i23		351.45	1.7 mg	484
254	DKC25i24		384.48	1.3 mg	338
255	DKC25i25		364.49	1.9 mg	521
256	DKC25i26		324.42	2.3 mg	709
257	DKC25i17		431.51	2.2 mg	510
258	DKC25i28		415.50	1.9 mg	457
259	DKC25i29		443.55	1.8 mg	406
260	DKC25i30		419.57	1.4 mg	334
261	DKC25i31		458.52	2.5 mg	545
262	DKC25i32		358.44	1.9 mg	530
263	DKC25i33		372.47	1.9 mg	510
264	DKC25i34		414.51	1.6 mg	386
265	DKC25i35		348.45	1.8 mg	517
266	DKC25i36		372.47	1.4 mg	376
267	DKC25i37		326.40	2.1 mg	643
268	DKC25i38		368.48	2.1 mg	570
269	DKC25i39		437.54	1.8 mg	411
270	DKC25i40		432.61	1.1 mg	254
271	DKC25i41		338.45	1.0 mg	295
272	DKC25i42		352.48	2.3 mg	653
273	DKC25i43		352.48	2.4 mg	681
274	DKC25i44		340.42	1.4 mg	411
275	DKC25i45		306.37	1.0 mg	326
276	DKC25i46		338.41	2.2 mg	650
277	DKC25i47		409.49	2.0 mg	488
278	DKC25i48		366.46	1.8 mg	491
279	DKC25i49		414.51	1.3 mg	314
280	DKC25i50		394.52	2.0 mg	507
281	DKC25i51		460.55	1.1 mg	239
282	DKC25i52		473.57	2.2 mg	465
283	DKC25i53		449.60	1.5 mg	334
284	DKC25i54		444.54	2.5 mg	562
285	DKC25i55		378.47	1.6 mg	423
286	DKC25i56		402.49	1.1 mg	273
287	DKC25i57		350.42	1.7 mg	499
288	DKC25i58		398.50	2.3 mg	577
289	DKC25i59		467.57	1.4 mg	299
290	DKC25i60		382.50	2.3 mg	601
291	DKC25i61		370.45	1.7 mg	459
292	DKC25i62		438.61	1.3 mg	296
293	DKC25i63		368.43	1.8 mg	489
294	DKC25i64		368.48	1.8 mg	488
295	DKC25i65		396.49	1.2 mg	303
296	DKC25i66		296.37	1.7 mg	574
297	DKC25i67		384.48	2.2 mg	572
298	DKC25i68		364.49	1.7 mg	466
299	DKC25i69		431.51	1.3 mg	301
300	DKC27i70		415.50	2.5 mg	602
301	DKC25i71		419.51	2.2 mg	524
302	DKC25i72		414.15	2.5 mg	604
303	DKC25i73		348.45	1.2 mg	344
304	DKC25i74		338.31	1.8 mg	532
305	DKC25i75		409.49	1.7 mg	415

Meanwhile, the compound of the present invention may exist in the form of a pharmaceutically acceptable salt. As the salt, an acid addition salt formed by a pharmaceutically acceptable free acid is useful. As used herein, the term “pharmaceutically acceptable salt” refers to any organic or inorganic addition salt of each of the compounds represented by Formulas 1 to 3 whose concentration has effective action because it is relatively non-toxic and harmless to a patient and whose side effects do not degrade the beneficial efficacy of the above compounds.

The acid addition salt is prepared by a conventional method, for example, by dissolving the compound in an excess of aqueous acid solution and precipitating the salt using a water-miscible organic solvent such as methanol, ethanol, acetone or acetonitrile. The acid addition salt may also be prepared by heating an equimolar amount of the compound and acid or alcohol (e.g., glycol monomethylether) in water, and then drying the mixture by evaporation or suction-filtering the precipitated salt.

As the free acid, an organic acid or inorganic acid may be used. Examples of the inorganic acid include, but are not limited to, hydrochloric acid, phosphoric acid, sulfuric acid, nitric acid, and stannic acid, and examples of the organic acid include, but are not limited to, methanesulfonic acid, p-toluenesulfonic acid, acetic acid, trifluoroacetic acid, maleic acid, succinic acid, oxalic acid, benzoic acid, tartaric acid, fumaric acid, mandelic acid, propionic acid, citric acid, lactic acid, glycolic acid, gluconic acid, galacturonic acid, glutamic acid, glutaric acid, glucuronic acid, aspartic acid, ascorbic acid, carbonic acid, vanillic acid, hydroiodic acid, etc.

In addition, a pharmaceutically acceptable metal salt may be prepared using a base. An alkali metal salt or an alkali earth metal salt is obtained, for example, by dissolving a compound in an excess amount of a solution of an alkali metal hydroxide or an alkali earth metal salt hydroxide, filtering undissolved compound salts, and drying the filtrate by evaporation. In particular, preparing a sodium salt, potassium salt or calcium salt as the salt is suitable from the pharmaceutical point of view, but is not limited thereto. Furthermore, the silver salt corresponding thereto may be obtained by reacting an alkali metal or alkali earth metal salt with an appropriate silver salt (e.g., silver nitrate).

The pharmaceutically acceptable salt of the compound of the present invention may include a salt of the acidic or basic group that can be present in the compound of Formula 1, unless indicated otherwise. Examples of the pharmaceutically acceptable salt includes sodium, potassium and calcium salts of a hydroxyl group, and other pharmaceutically acceptable salts of an amino group include hydrobromide, sulfate, hydrogen sulfate, phosphate, hydrogen phosphate, dihydrogen phosphate, acetate, succinate, citrate, tartrate, lactate, mandelate, methanesulfonate (mesylate), and p-toluenesulfonate (tosylate) salts. These may be prepared through the salt preparation methods known in the related art.

The salt of the compound of Formula 1 of the present invention is a pharmaceutically acceptable salt which exhibits pharmacological activity equivalent to that of the compound of Formula 1. For example, any salt of Formula 1 that delays death caused by metastasis of colorectal cancer cells or treats colorectal cancer by inhibiting the migration and invasion of colorectal cancer cells may be used without limitation.

In addition, the compounds represented by Formula 1 according to the present invention include, without limitation, pharmaceutically acceptable salts thereof, as well as possible solvates such as hydrates and all possible stereoisomers that can be prepared therefrom. Solvates and stereoisomers of the compound represented by Formula 1 may be prepared from the compound represented by Formula 1 using methods known in the art.

Furthermore, the compound represented by Formula 1 according to the present invention may be prepared in a crystalline form or an amorphous form, and when it is prepared in a crystalline form, it may be optionally hydrated or solvated. The present invention may encompass compounds containing various amounts of water as well as stoichiometric hydrates of the compound represented by Formula 1. Solvates of the compound represented by Formula 1 according to the present invention include both stoichiometric solvates and non-stoichiometric solvates.

The compound of Formula 1 according to the present invention may be prepared by the exemplary method to be described later, specific examples of which are shown in the reaction schemes described in the Examples below.

In the preparation method according to the present invention, as reactants used in the above reaction schemes, commercially available compounds may be purchased and used as they are, or compounds synthesized by carrying out one or more reactions known in the art or by performing an appropriate modification of the reactions may be used. For example, the reactants may be synthesized by performing one or more reactions in any order in consideration of the presence, type and/or position of a reactive functional group and/or hetero element included in the skeleton structure, without being limited thereto.

In another aspect, the present invention provides a composition for inhibiting cancer metastasis and invasion containing the compound of the present invention as an active ingredient. The present invention also provides a composition for treating cancer, preferably colorectal cancer, laryngeal cancer, lung cancer, gastric cancer, hepatocellular cancer, prostate cancer, or breast cancer, containing the compound and pharmaceutically acceptable salt thereof according to the present invention as an active ingredient. Preferably, the composition may be a pharmaceutical composition.

In specific examples of the present invention, specific compounds represented by Formula 1 were newly synthesized, and it was confirmed that these compounds had the effect of increasing KAI1 promoter gene expression and inhibiting cancer invasion.

As used herein, the term “treatment” or “treating” refers to any action of alleviating or beneficially changing colorectal cancer symptoms by administration of the pharmaceutical composition of the present invention.

As described above, the compound of the present invention not only increases the expression of the KAI1 promoter gene, but also exhibits an effect of inhibiting cancer metastasis and invasion. Thus, a pharmaceutical composition containing the compound as an active ingredient may be used for the inhibition of cancer metastasis and invasion and the treatment of colorectal cancer.

For example, the composition of the present invention may further contain a pharmaceutically acceptable carrier, diluent or excipient, and may be formulated in various forms such as oral dosage forms, for example, powders, granules, tablets, capsules, suspensions, emulsions, syrups and aerosols, as well as injections such as sterile injectable solutions, according to conventional methods depending on the intended use, and may be administered by various routes, including oral, intravenous, intraperitoneal, subcutaneous, rectal, and topical routes. Examples of a suitable carrier, excipient or diluent that may be contained in the composition include lactose, dextrose, sucrose, sorbitol, mannitol, xylitol, erythritol, maltitol, starch, acacia gum, alginate, gelatin, calcium phosphate, calcium silicate, cellulose, methylcellulose, microcrystalline cellulose, polyvinylpyrrolidone, water, methylhydroxybenzoate, propylhydroxybenzoate, talc, magnesium stearate, and mineral oil. In addition, the composition of the present invention may further contain a filler, an anti-agglomeration agent, a lubricant, a wetting agent, a fragrance, an emulsifier, a preservative, and the like.

Solid formulations for oral administration include tablets, pills, powders, granules, capsules, and the like, and such solid formulations are prepared by mixing the compound with one or more excipients, for example, starch, calcium carbonate, sucrose, lactose, gelatin, etc. In addition to simple excipients, lubricants such as magnesium stearate and talc may also be used.

Liquid formulations for oral administration include, for example, suspensions, solutions, emulsions, syrups, etc., and these formulations may contain various excipients, for example, a wetting agent, a sweetener, a fragrance and a preservative, in addition to commonly used simple diluents such as water and liquid paraffin.

Formulations for parenteral administration include sterile aqueous solutions, non-aqueous solutions, suspensions, emulsions, lyophilized formulations, and suppositories. Non-aqueous solvents and suspending agents include propylene glycol, polyethylene glycol, vegetable oils such as olive oil, and injectable esters such as ethyl oleate. As the base of the suppository, Witepsol, Macrogol, Tween 61, Cacao butter, laurin fat, glycerogelatin, etc. may be used. Meanwhile, injections may contain conventional additives such as a solubilizer, an isotonic agent, a suspending agent, an emulsifier, a stabilizer, and a preservative.

The formulation may be prepared by a conventional mixing, granulation or coating method, and contains the active ingredient in an amount effective for medical treatment, specifically, inhibition of cancer metastasis and invasion, or treatment of colorectal cancer.

The pharmaceutical composition of the present invention is administered in a pharmaceutically effective amount. As used herein, the term “pharmaceutically effective amount” refers to an amount sufficient to treat a disease at a reasonable benefit/risk ratio applicable to any medical treatment. The effective dose level of the pharmaceutical composition may be determined depending on factors, including the patient's health status, the kind and severity of the disease, the activity of the drug, sensitivity to the drug, the mode of administration, the time of administration, the route of administration, excretion rate, and drugs used in combination with the composition, as well as other factors well known in the medical field. The pharmaceutical composition of the present invention may be administered individually or in combination with other therapeutic agents, and may be administered sequentially or simultaneously with conventional therapeutic agents. The pharmaceutical composition may be administered in a single or multiple dosage form. It is important to administer the pharmaceutical composition in the minimum amount that can exhibit the maximum effect without causing side effects, in view of all the above-described factors, and this amount can be easily determined by a person skilled in the art.

For example, the dosage of the pharmaceutical composition may increase or decrease depending on the route of administration, the severity of the disease, the patient's sex, weight and age, etc., and thus the dosage is not intended to limit the scope of the present invention in any sense.

A preferred dosage of the compound of the present invention varies depending on the patient's condition and weight, the severity of the disease, the form of the drug, and the route and duration of administration, but may be appropriately selected by those skilled in the art.

In another aspect, the present invention provides a method for inhibiting cancer metastasis and invasion or treating colorectal cancer comprising a step of administering the pharmaceutical composition of the present invention to a subject in need thereof.

As used herein, the term “subject” refers to all animals, including humans, monkey, cows, horses, sheep, pigs, chicken, turkeys, quails, cats, dogs, mice, rats, rabbits or guinea pigs that are likely to develop cancer metastasis or invasion, or have cancer metastasis or invasion, or have developed colorectal cancer. When the pharmaceutical composition of the present invention is administered to a subject, it is possible to inhibit cancer metastasis and invasion or to effectively treat colorectal cancer. In addition, since the pharmaceutical composition of the present invention exhibits an effect of inhibiting cancer metastasis and invasion and treating colorectal cancer by increasing the expression of the KAI1 promoter gene, it may exhibit a synergistic effect when administered in combination with an existing therapeutic agent.

As used herein, the term “administration” or “administering” means providing a given substance to a patient by any suitable method. The pharmaceutical composition of the present invention may be administered through any general route as long as it can reach the target tissue. The pharmaceutical composition of the present invention may be administered intraperitoneally, intravenously, intramuscularly, subcutaneously, intradermally, orally, topically, intranasally, intrapulmonarily, or intrarectally administration, without being limited thereto. In addition, the composition of the present invention may also be administered using any device capable of delivering the active ingredient to target cells. Preferred administration modes and formulations are intravenous injections, subcutaneous injections, intradermal injections, intramuscular injections, drip injections, and the like. Injections may be prepared using aqueous solvents such as physiological saline and Ringer's solution, or non-aqueous solvents such as vegetable oil, higher fatty acid esters (e.g., ethyl oleate, etc.), or alcohols (e.g., ethanol, benzyl alcohol, propylene glycol, glycerin, etc.), and may contain pharmaceutical carriers, such as stabilizers (e.g., ascorbic acid, sodium hydrogen sulfite, sodium pyrosulfite, BHA, tocopherol, EDTA, etc.) for preventing deterioration, emulsifiers, buffers for pH adjustment, preservatives (e.g., phenylmercuric nitrate, thimerosal, benzalkonium chloride, phenol, cresol, benzyl alcohol, etc.) for inhibiting microbial growth, etc.

Hereinafter, the present invention will be described in more detail with reference to examples. These examples serve to explain the present invention in more detail, and the scope of the present invention is not limited by these examples.

Examples 1 to 87. Preparation of Compounds 1 to 87 (DKC1125a01 to 43 and DKC1125b01 to 44) According to the Present Invention

Compounds 1 to 87 (DKC1125a01 to 43 and DKC1125b01 to 44) of the present invention were synthesized according to the following Reaction Scheme 1.

General Preparation Method for Compounds 1 to 43 (DKC1125a01 to 43) and Compounds 44 to 87 (DKC1125b01 to 44)

CH₂Cl₂ (1 mL) and saturated NaHCO₃ (2 mL) were stirred vigorously and chilled in an ice bath. Each acid chloride (0.29 mmol) shown in Tables 2 and 3 below was added, followed immediately by addition of aminoacetophenone hydrochloride (50 mg, 0.29 mmol). Stirring was continued while warming to room temperature over a period of 1 hour. The organic layer was then separated, and dried with Na₂SO₄, and the solvent was evaporated (80 to 90% yield).

TABLE 2
Acid chlorides used in preparation of Compounds 1 to 43
(DKC1125a01 to 43)
Compounds  Acid chloride
DKC1125a01 4-Chlorobenzoyl chloride
DKC1125a02 2-Phenoxypropionyl chloride
DKC1125a03 2-Fluorobenzoyl chloride
DKC1125a04 4-Fluorobenzoyl chloride
DKC1125a05 2-Furoyl chloride
DKC1125a06 2-Chlorobenzoyl Chloride
DKC1125a07 3-Chlorobenzoyl chloride
DKC1125a08 Crotonyl chloride
DKC1125a09 3-Phenylpropionyl chloride
DKC1125a10 Acryloyl chloride
DKC1125a11 o-Toluoyl chloride
DKC1125a12 3-Methoxybenzoyl chloride
DKC1125a13 m-Toluoyl chloride
DKC1125a14 Propionyl chloride
DKC1125a15 Cyclohexanecarbonyl chloride
DKC1125a16 Cyclopropanecarbonylchloride
DKC1125a17 Cyclobutanecarbonyl chloride
DKC1125a18 Thiophene-2-carbonyl chloride
DKC1125a19 tert-butylacetyl chloride
DKC1125a20 Pentanoyl chloride
DKC1125a21 3-nitrobenzene-1-sulfonyl chloride
DKC1125a22 2,4-Difluorobenzoyl chloride
DKC1125a23 Methoxyacetyl chloride
DKC1125a24 Trimethylacetyl chloride
DKC1125a25 Methanesulfonyl chloride
DKC1125a26 4-Fluorobenzenesulfonyl chloride
DKC1125a27 p-Toluenesulfonyl chloride
DKC1125a28 a-Toluenesulfonyl chloride
DKC1125a29 3,5-Bis(trifluoromethyl)benzoyl chloride
DKC1125a30 2-(Trifluoromethyl)benzoyl chloride
DKC1125a31 3-(Trifluoromethyl)benzoyl chloride
DKC1125a32 4-(Trifluoromethyl)benzoyl chloride
DKC1125a33 2-Chloro-4-fluorobenzoyl chloride
DKC1125a34 3-Nitrobenzoyl chloride
DKC1125a35 3,4-Difluorobenzoyl chloride
DKC1125a36 3,5-Dichlorobenzoyl chloride
DKC1125a37 2,3-Dichlorobenzoyl chloride
DKC1125a38 4-(Trifluoromethoxy)benzoyl chloride
DKC1125a39 3-(Trifluoromethoxy)benzoyl chloride
DKC1125a40 3,5-Dimethylbenzoyl chloride
DKC1125a41 2-(Trifluoromethoxy)benzoyl chloride
DKC1125a42 3,5-Dimethoxybenzoyl chloride
DKC1125a43 4-Biphenylcarbonyl chloride

TABLE 3
Acid chlorides used in preparation of Compounds 44 to 87
(DKC1125b01 to 45)
Compounds  Acid chloride
DKC1125b01 2-Fluorobenzoyl chloride
DKC1125b02 4-Fluorobenzoyl chloride
DKC1125b03 2-Furoyl chloride
DKC1125b04 3-Chlorobenzoyl chloride
DKC1125b05 Crotonyl chloride
DKC1125b06 3-Phenylpropionyl chloride
DKC1125b07 Acryloyl chloride
DKC1125b08 o-Toluoyl chloride
DKC1125b09 3-Methoxybenzoyl chloride
DKC1125b10 m-Toluoyl chloride
DKC1125b11 Propionyl chloride
DKC1125b12 Cyclohexanecarbonyl chloride
DKC1125b13 Cyclopropanecarbonylchloride
DKC1125b14 Cyclobutanecarbonyl chloride
DKC1125b15 Thiophene-2-carbonyl chloride
DKC1125b16 2-Ethoxybenzoyl chloride
DKC1125b17 tert-butylacetyl chloride
DKC1125b18 Pentanoyl chloride
DKC1125b19 4-Methoxybenzoyl chloride
DKC1125b20 3-nitrobenzene-1-sulfonyl chloride
DKC1125b21 2,4-Difluorobenzoyl chloride
DKC1125b22 Methoxyacetyl chloride
DKC1125b23 Pivaloyl chloride
DKC1125b24 4-Fluorobenzenesulfonyl chloride
DKC1125b25 p-Toluenesulfonyl chloride
DKC1125b26 4-Chlorobenzenesulfonyl chloride
DKC1125b27 a-Toluenesulfonyl chloride
DKC1125b28 4-Methoxybenzenesulfonyl chloride
DKC1125b29 3,5-Bis(trifluoromethyl)benzoyl chloride
DKC1125b30 2-(Trifluoromethyl)benzoyl chloride
DKC1125b31 3-(Trifluoromethyl)benzoyl chloride
DKC1125b32 4-(Trifluoromethyl)benzoyl chloride
DKC1125b33 2-Chloro-4-fluorobenzoyl chloride
DKC1125b34 3-Nitrobenzoyl chloride
DKC1125b35 3,4-Difluorobenzoyl chloride
DKC1125b36 3,5-Dichlorobenzoyl chloride
DKC1125b37 2,3-Dichlorobenzoyl chloride
DKC1125b38 4-(Trifluoromethoxy)benzoyl chloride
DKC1125b39 3-(Trifluoromethoxy)benzoyl chloride
DKC1125b40 3,5-Dimethylbenzoyl chloride
DKC1125b41 2-(Trifluoromethoxy)benzoyl chloride
DKC1125b42 3,5-Dimethoxybenzoyl chloride
DKC1125b43 4-Biphenylcarbonyl chloride
DKC1125b44 4-Chlorobenzoyl chloride

Confirmation of Preparation of Compounds 1 to 87 (DKC1125a01 to 43 and DKC1125b01 to 44)

4-chloro-N-(2-oxo-2-phenylethyl)benzamide (DKC1125a01) ¹H-NMR (400 MHz, CDCl₃) δ 8.01 (dd, J=8.5, 1.1 Hz, 2H), 7.87-7.92 (m, 2H), 7.62-7.66 (m, 1H), 7.50-7.53 (m, 2H), 7.34 (s, 1H), 7.10-7.18 (m, 2H), 4.94 (d, J=4.1 Hz, 2H). MS(ESI): m/z 275 (M+1).

N-(2-oxo-2-phenylethyl)-2-phenoxypropanamide (DKC1125a02) ¹H-NMR (400 MHz, CDCl₃) δ 7.95-7.97 (m, 2H), 7.62 (tt, J=7.5, 1.4 Hz, 1H), 7.55 (s, 1H), 7.47-7.51 (m, 2H), 7.29-7.33 (m, 2H), 6.97-7.03 (m, 3H), 4.67-4.87 (m, 2H), 1.63 (d, J=6.9 Hz, 3H). MS(ESI): m/z 284 (M+1).

2-fluoro-N-(2-oxo-2-phenylethyl)benzamide (DKC1125a03) ¹H-NMR (400 MHz, CDCl₃) δ 8.13 (td, J=7.7, 1.9 Hz, 1H), 8.04 (dd, J=8.5, 1.1 Hz, 2H), 7.90 (d, J=11.4 Hz, 1H), 7.63-7.66 (m, 1H), 7.48-7.55 (m, 3H), 7.26-7.30 (m, 1H), 7.15-7.21 (m, 1H), 5.01 (dd, J=4.1, 0.9 Hz, 2H). MS(ESI): m/z 258 (M+1).

4-fluoro-N-(2-oxo-2-phenylethyl)benzamide (DKC1125a04) ¹H-NMR (400 MHz, CDCl₃) δ 8.02-8.04 (m, 2H), 7.88-7.93 (m, 2H), 7.63-7.67 (m, 1H), 7.53 (t, J=7.8 Hz, 2H), 7.29 (s, 1H), 7.11-7.17 (m, 2H), 4.95 (d, J=4.1 Hz, 2H). MS(ESI): m/z 258 (M+1).

N-(2-oxo-2-phenylethyl)furan-2-carboxamide (DKC1125a05) ¹H-NMR (400 MHz, CDCl₃) δ 7.98-8.00 (m, 2H), 7.58-7.62 (m, 1H), 7.47-7.50 (m, 3H), 7.45-7.31 (1H), 7.13-7.13 (m, 1H), 6.49 (q, J=1.8 Hz, 1H), 4.90 (d, J=4.6 Hz, 2H). MS(ESI): m/z 230 (M+1).

2-chloro-N-(2-oxo-2-phenylethyl)benzamide (DKC1125a06) ¹H-NMR (400 MHz, CDCl₃) δ 8.01 (dt, J=8.2, 1.6 Hz, 2H), 7.72 (dd, J=7.3, 1.8 Hz, 1H), 7.63 (tt, J=7.4, 1.4 Hz, 1H), 7.48-7.53 (m, 3H), 7.30-7.43 (m, 3H), 4.98 (d, J=4.6 Hz, 2H). MS(ESI): m/z 275 (M+1).

3-chloro-N-(2-oxo-2-phenylethyl)benzamide (DKC1125a07) ¹H-NMR (400 MHz, CDCl₃) δ 8.00-8.03 (m, 2H), 7.88 (t, J=1.8 Hz, 1H), 7.75 (dd, J=7.8, 0.9 Hz, 1H), 7.64 (t, J=7.3 Hz, 1H), 7.48-7.54 (m, 3H), 7.39 (t, J=8.0 Hz, 2H), 4.94 (d, J=4.1 Hz, 2H). MS(ESI): m/z 275 (M+1).

(E)-N-(2-oxo-2-phenylethyl)but-2-enamide (DKC1125a08) ¹H-NMR (400 MHz, CDCl₃) δ 8.00 (dt, J=8.4, 1.5 Hz, 2H), 7.63 (tt, J=7.5, 1.4 Hz, 1H), 7.49-7.52 (m, 2H), 6.92 (td, J=7.5, 6.4 Hz, 1H), 6.64 (s, 1H), 5.98 (dt, J=15.2, 1.7 Hz, 1H), 4.84 (d, J=4.6 Hz, 2H), 1.89 (dd, J=6.9, 1.8 Hz, 3H). MS(ESI): m/z 204 (M+1).

N-(2-oxo-2-phenylethyl)-3-phenylpropanamide (DKC1125a09) ¹H-NMR (400 MHz, CDCl₃) δ 7.95 (dt, J=8.4, 1.5 Hz, 2H), 7.58-7.62 (m, 1H), 7.45-7.49 (m, 2H), 7.16-7.29 (m, 5H), 6.69 (s, 1H), 4.74 (d, J=4.1 Hz, 2H), 3.00 (t, J=7.8 Hz, 2H), 2.62 (dd, J=8.7, 6.9 Hz, 2H). MS (ESI): m/z 268 (M+1).

N-(2-oxo-2-phenylethyl) acrylamide (DKC1125a10) ¹H-NMR (400 MHz, CDCl₃) δ 7.99-8.01 (m, 2H), 7.63 (tt, J=7.5, 1.4 Hz, 1H), 7.49-7.53 (m, 2H), 6.88 (s, 1H), 6.25-6.39 (m, 2H), 5.71 (dd, J=9.6, 1.8 Hz, 1H), 4.87 (d, J=4.6 Hz, 2H). MS(ESI): m/z 190 (M+1).

2-methyl-N-(2-oxo-2-phenylethyl)benzamide (DKC1125a11) ¹H-NMR (400 MHz, CDCl₃) δ 8.00 (dt, J=8.2, 1.6 Hz, 2H), 7.62 (tt, J=7.4, 1.4 Hz, 1H), 7.47-7.52 (m, 3H), 7.32 (td, J=7.4, 1.7 Hz, 1H), 7.21 (t, J=7.5 Hz, 2H), 6.97 (s, 1H), 4.92 (d, J=4.6 Hz, 2H), 2.48 (s, 3H). MS(ESI): m/z 254 (M+1).

4-methoxy-N-(2-oxo-2-phenylethyl)benzamide (DKC1125a12) ¹H-NMR (400 MHz, CDCl₃) δ 7.99-8.01 (m, 2H), 7.62 (tt, J=7.4, 1.4 Hz, 1H), 7.48-7.51 (m, 3H), 7.39-7.45 (m, 3H), 7.34 (t, J=7.8 Hz, 1H), 7.04 (dq, J=8.2, 1.2 Hz, 1H), 4.92 (d, J=4.1 Hz, 2H), 3.84 (t, J=4.6 Hz, 3H). MS(ESI): m/z 270 (M+1).

3-methyl-N-(2-oxo-2-phenylethyl)benzamide (DKC1125a13) ¹H-NMR (400 MHz, CDCl₃) δ 8.01-8.04 (m, 2H), 7.70 (s, 1H), 7.67 (td, J=4.0, 2.1 Hz, 1H), 7.63 (tt, J=7.4, 1.4 Hz, 1H), 7.49-7.53 (m, 2H), 7.32-7.36 (m, 3H), 4.94 (d, J=4.6 Hz, 2H), 2.38 (d, J=14.2 Hz, 3H). MS (ESI): m/z 254 (M+1).

N-(2-oxo-2-phenylethyl)propionamide (DKC1125a14) ¹H-NMR (400 MHz, CDCl₃) δ 7.99 (dt, J=8.2, 1.6 Hz, 2H), 7.63 (tt, J=7.4, 1.4 Hz, 1H), 7.49-7.53 (m, 2H), 6.63 (s, 1H), 4.78 (d, J=4.1 Hz, 2H), 2.36 (q, J=7.6 Hz, 2H), 1.22 (t, J=7.5 Hz, 3H). MS(ESI): m/z 192 (M+1).

N-(2-oxo-2-phenylethyl)cyclohexanecarboxamide (DKC1125a15) ¹H-NMR (400 MHz, CDCl₃) δ 7.97-8.01 (m, 2H), 7.59-7.64 (m, 1H), 7.47-7.51 (m, 2H), 6.68 (s, 1H), 4.58-4.78 (m, 2H), 2.21-2.29 (m, 1H), 1.95 (dd, J=22.2, 12.1 Hz, 2H), 1.76-1.84 (m, 2H), 1.49 (q, J=11.9 Hz, 2H), 1.19-1.35 (m, 4H). MS (ESI): m/z 246 (M+1).

N-(2-oxo-2-phenylethyl)cyclopropanecarboxamide (DKC1125a16) ¹H-NMR (400 MHz, CDCl₃) δ 7.99 (dt, J=8.2, 1.6 Hz, 2H), 7.63 (tt, J=7.4, 1.4 Hz, 1H), 7.48-7.53 (m, 2H), 6.82 (s, 1H), 4.80 (d, J=4.1 Hz, 2H), 1.57 (tt, J=8.4, 3.8 Hz, 1H), 0.99-1.03 (m, 2H), 0.80 (td, J=7.4, 4.3 Hz, 2H). MS(ESI): m/z 204 (M+1).

N-(2-oxo-2-phenylethyl)cyclobutanecarboxamide (DKC1125a17) ¹H-NMR (400 MHz, CDCl₃) δ 7.98 (dt, J=8.4, 1.5 Hz, 2H), 7.62 (tt, J=7.3, 1.5 Hz, 1H), 7.48-7.51 (m, 2H), 6.59 (s, 1H), 4.77 (d, J=4.3 Hz, 2H), 3.12-3.21 (m, 1H), 2.29-2.39 (m, 2H), 2.16-2.24 (m, 2H), 1.84-2.05 (m, 2H). MS(ESI): m/z 218 (M+1).

N-(2-oxo-2-phenylethyl)thiophene-2-carboxamide (DKC1125a18) ¹H-NMR (400 MHz, CDCl₃) δ 8.01-8.04 (m, 2H), 7.62-7.67 (m, 2H), 7.50-7.54 (m, 3H), 7.19 (s, 1H), 7.11 (dd, J=4.8, 3.9 Hz, 1H), 4.95 (d, J=4.6 Hz, 2H). MS (ESI): m/z 246 (M+1).

3,3-dimethyl-N-(2-oxo-2-phenylethyl) butanamide (DKC1125a19) ¹H-NMR (400 MHz, CDCl₃) δ 7.97-8.00 (m, 2H), 7.60-7.64 (m, 1H), 7.47-7.52 (m, 2H), 6.62 (d, J=13.7 Hz, 1H), 4.79 (dd, J=4.3, 1.1 Hz, 2H), 2.21 (S, 2H), 1.07 (d, J=1.4 Hz, 9H). MS(ESI): m/z 234 (M+1).

N-(2-oxo-2-phenylethyl)pentanamide (DKC1125a20) ¹H-NMR (400 MHz, CDCl₃) δ 7.99 (dt, J=8.4, 1.5 Hz, 2H), 7.60-7.64 (m, 1H), 7.48-7.52 (m, 2H), 6.68 (s, 1H), 4.78 (d, J=4.1 Hz, 2H), 2.32 (t, J=7.5 Hz, 2H), 1.64-1.71 (m, 2H), 1.34-1.41 (m, 2H), 0.93 (td, J=7.3, 2.3 Hz, 3H). MS (ESI): m/z 220 (M+1).

3-nitro-N-(2-oxo-2-phenylethyl)benzenesulfonamide (DKC1125a21) ¹H-NMR (400 MHz, CDCl₃) δ 8.76 (t, J=2.1 Hz, 1H), 8.40-8.43 (m, 1H), 8.23-8.25 (m, 1H), 7.85-7.87 (m, 2H), 7.74 (t, J=8.2 Hz, 1H), 7.63 (t, J=7.5 Hz, 1H), 7.49 (t, J=7.8 Hz, 2H), 5.94 (s, 1H), 4.57 (d, J=4.6 Hz, 2H). MS(ESI): m/z 321 (M+1).

2,4-difluoro-N-(2-oxo-2-phenylethyl)benzamide (DKC1125a22) ¹H-NMR (400 MHz, CDCl₃) δ 8.15 (td, J=8.8, 6.6 Hz, 1H), 8.03 (dd, J=8.5, 1.1 Hz, 2H), 7.83 (d, J=10.5 Hz, 1H), 7.64 (t, J=7.3 Hz, 1H), 7.52 (t, J=7.8 Hz, 2H), 6.89-7.03 (m, 2H), 4.99 (d, J=4.1 Hz, 2H). MS(ESI): m/z 276 (M+1).

2-methoxy-N-(2-oxo-2-phenylethyl) acetamide (DKC1125a23) ¹H-NMR (400 MHz, CDCl₃) δ 7.97-8.00 (m, 2H), 7.60-7.64 (m, 1H), 7.48-7.55 (m, 3H), 4.80 (d, J=5.0 Hz, 2H), 3.99 (s, 2H), 3.48 (s, 3H). MS(ESI): m/z 208 (M+1).

N-(2-oxo-2-phenylethyl)pivalamide (DKC1125a24) ¹H-NMR (400 MHz, CDCl₃) δ 7.97-8.07 (m, 2H), 7.62 (t, J=7.5 Hz, 1H), 7.50 (t, J=7.8 Hz, 2H), 6.85 (s, 1H), 4.74 (d, J=4.1 Hz, 2H), 1.12-1.34 (m, 9H). MS(ESI): m/z 220 (M+1).

N-(2-oxo-2-phenylethyl)methanesulfonamide (DKC1125a25) ¹H-NMR (400 MHz, CDCl₃) δ 7.94-7.97 (m, 2H), 7.64 (tt, J=7.4, 1.4 Hz, 1H), 7.49-7.53 (m, 2H), 5.60 (t, J=4.6 Hz, 1H), 4.69 (d, J=5.0 Hz, 2H), 3.03 (s, 3H). MS(ESI): m/z 214 (M+1).

4-fluoro-N-(2-oxo-2-phenylethyl)benzenesulfonamide (DKC1125a26) ¹H-NMR (400 MHz, CDCl₃) δ 7.93 (tt, J=7.2, 2.4 Hz, 2H), 7.84-7.87 (m, 2H), 7.60-7.64 (m, 1H), 7.46-7.50 (m, 2H), 7.14-7.20 (m, 2H), 5.80 (t, J=4.6 Hz, 1H), 4.49 (d, J=4.6 Hz, 2H). MS(ESI): m/z 294 (M+1).

4-methyl-N-(2-oxo-2-phenylethyl)benzenesulfonamide (DKC1125a27) ¹H-NMR (400 MHz, CDCl₃) δ 7.85 (dd, J=8.5, 1.1 Hz, 2H), 7.79 (d, J=8.7 Hz, 2H), 7.58-7.62 (m, 1H), 7.46 (t, J=7.8 Hz, 2H), 7.28 (d, J=8.2 Hz, 2H), 5.74 (t, J=4.3 Hz, 1H), 4.47 (d, J=4.6 Hz, 2H), 2.39 (s, 3H). MS (ESI): m/z 290 (M+1).

N-(2-oxo-2-phenylethyl)-1-phenylmethanesulfonamide (DKC1125a28) ¹H-NMR (400 MHz, CDCl₃) δ 7.78 (d, J=7.3 Hz, 2H), 7.60 (t, J=7.3 Hz, 1H), 7.42-7.47 (m, 4H), 7.29-7.34 (m, 3H), 5.55 (t, J=4.3 Hz, 1H), 4.35 (s, 2H), 4.31 (d, J=4.6 Hz, 2H). MS(ESI): m/z 290 (M+1).

N-(2-oxo-2-phenylethyl)-3,5-bis(trifluoromethyl)benzamide (DKC1125a29) ¹H-NMR (400 MHz, CDCl₃) δ 8.34 (s, 2H), 8.03-8.06 (m, 3H), 7.66-7.70 (m, 1H), 7.55 (t, J=7.5 Hz, 2H), 7.49 (s, 1H), 5.00 (d, J=4.6 Hz, 2H). MS(ESI): m/z 376 (M+1).

N-(2-oxo-2-phenylethyl)-2-(trifluoromethyl)benzamide (DKC1125a30) ¹H-NMR (400 MHz, CDCl₃) δ 7.97-7.99 (m, 2H), 7.48-7.71 (m, 7H), 7.07 (s, 1H), 4.95 (d, J=4.1 Hz, 2H). MS (ESI): m/z 308 (M+1).

N-(2-oxo-2-phenylethyl)-3-(trifluoromethyl)benzamide (DKC1125a31) ¹H-NMR (400 MHz, CDCl₃) δ 8.17 (s, 1H), 8.02-8.07 (m, 3H), 7.79 (d, J=8.2 Hz, 1H), 7.58-7.68 (m, 2H), 7.51-7.55 (m, 2H), 7.43 (s, 1H), 4.98 (d, J=4.6 Hz, 2H). MS(ESI): m/z 308 (M+1).

N-(2-oxo-2-phenylethyl)-4-(trifluoromethyl)benzamide (DKC1125a32) ¹H-NMR (400 MHz, CDCl₃) δ 8.00-8.06 (m, 4H), 7.75 (d, J=8.2 Hz, 2H), 7.65-7.69 (m, 1H), 7.55 (t, J=7.8 Hz, 2H), 7.37 (s, 1H), 4.98 (d, J=4.1 Hz, 2H). MS (ESI): m/z 308 (M+1).

2-chloro-4-fluoro-N-(2-oxo-2-phenylethyl)benzamide (DKC1125a33) ¹H-NMR (400 MHz, CDCl₃) δ 7.99-8.01 (m, 2H), 7.77 (dd, J=8.7, 5.9 Hz, 1H), 7.62-7.66 (m, 1H), 7.49-7.55 (m, 3H), 7.15 (dd, J=8.5, 2.5 Hz, 1H), 7.04 (td, J=8.2, 2.7 Hz, 1H), 4.97 (d, J=4.6 Hz, 2H). MS(ESI): m/z 293 (M+1).

3-nitro-N-(2-oxo-2-phenylethyl)benzamide (DKC1125a34) ¹H-NMR (400 MHz, CDCl₃) δ 8.73 (t, J=2.1 Hz, 1H), 8.37 (dd, J=7.8, 1.8 Hz, 1H), 8.23 (dt, J=7.9, 1.4 Hz, 1H), 8.02-8.04 (m, 2H), 7.64-7.69 (m, 2H), 7.51-7.55 (m, 3H), 5.00 (d, J=4.1 Hz, 2H). MS(ESI): m/z 285 (M+1).

3,4-difluoro-N-(2-oxo-2-phenylethyl)benzamide (DKC1125a35) ¹H-NMR (400 MHz, CDCl₃) δ 8.02-8.04 (m, 2H), 7.73-7.78 (m, 1H), 7.62-7.68 (m, 2H), 7.52-7.56 (m, 2H), 7.23-7.29 (m, 2H), 4.94-4.95 (m, 2H). MS(ESI): m/z 276 (M+1).

3,5-dichloro-N-(2-oxo-2-phenylethyl)benzamide (DKC1125a36) ¹H-NMR (400 MHz, CDCl₃) δ 8.01-8.03 (m, 2H), 7.75 (d, J=1.8 Hz, 2H), 7.66 (tt, J=7.4, 1.4 Hz, 1H), 7.50-7.55 (m, 3H), 7.33 (s, 1H), 4.94 (d, J=4.1 Hz, 2H) MS(ESI): m/z 309 (M+1).

2,3-dichloro-N-(2-oxo-2-phenylethyl)benzamide (DKC1125a37) ¹H-NMR (400 MHz, CDCl₃) δ 7.99-8.01 (m, 2H), 7.63-7.67 (m, 1H), 7.51-7.55 (m, 4H), 7.27 (t, J=8.0 Hz, 2H), 4.98 (d, J=4.1 Hz, 2H). MS(ESI): m/z 309 (M+1).

N-(2-oxo-2-phenylethyl)-4-(trifluoromethoxy)benzamide (DKC1125a38) (DKC1125a38) ¹H-NMR (400 MHz, CDCl₃) δ 8.01-8.03 (m, 2H), 7.93 (dt, J=9.3, 2.3 Hz, 2H), 7.64 (t, J=7.5 Hz, 1H), 7.52 (t, J=7.8 Hz, 2H), 7.39 (s, 1H), 7.28 (d, J=8.2 Hz, 2H), 4.95 (d, J=4.1 Hz, 2H). MS(ESI): m/z 324 (M+1).

N-(2-oxo-2-phenylethyl)-3-(trifluoromethoxy)benzamide (DKC1125a39) ¹H-NMR (400 MHz, CDCl₃) δ 8.01 (dd, J=8.5, 1.1 Hz, 2H), 7.77-7.81 (m, 2H), 7.61-7.66 (m, 1H), 7.46-7.53 (m, 4H), 7.37 (dt, J=8.4, 1.1 Hz, 1H), 4.95 (d, J=4.6 Hz, 2H). MS(ESI): m/z 324 (M+1).

3,5=dimethyl-N-(2-oxo-2-phenylethyl)benzamide (DKC1125a40) ¹H-NMR (400 MHz, CDCl₃) δ 8.00-8.02 (m, 2H), 7.60-7.64 (m, 1H), 7.50 (t, J=7.5 Hz, 4H), 7.34 (s, 1H), 7.13 (s, 1H), 4.93 (d, J=4.1 Hz, 2H), 2.31-2.36 (m, 6H) MS(ESI): m/z 268 (M+1).

N-(2-oxo-2-phenylethyl)-2-(trifluoromethoxy)benzamide (DKC1125a41) ¹H-NMR (400 MHz, CDCl₃) δ 8.03 (tt, J=5.3, 1.9 Hz, 3H), 7.80 (s, 1H), 7.63 (tt, J=7.4, 1.4 Hz, 1H), 7.49-7.55 (m, 3H), 7.40 (td, J=7.5, 1.1 Hz, 1H), 7.34 (dt, J=8.2, 1.4 Hz, 1H), 4.99 (d, J=4.6 Hz, 2H). MS(ESI): m/z 324 (M+1).

3,5-dimethoxy-N-(2-oxo-2-phenylethyl)benzamide (DKC1125a42) ¹H-NMR (400 MHz, CDCl₃) δ 7.99-8.02 (m, 2H), 7.63 (tt, J=7.4, 1.4 Hz, 1H), 7.48-7.52 (m, 2H), 7.36 (d, J=3.7 Hz, 1H), 7.00 (d, J=2.3 Hz, 2H), 6.59 (t, J=2.3 Hz, 1H), 4.92 (d, J=4.1 Hz, 2H), 3.80 (d, J=10.1 Hz, 6H). MS(ESI): m/z 300 (M+1).

N-(2-oxo-2-phenylethyl)-[1,1′-biphenyl]-4-carboxamide (DKC1125a43) ¹H-NMR (400 MHz, CDCl₃) δ 8.04-8.06 (m, 2H), 7.97 (dt, J=8.4, 1.9 Hz, 2H), 7.61-7.71 (m, 5H), 7.53 (t, J=7.8 Hz, 2H), 7.45-7.49 (m, 2H), 7.37-7.41 (m, 2H), 4.99 (d, J=4.1 Hz, 2H). MS(ESI): m/z 316 (M+1).

N-(2-(4-chlorophenyl)-2-oxoethyl)-2-fluorobenzamide (DKC1125b01) ¹H-NMR (400 MHz, CDCl₃) δ 8.11 (tt, J=7.9, 2.4 Hz, 1H), 7.97 (dt, J=9.0, 2.1 Hz, 2H), 7.84-7.87 (m, 1H), 7.47-7.53 (m, 3H), 7.25-7.29 (m, 1H), 7.10-7.19 (m, 1H), 4.97 (dd, J=4.3, 1.1 Hz, 2H). MS(ESI): m/z 293 (M+1)

N-(2-(4-chlorophenyl)-2-oxoethyl)-4-fluorobenzamide (DKC1125b02) ¹H-NMR (400 MHz, CDCl₃) δ 7.88-7.97 (m, 4H), 7.50 (dd, J=8.0, 1.6 Hz, 2H), 7.26 (s, 1H), 7.12-7.16 (m, 2H), 4.91 (d, J=2.7 Hz, 2H). MS(ESI): m/z 293 (M+1).

N-(2-(4-chlorophenyl)-2-oxoethyl)furan-2-carboxamide (DKC1125b03) ¹H-NMR (400 MHz, CDCl₃) δ 7.96-7.98 (m, 2H), 7.48-7.51 (m, 2H), 7.28-7.39 (m, 1H), 7.16 (d, J=1.8 Hz, 1H), 6.52 (s, 1H), 4.90 (t, J=2.1 Hz, 2H). MS(ESI): m/z 265 (M+1).

3-chloro-N-(2-(4-chlorophenyl)-2-oxoethyl)benzamide (DKC1125b04) ¹H-NMR (400 MHz, CDCl₃) δ 7.94-7.96 (m, 2H), 7.86 (t, J=1.6 Hz, 1H), 7.73 (dd, J=7.8, 0.9 Hz, 1H), 7.47-7.50 (m, 3H), 7.35-7.41 (m, 2H), 4.91 (d, J=4.1 Hz, 2H). MS(ESI): m/z 309 (M+1).

(E)-N-(2-(4-chlorophenyl)-2-oxoethyl)but-2-enamide (DKC1125b05) ¹H-NMR (400 MHz, CDCl₃) δ 7.93-7.96 (m, 2H), 7.47-7.50 (m, 2H), 6.92 (q, J=7.3 Hz, 1H), 6.59 (s, 1H), 5.97 (dd, J=15.1, 1.8 Hz, 1H), 4.81 (d, J=4.6 Hz, 2H), 1.89 (dd, J=6.9, 1.8 Hz, 3H). MS(ESI): m/z 239 (M+1).

N-(2-(4-chlorophenyl)-2-oxoethyl)-3-phenylpropanamide (DKC1125b06) ¹H-NMR (400 MHz, CDCl₃) δ 7.89 (dt, J=9.0, 2.3 Hz, 2H), 7.45 (dt, J=8.8, 2.3 Hz, 2H), 7.25-7.30 (m, 2H), 7.17-7.22 (m, 3H), 6.62 (s, 1H), 4.70 (d, J=4.1 Hz, 2H), 3.00 (t, J=7.9 Hz, 2H), 2.62 (dd, J=8.7, 6.9 Hz, 2H). MS(ESI): m/z 303 (M+1).

N-(2-(4-chlorophenyl)-2-oxoethyl)acrylamide (DKC1125b07) ¹H-NMR (400 MHz, CDCl₃) δ 7.93-7.96 (m, 2H), 7.48-7.51 (m, 2H), 6.78 (s, 1H), 6.23-6.39 (m, 2H), 5.73 (dd, J=10.1, 1.8 Hz, 1H), 4.83 (d, J=4.6 Hz, 2H). MS (ESI): m/z 225 (M+1).

N-(2-(4-chlorophenyl)-2-oxoethyl)-2-methylbenzamide (DKC1125b08) ¹H-NMR (400 MHz, CDCl₃) δ 7.95 (dt, J=9.0, 2.1 Hz, 2H), 7.46-7.51 (m, 3H), 7.32-7.36 (m, 1H), 7.21-7.27 (m, 2H), 6.90 (s, 1H), 4.90 (d, J=4.6 Hz, 2H), 2.47 (d, J=4.6 Hz, 3H). MS(ESI): m/z 289 (M+1).

N-(2-(4-chlorophenyl)-2-oxoethyl)-4-methoxybenzamide (DKC1125b09) ¹H-NMR (400 MHz, CDCl₃) δ 7.94 (dt, J=9.0, 2.1 Hz, 2H), 7.48 (dt, J=8.7, 1.9 Hz, 2H), 7.40-7.43 (m, 2H), 7.31-7.37 (m, 2H), 7.04-7.07 (m, 1H), 4.90 (d, J=4.1 Hz, 2H), 3.84 (s, 3H). MS(ESI): m/z 305 (M+1).

N-(2-(4-chlorophenyl)-2-oxoethyl)-3-methylbenzamide (DKC1125b10) ¹H-NMR (400 MHz, CDCl₃) δ 7.96 (dt, J=9.0, 2.1 Hz, 2H), 7.64-7.69 (m, 2H), 7.48 (dt, J=9.0, 2.1 Hz, 2H), 7.30-7.34 (m, 3H), 4.91 (d, J=4.3 Hz, 2H), 2.39 (d, J=10.1 Hz, 3H). MS(ESI): m/z 289 (M+1).

N-(2-(4-chlorophenyl)-2-oxoethyl) propionamide (DKC1125b11) ¹H-NMR (400 MHz, CDCl₃) δ 7.92-7.95 (m, 2H), 7.47-7.50 (m, 2H), 6.60 (s, 1H), 4.75 (d, J=4.6 Hz, 2H), 2.35 (q, J=7.6 Hz, 2H), 1.22 (t, J=7.5 Hz, 3H). MS (ESI): m/z 227 (M+1).

N-(2-(4-chlorophenyl)-2-oxoethyl)cyclohexanecarboxamide (DKC1125b12) ¹H-NMR (400 MHz, CDCl₃) δ 7.92 (dt, J=8.8, 2.2 Hz, 2H), 7.48 (dt, J=9.0, 2.1 Hz, 2H), 6.62 (s, 1H), 4.73 (d, J=4.6 Hz, 2H), 2.24 (tt, J=11.7, 3.6 Hz, 1H), 1.92 (dd, J=13.5, 2.1 Hz, 2H), 1.80-1.84 (m, 2H), 1.67-1.71 (m, 1H), 1.49 (qd, J=12.2, 2.9 Hz, 2H), 1.21-1.36 (m, 3H). MS(ESI): m/z 281 (M+1).

N-(2-(4-chlorophenyl)-2-oxoethyl)cyclopropanecarboxamide (DKC1125b13) ¹H-NMR (400 MHz, CDCl₃) δ 7.92-7.95 (m, 2H), 7.48-7.50 (m, 2H), 6.70 (s, 1H), 4.76 (d, J=4.6 Hz, 2H), 1.51-1.56 (m, 1H), 1.01 (dt, J=8.2, 3.5 Hz, 2H), 0.81 (td, J=7.4, 4.3 Hz, 2H). MS (ESI): m/z 239 (M+1).

N-(2-(4-chlorophenyl)-2-oxoethyl)cyclobutanecarboxamide (DKC1125b14) ¹H-NMR (400 MHz, CDCl₃) δ 7.91-7.94 (m, 2H), 7.46-7.49 (m, 2H), 6.50 (s, 1H), 4.74 (d, J=4.1 Hz, 2H), 3.11-3.20 (m, 1H), 1.85-2.38 (m, 6H). MS (ESI): m/z 253 (M+1).

N-(2-(4-chlorophenyl)-2-oxoethyl)thiophene-2-carboxamide (DKC1125b15) ¹H-NMR (400 MHz, CDCl₃) δ 7.94-7.97 (m, 2H), 7.64 (dd, J=3.7, 0.9 Hz, 1H), 7.47-7.52 (m, 3H), 7.09-7.19 (m, 2H), 4.90 (d, J=4.1 Hz, 2H). MS(ESI): m/z 281 (M+1).

N-(2-(4-chlorophenyl)-2-oxoethyl)-2-(methoxymethyl)benzamide (DKC1125b16) ¹H-NMR (400 MHz, CDCl₃) δ 9.19 (s, 1H), 8.25 (dd, J=7.8, 1.8 Hz, 1H), 7.97 (dt, J=9.0, 2.1 Hz, 2H), 7.42-7.49 (m, 3H), 6.98-7.08 (m, 2H), 4.97 (d, J=4.1 Hz, 2H), 4.25 (q, J=7.0 Hz, 2H), 1.70 (t, J=7.1 Hz, 3H). MS(ESI): m/z 319 (M+1).

N-(2-(4-chlorophenyl)-2-oxoethyl)-3,3-dimethylbutanamide (DKC1125b17) ¹H-NMR (400 MHz, CDCl₃) δ 7.93 (dt, J=9.0, 2.1 Hz, 2H), 7.48 (dt, J=9.0, 2.3 Hz, 2H), 6.52 (s, 1H), 4.75 (d, J=4.6 Hz, 2H), 2.20 (s, 2H), 1.07 (d, J=2.3 Hz, 9H). MS(ESI): m/z 269 (M+1).

N-(2-(4-chlorophenyl)-2-oxoethyl)pentanamide (DKC1125b18) ¹H-NMR (400 MHz, CDCl₃) δ 7.93 (dt, J=9.0, 2.3 Hz, 2H), 7.47-7.50 (m, 2H), 6.63 (s, 1H), 4.75 (d, J=4.6 Hz, 2H), 2.32 (t, J=7.5 Hz, 2H), 1.62-1.71 (m, 2H), 1.33-1.43 (m, 2H), 0.93 (td, J=7.2, 4.3 Hz, 3H). MS(ESI): m/z 255 (M+1).

N-(2-(4-chlorophenyl)-2-oxoethyl)-4-methoxybenzamide (DKC1125b19) ¹H-NMR (400 MHz, CDCl₃) δ 7.96-7.99 (m, 2H), 7.84-7.87 (m, 2H), 7.49-7.51 (m, 2H), 7.19 (s, 1H), 6.94-6.97 (m, 2H), 4.92 (d, J=4.1 Hz, 2H), 3.86 (d, J=4.1 Hz, 3H). MS(ESI): m/z 305 (M+1).

N-(2-(4-chlorophenyl)-2-oxoethyl)-3-nitrobenzenesulfonamide (DKC1125b20) ¹H-NMR (400 MHz, CDCl₃) δ 8.75 (t, J=1.8 Hz, 1H), 8.42-8.44 (m, 1H), 8.23 (d, J=7.8 Hz, 1H), 7.81 (d, J=8.2 Hz, 2H), 7.75 (t, J=8.0 Hz, 1H), 7.47 (d, J=8.7 Hz, 2H), 5.81 (s, 1H), 4.53 (d, J=4.1 Hz, 2H). MS(ESI): m/z 356 (M+1).

N-(2-(4-chlorophenyl)-2-oxoethyl)-2,4ifluorobenzamide (DKC1125b21) ¹H-NMR (400 MHz, CDCl₃) δ 8.11-8.18 (m, 1H), 7.97 (dt, J=9.0, 2.3 Hz, 2H), 7.77-7.80 (m, 1H), 7.50 (dt, J=9.0, 2.3 Hz, 2H), 6.98-7.03 (m, 1H), 6.88-6.95 (m, 1H), 4.96 (dd, J=4.1, 0.9 Hz, 2H). MS(ESI): m/z 311 (M+1).

N-(2-(4-chlorophenyl)-2-oxoethyl)-2-methoxyacetamide (DKC1125b22) ¹H-NMR (400 MHz, CDCl₃) δ 7.93 (dt, J=8.8, 2.2 Hz, 2H), 7.49 (dt, J=9.0, 2.1 Hz, 3H), 4.77 (d, J=4.6 Hz, 2H), 3.99 (s, 2H), 3.49 (s, 3H). MS(ESI): m/z 243 (M+1).

N-(2-(4-chlorophenyl)-2-oxoethyl)pivalamide (DKC1125b23) ¹H-NMR (400 MHz, CDCl₃) δ 7.92-7.95 (m, 2H), 7.47-7.50 (m, 2H), 6.79 (s, 1H), 4.71 (d, J=4.1 Hz, 2H), 1.27 (d, J=5.5 Hz, 9H). MS(ESI): m/z 255 (M+1).

N-(2-(4-chlorophenyl)-2-oxoethyl)-4-fluorobenzenesulfonamide (DKC1125b24) ¹H-NMR (400 MHz, CDCl₃) δ 7.92 (tt, J=7.3, 2.3 Hz, 2H), 7.80 (dt, J=9.0, 2.1 Hz, 2H), 7.45 (dt, J=8.8, 2.3 Hz, 2H), 7.18 (tt, J=8.8, 2.7 Hz, 2H), 5.73 (t, J=4.3 Hz, 1H), 4.46 (d, J=4.6 Hz, 2H). MS(ESI): m/z 329 (M+1).

N-(2-(4-chlorophenyl)-2-oxoethyl)-4-methylbenzenesulfonamide (DKC1125b25) ¹H-NMR (400 MHz, CDCl₃) δ 7.77-7.81 (m, 4H), 7.44 (dd, J=6.6, 1.6 Hz, 2H), 7.29 (d, J=8.2 Hz, 2H), 5.66 (s, 1H), 4.43 (d, J=4.6 Hz, 2H), 2.40 (s, 3H). MS(ESI): m/z 325 (M+1).

4-chloro-N-(2-(4-chlorophenyl)-2-oxoethyl)benzenesulfonamide (DKC1125b26) ¹H-NMR (400 MHz, CDCl₃) δ 7.99 (dt, J=9.3, 2.3 Hz, 1H), 7.78-7.85 (m, 3H), 7.61 (dt, J=9.0, 2.3 Hz, 1H), 7.44-7.49 (m, 3H), 5.71 (t, J=4.3 Hz, 1H), 4.45 (d, J=4.6 Hz, 2H). MS(ESI): m/z 345 (M+1).

N-(2-(4-chlorophenyl)-2-oxoethyl)-1-phenylmethanesulfonamide (DKC1125b27) ¹H-NMR (400 MHz, CDCl₃) δ 7.72 (dt, J=9.0, 2.1 Hz, 2H), 7.41-7.46 (m, 4H), 7.32-7.36 (m, 3H), 5.36 (t, J=4.3 Hz, 1H), 4.35 (s, 2H), 4.24 (d, J=4.6 Hz, 2H). MS(ESI): m/z 325 (M+1).

N-(2-(4-chlorophenyl)-2-oxoethyl)-4-methoxybenzenesulfonamide (DKC1125b28) ¹H-NMR (400 MHz, CDCl₃) δ 7.78-7.84 (m, 4H), 7.45 (dt, J=9.0, 2.3 Hz, 2H), 6.96 (dt, J=9.6, 2.5 Hz, 2H), 4.42 (d, J=4.6 Hz, 2H), 3.84 (s, 3H). MS(ESI): m/z 341 (M+1).

N-(2-(4-chlorophenyl)-2-oxoethyl)-3,5-bis(trifluoromethyl)benzamide (DKC1125b29) ¹H-NMR (400 MHz, CDCl₃) δ 8.33 (s, 2H), 8.04 (s, 1H), 7.98 (dd, J=6.9, 1.8 Hz, 2H), 7.53 (dd, J=6.9, 1.8 Hz, 2H), 7.46 (s, 1H), 4.97 (d, J=4.1 Hz, 2H). MS(ESI): m/z 411 (M+1).

N-(2-(4-chlorophenyl)-2-oxoethyl)-2-(trifluoromethyl)benzamide (DKC1125b30) ¹H-NMR (400 MHz, CDCl₃) δ 7.94 (d, J=8.7 Hz, 2H), 7.72 (d, J=7.3 Hz, 1H), 7.54-7.63 (m, 3H), 7.50 (d, J=8.7 Hz, 2H), 6.98 (s, 1H), 4.93 (d, J=4.6 Hz, 2H). MS(ESI): m/z 343 (M+1).

N-(2-(4-chlorophenyl)-2-oxoethyl)-3-(trifluoromethyl)benzamide (DKC1125b31) ¹H-NMR (400 MHz, CDCl₃) δ 8.15 (s, 1H), 8.05 (d, J=7.8 Hz, 1H), 7.96 (dt, J=9.0, 2.1 Hz, 2H), 7.76-7.79 (m, 1H), 7.59 (t, J=7.8 Hz, 1H), 7.48-7.51 (m, 2H), 4.94 (d, J=4.6 Hz, 2H). MS (ESI): m/z 343 (M+1).

N-(2-(4-chlorophenyl)-2-oxoethyl)-4-(trifluoromethyl)benzamide (DKC1125b32) ¹H-NMR (400 MHz, CDCl₃) δ 7.96-8.00 (m, 4H), 7.74 (d, J=8.2 Hz, 2H), 7.52 (dt, J=8.8, 2.2 Hz, 2H), 7.36 (s, 1H), 4.94 (d, J=4.1 Hz, 2H). MS(ESI): m/z 343 (M+1).

2-chloro-N-(2-(4-chlorophenyl)-2-oxoethyl)-4-fluorobenzamide (DKC1125b33) ¹H-NMR (400 MHz, CDCl₃) δ 7.96 (dt, J=9.0, 2.1 Hz, 2H), 7.80 (dd, J=8.7, 5.9 Hz, 1H), 7.51 (dt, J=9.0, 2.3 Hz, 2H), 7.46 (s, 1H), 7.19 (dd, J=8.5, 2.5 Hz, 1H), 7.05-7.10 (m, 1H), 4.95 (d, J=4.1 Hz, 2H). MS(ESI): m/z 327 (M+1).

N-(2-(4-chlorophenyl)-2-oxoethyl)-3-nitrobenzamide (DKC1125b34) ¹H-NMR (400 MHz, CDCl₃) δ 8.74 (t, J=1.8 Hz, 1H), 8.41 (dq, J=8.2, 1.1 Hz, 1H), 8.23 (dd, J=7.8, 0.9 Hz, 1H), 7.98-8.01 (m, 2H), 7.70 (t, J=8.0 Hz, 1H), 7.52-7.55 (m, 2H), 7.38 (s, 1H), 4.97 (d, J=4.1 Hz, 2H). MS(ESI): m/z 320 (M+1).

N-(2-(4-chlorophenyl)-2-oxoethyl)-3,4ifluorobenzamide (DKC1125b35) ¹H-NMR (400 MHz, CDCl₃) δ 7.97 (dt, J=9.0, 2.3 Hz, 2H), 7.75 (ddd, J=10.6, 7.4, 2.2 Hz, 1H), 7.61-7.65 (m, 1H), 7.51 (dt, J=9.0, 2.1 Hz, 2H), 7.23-7.29 (m, 2H), 4.91 (d, J=4.1 Hz, 2H). MS(ESI): m/z 311 (M+1).

3,5-dichloro-N-(2-(4-chlorophenyl)-2-oxoethyl)benzamide (DKC1125b36) ¹H-NMR (400 MHz, CDCl₃) δ 7.98 (dt, J=9.0, 2.3 Hz, 2H), 7.74 (d, J=1.8 Hz, 2H), 7.53 (td, J=4.5, 2.1 Hz, 3H), 7.21 (s, 1H), 4.91 (d, J=4.1 Hz, 2H). MS(ESI): m/z 344 (M+1).

2,3-dichloro-N-(2-(4-chlorophenyl)-2-oxoethyl)benzamide (DKC1125b37) ¹H-NMR (400 MHz, CDCl₃) δ 7.95 (d, J=7.8 Hz, 2H), 7.49-7.55 (m, 4H), 7.28 (t, J=7.5 Hz, 2H), 4.94 (d, J=4.1 Hz, 2H). MS(ESI): m/z 344 (M+1).

N-(2-(4-chlorophenyl)-2-oxoethyl)-4-(trifluoromethoxy)benzamide (DKC1125b38) ¹H-NMR (400 MHz, CDCl₃) δ 7.97 (dt, J=9.0, 2.1 Hz, 2H), 7.93 (dt, J=9.1, 2.4 Hz, 2H), 7.50 (dt, J=9.1, 2.0 Hz, 2H), 7.26-7.32 (m, 3H), 4.92 (d, J=4.1 Hz, 2H). MS(ESI): m/z 359 (M+1).

N-(2-(4-chlorophenyl)-2-oxoethyl)-3-(trifluoromethoxy)benzamide (DKC1125b39) ¹H-NMR (400 MHz, CDCl₃) δ 7.96 (dt, J=8.8, 2.2 Hz, 2H), 7.77-7.79 (m, 1H), 7.75 (s, 1H), 7.48-7.52 (m, 3H), 7.36-7.40 (m, 2H), 4.92 (d, J=4.1 Hz, 2H). MS(ESI): m/z 359 (M+1).

N-(2-(4-chlorophenyl)-2-oxoethyl)-3,5-dimethylbenzamide (DKC1125b40) ¹H-NMR (400 MHz, CDCl₃) δ 7.98 (dt, J=9.0, 2.1 Hz, 2H), 7.50 (dt, J=9.0, 2.1 Hz, 2H), 7.47 (s, 2H), 7.23 (s, 1H), 7.16 (s, 1H), 4.92 (d, J=4.1 Hz, 2H), 2.37 (s, 6H). MS(ESI): m/z 303 (M+1).

N-(2-(4-chlorophenyl)-2-oxoethyl)-2-(trifluoromethoxy)benzamide (DKC1125b41) ¹H-NMR (400 MHz, CDCl₃) δ 8.04 (dd, J=7.8, 1.4 Hz, 1H), 7.97 (dt, J=9.1, 2.1 Hz, 2H), 7.76 (s, 1H), 7.48-7.56 (m, 3H), 7.41 (td, J=7.5, 1.2 Hz, 1H), 7.35 (dd, J=8.2, 1.4 Hz, 1H), 4.96 (d, J=4.6 Hz, 2H). MS(ESI): m/z 359 (M+1).

N-(2-(4-chlorophenyl)-2-oxoethyl)-3,5imethoxybenzamide (DKC1125b42) ¹H-NMR (400 MHz, CDCl₃) δ 7.95 (dt, J=9.0, 2.1 Hz, 2H), 7.48 (dt, J=9.0, 2.3 Hz, 2H), 7.31 (t, J=3.9 Hz, 1H), 6.99 (d, J=2.3 Hz, 2H), 6.59 (t, J=2.3 Hz, 1H), 4.89 (d, J=4.6 Hz, 2H), 3.82 (s, 6H). MS(ESI): m/z 335 (M+1).

N-(2-(4-chlorophenyl)-2-oxoethyl)-[1,1′-biphenyl]-4-carboxamide (DKC1125b43) ¹H-NMR (400 MHz, CDCl₃) δ 7.95-8.01 (m, 4H), 7.70 (d, J=8.2 Hz, 2H), 7.62-7.65 (m, 2H), 7.46-7.54 (m, 4H), 7.40-7.42 (m, 1H), 7.31 (s, 1H), 4.96 (d, J=4.1 Hz, 2H). MS(ESI): m/z 351 (M+1).

4-chloro-N-(2-(4-chlorophenyl)-2-oxoethyl)benzamide (DKC1125b44) ¹H-NMR (400 MHz, CDCl₃) δ 7.90 (dd, J=6.6, 2.1 Hz, 2H), 7.75 (dd, J=8.7, 2.3 Hz, 2H), 7.36-7.45 (m, 4H), 7.23 (s, 1H), 4.85 (d, J=4.6 Hz, 2H). MS(ESI): m/z 309 (M+1).

Examples 88 to 121. Preparation of Compounds 88 to 122 (DKC1125c01 to 34) According to the Present Invention

Compounds 88 to 122 (DKC1125c01 to 34) of the present invention were synthesized according to the following Reaction Scheme 2.

Synthesis of 2-bromo-1-(4-(dimethylamino)phenyl)ethan-1-one (1)

To a solution of 1-(4-(dimethylamino)phenyl)ethan-1-one (5 g, 30.63 mmol) in HBr (100 mL) at 0° C. was added Br₂ (4.9 g, 30.63 mmol) dropwise over 1 hour. After the reaction was complete, the product was extracted twice with CH₂Cl₂ and washed with saturated NaHCO₃. The organic layer was dried with MgSO₄, and the solvent was evaporated. The resulting crude product was purified by column chromatography to obtain compound (1) (7.09 g, 95%) of reaction scheme 2.

¹H NMR (400 MHz, CDCl₃) δ 7.89 (d, J=9.0 Hz, 2H), 6.66 (d, J=9.0 Hz, 2H), 4.36 (s, 2H), 3.08 (s, 6H).

Synthesis of 2-amino-1-(4-(dimethylamino)phenyl)ethan-1-one hydrochloride (2)

2-bromo-1-(4-(dimethylamino)phenyl) ethan-1-one (1.6 g, 24.78 mmol) was dissolved in 20 mL of dry potassium phthalimide (5.05 g, 27.26 mmol) solution, and held at 75° C. for 18 hrs. The suspension was quenched in 90 mL of water with stirring, which was maintained for 40 min, and the product was collected, washed with 50 mL of water, and recrystallized from 50 mL of acetonitrile at 0° C. overnight. (4.58 g, 60%). The solid was dissolved in a solution (90 mL) of 1:2 of concentrated HCl and EtOH. The reaction was boiled under reflux for 2 hrs. The precipitate was filtered out and washed with water and then EtOH (2.61 g, 70%).

¹H NMR (400 MHz, (CD₃)₂SO) δ 7.91 (d, J=9.5 Hz, 2H) 6.66 (d, J=9.5 Hz, 2H), 5.06 (s, 2H), 1.22 (s, 6H).

General Preparation Method for Compounds 88 to 121 (DKC1125c01 to 34)

CH₂Cl₂ (1 mL) and saturated NaHCO₃ (2 mL) were stirred vigorously and chilled in an ice bath. Each acid chloride (0.29 mmol) described in Table 4 below was added, followed immediately by addition of 2-amino-1-(4-(dimethylamino)phenyl)ethan-1-one dihydrochloride (2, 50 mg, 0.29 mmol). Stirring was continued while warming to room temperature over period of 1 hour. The organic layer was then separated, and dried with Na₂SO₄, and the solvent was evaporated. The residue was purified by column chromatography (yield: 70 to 80%).

TABLE 4
Acid chlorides for preparation of compounds 88 to 121
(DKC1125c01 to 34)
Compounds  Acid chloride
DKC1125c01 4-Chlorobenzoyl chloride
DKC1125c02 2-Phenoxypropionyl chloride
DKC1125c03 2-Fluorobenzoyl chloride
DKC1125c04 4-Fluorobenzoyl chloride
DKC1125c05 2-Furoyl chloride
DKC1125c06 2-Chlorobenzoyl Chloride
DKC1125c07 3-Chlorobenzoyl chloride
DKC1125c08 Acryloyl chloride
DKC1125c09 o-Toluoyl chloride
DKC1125c10 3-Methoxybenzoyl chloride
DKC1125c11 m-Toluoyl chloride
DKC1125c12 Propionyl chloride
DKC1125c13 Cyclopropanecarbonylchloride
DKC1125c14 Thiophene-2-carbonyl chloride
DKC1125c15 tert-butylacetyl chloride
DKC1125c16 Pentanoyl chloride
DKC1125c17 4-Methoxybenzoyl chloride
DKC1125c18 2,4-Difluorobenzoyl chloride
DKC1125c19 Methoxyacetyl chloride
DKC1125c20 4-Fluorobenzenesulfonyl chloride
DKC1125c21 4-Chlorobenzenesulfonyl chloride
DKC1125c22 Benzenesulfonyl chloride
DKC1125c23 a-Toluenesulfonyl chloride
DKC1125c24 4-Methoxybenzenesulfonyl chloride
DKC1125c25 2-(Trifluoromethyl)benzoyl chloride
DKC1125c26 3-(Trifluoromethyl)benzoyl chloride
DKC1125c27 4-(Trifluoromethyl)benzoyl chloride
DKC1125c28 2-Chloro-4-fluorobenzoyl chloride
DKC1125c29 3,4-Difluorobenzoyl chloride
DKC1125c30 3,5-Dichlorobenzoyl chloride
DKC1125c31 2,3-Dichlorobenzoyl chloride
DKC1125c32 4-(Trifluoromethoxy)benzoyl chloride
DKC1125c33 3,5-Dimethylbenzoyl chloride
DKC1125c34 3,5-Dimethoxybenzoyl chloride

Confirmation of Preparation of Compounds 88 to 121 (DKC1125c01 to 34)

4-chloro-N-(2-(4-(dimethylamino)phenyl)-2-oxoethyl)benzamide (DKC1125c01) ¹H-NMR (400 MHz, CDCl₃) δ 7.90-7.92 (m, 2H), 7.83 (dd, J=6.4, 1.8 Hz, 2H), 7.42-7.44 (m, 3H), 6.68 (d, J=9.1 Hz, 2H), 4.83 (d, J=4.1 Hz, 2H), 3.09 (s, 6H). MS(ESI): m/z 318 (M+1).

N-(2-(4-(dimethylamino)phenyl)-2-oxoethyl)-2-phenoxypropanamide (DKC1125c02) ¹H-NMR (400 MHz, CDCl₃) δ 7.85 (dt, J=9.8, 2.5 Hz, 2H), 7.68 (s, 1H), 7.27-7.33 (m, 2H), 6.97-7.01 (m, 3H), 6.64 (dt, J=9.8, 2.5 Hz, 2H), 4.56-4.80 (m, 2H), 3.06 (d, J=7.3 Hz, 6H), 1.62 (d, J=6.4 Hz, 3H). MS(ESI): m/z 327 (M+1).

N-(2-(4-(dimethylamino)phenyl)-2-oxoethyl)-2-fluorobenzamide (DKC1125c03) ¹H-NMR (400 MHz, CDCl₃) δ 8.12 (td, J=7.8, 1.8 Hz, 1H), 8.01-8.04 (m, 1H), 7.93 (dt, J=9.6, 2.5 Hz, 2H), 7.46-7.52 (m, 1H), 7.25-7.29 (m, 1H), 7.14-7.19 (m, 1H), 6.66-6.70 (m, 2H), 4.89-4.90 (m, 2H), 3.08 (s, 6H). MS(ESI): m/z 301 (M+1).

N-(2-(4-(dimethylamino)phenyl)-2-oxoethyl)-4-fluorobenzamide (DKC1125c04) ¹H-NMR (400 MHz, CDCl₃) δ 7.87-7.94 (m, 4H), 7.42 (d, J=11.0 Hz, 1H), 7.11-7.16 (m, 2H), 6.68 (dd, J=12.1, 3.0 Hz, 2H), 4.84 (d, J=4.1 Hz, 2H), 3.11 (d, J=15.1 Hz, 6H). MS(ESI): m/z 301 (M+1).

N-(2-(4-(dimethylamino)phenyl)-2-oxoethyl)furan-2-carboxamide (DKC1125c05) ¹H-NMR (400 MHz, CDCl₃) δ 7.90-7.93 (m, 2H), 7.56 (s, 1H), 7.50 (t, J=0.9 Hz, 1H), 7.15 (d, J=3.7 Hz, 1H), 6.67-6.70 (m, 2H), 6.51 (q, J=1.7 Hz, 1H), 4.82 (d, J=4.1 Hz, 2H), 3.09 (s, 6H). MS(ESI): m/z 273 (M+1).

2-chloro-N-(2-(4-(dimethylamino)phenyl)-2-oxoethyl)benzamide (DKC1125c06) ¹H-NMR (400 MHz, CDCl₃) δ 7.90-7.93 (m, 2H), 7.72 (dd, J=7.5, 2.1 Hz, 1H), 7.54 (s, 1H), 7.31-7.45 (m, 3H), 6.67-6.70 (m, 2H), 4.88 (d, J=4.1 Hz, 2H), 3.09 (s, 6H). MS(ESI): m/z 318 (M+1).

3-chloro-N-(2-(4-(dimethylamino)phenyl)-2-oxoethyl)benzamide (DKC1125c07) ¹H-NMR (400 MHz, CDCl₃) δ 7.88-7.94 (m, 3H), 7.75 (dt, J=7.8, 1.4 Hz, 1H), 7.50 (dq, J=8.1, 1.0 Hz, 1H), 7.38-7.44 (m, 2H), 6.68-6.70 (m, 2H), 4.84 (d, J=4.1 Hz, 2H), 3.10 (s, 6H). MS(ESI): m/z 318 (M+1).

N-(2-(4-(dimethylamino)phenyl)-2-oxoethyl)acrylamide (DKC1125c08) ¹H-NMR (400 MHz, CDCl₃) δ 7.86-7.91 (m, 2H), 6.86 (s, 1H), 6.67 (dt, J=9.8, 2.5 Hz, 2H), 6.35 (dd, J=16.9, 1.8 Hz, 1H), 6.25 (dd, J=17.2, 9.8 Hz, 1H), 5.70 (dd, J=10.1, 1.8 Hz, 1H), 4.74 (d, J=4.1 Hz, 2H), 3.09 (s, 6H). MS(ESI): m/z 233 (M+1).

N-(2-(4-(dimethylamino)phenyl)-2-oxoethyl)-2-methylbenzamide (DKC1125c09) ¹H-NMR (400 MHz, CDCl₃) δ 7.91 (dt, J=9.8, 2.5 Hz, 2H), 7.49 (d, J=7.3 Hz, 1H), 7.33 (td, J=7.5, 1.5 Hz, 1H), 7.23-7.26 (m, 2H), 7.04 (s, 1H), 6.66-6.70 (m, 2H), 4.86 (d, J=4.1 Hz, 2H), 3.09 (s, 6H), 2.50 (s, 3H). MS(ESI): m/z 297 (M+1).

N-(2-(4-(dimethylamino)phenyl)-2-oxoethyl)-4-methoxybenzamide (DKC1125c10) ¹H-NMR (400 MHz, CDCl₃) δ 7.93 (dt, J=9.6, 2.5 Hz, 2H), 7.42-7.46 (m, 3H), 7.37 (t, J=8.0 Hz, 1H), 7.05-7.08 (m, 1H), 6.69 (dt, J=9.8, 2.3 Hz, 2H), 4.85 (d, J=3.7 Hz, 2H), 3.87 (s, 3H), 3.10 (s, 6H) MS(ESI): m/z 313 (M+1).

N-(2-(4-(dimethylamino)phenyl)-2-oxoethyl)-3-methylbenzamide (DKC1125c11) ¹H-NMR (400 MHz, CDCl₃) δ 7.91-7.94 (m, 2H), 7.69 (dd, J=8.2, 6.4 Hz, 2H), 7.44 (s, 1H), 7.32-7.37 (m, 2H), 6.69 (d, J=9.1 Hz, 2H), 4.85 (d, J=3.7 Hz, 2H), 3.11 (d, J=14.6 Hz, 6H), 2.40 (d, J=14.2 Hz, 3H). MS(ESI): m/z 297 (M+1).

N-(2-(4-(dimethylamino)phenyl)-2-oxoethyl)propionamide (DKC1125c12) ¹H-NMR (400 MHz, CDCl₃) δ 7.86-7.92 (m, 2H), 6.65-6.71 (m, 3H), 4.66 (d, J=4.1 Hz, 2H), 3.08 (t, J=15.3 Hz, 6H), 2.34 (q, J=7.6 Hz, 2H), 1.18-1.25 (m, 3H). MS (ESI): m/z 235 (M+1).

N-(2-(4-(dimethylamino)phenyl)-2-oxoethyl)cyclopropanecarboxamide (DKC1125c13) ¹H-NMR (400 MHz, CDCl₃) δ 7.86-7.91 (m, 2H), 6.86 (s, 1H), 6.67 (dt, J=9.8, 2.5 Hz, 2H), 4.68 (d, J=4.3 Hz, 2H), 3.08 (s, 6H), 1.54 (tt, J=8.4, 3.8 Hz, 1H), 1.00 (dt, J=8.1, 3.3 Hz, 2H), 0.78 (dt, J=11.6, 3.4 Hz, 2H). MS(ESI): m/z 247 (M+1).

N-(2-(4-(dimethylamino)phenyl)-2-oxoethyl)thiophene-2-carboxamide (DKC1125c14) ¹H-NMR (400 MHz, CDCl₃) δ 7.92 (dt, J=9.6, 2.4 Hz, 2H), 7.63 (dd, J=3.9, 1.1 Hz, 1H), 7.50 (dd, J=5.0, 0.9 Hz, 1H), 7.29 (s, 1H), 7.11 (dd, J=5.0, 3.7 Hz, 1H), 6.68 (dt, J=9.8, 2.3 Hz, 2H), 4.83 (d, J=4.1 Hz, 2H), 3.09 (s, 6H). MS(ESI): m/z 289 (M+1).

N-(2-(4-(dimethylamino)phenyl)-2-oxoethyl)-3,3-dimethylbutanamide (DKC1125c15) ¹H-NMR (400 MHz, CDCl₃) δ 7.87 (dt, J=9.6, 2.5 Hz, 2H), 6.66 (dt, J=9.8, 2.5 Hz, 2H), 6.61 (s, 1H), 4.67 (d, J=4.1 Hz, 2H), 3.07 (d, J=8.7 Hz, 6H), 2.19 (s, 2H), 1.07 (s, 9H). MS(ESI): m/z 277 (M+1).

N-(2-(4-(dimethylamino)phenyl)-2-oxoethyl)pentanamide (DKC1125c16) ¹H-NMR (400 MHz, CDCl₃) δ 7.87-7.90 (m, 2H), 6.65-6.68 (m, 3H), 4.66 (d, J=4.1 Hz, 2H), 3.08 (s, 6H), 2.30 (t, J=7.5 Hz, 2H), 1.63-1.71 (m, 2H), 1.34-1.41 (m, 3H), 0.93 (t, J=7.3 Hz, 3H). MS(ESI): m/z 263 (M+1).

N-(2-(4-(dimethylamino)phenyl)-2-oxoethyl)-4-methoxybenzamide (DKC1125c17) ¹H-NMR (400 MHz, CDCl₃) δ 7.93 (dt, J=9.8, 2.5 Hz, 2H), 7.86 (dt, J=9.5, 2.5 Hz, 2H), 7.36 (s, 1H), 6.93-6.97 (m, 2H), 6.68-6.71 (m, 2H), 4.84 (d, J=4.1 Hz, 2H), 3.87 (d, J=4.1 Hz, 3H), 3.09 (s, 6H). MS(ESI): m/z 313 (M+1).

N-(2-(4-(dimethylamino)phenyl)-2-oxoethyl)-2,4ifluorobenzamide (DKC1125c18) ¹H-NMR (400 MHz, CDCl₃) δ 8.15 (td, J=8.9, 6.7 Hz, 1H), 7.91-7.97 (m, 3H), 6.98-7.02 (m, 1H), 6.89-6.95 (m, 1H), 6.69 (dt, J=9.8, 2.3 Hz, 2H), 4.88-4.89 (m, 2H), 3.10 (s, 6H). MS(ESI): m/z 319 (M+1).

N-(2-(4-(dimethylamino)phenyl)-2-oxoethyl)-2-methoxyacetamide (DKC1125c19) ¹H-NMR (400 MHz, CDCl₃) δ 7.88 (dt, J=9.8, 2.5 Hz, 2H), 7.64 (s, 1H), 6.67 (dt, J=9.6, 2.4 Hz, 2H), 4.70 (d, J=4.6 Hz, 2H), 3.98 (s, 2H), 3.48 (s, 3H), 3.08 (s, 6H). MS(ESI): m/z 251 (M+1).

N-(2-(4-(dimethylamino)phenyl)-2-oxoethyl)-4-fluorobenzenesulfonamide (DKC1125c20) ¹H-NMR (400 MHz, CDCl₃) δ 7.88-7.94 (m, 2H), 7.73 (dt, J=9.8, 2.5 Hz, 2H), 7.13-7.18 (m, 2H), 6.60-6.63 (m, 2H), 5.83 (t, J=4.1 Hz, 1H), 4.35 (d, J=4.1 Hz, 2H), 3.02-3.09 (m, 6H). MS(ESI): m/z 337 (M+1).

4-chloro-N-(2-(4-(dimethylamino)phenyl)-2-oxoethyl)benzenesulfonamide (DKC1125c21) ¹H-NMR (400 MHz, CDCl₃) δ 7.83 (dt, J=9.0, 2.3 Hz, 2H), 7.72 (dt, J=9.8, 2.5 Hz, 2H), 7.45 (dt, J=9.0, 2.3 Hz, 2H), 6.61 (dt, J=9.7, 2.5 Hz, 2H), 5.85 (t, J=4.1 Hz, 1H), 4.35 (d, J=4.1 Hz, 2H), 3.02-3.09 (m, 6H). MS(ESI): m/z 354 (M+1).

N-(2-(4-(dimethylamino)phenyl)-2-oxoethyl)benzenesulfonamide (DKC1125c22) ¹H-NMR (400 MHz, CDCl₃) δ 7.88-7.93 (m, 2H), 7.73 (dt, J=9.6, 2.4 Hz, 2H), 7.46-7.57 (m, 3H), 6.59-6.63 (m, 2H), 5.82 (t, J=3.9 Hz, 1H), 4.35 (d, J=4.6 Hz, 2H), 3.02-3.07 (m, 6H). MS(ESI): m/z 319 (M+1).

N-(2-(4-(dimethylamino)phenyl)-2-oxoethyl)-1-phenylmethanesulfonamide (DKC1125c23) ¹H-NMR (400 MHz, CDCl₃) δ 7.67-7.71 (m, 2H), 7.39-7.43 (m, 2H), 7.32-7.34 (m, 3H), 6.60-6.64 (m, 2H), 5.46 (t, J=4.1 Hz, 1H), 4.33 (d, J=8.7 Hz, 2H), 4.23 (d, J=4.1 Hz, 2H), 3.08 (s, 6H). MS(ESI): m/z 333 (M+1).

N-(2-(4-(dimethylamino)phenyl)-2-oxoethyl)-4-methoxybenzenesulfonamide (DKC1125c24) ¹H-NMR (400 MHz, CDCl₃) δ 7.80 (dt, J=9.5, 2.5 Hz, 2H), 7.71 (dt, J=9.9, 2.4 Hz, 2H), 6.92 (dt, J=9.5, 2.5 Hz, 2H), 6.58-6.61 (m, 2H), 5.73 (t, J=4.3 Hz, 1H), 4.31 (d, J=4.6 Hz, 2H), 3.81 (s, 3H), 3.02 (d, J=17.4 Hz, 6H). MS(ESI): m/z 349 (M+1).

N-(2-(4-(dimethylamino)phenyl)-2-oxoethyl)-2-(trifluoromethyl)benzamide (DKC1125c25) ¹H-NMR (400 MHz, CDCl₃) δ 7.91 (dt, J=9.6, 2.4 Hz, 2H), 7.72-7.75 (m, 1H), 7.61-7.65 (m, 2H), 7.55-7.60 (m, 1H), 7.11 (s, 1H), 6.69 (dt, J=9.8, 2.5 Hz, 2H), 4.87 (d, J=4.1 Hz, 2H), 3.10 (d, J=6.4 Hz, 6H). MS(ESI): m/z 351 (M+1).

N-(2-(4-(dimethylamino)phenyl)-2-oxoethyl)-3-(trifluoromethyl)benzamide (DKC1125c26) ¹H-NMR (400 MHz, CDCl₃) δ 8.18 (s, 1H), 8.07 (d, J=7.8 Hz, 1H), 7.94 (dt, J=9.8, 2.3 Hz, 2H), 7.79 (d, J=7.8 Hz, 1H), 7.62 (t, J=7.8 Hz, 1H), 7.51 (s, 1H), 6.71 (dt, J=9.8, 2.5 Hz, 2H), 4.87 (d, J=4.1 Hz, 2H), 3.11 (s, 6H). MS(ESI): m/z 351 (M+1).

N-(2-(4-(dimethylamino)phenyl)-2-oxoethyl)-4-(trifluoromethyl)benzamide (DKC1125c27) ¹H-NMR (400 MHz, CDCl₃) δ 8.00 (d, J=8.2 Hz, 2H), 7.92 (dd, J=7.1, 2.1 Hz, 2H), 7.73 (d, J=7.8 Hz, 2H), 7.52 (s, 1H), 6.68-6.70 (m, 2H), 4.86 (d, J=4.1 Hz, 2H), 3.10 (s, 6H). MS(ESI): m/z 351 (M+1).

2-chloro-N-(2-(4-(dimethylamino)phenyl)-2-oxoethyl)-4-fluorobenzamide (DKC1125c28) ¹H-NMR (400 MHz, CDCl₃) δ 7.90-7.93 (m, 2H), 7.79 (dd, J=8.5, 6.2 Hz, 1H), 7.58 (s, 1H), 7.19 (dd, J=8.5, 2.5 Hz, 1H), 7.05-7.10 (m, 1H), 6.69 (dd, J=9.4, 2.5 Hz, 2H), 4.88 (d, J=4.1 Hz, 2H), 3.10 (d, J=3.7 Hz, 6H). MS(ESI): m/z 336 (M+1).

N-(2-(4-(dimethylamino)phenyl)-2-oxoethyl)-3,4ifluorobenzamide (DKC1125c29) ¹H-NMR (400 MHz, CDCl₃) δ 7.90-7.93 (m, 2H), 7.74-7.79 (m, 1H), 7.64 (tt, J=6.1, 2.0 Hz, 1H), 7.42 (s, 1H), 7.22-7.29 (m, 1H), 6.68-6.71 (m, 2H), 4.83-4.89 (m, 2H), 3.13 (d, J=15.1 Hz, 5H). MS(ESI): m/z 319 (M+1).

3,5-dichloro-N-(2-(4-(dimethylamino)phenyl)-2-oxoethyl)benzamide (DKC1125c30) ¹H-NMR (400 MHz, CDCl₃) δ 7.93 (dt, J=9.8, 2.5 Hz, 2H), 7.75-7.77 (m, 2H), 7.52 (q, J=2.3 Hz, 1H), 7.42 (s, 1H), 6.68-6.72 (m, 2H), 4.83 (d, J=3.7 Hz, 2H), 3.10-3.15 (m, 6H). MS(ESI): m/z 352 (M+1).

2,3-dichloro-N-(2-(4-(dimethylamino)phenyl)-2-oxoethyl)benzamide (DKC1125c31) ¹H-NMR (400 MHz, CDCl₃) δ 7.91 (dt, J=9.8, 2.5 Hz, 2H), 7.54 (ddd, J=10.6, 7.9, 1.5 Hz, 2H), 7.33 (s, 1H), 7.27-7.31 (m, 1H), 6.69 (dt, J=9.6, 2.5 Hz, 2H), 4.88 (d, J=4.1 Hz, 2H), 3.11 (s, 6H). MS (ESI): m/z 352 (M+1).

N-(2-(4-(dimethylamino)phenyl)-2-oxoethyl)-4-(trifluoromethoxy)benzamide (DKC1125c32) ¹H-NMR (400 MHz, CDCl₃) δ 7.91-7.97 (m, 4H), 7.45 (s, 1H), 7.30-7.32 (m, 2H), 6.70 (dt, J=9.8, 2.5 Hz, 2H), 4.85 (d, J=4.1 Hz, 2H), 3.11 (s, 6H). MS(ESI): m/z 367 (M+1).

N-(2-(4-(dimethylamino)phenyl)-2-oxoethyl)-3,5-dimethylbenzamide (DKC1125c33) ¹H-NMR (400 MHz, CDCl₃) δ 7.91-7.95 (m, 2H), 7.49 (s, 2H), 7.42 (d, J=3.7 Hz, 1H), 7.15 (s, 1H), 6.69 (dd, J=11.9, 2.7 Hz, 2H), 4.84 (d, J=4.1 Hz, 2H), 3.11 (d, J=15.1 Hz, 6H), 2.34-2.37 (m, 6H) MS(ESI): m/z 311 (M+1).

N-(2-(4-(dimethylamino)phenyl)-2-oxoethyl)-3,5imethoxybenzamide (DKC1125c34) ¹H-NMR (400 MHz, CDCl₃) δ 7.93 (dd, J=11.9, 2.7 Hz, 2H), 7.39 (s, 1H), 7.01 (d, J=2.3 Hz, 2H), 6.69 (dd, J=11.9, 2.7 Hz, 2H), 6.60 (t, J=2.3 Hz, 1H), 4.84 (d, J=4.1 Hz, 2H), 3.83-3.89 (m, 6H), 3.10 (s, 6H). MS(ESI): m/z 343 (M+1).

Examples 122 to 129. Preparation of Compounds 122 to 129 (DKC1125d01 to 08) According to the Present Invention

Compounds 122 to 129 (DKC1125d01 to 08) of the present invention were synthesized according to the following Reaction Scheme 3.

Synthesis of 2-amino-1-(3-methoxyphenyl)ethan-1-one hydrochloride (3)

2-bromo-1-(3-methoxyphenyl)ethan-1-one (5 g, 21.83 mmol) was dissolved in 25 mL of CH₂Cl₂ and treated with hexamethylenetetramine (3.06 g, 21.83 mmol). After overnight at room temperature, the reaction product was cooled with an ice bath and the formed precipitate was washed with CH₂Cl₂ and EtOH to obtain the hexamethylenetetramine salt. The desired amine was obtained by treating the salt with a solution (90 mL) of concentrated HCl and EtOH (1:2). The formed precipitate was filtered out and washed with water and then EtOH (2.95 g, 65%).

¹H NMR (400 MHz, (CD₃)₂SO) δ 8.50 (s, 3H), 7.61 (dd, J=0.9, 7.8 Hz, 1H), 7.50-7.53 (m, 2H), 7.31 (m, 1H), 4.58 (d, J=4.4 Hz, 2H), 3.85 (s, 3H).

General Preparation Method for Compounds 122 to 129 (DKC1125d01 to 08)

CH₂Cl₂ (1 mL) and saturated NaHCO₃ (2 mL) were stirred vigorously and chilled in an ice bath. Each acid chloride (0.29 mmol) described in Table 5 below was added, followed immediately by addition of 2-amino-1-(3-methoxyphenyl)ethan-1-one hydrochloride (3, 50 mg, 0.29 mmol). Stirring was continued while warming to room temperature over a period of 1 hour. The organic layer was then separated, and dried with Na₂SO₄, and the solvent was evaporated (yield: 80 to 90%).

TABLE 5
Acid chlorides used in preparation of 122 to 129
(DKC1125d01 to 08)
Compounds  Acid chloride
DKC1125d01 4-Chlorobenzoyl chloride
DKC1125d02 Crotonyl chloride
DKC1125d03 Propionyl chloride
DKC1125d04 Cyclopropanecarbonylchloride
DKC1125d05 Cyclobutanecarbonyl chloride
DKC1125d06 Thiophene-2-carbonyl chloride
DKC1125d07 Pentanoyl chloride
DKC1125d08 Benzenesulfonyl chloride

Confirmation of Preparation of Compounds 122 to 129 (DKC1125d01 to 08)

4-chloro-N-(2-(3-methoxyphenyl)-2-oxoethyl)benzamide (DKC1125d01) ¹H-NMR (400 MHz, CDCl₃) δ 7.83 (dd, J=8.7, 2.3 Hz, 2H), 7.61 (dd, J=7.7, 0.8 Hz, 1H), 7.52-7.54 (m, 2H), 7.44 (dd, J=8.2, 1.8 Hz, 3H), 7.29 (s, 1H), 7.19 (dd, J=8.2, 2.7 Hz, 1H), 4.94 (d, J=4.1 Hz, 2H). MS(ESI): m/z 305 (M+1).

(E)-N-(2-(3-methoxyphenyl)-2-oxoethyl)but-2-enamide (DKC1125d02) ¹H-NMR (400 MHz, CDCl₃) δ 7.58 (d, J=7.8 Hz, 1H), 7.50 (t, J=2.1 Hz, 1H), 7.41 (t, J=8.0 Hz, 1H), 7.17 (dd, J=8.0, 2.5 Hz, 1H), 6.92 (q, J=7.3 Hz, 1H), 5.98 (dd, J=15.3, 1.6 Hz, 1H), 4.83 (d, J=4.1 Hz, 2H), 3.87 (s, 3H), 1.89 (dd, J=6.9, 1.4 Hz, 3H), 1.61 (d, J=6.4 Hz, 1H). MS(ESI): m/z 234 (M+1).

N-(2-(3-methoxyphenyl)-2-oxoethyl) propionamide (DKC1125d03) ¹H-NMR (400 MHz, CDCl₃) δ 7.64-7.50 (1H), 7.50-7.43 (1H), 7.43-7.33 (1H), 7.20-7.07 (1H), 6.72-6.46 (1H), 4.77-4.68 (2H), 3.87-3.77 (3H), 2.38-2.25 (2H), 1.25-1.08 (3H). MS(ESI): m/z 222 (M+1).

N-(2-(3-methoxyphenyl)-2-oxoethyl)cyclopropanecarboxamide (DKC1125d04) ¹H-NMR (400 MHz, CDCl₃) δ 7.56 (d, J=7.8 Hz, 1H), 7.49 (t, J=2.1 Hz, 1H), 7.41 (q, J=7.8 Hz, 1H), 7.16 (dd, J=8.2, 2.3 Hz, 1H), 6.79 (s, 1H), 4.78 (d, J=4.1 Hz, 2H), 3.86 (s, 3H), 1.53-1.59 (m, 1H), 0.99-1.04 (m, 2H), 0.78-0.84 (m, 2H) MS (ESI): m/z 234 (M+1).

N-(2-(3-methoxyphenyl)-2-oxoethyl)cyclobutanecarboxamide (DKC1125d05) ¹H-NMR (400 MHz, CDCl₃) δ 7.56 (dd, J=7.8, 1.4 Hz, 1H), 7.49 (q, J=1.4 Hz, 1H), 7.41 (t, J=8.0 Hz, 1H), 7.16 (dt, J=8.2, 1.4 Hz, 1H), 6.51 (s, 1H), 4.75 (d, J=4.1 Hz, 2H), 3.86 (s, 3H), 3.11-3.20 (m, 1H), 2.29-2.39 (m, 2H), 2.17-2.25 (m, 2H), 1.85-2.05 (m, 2H). MS(ESI): m/z 248 (M+1).

N-(2-(3-methoxyphenyl)-2-oxoethyl)thiophene-2-carboxamide (DKC1125d06) ¹H-NMR (400 MHz, CDCl₃) δ 7.62 (d, J=3.7 Hz, 1H), 7.59 (d, J=7.8 Hz, 1H), 7.49-7.51 (m, 2H), 7.41 (t, J=8.0 Hz, 1H), 7.17 (dd, J=8.2, 2.7 Hz, 1H), 7.13 (s, 1H), 7.10 (t, J=4.3 Hz, 1H), 4.91 (d, J=4.1 Hz, 2H). MS(ESI): m/z 276 (M+1).

N-(2-(3-methoxyphenyl)-2-oxoethyl)pentanamide (DKC1125d07) ¹H-NMR (400 MHz, CDCl₃) δ 7.56 (dd, J=6.4, 1.4 Hz, 1H), 7.49 (q, J=1.4 Hz, 1H), 7.40 (t, J=8.0 Hz, 1H), 7.16 (dq, J=8.2, 1.2 Hz, 1H), 6.64 (s, 1H), 4.76 (d, J=4.6 Hz, 2H), 3.86 (s, 3H), 2.32 (t, J=7.8 Hz, 2H), 1.64-1.71 (m, 2H), 1.34-1.41 (m, 2H), 0.94 (t, J=7.3 Hz, 3H). MS(ESI): m/z 250 (M+1).

N-(2-(3-methoxyphenyl)-2-oxoethyl)benzenesulfonamide (DKC1125d08) ¹H-NMR (400 MHz, CDCl₃) δ 7.89-7.92 (m, 2H), 7.48-7.58 (m, 3H), 7.34-7.42 (m, 3H), 7.14 (dq, J=8.0, 1.2 Hz, 1H), 5.77 (t, J=4.3 Hz, 1H), 4.47 (d, J=4.6 Hz, 2H), 3.83 (s, 3H). MS(ESI): m/z 306 (M+1).

Examples 130 to 136. Preparation of Compounds 130 to 129 (DKC1125e01 to 07) According to the Present Invention

Synthesis of Compounds 130 to 136 (DKC1125e01 to 07)

Compounds 130 to 136 (DKC1125e01-07) of the present invention were synthesized according to the following Reaction Scheme 4.

Synthesis of 2-amino-1-(pyridin-3-yl) ethan-1-one hydrochloride (4)

2-bromo-1-(pyridin-3-yl)ethan-1-one (5 g, 25.00 mmol) was dissolved in 25 mL of CH₂Cl₂ and treated with a solution of hexamethylenetetramine (3.50 g, 25.00 mmol) in 25 mL of CH₂Cl₂. After overnight at room temperature, the reaction product was cooled with an ice bath and the formed precipitate was washed with CH₂Cl₂ and EtOH to obtain the hexamethylenetetramine salt. The desired amine was obtained by treating the salt with a solution (90 mL) of concentrated hydrochloric acid and ethanol (1:2). The formed precipitate was filtered out and washed with water and then ethanol to obtain the title compound (1.30 g, 30%).

¹H-NMR (400 MHz, (CD₃)₂SO) δ 9.24 (t, J=1.1 Hz, 1H), 8.93 (q, J=2.3 Hz, 1H), 8.57 (s, 2H), 8.49 (dt, J=8.1, 1.9 Hz, 1H), 7.73-7.76 (m, 1H), 4.67 (d, J=5.5 Hz, 2H).

General Preparation Method for Compounds 130 to 136 (DKC1125e01 to 07)

CH₂Cl₂ (1 mL) and saturated NaHCO₃ (2 mL) were stirred vigorously and chilled in an ice bath. Each acid chloride (0.29 mmol) described in Table 6 below was added, followed immediately by addition of 2-amino-1-(pyridin-3-yl)ethan-1-one hydrochloride (4, 50 mg, 0.29 mmol). Stirring was continued while warming to room temperature over a period of 1 hour. The organic layer was then separated, and dried with Na₂SO₄, and the solvent was evaporated. The residue was purified by column chromatography (yield: 30 to 40%).

TABLE 6
Acid chlorides used in preparation
of compounds 130 to 136
(DKC1125e01 to 07)
Compounds  Acid chloride
DKC1125e01 4-Chlorobenzoyl chloride
DKC1125e02 2-Phenoxypropiony chloride
DKC1125e03 2-Fluorobenzoyl chloride
DKC1125e04 4-Fluorobenzoyl chloride
DKC1125e05 Crotonyl chloride
DKC1125e06 o-Toluoyl chloride
DKC1125e07 Propionyl chloride

Confirmation of Preparation of Compounds 130 to 136 (DKC1125e01 to 07)

4-chloro-N-(2-oxo-2-(pyridin-3-yl)ethyl)benzamide (DKC1125e01) ¹H-NMR (400 MHz, CDCl₃) δ 9.23 (s, 1H), 8.84 (d, J=3.7 Hz, 1H), 8.27 (dt, J=7.9, 1.9 Hz, 1H), 7.80 (dt, J=9.0, 2.1 Hz, 2H), 7.47 (dd, J=8.0, 4.8 Hz, 1H), 7.42 (dt, J=9.0, 2.1 Hz, 2H), 7.25 (s, 1H), 4.95 (d, J=4.6 Hz, 2H). MS(ESI): m/z 276 (M+1).

N-(2-oxo-2-(pyridin-3-yl)ethyl)-2-phenoxypropanamide (DKC1125e02) ¹H-NMR (400 MHz, CDCl₃) δ 9.18 (d, J=1.8 Hz, 1H), 8.83 (dd, J=4.8, 1.6 Hz, 1H), 8.24 (dt, J=7.8, 1.8 Hz, 1H), 7.45-7.51 (m, 2H), 7.31 (t, J=8.0 Hz, 2H), 6.96-7.04 (m, 3H), 4.68-4.87 (m, 3H), 1.63 (d, J=6.9 Hz, 3H) MS(ESI): m/z 285 (M+1).

2-fluoro-N-(2-oxo-2-(pyridin-3-yl)ethyl)benzamide (DKC1125e03) ¹H-NMR (400 MHz, CDCl₃) δ 9.27 (s, 1H), 8.87 (d, J=3.7 Hz, 1H), 8.32 (dt, J=8.2, 1.8 Hz, 1H), 8.11 (td, J=8.0, 1.8 Hz, 1H), 7.84 (d, J=11.9 Hz, 1H), 7.49-7.54 (m, 2H), 7.26-7.30 (m, 1H), 7.18 (ddd, J=11.9, 8.2, 0.9 Hz, 1H), 5.02-5.03 (m, 2H). MS(ESI): m/z 259 (M+1).

4-fluoro-N-(2-oxo-2-(pyridin-3-yl)ethyl)benzamide (DKC1125e04) ¹H-NMR (400 MHz, CDCl₃) δ 9.22 (s, 1H), 8.83 (d, J=3.7 Hz, 1H), 8.27 (dt, J=8.2, 1.8 Hz, 1H), 7.85-7.88 (m, 2H), 7.46 (q, J=4.1 Hz, 1H), 7.24 (d, J=4.1 Hz, 1H), 7.09-7.13 (m, 2H), 4.94 (d, J=4.6 Hz, 2H). MS(ESI): m/z 259 (M+1).

(E)-N-(2-oxo-2-(pyridin-3-yl)ethyl)but-2-enamide (DKC1125e05) ¹H-NMR (400 MHz, CDCl₃) δ 9.32-9.09 (1H), 8.92-8.71 (1H), 8.35-8.16 (1H), 7.60-7.35 (1H), 6.96-6.84 (1H), 6.00-5.89 (1H), 4.88-4.81 (2H), 1.92-1.75 (3H). MS(ESI): m/z 205 (M+1).

2-methyl-N-(2-oxo-2-(pyridin-3-yl)ethyl)benzamide (DKC1125e06) ¹H-NMR (400 MHz, CDCl₃) δ 9.24 (d, J=1.8 Hz, 1H), 8.86 (dd, J=4.8, 1.1 Hz, 1H), 8.30 (dt, J=7.9, 1.9 Hz, 1H), 7.50 (q, J=4.1 Hz, 2H), 7.34-7.38 (m, 1H), 7.23-7.27 (m, 2H), 6.88 (s, 1H), 4.98 (d, J=4.6 Hz, 2H), 2.50 (s, 3H). MS(ESI): m/z 255 (M+1).

N-(2-oxo-2-(pyridin-3-yl)ethyl) propionamide (DKC1125e07) ¹H-NMR (400 MHz, CDCl₃) δ 9.21 (d, J=2.3 Hz, 1H), 8.85 (dd, J=4.8, 1.6 Hz, 1H), 8.27 (dt, J=8.1, 1.9 Hz, 1H), 7.46-7.50 (m, 1H), 6.57 (s, 1H), 4.80 (d, J=4.1 Hz, 2H), 2.37 (q, J=7.6 Hz, 2H), 1.20-1.26 (m, 3H). MS(ESI): m/z 193 (M+1).

Examples 137 to 150. Preparation of Compounds 137 to 150 (DKC1125f01 to 14) According to the Present Invention

Synthesis of Compounds 137-150 (DKC1125f01 to 14)

Compounds 137 to 140 (DKC1125f01 to 14) of the present invention were synthesized according to the following Reaction Scheme 5.

Synthesis of 2-bromo-1-(4-morpholinophenyl)ethan-1-one (5)

To a solution of 1-(4-morpholinophenyl)ethan-1-one (5 g, 24.36 mmol) in HBr (100 mL) at 0° C. was added Br₂ (3.89 g, 24.36 mmol) dropwise over 1 hour. After the reaction was complete, the product was extracted twice with CH₂Cl₂ and washed with saturated NaHCO₃. The organic layer was dried with MgSO₄, and the solvent was evaporated. The resulting crude product was purified by column chromatography to give compound (1) of Reaction Scheme 5 (6.23 g, 90%).

¹H NMR (400 MHz, CDCl₃) δ 7.95 (d, J=4.0 Hz, 2H), 7.04 (d, J=4.0 Hz, 2H), 4.60 (s, 2H), 3.83 (m, 4H), 3.65 (m, 4H).

Synthesis of 2-Amino-1-[4-(morpholin-4-yl)phenyl]ethan-1-one dihydrochloride (6)

The 2-bromo-1-(4-morpholinophenyl)ethan-1-one (5, 6 g, 21.11 mmol) was dissolved in 20 mL of dry potassium phthalimide solution (4.30 g, 23.22 mmol), and held at 75° C. for 18 hrs. The suspension was quenched in 90 mL of water with stirring, which was maintained for 40 min, and the product was collected, washed with 50 mL of water, and recrystallized from 50 mL of acetonitrile at 0° C. overnight. (4.58 g, 60%). The solid was dissolved in a solution (90 mL) of concentrated HCl and EtOH (1:2). The reaction product was boiled under reflux for 2 hrs. The precipitate was filtered out and washed with water and then EtOH (3.79 g, 70%).

¹H-NMR (400 MHz, (CD₃)₂SO) δ 1.87 (d, J=9.0 Hz, 2H), 7.03 (d, J=9.0 Hz, 2H), 4.45 (d, J=4.5 Hz, 2H), 3.73 (dd, J=4.0, 5.0 Hz, 4H), 3.35 (dd, J=4.0, 5.0 Hz, 4H).

General Preparation Method for Compounds 137 to 150 (DKC1125f01 to 14)

CH₂Cl₂ (1 mL) and saturated NaHCO₃ (2 mL) were stirred vigorously and chilled in an ice bath. Each acid chloride (0.29 mmol) shown in Table 7 below was added, followed immediately by addition of 2-amino-1-(4-morpholinophenyl)ethan-1-one dihydrochloride (6, 50 mg, 0.29 mmol). Stirring was continued while warming to room temperature over a period of 1 hr. The organic layer was then separated, and dried with Na₂SO₄, and the solvent was evaporated. The residue was purified by column chromatography (yield: 65 to 80%).

TABLE 7
Acid chlorides used in preparation
of compounds 137 to 150
(DKC1125f01 to 14)
Compounds  Acid chloride
DCK1125f01 2-Fluorobenzoyl chloride
DCK1125f02 2-Chlorobenzoyl Chloride
DCK1125f03 Crotonyl chloride
DCK1125f04 3-Methoxybenzoyl chloride
DCK1125f05 m-Toluoyl chloride
DCK1125f06 Propionyl chloride
DCK1125f07 Cyclopropanecarbonylchloride
DCK1125f08 Cyclobutanecarbonyl chloride
DCK1125f09 Pentanoyl chloride
DCK1125f10 4-Fluorobenzenesulfonyl chloride
DCK1125f11 4-Chlorobenzenesulfonyl chloride
DCK1125f12 Benzenesulfonyl chloride
DCK1125f13 a-Toluenesulfonyl chloride
DCK1125f14 4-Methoxybenzenesulfonyl chloride

Confirmation of Preparation of Compounds 137 to 150 (DKC1125f01 to 14)

2-fluoro-N-(2-(4-morpholinophenyl)-2-oxoethyl)benzamide (DKC1125f01) ¹H-NMR (400 MHz, CDCl₃) δ 8.13 (td, J=7.8, 1.8 Hz, 1H), 7.95-7.99 (m, 3H), 7.48-7.53 (m, 1H), 7.26-7.30 (m, 1H), 7.16-7.21 (m, 1H), 6.91 (dt, J=9.6, 2.4 Hz, 2H), 4.92 (dd, J=4.1, 0.9 Hz, 2H), 3.88 (t, J=5.0 Hz, 4H), 3.36 (t, J=4.8 Hz, 4H). MS (ESI): m/z 343 (M+1).

2-chloro-N-(2-(4-morpholinophenyl)-2-oxoethyl)benzamide (DKC1125f02) ¹H-NMR (400 MHz, CDCl₃) δ 7.94 (dt, J=9.6, 2.4 Hz, 2H), 7.73 (dd, J=7.8, 1.8 Hz, 1H), 7.49 (s, 1H), 7.32-7.45 (m, 3H), 6.90 (dd, J=11.9, 2.7 Hz, 2H), 4.90 (d, J=4.6 Hz, 2H), 3.86 (t, J=5.0 Hz, 4H), 3.36 (t, J=5.0 Hz, 4H). MS(ESI): m/z 360 (M+1).

(E)-N-(2-(4-morpholinophenyl)-2-oxoethyl)but-2-enamide (DKC1125f03) ¹H-NMR (400 MHz, CDCl₃) δ 7.92 (d, J=8.7 Hz, 2H), 6.87-6.95 (m, 3H), 6.65 (s, 1H), 5.96 (dd, J=15.3, 1.6 Hz, 1H), 4.75 (d, J=4.1 Hz, 2H), 3.86 (t, J=4.8 Hz, 4H), 3.35 (t, J=4.8 Hz, 4H), 1.89 (d, J=6.9 Hz, 3H). MS(ESI): m/z 289 (M+1).

4-methoxy-N-(2-(4-morpholinophenyl)-2-oxoethyl)benzamide (DKC1125f04) ¹H-NMR (400 MHz, CDCl₃) δ 7.96 (d, J=9.1 Hz, 2H), 7.33-7.45 (m, 4H), 7.06-7.08 (m, 1H), 6.91 (d, J=8.7 Hz, 2H), 4.87 (d, J=4.1 Hz, 2H), 3.86-3.88 (m, 8H), 3.36 (t, J=5.0 Hz, 3H). MS(ESI): m/z 355 (M+1).

3-methyl-N-(2-(4-morpholinophenyl)-2-oxoethyl)benzamide (DKC1125f05) ¹H-NMR (400 MHz, CDCl₃) δ 7.97 (d, J=9.1 Hz, 2H), 7.69 (dd, J=8.9, 6.6 Hz, 2H), 7.35-7.38 (m, 3H), 6.92 (d, J=8.7 Hz, 2H), 4.88 (d, J=4.1 Hz, 2H), 3.88 (t, J=4.8 Hz, 4H), 3.37 (t, J=4.8 Hz, 4H), 2.43 (s, 3H). MS(ESI): m/z 339 (M+1).

N-(2-(4-morpholinophenyl)-2-oxoethyl)propionamide (DKC1125f06) ¹H-NMR (400 MHz, CDCl₃) δ 7.89-7.93 (m, 2H), 6.89 (dt, J=11.9, 2.3 Hz, 2H), 6.65 (s, 1H), 4.69 (d, J=4.1 Hz, 2H), 3.87 (t, J=5.0 Hz, 4H), 3.35 (t, J=5.0 Hz, 4H), 2.35 (q, J=7.6 Hz, 2H), 1.22 (t, J=7.5 Hz, 4H). MS (ESI): m/z 377 (M+1).

N-(2-(4-morpholinophenyl)-2-oxoethyl)cyclopropanecarboxamide (DKC1125f07) ¹H-NMR (400 MHz, CDCl₃) δ 7.92 (d, J=9.1 Hz, 2H), 6.89 (d, J=9.1 Hz, 2H), 6.81 (s, 1H), 4.71 (d, J=4.1 Hz, 2H), 3.87 (t, J=5.0 Hz, 4H), 3.35 (t, J=5.0 Hz, 4H), 1.52-1.58 (m, 1H), 0.99-1.03 (m, 2H), 0.80 (dt, J=11.6, 3.4 Hz, 2H). MS (ESI): m/z 289 (M+1).

N-(2-(4-morpholinophenyl)-2-oxoethyl)cyclobutanecarboxamide (DKC1125f08) ¹H-NMR (400 MHz, CDCl₃) δ 7.90-7.93 (m, 2H), 6.89 (dd, J=11.9, 2.7 Hz, 2H), 6.56 (s, 1H), 4.68 (d, J=4.1 Hz, 2H), 3.87 (t, J=5.0 Hz, 4H), 3.35 (t, J=5.0 Hz, 4H), 3.11-3.19 (m, 1H), 2.29-2.39 (m, 2H), 2.17-2.25 (m, 2H), 1.88-2.06 (m, 2H). MS (ESI): m/z 303 (M+1).

N-(2-(4-morpholinophenyl)-2-oxoethyl)pentanamide (DKC1125f09) ¹H-NMR (400 MHz, CDCl₃) δ 7.91 (d, J=9.1 Hz, 2H), 6.89 (d, J=9.1 Hz, 2H), 6.64 (s, 1H), 4.69 (d, J=4.1 Hz, 2H), 3.87 (t, J=4.8 Hz, 4H), 3.35 (t, J=5.0 Hz, 4H), 2.32 (t, J=7.5 Hz, 2H), 1.64-1.72 (m, 2H), 1.36-1.44 (m, 2H), 0.94 (t, J=7.3 Hz, 3H). MS(ESI): m/z 305 (M+1).

4-fluoro-N-(2-(4-morpholinophenyl)-2-oxoethyl)benzenesulfonamide (DKC1125f10) ¹H-NMR (400 MHz, CDCl₃) δ 7.92 (qd, J=4.8, 2.5 Hz, 2H), 7.76-7.79 (m, 2H), 7.15-7.20 (m, 2H), 6.83-6.86 (m, 2H), 4.38 (d, J=4.1 Hz, 2H), 3.86 (t, J=4.8 Hz, 4H), 3.34 (t, J=5.0 Hz, 4H). MS(ESI): m/z 379 (M+1).

4-chloro-N-(2-(4-morpholinophenyl)-2-oxoethyl)benzenesulfonamide (DKC1125f11) ¹H-NMR (400 MHz, CDCl₃) δ 7.82-7.92 (m, 2H), 7.75-7.78 (m, 2H), 7.47 (dt, J=9.1, 2.3 Hz, 2H), 6.82-6.85 (m, 2H), 5.78 (t, J=4.3 Hz, 1H), 4.38 (d, J=4.6 Hz, 2H), 3.84-3.89 (m, 4H), 3.34 (t, J=5.0 Hz, 4H). MS(ESI): m/z 396 (M+1).

N-(2-(4-morpholinophenyl)-2-oxoethyl)benzenesulfonamide (DKC1125f12) ¹H-NMR (400 MHz, CDCl₃) δ 7.89-7.94 (m, 2H), 7.77 (dd, J=7.1, 2.1 Hz, 2H), 7.48-7.57 (m, 4H), 6.84 (d, J=9.1 Hz, 2H), 4.39 (d, J=4.6 Hz, 2H), 3.84-3.88 (m, 5H), 3.33 (t, J=5.0 Hz, 4H). MS (ESI): m/z 361 (M+1).

N-(2-(4-morpholinophenyl)-2-oxoethyl)-1-phenylmethanesulfonamide (DKC1125f13) ¹H-NMR (400 MHz, CDCl₃) δ 7.72 (dt, J=9.6, 2.4 Hz, 2H), 7.40-7.45 (m, 2H), 7.33-7.37 (m, 3H), 6.83-6.86 (m, 2H), 4.33 (s, 2H), 4.25 (d, J=4.6 Hz, 2H), 3.87 (t, J=4.8 Hz, 4H), 3.35 (t, J=5.0 Hz, 4H). MS(ESI): m/z 375 (M+1).

4-methoxy-N-(2-(4-morpholinophenyl)-2-oxoethyl)benzenesulfonamide (DKC1125f14) ¹H-NMR (400 MHz, CDCl₃) δ 7.82 (dt, J=9.5, 2.4 Hz, 2H), 7.76 (d, J=9.1 Hz, 2H), 6.94 (dt, J=9.6, 2.5 Hz, 2H), 6.83 (d, J=9.1 Hz, 2H), 5.72 (t, J=4.1 Hz, 1H), 4.35 (d, J=4.6 Hz, 2H), 3.85 (dd, J=8.9, 3.9 Hz, 7H), 3.32 (t, J=5.0 Hz, 4H). MS(ESI): m/z 391 (M+1).

Examples 151 to 200. Preparation of Compounds 151 to 200 (DKC1125 g01 to 50) According to the Present Invention

Synthesis of Compounds 151 to 200 (DKC1125 g01 to 50)

Compounds 151 to 200 (DKC1125 g01 to 50) of the present invention were synthesized according to the following Reaction Scheme 6.

Synthesis of 2-((1-(tert-butoxycarbonyl)) piperidin-4-yl) oxy) benzoic acid (1)

To a solution of tert-butyl 4-(2-(methoxycarbonyl)phenoxy)piperidine-1-carboxylate (2.0 g, 5.69 mol) in methanol (20 mL) was added 4N NaOH (6 mL). The resulting solution was stirred at 65° C. for 6 hrs. The reaction monitored by checking TLC. After completion of the reaction, to the resulting mixture added water and HCl to maintain acidic pH, followed by extraction with EA. The organic layer was separated and washed with brine (3×100 mL). The washed solution was dried with anhydrous Na₂SO₄, and the solvent was evaporated in vacuum. The residue was purified by column chromatography (EtOAc:Hexane 1:1) to give the title compound (1) as white powder (1.8 g, 90%).

¹H-NMR (400 MHz, CDCl₃) δ 8.20 (dd, J=7.8, 1.8 Hz, 1H), 7.52-7.57 (m, 1H), 7.12-7.17 (m, 1H), 7.06 (d, J=8.2 Hz, 1H), 4.73-4.79 (m, 1H), 4.09-4.14 (m, 1H), 3.83 (q, J=4.4 Hz, 2H), 3.29 (tt, J=13.3, 4.4 Hz, 2H), 2.04 (d, J=3.7 Hz, 8H), 1.84 (tt, J=13.0, 4.3 Hz, 2H), 1.47 (s, 9H). MS (ESI): m/z 322 (M+1).

Synthesis of tert-butyl 4-(2-((2-oxo-2-phenylethyl) carbonyl) phenoxy) piperidine-1-carboxylate (2)

To a solution of 2-((1-(tert-butoxycarbonyl))piperidin-4-yl)oxy)benzoic acid (1, 1.0 g, 3.11 mol) (1.0 g, 3.11 mol) and 2-amino-1-phenylethan-1-one (534 mg, 3.11 mol) in DMF (10 mL) was added DIEA (1.3 mL, 7.78 mol) with stirring, followed by addition of HATU (1.1 g, 3.11 mmol). The resulting solution was stirred at room temperature for 10 hrs. The reaction was monitored by checking TLC. After completions of reaction, to the resulting mixture was added water, followed by extraction with EA. The organic layer was separated and washed with brine (3×100 mL). The washed solution was dried with anhydrous sodium sulphate, and the solvent was evaporated. The residue was purified by column chromatography (EtOAc: Hexane 2:3) to give the title compound (2) as white powder (1.3 g, 76%).

¹H-NMR (400 MHz, CDCl₃) δ 9.00 (s, 1H), 8.24 (dd, J=8.0, 2.1 Hz, 1H), 7.63 (tt, J=7.4, 1.4 Hz, 2H), 7.50-7.54 (m, 2H), 7.44 (dd, J=8.7, 1.4 Hz, 2H), 7.02-7.10 (m, 2H), 5.01 (d, J=3.7 Hz, 2H), 4.66-4.71 (m, 1H), 3.95 (s, 2H), 3.17-3.23 (m, 2H), 2.96 (d, J=5.5 Hz, 4H), 1.47 (s, 9H) MS (ESI): m/z 439 (M+1).

Synthesis of N-(2-oxo-2-phenylethyl)-2-(piperidin-4-yloxy) benzamine (3)

To a solution of tert-butyl 4-(2-((2-oxo-2-phenylethyl) carbonyl) phenyl) piperidine-1-carboxylate (2, 1.0 g, 3.11 mol) in anhydrous dichloromethane (20 mL) was added trifluoroacetic acid (1.3 mL, 7.78 mol) under nitrogen gas. The resulting solution was stirred at room temperature for 2 hrs. After completion of the reaction, the solvent was evaporated from the mixture, and the residue was purified by column chromatography to give the title compound (3) as a yellow solid (0.9 g, 90%).

¹H-NMR (400 MHz, CDCl₃) δ 9.12 (s, 1H), 8.25 (dd, J=7.8, 1.8 Hz, 1H), 8.03-8.05 (m, 2H), 7.61-7.65 (m, 1H), 7.50-7.54 (m, 2H), 7.44 (dd, J=8.7, 1.4 Hz, 1H), 7.03-7.09 (m, 2H), 5.30 (s, 1H), 5.02 (d, J=4.1 Hz, 2H), 4.61-4.68 (m, 1H), 3.26 (td, J=8.7, 4.3 Hz, 2H), 2.78-2.84 (m, 2H), 2.17-2.25 (m, 4H). MS (ESI): m/z 339 (M+1).

General Preparation Method for Compounds 150 to 200 (DKC1125 g01 to 50)

To a solution of N-(2-oxo-2-phenylethyl)-2-(piperidin-4-yloxy)benzamine (3, 10 mg, 0.029 mmol) and each acid chloride (10 μL, 0.07 mmol) shown in Table 8 below in dichloromethane was added triethylamine (3.7 μL, 0.029 mmol). The reaction mixture was stirred at room temperature for 1 hr. After completion of the reaction, the mixture was evaporated and purified by column chromatography to give (EtOAc: Hexane 1:2) to obtain the title compound as a solid (12 mg, 83%).

TABLE 8
Acid chlorides used in preparation of compounds 150 to 200
(DKC1125g01 to 50)
Compounds  Acid Chloride
DKC1125g01 4-Chlorobenzoyl chloride
DKC1125g02 2-Phenoxypropionyl chloride
DKC1125g03 2-Fluorobenzoyl chloride
DKC1125g04 4-Fluorobenzoyl chloride
DKC1125g05 2-Furoyl chloride
DKC1125g06 2-Chlorobenzoyl Chloride
DKC1125g07 3-Chlorobenzoyl chloride
DKC1125g08 Crotonyl chloride
DKC1125g09 3-Phenylpropionyl chloride
DKC1125g10 Acryloyl chloride
DKC1125g11 o-Toluoyl chloride
DKC1125g12 3-Methoxybenzoyl chloride
DKC1125g13 m-Toluoyl chloride
DKC1125g14 Propionyl chloride
DKC1125g15 Cyclohexanecarbonyl chloride
DKC1125g16 Cyclopropanecarbonylchloride
DKC1125g17 Cyclobutanecarbonyl chloride
DKC1125g18 Thiophene-2-carbonyl chloride
DKC1125g19 2-Ethoxybenzoyl chloride
DKC1125g20 tert-butylacetyl chloride
DKC1125g21 4-Morpholinecarbonyl chloride
DKC1125g22 Pentanoyl chloride
DKC1125g23 4-Methoxybenzoyl chloride
DKC1125g24 4-Cyanobenzoyl chloride
DKC1125g25 3-nitrobenzene-1-sulfonyl chloride
DKC1125g26 O-Acetylsalicyloyl chloride
DKC1125g27 2,4-Difluorobenzoyl chloride
DKC1125g28 Methoxyacetyl chloride
DKC1125g29 Pivaloyl chloride
DKC1125g30 Dimethylcarbamyl chloride
DKC1125g31 4-Bromobenzoyl chloride
DKC1125g32 Acetyl chloride
DKC1125g33 Methanesulfonyl chloride
DKC1125g34 4-Fluorobenzenesulfonyl chloride
DKC1125g35 p-Toluenesulfonyl chloride
DKC1125g36 4-Chlorobenzenesulfonyl chloride
DKC1125g37 Benzenesulfonyl chloride
DKC1125g38 a-Toluenesulfonyl chloride
DKC1125g39 4-Methoxybenzenesulfonyl chloride
DKC1125g40 3,5-Bis(trifluoromethyl)benzoyl chloride
DKC1125g41 2-(Trifluoromethyl)benzoyl chloride
DKC1125g42 3-(Trifluoromethyl)benzoyl chloride
DKC1125g43 4-(Trifluoromethyl)benzoyl chloride
DKC1125g44 2-Chloro-4-fluorobenzoyl chloride
DKC1125g45 3-Nitrobenzoyl chloride
DKC1125g46 3,4-Difluorobenzoyl chloride
DKC1125g47 3,5-Dichlorobenzoyl chloride
DKC1125g48 2,3-Dichlorobenzoyl chloride
DKC1125g49 4-(Trifluoromethoxy)benzoyl chloride
DKC1125g50 3-(Trifluoromethoxy)benzoyl chloride

Confirmation of Preparation of Compounds 150 to 200 (DKC1125 g01 to 50)

2-((1-(4-chlorobenzoyl)piperidin-4-yl)oxy)-N-(2-oxo-2-phenylethyl)benzamide (DKC1125 g01) ¹H-NMR (400 MHz, CDCl₃) δ 8.98 (s, 1H), 8.25 (dd, J=7.8, 1.8 Hz, 1H), 8.00-8.08 (m, 2H), 7.63-7.67 (m, 1H), 7.61-7.65 (m, 1H), 7.53-7.57 (m, 2H), 7.36-7.43 (m, 2H), 7.28-7.32 (m, 2H), 7.03-7.12 (m, 2H), 5.02 (d, J=4.1 Hz, 2H), 4.61-4.68 (m, 1H), 3.26 (td, J=8.7, 4.3 Hz, 2H), 2.78-2.84 (m, 2H), 2.17-2.25 (m, 4H). MS (ESI): m/z 477 (M+1).

N-(2-oxo-2-phenylethyl)-2-((1-(2-phenoxypropanoyl)piperidin-4-yl)oxy)benzamide (DKC1125 g02) ¹H-NMR (400 MHz, CDCl₃) δ 8.96 (s, 1H), 8.20 (dd, J=7.8, 1.8 Hz, 1H), 7.80-8.91 (m, 2H), 7.64-7.68 (m, 2H), 7.53-7.57 (m, 2H), 7.36-7.43 (m, 2H), 7.28-7.34 (m, 2H), 7.03-7.12 (m, 2H), 5.01 (d, J=4.1 Hz, 2H), 4.7-4.9 (m, 1H), 4.61-4.68 (m, 1H), 3.26 (td, J=8.7, 4.3 Hz, 2H), 2.87 (s, 3H), 2.78-2.84 (m, 2H), 2.17-2.25 (m, 4H). MS (ESI): m/z 487 (M+1).

2-((1-(2-fluorobenzoyl)piperidin-4-yl)oxy)-N-(2-oxo-2-phenylethyl)benzamide (DKC1125 g03) ¹H-NMR (400 MHz, CDCl₃) δ 8.99 (s, 1H), 8.28 (dd, J=7.8, 1.8 Hz, 1H), 8.30-8.08 (m, 2H), 7.68-7.69 (m, 2H), 7.53-7.57 (m, 2H), 7.36-7.43 (m, 2H), 7.28-7.34 (m, 2H), 7.03-7.12 (m, 2H), 5.02 (d, J=4.1 Hz, 2H), 4.61-4.68 (m, 1H), 3.26 (td, J=8.7, 4.3 Hz, 2H), 2.78-2.84 (m, 2H), 2.17-2.25 (m, 4H). MS (ESI): m/z 461 (M+1).

2-((1-(4-fluorobenzoyl)piperidin-4-yl)oxy)-N-(2-oxo-2-phenylethyl)benzamide (DKC1125 g04) ¹H-NMR (400 MHz, CDCl₃) δ 8.98 (s, 1H), 8.25 (dd, J=7.8, 1.8 Hz, 1H), 8.00-8.08 (m, 2H), 7.63-7.67 (m, 2H), 7.54-7.58 (m, 2H), 7.36-7.43 (m, 2H), 7.28-7.34 (m, 2H), 7.06-7.14 (m, 2H), 5.02 (d, J=4.1 Hz, 2H), 4.61-4.68 (m, 1H), 3.26 (td, J=8.7, 4.3 Hz, 2H), 2.78-2.84 (m, 2H), 2.17-2.25 (m, 4H). MS (ESI): m/z 461 (M+1).

2-((1-(furan-2-carbonyl)piperidin-4-yl)oxy)-N-(2-oxo-2-phenylethyl)benzamide (DKC1125 g05) ¹H-NMR (400 MHz, CDCl₃) δ 8.98 (s, 1H), 8.25 (dd, J=7.8, 1.8 Hz, 1H), 8.10-8.18 (m, 2H), 7.63-7.67 (m, 2H), 7.53-7.57 (m, 2H), 7.36-7.43 (m, 2H), 7.28-7.32 (m, 2H), 7.03-7.12 (m, 1H), 5.02 (d, J=4.1 Hz, 2H), 4.61-4.68 (m, 1H), 3.26 (td, J=8.7, 4.3 Hz, 2H), 2.78-2.84 (m, 2H), 2.17-2.25 (m, 4H). MS (ESI): m/z 433 (M+1).

2-((1-(2-chlorobenzoyl)piperidin-4-yl)oxy)-N-(2-oxo-2-phenylethyl)benzamide (DKC1125 g06) ¹H-NMR (400 MHz, CDCl₃) δ 8.98 (s, 1H), 8.25 (dd, J=7.8, 1.8 Hz, 1H), 8.00-8.08 (m, 2H), 7.61-7.65 (m, 2H), 7.53-7.57 (m, 2H), 7.36-7.43 (m, 2H), 7.28-7.32 (m, 2H), 7.06-7.12 (m, 2H), 5.02 (d, J=4.1 Hz, 2H), 4.61-4.68 (m, 1H), 3.26 (td, J=8.7, 4.3 Hz, 2H), 2.78-2.84 (m, 2H), 2.17-2.25 (m, 4H). MS (ESI): m/z 477 (M+1).

2-((1-(3-chlorobenzoyl)piperidin-4-yl)oxy)-N-(2-oxo-2-phenylethyl)benzamide (DKC1125 g07) ¹H-NMR (400 MHz, CDCl₃) δ 8.98 (s, 1H), 8.25 (dd, J=7.8, 1.8 Hz, 1H), 8.00-8.08 (m, 2H), 7.63-7.67 (m, 1H), 7.61-7.65 (m, 1H), 7.53-7.57 (m, 2H), 7.36-7.43 (m, 2H), 7.20-7.30 (m, 2H), 7.03-7.12 (m, 2H), 5.02 (d, J=4.1 Hz, 2H), 4.61-4.68 (m, 1H), 3.26 (td, J=8.7, 4.3 Hz, 2H), 2.78-2.84 (m, 2H), 2.17-2.25 (m, 4H). MS (ESI): m/z 477 (M+1).

(E)-2-((1-(but-2-enoyl)piperidin-4-yl)oxy)-N-(2-oxo-2-phenylethyl)benzamide (DKC1125 g08) ¹H-NMR (400 MHz, CDCl₃) δ 9.12 (s, 1H), 8.20 (dd, J=7.8, 1.8 Hz, 1H), 8.08-8.12 (m, 2H), 7.61-7.65 (m, 1H), 7.50-7.54 (m, 2H), 7.44 (dd, J=8.7, 1.4 Hz, 1H), 7.03-7.09 (m, 2H), 5.30 (s, 1H), 5.02 (d, J=4.1 Hz, 2H), 4.61-4.68 (m, 1H), 3.26 (td, J=8.7, 4.3 Hz, 2H), 2.88 (s, 1H), 2.78-2.84 (m, 1H), 2.6 (s, 3H), 2.17-2.25 (m, 4H), 2.16 (s, 1H), 1.94-2.03 (m, 2H). MS (ESI): m/z 407 (M+1).

N-(2-oxo-2-phenylethyl)-2-((1-(3-phenylpropanoyl) piperidin-4-yl)oxy)benzamide (DKC1125 g09) ¹H-NMR (400 MHz, CDCl₃) δ 8.95 (s, 1H), 8.25 (dd, J=7.8, 1.8 Hz, 1H), 8.02-8.08 (m, 2H), 7.63-7.67 (m, 1H), 7.61-7.65 (m, 2H), 7.53-7.57 (m, 2H), 7.36-7.43 (m, 2H), 7.22-7.32 (m, 2H), 7.03-7.12 (m, 2H), 5.01 (d, J=4.1 Hz, 2H), 4.60-4.64 (m, 1H), 3.26 (td, J=8.7, 4.3 Hz, 2H), 2.78-2.84 (m, 2H), 2.58-2.70 (m, 2H), 2.54 (d, J=2.4 Hz, 2H), 2.17-2.25 (m, 4H). MS (ESI): m/z 471 (M+1).

2-((1-acryloylpiperidin-4-yl)oxy)-N-(2-oxo-2-phenylethyl)benz amide (DKC1125 g10) ¹H-NMR (400 MHz, CDCl₃) δ 9.12 (s, 1H), 8.25 (dd, J=7.8, 1.8 Hz, 1H), 8.03-8.05 (m, 2H), 7.61-7.65 (m, 1H), 7.50-7.54 (m, 2H), 7.42 (dd, J=8.6, 1.3 Hz, 1H), 7.03-7.09 (m, 2H), 6.20 (s, 2H), 5.02 (s, 2H), 4.61-4.68 (m, 1H), 3.26 (td, J=8.7, 4.3 Hz, 2H), 2.6 (s, 2H), 2.17-2.25 (m, 4H), 1.94-2.03 (m, 3H). MS (ESI): m/z 393 (M+1).

2-((1-(2-methylbenzoyl)piperidin-4-yl)oxy)-N-(2-oxo-2-phenylethyl)benzamide (DKC1125 g11) ¹H-NMR (400 MHz, CDCl₃) δ 8.93 (s, 1H), 8.20 (dd, J=7.4, 1.8 Hz, 1H), 8.02-8.06 (m, 2H), 7.62-7.64 (m, 1H), 7.60-7.63 (m, 1H), 7.53-7.57 (m, 2H), 7.36-7.43 (m, 2H), 7.20-7.30 (m, 2H), 7.03-7.12 (m, 2H), 5.02 (d, J=4.1 Hz, 2H), 4.61-4.68 (m, 1H), 3.26 (td, J=8.7, 4.3 Hz, 2H), 2.9 (s, 3H), 2.78-2.84 (m, 2H), 2.17-2.25 (m, 4H). MS (ESI): m/z 457 (M+1).

2-((1-(2-methoxybenzoyl)piperidin-4-yl)oxy)-N-(2-oxo-2-phenylethyl)benzamide (DKC1125 g12) ¹H-NMR (400 MHz, CDCl₃) δ 8.90 (s, 1H), 8.24 (dd, J=7.8, 1.8 Hz, 1H), 8.01-8.07 (m, 2H), 7.64-7.69 (m, 1H), 7.61-7.65 (m, 1H), 7.53-7.57 (m, 2H), 7.36-7.43 (m, 2H), 7.20-7.30 (m, 2H), 7.03-7.12 (m, 2H), 5.02 (d, J=4.1 Hz, 2H), 4.61-4.68 (m, 1H), 3.9 (s, 3H), 3.26 (td, J=8.7, 4.3 Hz, 2H), 2.78-2.84 (m, 2H), 2.17-2.25 (m, 4H). MS (ESI): m/z 473 (M+1).

2-((1-(3-methylbenzoyl)piperidin-4-yl)oxy)-N-(2-oxo-2-phenylethyl)benzamide (DKC1125 g13) ¹H-NMR (400 MHz, CDCl₃) δ 8.98 (s, 1H), 8.25 (dd, J=7.8, 1.8 Hz, 1H), 8.12-8.18 (m, 2H), 7.63-7.67 (m, 1H), 7.61-7.65 (m, 1H), 7.53-7.57 (m, 2H), 7.36-7.43 (m, 2H), 7.22-7.32 (m, 2H), 7.03-7.12 (m, 2H), 5.02 (d, J=4.1 Hz, 2H), 4.61-4.68 (m, 1H), 3.26 (td, J=8.7, 4.3 Hz, 2H), 2.9 (s, 3H), 2.78-2.84 (m, 2H), 2.17-2.25 (m, 4H). MS (ESI): m/z 457 (M+1).

N-(2-oxo-2-phenylethyl)-2-((1-propionylpiperidin-4-yl)oxy)benzamide (DKC1125 g14) ¹H-NMR (400 MHz, CDCl₃) δ 9.12 (s, 1H), 8.25 (dd, J=7.8, 1.8 Hz, 1H), 8.03-8.05 (m, 2H), 7.61-7.65 (m, 1H), 7.50-7.54 (m, 2H), 7.42 (dd, J=8.6, 1.3 Hz, 1H), 7.03-7.09 (m, 2H), 5.30 (s, 2H), 4.61-4.68 (m, 1H), 3.26 (td, J=8.7, 4.3 Hz, 2H), 2.79 (m, 2H), 2.78-2.84 (m, 2H), 2.17-2.25 (m, 4H), 1.94-2.03 (m, 3H). MS (ESI): m/z 395 (M+1).

2-((1-(cyclohexanecarbonyl)piperidin-4-yl)oxy)-N-(2-oxo-2-phenylethyl)benzamide (DKC1125 g15) ¹H-NMR (400 MHz, CDCl₃) δ 9.12 (s, 1H), 8.25 (dd, J=7.8, 1.8 Hz, 1H), 8.03-8.05 (m, 2H), 7.61-7.65 (m, 1H), 7.50-7.54 (m, 2H), 7.44 (dd, J=8.7, 1.4 Hz, 1H), 7.03-7.09 (m, 2H), 5.30 (s, 1H), 4.61-4.68 (m, 1H), 4.20-4.40 (m, 1H), 3.26 (td, J=8.7, 4.3 Hz, 2H), 2.88 (s, 2H), 2.78-2.84 (m, 2H), 2.50-2.68 (m, 4H), 2.22-2.46 (m, 2H), 2.17-2.25 (m, 4H), 2.06-2.14 (m, 2H). MS (ESI): m/z 449 (M+1).

2-((1-(cyclopropanecarbonyl) piperidin-4-yl)oxy)-N-(2-oxo-2-phenylethyl)benzamide (DKC1125 g16) ¹H-NMR (400 MHz, CDCl₃) δ 9.12 (s, 1H), 8.25 (dd, J=7.8, 1.8 Hz, 1H), 8.03-8.05 (m, 2H), 7.61-7.65 (m, 1H), 7.50-7.54 (m, 2H), 7.42 (dd, J=8.7, 1.4 Hz, 1H), 7.03-7.09 (m, 2H), 5.30 (s, 2H), 4.61-4.68 (m, 1H), 4.26-4.44 (m, 1H), 3.26-4.10 (m, 2H), 2.78-2.84 (m, 2H), 2.54-2.62 (m, 4H), 2.16-2.24 (m, 4H). MS (ESI): m/z 407 (M+1).

2-((1-(cyclobutanecarbonyl)piperidin-4-yl)oxy)-N-(2-oxo-2-phenylethyl)benzamide (DKC1125 g17) ¹H-NMR (400 MHz, CDCl₃) δ 9.12 (s, 1H), 8.25 (dd, J=7.8, 1.8 Hz, 1H), 8.03-8.05 (m, 2H), 7.61-7.65 (m, 1H), 7.50-7.54 (m, 2H), 7.47 (dd, J=8.7, 1.4 Hz, 1H), 7.03-7.09 (m, 2H), 5.30 (s, 2H), 5.02 (d, J=4.1 Hz, 1H), 4.61-4.68 (m, 1H), 3.26 (td, J=8.7, 4.3 Hz, 2H), 2.78-2.84 (m, 2H), 2.40-2.64 (m, 4H), 2.30-2.34 (m, 2H), 2.06-2.14 (m, 4H), MS (ESI): m/z 421 (M+1).

N-(2-oxo-2-phenylethyl)-2-((1-(thiophene-2-carbonyl)piperidin-4-yl)oxy)benzamide (DKC1125 g18) ¹H-NMR (400 MHz, CDCl₃) δ 8.98 (s, 1H), 8.25 (dd, J=7.8, 1.8 Hz, 1H), 8.12-8.16 (m, 2H), 7.63-7.67 (m, 1H), 7.61-7.65 (m, 1H), 7.53-7.57 (m, 2H), 7.36-7.43 (m, 2H), 7.22-7.30 (m, 2H), 7.03-7.12 (m, 1H), 5.02 (d, J=4.1 Hz, 2H), 4.61-4.68 (m, 1H), 3.26 (td, J=8.7, 4.3 Hz, 2H), 2.78-2.84 (m, 2H), 2.17-2.25 (m, 4H). MS (ESI): m/z 449 (M+1).

2-((1-(2-(methoxymethyl)benzoyl) piperidin-4-yl)oxy)-N-(2-oxo-2-phenylethyl)benzamide (DKC1125 g19) H-NMR (400 MHz, CDCl₃) δ 8.98 (s, 1H), 8.25 (dd, J=7.8, 1.8 Hz, 1H), 8.12-8.18 (m, 2H), 7.63-7.67 (m, 1H), 7.61-7.65 (m, 1H), 7.53-7.57 (m, 2H), 7.36-7.43 (m, 2H), 7.20-7.29 (m, 2H), 7.03-7.12 (m, 2H), 5.02 (d, J=4.1 Hz, 2H), 4.61-4.68 (m, 1H), 3.92 (s, 3H), 3.26 (td, J=8.7, 4.3 Hz, 2H), 2.96 (s, 2H), 2.78-2.84 (m, 2H), 2.17-2.25 (m, 4H). MS (ESI): m/z 487 (M+1).

2-((1-(3,3-dimethylbutanoyl)piperidin-4-yl)oxy)-N-(2-oxo-2-phenylethyl)benzamide (DKC1125 g20) ¹H-NMR (400 MHz, CDCl₃) δ 9.12 (s, 1H), 8.25 (dd, J=7.8, 1.8 Hz, 1H), 8.10-8.16 (m, 2H), 7.61-7.65 (m, 1H), 7.50-7.54 (m, 2H), 7.46 (dd, J=8.7, 1.4 Hz 1H), 7.03-7.09 (m, 2H), 5.02 (d, J=4.1 Hz, 2H), 4.61-4.68 (m, 1H), 3.26 (td, J=8.7, 4.3 Hz, 2H), 2.9 (m, 2H), 2.78-2.84 (m, 2H), 2.17-2.25 (m, 4H). 1.97 (s, 9H). MS (ESI): m/z 437 (M+1).

2-((1-(morpholine-4-carbonyl)piperidin-4-yl)oxy)-N-(2-oxo-2-phenylethyl)benzamide (DKC1125 g21) ¹H-NMR (400 MHz, CDCl₃) δ 9.12 (s, 1H), 8.25 (dd, J=7.8, 1.8 Hz, 1H), 8.03-8.05 (m, 2H), 7.61-7.65 (m, 1H), 7.50-7.54 (m, 2H), 7.44 (dd, J=8.7, 1.4 Hz, 1H), 7.03-7.09 (m, 2H), 5.30 (s, 2H), 4.61-4.68 (m, 1H), 3.26 (td, J=8.7, 4.3 Hz, 2H), 2.8 (m, 2H), 2.78-2.84 (m, 2H), 2.20-2.27 (m, 4H), 2.14-2.18 (m, 2H), 2.10-2.14 (m, 4H). MS (ESI): m/z 452 (M+1).

N-(2-oxo-2-phenylethyl)-2-((1-pentanoylpiperidin-4-yl)oxy)benzamide (DKC1125 g22) ¹H-NMR (400 MHz, CDCl₃) δ 9.12 (s, 1H), 8.25 (dd, J=7.8, 1.8 Hz, 1H), 8.03-8.05 (m, 2H), 7.61-7.65 (m, 1H), 7.50-7.54 (m, 2H), 7.48 (dd, J=8.7, 1.4 Hz, 1H), 7.03-7.09 (m, 2H), 5.30 (s, 2H), 4.61-4.68 (m, 1H), 3.26 (td, J=8.7, 4.3 Hz, 2H), 2.89 (s, 2H), 2.78-2.84 (m, 2H), 2.24-2.29 (m, 2H), 2.17-2.25 (m, 4H), 2.16 (s, 2H), 1.79 (s, 3H). MS (ESI): m/z 523 (M+1).

2-((1-(4-methoxybenzoyl)piperidin-4-yl)oxy)-N-(2-oxo-2-phenylethyl)benzamide (DKC1125 g23) ¹H-NMR (400 MHz, CDCl₃) δ 8.98 (s, 1H), 8.25 (dd, J=7.8, 1.8 Hz, 1H), 8.00-8.08 (m, 2H), 7.63-7.67 (m, 1H), 7.61-7.65 (m, 1H), 7.53-7.57 (m, 2H), 7.36-7.43 (m, 2H), 7.22-7.28 (m, 2H), 7.03-7.12 (m, 2H), 5.02 (d, J=4.1 Hz, 2H), 4.61-4.68 (m, 1H), 3.23 (s, 3H), 3.26 (td, J=8.7, 4.3 Hz, 2H), 2.78-2.84 (m, 2H), 2.17-2.25 (m, 4H). MS (ESI): m/z 573 (M+1).

2-((1-(4-cyanobenzoyl)piperidin-4-yl)oxy)-N-(2-oxo-2-phenylethyl)benzamide (DKC1125 g24) ¹H-NMR (400 MHz, CDCl₃) δ 8.98 (s, 1H), 8.25 (dd, J=7.8, 1.8 Hz, 1H), 8.00-8.08 (m, 2H), 7.63-7.67 (m, 1H), 7.61-7.65 (m, 1H), 7.53-7.57 (m, 2H), 7.36-7.43 (m, 2H), 7.22-7.28 (m, 2H), 7.03-7.12 (m, 2H), 5.02 (d, J=4.1 Hz, 2H), 4.61-4.68 (m, 1H), 3.26 (td, J=8.7, 4.3 Hz, 2H), 2.78-2.84 (m, 2H), 2.17-2.25 (m, 4H). MS (ESI): m/z 471 (M+1).

2-((1-((3-(dioxo-15-sulfanyl)phenyl)sulfonyl)piperidin-4-yl)oxy)-N-(2-oxo-2-phenylethyl)benzamide (DKC1125 g25) ¹H-NMR (400 MHz, CDCl₃) δ 8.98 (s, 1H), 8.25 (dd, J=7.8, 1.8 Hz, 1H), 8.00-8.08 (m, 2H), 7.63-7.67 (m, 1H), 7.61-7.65 (m, 1H), 7.53-7.57 (m, 2H), 7.36-7.43 (m, 2H), 7.24-7.32 (m, 2H), 7.03-7.12 (m, 2H), 5.02 (d, J=4.1 Hz, 2H), 4.61-4.68 (m, 1H), 3.26 (td, J=8.7, 4.3 Hz, 2H), 2.78-2.84 (m, 2H), 2.17-2.25 (m, 4H) MS (ESI): m/z 542 (M+1).

2-(4-(2-((2-oxo-2-phenylethyl) carbamoyl) phenoxy) piperidine-1-carbonyl)phenylacetate (DKC112526 g) ¹H-NMR (400 MHz, CDCl₃) δ 8.98 (s, 1H), 8.25 (dd, J=7.8, 1.8 Hz, 1H), 8.00-8.08 (m, 2H), 7.63-7.67 (m, 1H), 7.61-7.65 (m, 1H), 7.53-7.57 (m, 2H), 7.36-7.43 (m, 2H), 7.10-7.34 (m, 2H), 7.03-7.12 (m, 2H), 5.02 (d, J=4.1 Hz, 2H), 4.61-4.68 (m, 1H), 4.21-4.30 (m, 1H), 3.26 (td, J=8.7, 4.3 Hz, 2H), 2.78-2.84 (m, 2H), 2.17-2.25 (m, 4H). MS (ESI): m/z 520 (M+1).

2-((1-(2,4-difluorobenzoyl)piperidin-4-yl)oxy)-N-(2-oxo-2-phenylethyl)benzamide (DKC1125 g27) ¹H-NMR (400 MHz, CDCl₃) δ 8.98 (s, 1H), 8.25 (dd, J=7.8, 1.8 Hz, 1H), 8.00-8.08 (m, 2H), 7.61-7.65 (m, 1H), 7.53-7.57 (m, 2H), 7.36-7.43 (m, 2H), 7.20-7.36 (m, 2H), 7.03-7.12 (m, 2H), 5.02 (d, J=4.1 Hz, 2H), 4.61-4.68 (m, 1H), 3.26 (td, J=8.7, 4.3 Hz, 2H), 2.78-2.84 (m, 2H), 2.17-2.25 (m, 4H). MS (ESI): m/z 479 (M+1).

2-((1-(2-methoxyacetyl)piperidin-4-yl)oxy)-N-(2-oxo-2-phenylethyl)benzamide (DKC1125 g28) ¹H-NMR (400 MHz, CDCl₃) δ 9.12 (s, 1H), 8.25 (dd, J=7.8, 1.8 Hz, 1H), 8.03-8.05 (m, 2H), 7.61-7.65 (m, 1H), 7.50-7.54 (m, 2H), 7.44 (ddd, J=8.7, 6.9, 1.4 Hz, 1H), 7.03-7.09 (m, 2H), 5.30 (m, 1H), 5.02 (d, J=4.1 Hz, 2H), 4.61-4.68 (m, 2H), 3.97 (s, 3H), 3.26 (td, J=8.7, 4.3 Hz, 2H), 2.78-2.84 (m, 2H), 2.17-2.25 (m, 4H). MS (ESI): m/z 411 (M+1).

N-(2-oxo-2-phenylethyl)-2-((1-pivaloylpiperidin-4-yl)oxy)benzamide (DKC1125 g29) ¹H-NMR (400 MHz, CDCl₃) δ 9.12 (s, 1H), 8.25 (dd, J=7.8, 1.8 Hz, 1H), 8.03-8.05 (m, 2H), 7.61-7.65 (m, 1H), 7.50-7.54 (m, 2H), 7.44 (dd, J=8.7, 1.4 Hz, 1H), 7.03-7.09 (m, 2H), 5.02 (d, J=4.1 Hz, 2H), 4.61-4.68 (m, 1H), 3.26 (td, J=8.7, 4.3 Hz, 2H), 2.78-2.84 (m, 2H), 2.17-2.25 (m, 4H). 1.92 (s, 9H). MS (ESI): m/z 423 (M+1).

N,N-dimethyl-4-(2-((2-oxo-2-phenylethyl) carbamoyl) phenoxy) piperidine-1-carboxamide (DKC1125 g30) ¹H-NMR (400 MHz, CDCl₃) δ 9.12 (s, 1H), 8.25 (dd, J=7.8, 1.8 Hz, 1H), 8.03-8.05 (m, 2H), 7.61-7.65 (m, 1H), 7.50-7.54 (m, 2H), 7.44 (dd, J=8.7, 1.4 Hz, 1H), 7.03-7.09 (m, 2H), 5.30 (s, 2H), 4.61-4.68 (m, 1H), 4.62-4.66 (m, 6H), 3.28 (s, 2H), 2.79 (m, 2H), 2.17-2.25 (m, 4H). MS (ESI): m/z 410 (M+1).

2-((1-(4-bromobenzoyl)piperidin-4-yl)oxy)-N-(2-oxo-2-phenylethyl)benzamide (DKC1125 g31) ¹H-NMR (400 MHz, CDCl₃) δ 8.98 (s, 1H), 8.25 (dd, J=7.8, 1.8 Hz, 1H), 8.00-8.08 (m, 2H), 7.63-7.67 (m, 1H), 7.61-7.65 (m, 1H), 7.53-7.57 (m, 2H), 7.36-7.43 (m, 2H), 7.24-7.34 (m, 2H), 7.03-7.12 (m, 2H), 5.02 (d, J=4.1 Hz, 2H), 4.61-4.68 (m, 1H), 3.26 (td, J=8.7, 4.3 Hz, 2H), 2.78-2.84 (m, 2H), 2.17-2.25 (m, 4H). MS (ESI): m/z 521 (M+1).

2-((1-acetylpiperidin-4-yl)oxy)-N-(2-oxo-2-phenylethyl)benzamide (DKC1125 g32) ¹H-NMR (400 MHz, CDCl₃) δ 9.12 (s, 1H), 8.25 (dd, J=7.8, 1.8 Hz, 1H), 8.03-8.05 (m, 2H), 7.61-7.65 (m, 1H), 7.50-7.54 (m, 2H), 7.44 (dd, J=8.7, 1.4 Hz, 1H), 7.03-7.09 (m, 2H), 5.02 (d, J=4.1 Hz, 2H), 4.61-4.68 (m, 1H), 3.26 (td, J=8.7, 4.3 Hz, 2H), 2.9 (s, 3H), 2.78-2.84 (m, 2H), 2.17-2.25 (m, 4H). MS (ESI): m/z 381 (M+1).

2-((1-(methylsulfonyl)piperidin-4-yl)oxy)-N-(2-oxo-2-phenylethyl)benzamide (DKC1125 g33) ¹H-NMR (400 MHz, CDCl₃) δ 9.12 (s, 1H), 8.25 (dd, J=7.8, 1.8 Hz, 1H), 8.03-8.05 (m, 2H), 7.61-7.65 (m, 1H), 7.50-7.54 (m, 2H), 7.44 (dd, J=8.7, 1.4 Hz, 1H), 7.03-7.09 (m, 2H), 5.02 (d, J=4.1 Hz, 2H), 4.61-4.68 (m, 1H), 3.8 (s, 3H), 3.26 (td, J=8.7, 4.3 Hz, 2H), 2.78-2.84 (m, 2H), 2.17-2.25 (m, 4H). MS (ESI): m/z 417 (M+1).

2-((1-((4-fluorophenyl)sulfonyl)piperidin-4-yl)oxy)-N-(2-oxo-2-phenylethyl)benzamide (DKC1125 g34) ¹H-NMR (400 MHz, CDCl₃) δ 8.98 (s, 1H), 8.25 (dd, J=7.8, 1.8 Hz, 1H), 8.00-8.08 (m, 2H), 7.63-7.67 (m, 1H), 7.61-7.65 (m, 1H), 7.53-7.57 (m, 2H), 7.36-7.43 (m, 2H), 7.24-7.34 (m, 2H), 7.03-7.12 (m, 2H), 5.02 (d, J=4.1 Hz, 2H), 4.61-4.68 (m, 1H), 3.26 (td, J=8.7, 4.3 Hz, 2H), 2.78-2.84 (m, 2H), 2.17-2.25 (m, 4H). MS (ESI): m/z 497 (M+1).

N-(2-oxo-2-phenylethyl)-2-((1-tosylpiperidin-4-yl)oxy)benzamide (DKC1125 g35) ¹H-NMR (400 MHz, CDCl₃) δ 8.98 (s, 1H), 8.25 (dd, J=7.8, 1.8 Hz, 1H), 8.00-8.08 (m, 2H), 7.63-7.67 (m, 2H), 7.53-7.57 (m, 2H), 7.36-7.43 (m, 2H), 7.24-7.34 (m, 2H), 7.03-7.12 (m, 2H), 5.02 (d, J=4.1 Hz, 2H), 4.61-4.68 (m, 1H), 3.26 (td, J=8.7, 4.3 Hz, 2H), 2.96 (s, 3H), 2.78-2.84 (m, 2H), 2.17-2.25 (m, 4H). MS (ESI): m/z 493 (M+1).

2-((1-((4-chlorophenyl) sulfonyl) piperidin-4-yl)oxy)-N-(2-oxo-2-phenylethyl)benzamide (DKC1125 g36) H-NMR (400 MHz, CDCl₃) δ 8.98 (s, 1H), 8.25 (dd, J=7.8, 1.8 Hz, 1H), 8.00-8.08 (m, 2H), 7.63-7.67 (m, 2H), 7.53-7.57 (m, 2H), 7.36-7.43 (m, 2H), 7.24-7.34 (m, 2H), 7.03-7.12 (m, 2H), 5.02 (d, J=4.1 Hz, 2H), 4.61-4.68 (m, 1H), 3.26 (td, J=8.7, 4.3 Hz, 2H), 2.78-2.84 (m, 2H), 2.17-2.25 (m, 4H). MS (ESI): m/z 513 (M+1).

N-(2-oxo-2-phenylethyl)-2-((1-(phenylsulfonyl)piperidin-4-yl)oxy)benzamide (DKC1125 g37) ¹H-NMR (400 MHz, CDCl₃) δ 8.98 (s, 1H), 8.25 (dd, J=7.8, 1.8 Hz, 1H), 8.00-8.08 (m, 2H), 7.63-7.67 (m, 1H), 7.61-7.65 (m, 2H), 7.53-7.57 (m, 2H), 7.36-7.43 (m, 2H), 7.24-7.34 (m, 2H), 7.03-7.12 (m, 2H), 5.02 (d, J=4.1 Hz, 2H), 4.61-4.68 (m, 1H), 3.26 (td, J=8.7, 4.3 Hz, 2H), 2.78-2.84 (m, 2H), 2.17-2.25 (m, 4H). MS (ESI): m/z 479 (M+1).

2-((1-(benzylsulfonyl)piperidin-4-yl)oxy)-N-(2-oxo-2-phenylethyl)benzamide (DKC1125 g38) ¹H-NMR (400 MHz, CDCl₃) δ 8.98 (s, 1H), 8.25 (dd, J=7.8, 1.8 Hz, 1H), 8.00-8.08 (m, 2H), 7.63-7.67 (m, 1H), 7.61-7.65 (m, 2H), 7.53-7.57 (m, 2H), 7.36-7.43 (m, 2H), 7.2-7.3 (m, 2H), 7.03-7.12 (m, 2H), 5.04 (s, 2H), 5.02 (d, J=4.1 Hz, 2H), 4.61-4.68 (m, 1H), 3.26 (td, J=8.7, 4.3 Hz, 2H), 2.78-2.84 (m, 2H), 2.17-2.25 (m, 4H). MS (ESI): m/z 457 (456.18+1). MS (ESI): m/z 493 (M+1).

2-((1-((4-methoxyphenyl) sulfonyl) piperidin-4-yl)oxy)-N-(2-oxo-2-phenylethyl)benzamide (DKC1125 g39) H-NMR (400 MHz, CDCl₃) δ 8.98 (s, 1H), 8.25 (dd, J=7.8, 1.8 Hz, 1H), 8.00-8.08 (m, 2H), 7.63-7.67 (m, 1H), 7.61-7.65 (m, 1H), 7.53-7.57 (m, 2H), 7.36-7.43 (m, 2H), 7.28-7.30 (m, 2H), 7.03-7.12 (m, 2H), 5.02 (d, J=4.1 Hz, 2H), 4.61-4.68 (m, 1H), 3.91 (s, 3H), 3.26 (td, J=8.7, 4.3 Hz, 2H), 2.78-2.84 (m, 2H), 2.17-2.25 (m, 4H). MS (ESI): m/z 409 (M+1).

2-((1-(3,5-bis(trifluoromethyl)benzoyl)piperidin-4-yl)oxy)-N-(2-oxo-2-phenylethyl)benzamide (DKC1125 g40) ¹H-NMR (400 MHz, CDCl₃) δ 8.98 (s, 1H), 8.25 (dd, J=7.8, 1.8 Hz, 1H), 8.00-8.08 (m, 2H), 7.63-7.67 (m, 1H), 7.61-7.65 (m, 1H), 7.53-7.57 (m, 2H), 7.36-7.43 (m, 2H), 7.28-7.30 (m, 2H), 7.03-7.12 (m, 1H), 5.02 (d, J=4.1 Hz, 2H), 4.61-4.68 (m, 1H), 3.26 (td, J=8.7, 4.3 Hz, 2H), 2.78-2.84 (m, 2H), 2.17-2.25 (m, 4H). MS (ESI): m/z 579 (M+1).

N-(2-oxo-2-phenylethyl)-2-((1-(2-(trifluoromethyl)benzoyl) piperidin-4-yl)oxy)benzamide (DKC1125 g41) ¹H-NMR (400 MHz, CDCl₃) δ 8.98 (s, 1H), 8.25 (dd, J=7.8, 1.8 Hz, 1H), 8.00-8.08 (m, 2H), 7.63-7.67 (m, 1H), 7.61-7.65 (m, 1H), 7.53-7.57 (m, 2H), 7.36-7.43 (m, 2H), 7.28-7.30 (m, 2H), 7.03-7.12 (m, 2H), 5.02 (d, J=4.1 Hz, 2H), 4.61-4.68 (m, 1H), 3.26 (td, J=8.7, 4.3 Hz, 2H), 2.78-2.84 (m, 2H), 2.17-2.25 (m, 4H). MS (ESI): m/z 511 (M+1).

N-(2-oxo-2-phenylethyl)-2-((1-(3-(trifluoromethyl)benzoyl) piperidin-4-yl)oxy)benzamide (DKC1125 g42) ¹H-NMR (400 MHz, CDCl₃) δ 8.98 (s, 1H), 8.25 (dd, J=7.8, 1.8 Hz, 1H), 8.00-8.08 (m, 2H), 7.63-7.67 (m, 1H), 7.61-7.65 (m, 1H), 7.53-7.57 (m, 2H), 7.36-7.43 (m, 2H), 7.28-7.30 (m, 2H), 7.03-7.12 (m, 2H), 5.40 (d, J=4.2 Hz, 2H), 4.61-4.68 (m, 1H), 3.26 (td, J=8.7, 4.3 Hz, 2H), 2.78-2.84 (m, 2H), 2.17-2.25 (m, 4H). MS (ESI): m/z 511 (M+1).

N-(2-oxo-2-phenylethyl)-2-((1-(4-(trifluoromethyl)benzoyl) piperidin-4-yl)oxy)benzamide (DKC1125 g43) ¹H-NMR (400 MHz, CDCl₃) δ 8.98 (s, 1H), 8.25 (dd, J=7.8, 1.8 Hz, 1H), 8.00-8.08 (m, 2H), 7.63-7.67 (m, 1H), 7.61-7.65 (m, 1H), 7.53-7.57 (m, 2H), 7.36-7.43 (m, 2H), 7.22-7.30 (m, 2H), 7.08-7.12 (m, 2H), 5.02 (d, J=4.1 Hz, 2H), 4.61-4.68 (m, 1H), 3.26 (td, J=8.7, 4.3 Hz, 2H), 2.78-2.84 (m, 2H), 2.17-2.25 (m, 4H). MS (ESI): m/z 511 (M+1).

2-((1-(2-chloro-4-fluorobenzoyl) piperidin-4-yl)oxy)-N-(2-oxo-2-phenylethyl)benzamide (DKC1125 g44) H-NMR (400 MHz, CDCl₃) δ 8.98 (s, 1H), 8.25 (dd, J=7.8, 1.8 Hz, 1H), 8.00-8.08 (m, 2H), 7.63-7.67 (m, 1H), 7.61-7.65 (m, 1H), 7.53-7.57 (m, 2H), 7.36-7.43 (m, 2H), 7.25-7.32 (m, 2H), 7.03-7.12 (m, 2H), 5.02 (d, J=4.1 Hz, 2H), 4.61-4.68 (m, 1H), 3.26 (td, J=8.7, 4.3 Hz, 2H), 2.78-2.84 (m, 2H), 2.17-2.25 (m, 4H). MS (ESI): m/z 495 (M+1).

2-((1-(3-nitrobenzoyl)piperidin-4-yl)oxy)-N-(2-oxo-2-phenylethyl)benzamide (DKC1125 g45) ¹H-NMR (400 MHz, CDCl₃) δ 8.98 (s, 1H), 8.25 (dd, J=7.8, 1.8 Hz, 1H), 8.00-8.08 (m, 2H), 7.62-7.66 (m, 1H), 7.61-7.65 (m, 1H), 7.53-7.57 (m, 2H), 7.36-7.43 (m, 2H), 7.28-7.30 (m, 2H), 7.03-7.12 (m, 2H), 5.02 (d, J=4.1 Hz, 2H), 4.61-4.68 (m, 1H), 3.26 (td, J=8.7, 4.3 Hz, 2H), 2.78-2.84 (m, 2H), 2.17-2.25 (m, 4H). MS (ESI): m/z 488 (M+1).

2-((1-(3,4-difluorobenzoyl)piperidin-4-yl)oxy)-N-(2-oxo-2-phenylethyl)benzamide (DKC1125 g46) ¹H-NMR (400 MHz, CDCl₃) δ 8.98 (s, 1H), 8.25 (dd, J=7.8, 1.8 Hz, 1H), 8.00-8.08 (m, 2H), 7.63-7.67 (m, 1H), 7.61-7.65 (m, 1H), 7.53-7.57 (m, 2H), 7.38-7.48 (m, 2H), 7.23-7.34 (m, 2H), 7.03-7.12 (m, 1H), 5.02 (d, J=4.1 Hz, 2H), 4.61-4.68 (m, 1H), 3.26 (td, J=8.7, 4.3 Hz, 2H), 2.78-2.84 (m, 2H), 2.17-2.25 (m, 4H). MS (ESI): m/z 479 (M+1).

2-((1-(3,5-dichlorobenzoyl)piperidin-4-yl)oxy)-N-(2-oxo-2-phenylethyl)benzamide (DKC1125 g47) ¹H-NMR (400 MHz, CDCl₃) δ 8.98 (s, 1H), 8.25 (dd, J=7.8, 1.8 Hz, 1H), 8.10-8.18 (m, 2H), 7.64-7.68 (m, 1H), 7.61-7.65 (m, 1H), 7.53-7.57 (m, 2H), 7.36-7.43 (m, 2H), 7.25-7.32 (m, 1H), 7.03-7.12 (m, 2H), 5.02 (d, J=4.1 Hz, 2H), 4.61-4.68 (m, 1H), 3.26 (td, J=8.7, 4.3 Hz, 2H), 2.78-2.84 (m, 2H), 2.17-2.25 (m, 4H). MS (ESI): m/z 511 (M+1).

2-((1-(2,3-dichlorobenzoyl)piperidin-4-yl)oxy)-N-(2-oxo-2-phenylethyl)benzamide (DKC1125 g48) ¹H-NMR (400 MHz, CDCl₃) δ 8.98 (s, 1H), 8.25 (dd, J=7.8, 1.8 Hz, 1H), 8.22-8.26 (m, 1H), 7.63-7.67 (m, 1H), 7.61-7.65 (m, 1H), 7.53-7.57 (m, 2H), 7.36-7.43 (m, 2H), 7.25-7.32 (m, 2H), 7.03-7.12 (m, 2H), 5.02 (d, J=4.1 Hz, 2H), 4.61-4.68 (m, 1H), 3.26 (td, J=8.7, 4.3 Hz, 2H), 2.78-2.84 (m, 2H), 2.17-2.25 (m, 4H). MS (ESI): m/z 511 (M+1).

N-(2-oxo-2-phenylethyl)-2-((1-(4-(trifluoromethoxy)benzoyl) piperidin-4-yl)oxy)benzamide (DKC1125 g49) ¹H-NMR (400 MHz, CDCl₃) δ 8.98 (s, 1H), 8.25 (dd, J=7.8, 1.8 Hz, 1H), 8.10-8.16 (m, 2H), 7.62-7.64 (m, 1H), 7.61-7.65 (m, 1H), 7.53-7.57 (m, 2H), 7.36-7.43 (m, 2H), 7.21-7.30 (m, 1H), 7.03-7.12 (m, 2H), 5.02 (d, J=4.1 Hz, 2H), 4.61-4.68 (m, 1H), 3.26 (td, J=8.7, 4.3 Hz, 2H), 2.78-2.84 (m, 2H), 2.17-2.25 (m, 4H). MS (ESI): m/z 527 (M+1).

N-(2-oxo-2-phenylethyl)-2-((1-(3-(trifluoromethoxy)benzoyl)piperidin-4-yl)oxy)benzamide (DKC1125 g50) ¹H-NMR (400 MHz, CDCl₃) δ 8.98 (s, 1H), 8.25 (dd, J=7.8, 1.8 Hz, 1H), 8.10-8.18 (m, 2H), 7.63-7.67 (m, 1H), 7.61-7.65 (m, 1H), 7.53-7.57 (m, 2H), 7.36-7.43 (m, 2H), 7.21-7.30 (m, 2H), 7.03-7.12 (m, 2H), 5.02 (d, J=4.1 Hz, 2H), 4.61-4.68 (m, 1H), 3.26 (td, J=8.7, 4.3 Hz, 2H), 2.78-2.84 (m, 2H), 2.17-2.25 (m, 4H). MS (ESI): m/z 527 (M+1).

Examples 201 to 230. Preparation of Compounds 201 to 230 (DKC1125h01 to 30) According to the Present Invention

Synthesis of Compounds 201 to 230 (DKC1125h01 to 30)

Compounds 201 to 230 (DKC1125h01 to 30) of the present invention were synthesized according to the following Reaction Scheme 7.

Synthesis of methyl 2-(2((-oxo-2-phenylethyl)carbomyl)phenoxy)acetate (1)

To a solution of 2-hydroxy-N-(2-oxo-2-phenylethyl)benzamide (500 mg, 1.97 mmol) and methyl 2-bromoacetate (240 μL, 2.97 mol) in DMF (8 mL) was added potassium carbonate (677 mg, 4.97 mol). The resulting solution was stirred at 50° C. for 9 hrs. The reaction was monitored by checking TLC. After completion of the reaction, to the mixture were added water and HCl to maintain acidic pH, followed by extraction with EtOAc. The organic layer was washed with brine (3×100 mL), and dried the solution with Na₂SO₄, and the solvent was evaporated. The residue was purified by column chromatography to give the title compound (1) as a white powder (0.6 g, 84%).

¹H-NMR (400 MHz, CDCl₃) δ 9.89 (d, J=10.5 Hz, 1H), 8.14-8.20 (m, 1H), 7.74-7.80 (m, 1H), 7.51-7.58 (m, 1H), 7.38-7.49 (m, 2H), 6.96-6.99 (m, 2H), 6.83 (d, J=7.8 Hz, 1H), 6.75 (d, J=8.2 Hz, 1H), 4.74 (d, J=5.9 Hz, 2H), 4.51 (s, 2H), 3.88 (q, J=7.2 Hz, 3H). MS (ESI): m/z 328 (M+1).

Synthesis of 2-(2 ((-oxo-2-phenylethyl)carbomyl)phenoxy)acetic acid (2)

To a solution of methyl 2-(2((-oxo-2-phenylethyl)carbomyl)phenoxy)acetate (1, 0.6 g, 1.77 mol) in EtOH (10 mL) was added 4N NaOH (6 mL) with stirring, followed by addition of 2N HCl (1 mL). The resulting solution was stirred at room temperature for 4 hrs. The reaction was monitored by checking TLC. After completion of the reaction, to the mixture were added water and HCl to maintain acidic pH, followed by extraction with EA. The organic layer was separated, washed with brine (3×100 mL). The washed solution was dried with anhydrous sodium sulphate, and the solvent was evaporated in vacuo. The residue was purified by column chromatography (EtOAc: Hexane 2:3) to give the title compounds (2) as a white powder (567 mg, 83%).

¹H-NMR (400 MHz, CDCl₃) δ 9.01 (t, J=5.3 Hz, 1H), 8.03-8.06 (m, 2H), 7.93 (dd, J=7.3, 1.8 Hz, 1H), 7.67-7.71 (m, 2H), 7.55-7.59 (m, 1H), 7.49-7.53 (m, 1H), 7.09-7.14 (m, 2H), 4.93 (s, 2H), 4.87 (d, J=5.5 Hz, 2H). MS (ESI): m/z 314 (M+1).

General Preparation Method for Compounds 201 to 230 (DKC1125h01 to 30)

To a solution of 2-(2((-oxo-2-phenylethyl)carbomyl)phenoxy)acetic acid (2, 20 mg, 0.069 mmol) and each amine (10 μL, 0.069 mmol) shown in Table 9 below in DMF was added HATU (18 mg, 0.069 mmol). Finally, DIEA (24 μL, 0.143 mmol) was added thereto, and the reaction mixture was stirred at room temperature for 1 hr. After completion of the reaction, the mixture was evaporated by using Rota vapor and purified by column chromatography to obtain the title compound as a solid (12 mg, 80 to 90%).

TABLE 9
Amines used in preparation of compounds 201 to 230
(DKC1125h01 to 30)
Compounds  Amine
DKC1125h01 Aniline
DKC1125h02 o-toluidine
DKC1125h03 Allylamine
DKC1125h04 Benzylamine
DKC1125h05 3-fluorobenzylamine
DKC1125h06 2-methoxy-5-methylaniline
DKC1125h07 3-Fluoro-4-methoxyaniline
DKC1125h08 3-aminopyridine
DKC1125h09 m-anisidine
DKC1125h10 2-propylaniline
DKC1125h11 4-fluoro-3-nitroaniline
DKC1125h12 3,4-(methylenedioxy)benzylamine
DKC1125h13 4-n-propylaniline
DKC1125h14 3-phenoxyaniline
DKC1125h15 3,4-Dimethoxybenzylamine
DKC1125h16 3,4-Dimethoxyaniline
DKC1125h17 3,4-(methylenedioxy)aniline
DKC1125h18 1,4-benzodioxan-6-amine
DKC1125h19 5-aminoindane
DKC1125h20 3-isopropoxyaniline
DKC1125h21 4-phenoxyaniline
DKC1125h22 3-Amino-4-fluorobenzotrifluoride
DKC1125h23 3-aminophenol
DKC1125h24 2-chloroaniline
DKC1125h25 2-aminophenol
DKC1125h26 isopropylamine
DKC1125h27 1,2,3,4-tetrahydroisoquinoline
DKC1125h28 1-propylamine
DKC1125h29 isoamylamine
DKC1125h30 cyclohexylamine

Confirmation of Preparation of Compounds 201 to 230 (DKC1125h01 to 30)

2-(2-oxo-2-(phenylamino) ethoxy)-N-(2-oxo-2-phenylethyl)benzamide (DKC1125h01) ¹H-NMR (400 MHz, CDCl₃) δ 9.76 (s, 1H), 8.48 (s, 1H), 8.01-8.03 (m, 1H), 7.81-7.84 (m, 1H), 7.74-7.77 (m, 2H), 7.49-7.56 (m, 3H), 7.29 (dd, J=7.2, 1.8 Hz, 3H), 7.10-7.15 (m, 2H), 7.05-7.08 (m, 1H), 5.03 (t, J=3.9 Hz, 2H), 4.83 (s, 2H). MS (ESI): m/z 389 (M+1).

2-(2-oxo-2-(o-toylamino) ethoxy)-N-(2-oxo-2-phenylethyl)benzamide (DKC1125h02) ¹H-NMR (400 MHz, CDCl₃) δ 9.74 (s, 1H), 8.38 (s, 1H), 8.01-8.03 (m, 2H), 7.81-7.84 (m, 1H), 7.74-7.77 (m, 1H), 7.49-7.56 (m, 3H), 7.29 (dd, J=7.2, 1.8 Hz, 3H), 7.10-7.15 (m, 2H), 7.05-7.08 (m, 1H), 5.03 (t, J=3.9 Hz, 2H), 4.83 (s, 2H), 2.9 (s, 3H). MS (ESI): m/z 403 (M+1).

2-(2-(allylamino)-2-oxoethoxy)-N-(2-oxo-2-phenylethyl)benzamide (DKC1125h03) ¹H-NMR (400 MHz, CDCl₃) 9.70 (s, 1H), 8.64 (s, 1H), 8.02 (d, J=7.3 Hz, 1H), 7.79 (dd, J=7.8, 1.4 Hz, 1H), 7.71 (d, J=3.2 Hz, 3H), 7.52-7.56 (m, 3H), 6.89-6.94 (m, 1H), 5.03 (t, J=3.9 Hz, 2H), 4.83 (s, 2H), 4.66 (s, 1H), 4.04-4.10 (m, 2H), 3.95 (t, J=5.7 Hz, 2H). MS (ESI): m/z 353(M+1).

2-(2-(benzylamino)-2-oxoethoxy)-N-(2-oxo-2-phenylethyl)benzamide (DKC1125h04) ¹H-NMR (400 MHz, CDCl₃) 9.76 (s, 1H), 8.01-8.03 (m, 2H), 7.81-7.84 (m, 1H), 7.74-7.77 (m, 2H), 7.49-7.56 (m, 3H), 7.18 (dd, J=7.2, 1.8 Hz, 3H), 7.10-7.15 (m, 2H), 7.05-7.08 (m, 1H), 5.24 (s, 2H), 5.01 (t, J=3.9 Hz, 2H), 4.67 (s, 2H). MS (ESI): m/z 403(M+1).

2-(2-((fluorobenzyl)amino)-2-oxoethoxy)-N-(2-oxo-2-phenylethyl)benzamide (DKC1125h05) ¹H-NMR (400 MHz, CDCl₃) δ 9.76 (s, 1H), 8.71 (s, 1H), 8.01-8.03 (m, 2H), 7.81-7.84 (m, 1H), 7.74-7.77 (m, 1H), 7.49-7.56 (m, 3H), 7.30 (dd, J=7.4, 1.8 Hz, 3H), 7.10-7.15 (m, 2H), 7.05-7.08 (m, 1H), 5.03 (t, J=3.9 Hz, 2H), 4.83 (s, 2H). MS (ESI): m/z 421(M+1).

2-(2-((2-methoxy-4-methylphenyl)amino)-2-oxoethoxy)-N-(2-oxo-2-phenylethyl)benzamide (DKC1125h06) ¹H-NMR (400 MHz, CDCl₃) δ 8.81 (s, 2H), 8.17 (q, J=2.3 Hz, 1H), 8.14 (dd, J=7.8, 1.8 Hz, 1H), 7.90-7.92 (m, 2H), 7.60-7.64 (m, 1H), 7.46-7.53 (m, 3H), 7.15-7.19 (m, 1H), 7.03 (d, J=8.2 Hz, 1H), 6.82 (dd, J=8.2, 1.4 Hz, 1H), 6.57-6.61 (m, 1H), 5.42 (d, J=4.1 Hz, 2H), 4.79 (s, 2H). 3.96 (s, 3H), 3.12 (s, 1H). MS (ESI): m/z 433 (M+1).

2-(2-((3-fluoro-4-methoxyphenyl)amino)-2-oxoethoxy)-N-(2-oxo-2-phenylethyl)benzamide (DKC1125h07) ¹H-NMR (400 MHz, CDCl₃) δ 8.78 (s, 2H), 8.17 (q, J=2.3 Hz, 2H), 8.15 (dd, J=7.8, 1.8 Hz, 2H), 7.90-7.92 (m, 2H), 7.62-7.64 (m, 2H), 7.03 (d, J=8.2 Hz, 2H), 6.82 (dd, J=8.2, 1.4 Hz, 1H), 6.57-6.61 (m, 1H), 5.03 (d, J=4.1 Hz, 2H), 4.89 (s, 2H), 3.68 (d, J=3.2 Hz, 3H). MS (ESI): m/z 437 (M+1).

2-(2-oxo-2-(pyridin-3-ylamino)ethoxy)-N-(2-oxo-2-phenylethyl)benzamide (DKC1125h08) ¹H-NMR (400 MHz, CDCl₃) δ 9.76 (s, 1H), 8.84 (s, 1H), 8.01-8.03 (m, 2H), 7.81-7.84 (m, 1H), 7.74-7.77 (m, 1H), 7.89-7.59 (m, 3H), 7.48-7.42 (dd, J=7.4, 1.8 Hz, 3H), 7.20-7.25 (m, 2H), 7.05-7.08 (m, 1H), 5.47 (t, J=3.9 Hz, 2H), 4.87 (s, 2H). MS (ESI): m/z 390 (M+1).

2-(2-((3-methoxyphenyl)amino)-2-oxoethoxy)-N-(2-oxo-2-phenylethyl)benzamide (DKC1125h09) ¹H-NMR (400 MHz, CDCl₃) 8.62 (s, 1H), 8.17 (q, J=2.3 Hz, 1H), 8.14 (dd, J=7.8, 1.8 Hz, 2H), 7.90-7.92 (m, 2H), 7.60-7.64 (m, 1H), 7.46-7.53 (m, 3H), 7.15-7.19 (m, 1H), 7.03 (d, J=8.2 Hz, 1H), 6.82 (dd, J=8.2, 1.4 Hz, 1H), 6.57-6.61 (m, 1H), 5.03 (d, J=4.1 Hz, 2H), 4.89 (s, 2H), 3.61 (d, J=3.2 Hz, 3H). MS (ESI): m/z 419 (M+1).

2-(2-oxo-2-((2-propylphenyl)amino) ethoxy)-N-(2-oxo-2-phenylethyl)benzamide (DKC1125h10) ¹H-NMR (400 MHz, CDCl₃) δ 8.91 (s, 1H), 8.60 (s, 1H), 8.17 (q, J=2.3 Hz, 1H), 8.15 (dd, J=7.8, 1.8 Hz, 2H), 7.90-7.92 (m, 2H), 7.60-7.64 (m, 1H), 7.15-7.19 (m, 1H), 7.03 (d, J=8.2 Hz, 2H), 6.82 (dd, J=8.2, 1.4 Hz, 2H), 6.57-6.61 (m, 2H), 5.03 (d, J=4.1 Hz, 2H), 4.89 (s, 2H), 3.61 (d, J=3.2 Hz, 3H), 2.66-2.72 (m, 2H), 2.42-2.50 (m, 2H). MS (ESI): m/z 431 (M+1).

2-(2-((1-fluoro-3-nitrophenyl)amino)-2-oxoethoxy)-N-(2-oxo-2-phenylethylbenzamide (DKC1125h11) ¹H-NMR (400 MHz, CDCl₃) δ 8.80 (s, 1H), 8.68 (s, 1H), 8.17 (q, J=2.3 Hz, 2H), 8.14 (dd, J=7.8, 1.8 Hz, 2H), 7.90-7.92 (m, 2H), 7.60-7.64 (m, 1H), 7.05-7.16 (m, 1H), 7.03 (d, J=8.2 Hz, 2H), 6.82 (dd, J=8.2, 1.4 Hz, 1H), 6.57-6.61 (m, 1H), 5.52 (d, J=4.1 Hz, 2H), 4.90 (s, 2H). MS (ESI): m/z 452 (M+1).

2-(2-((benzo [1,3]dioxol-5-ylmethyl)amino)-2-oxoethoxy)-N-(2-oxo-2-phenylethylbenzamide (DKC1125h12) ¹H-NMR (400 MHz, CDCl₃) δ 8.90 (s, 1H), 8.71 (s, 1H), 8.17 (q, J=2.3 Hz, 1H), 8.14 (dd, J=7.8, 1.8 Hz, 1H), 7.90-7.92 (m, 2H), 7.60-7.64 (m, 1H), 7.46-7.53 (m, 3H), 7.15-7.19 (m, 1H), 7.03 (d, J=8.2 Hz, 1H), 6.82 (dd, J=8.2, 1.4 Hz, 1H), 6.57-6.61 (m, 1H), 6.0 (s, 2H), 5.01 (d, J=4.1 Hz, 2H), 4.68 (s, 2H). MS (ESI): m/z 447 (M+1).

2-(2-oxo-2-((4-propylphenyl)amino)ethoxy)-N-(2-oxo-2-phenylethyl)benzamide (DKC1125h13) ¹H-NMR (400 MHz, CDCl₃) δ 9.02 (s, 1H), 8.71 (s, 1H), 8.17 (q, J=2.3 Hz, 1H), 8.03 (dd, J=7.8, 1.8 Hz, 2H), 7.91-7.92 (m, 2H), 7.62-7.64 (m, 1H), 7.44-7.50 (m, 2H), 7.16-7.19 (m, 1H), 7.03 (d, J=8.2 Hz, 1H), 6.82 (dd, J=8.2, 1.4 Hz, 1H), 6.57-6.61 (m, 2H), 5.20 (d, J=4.1 Hz, 2H), 4.54 (s, 2H), 3.61 (d, J=3.2 Hz, 3H). 2.66-2.8 (m, 2H), 2.42-2.48 (m, 2H). MS (ESI): m/z 431 (M+1).

2-(2-oxo-2-((3-phenoxyphenyl)amino)ethoxy)-N-(2-oxo-2-phenylethyl)benzamid (DKC1125h14) ¹H-NMR (400 MHz, CDCl₃) δ 8.71 (s, 1H), 8.17 (q, J=2.3 Hz, 1H), 8.14 (dd, J=7.8, 1.8 Hz, 1H), 7.90-7.92 (m, 2H), 7.70-7.80 (m, 2H), 7.61-7.64 (m, 2H), 7.50-7.60 (m, 2H), 7.46-7.53 (m, 3H), 7.15-7.19 (m, 2H), 7.03 (d, J=8.2 Hz, 2H), 6.57-6.61 (m, 1H), 5.02 (d, J=4.1 Hz, 2H), 4.67 (s, 2H). MS (ESI): m/z 481 (M+1).

2-(2-((3,4-dimethoxybenzyl)amino)-2-oxoethoxy)-N-(2-oxo-2-phenylethyl)benzamide (DKC1125h15) ¹H-NMR (400 MHz, CDCl₃) δ 8.22 (s, 2H), 8.18 (q, J=2.3 Hz, 2H), 8.12 (dd, J=7.8, 1.8 Hz, 2H), 7.90-7.91 (m, 2H), 7.60-7.64 (m, 1H), 7.15-7.19 (m, 1H), 7.03 (d, J=8.2 Hz, 2H), 6.82 (dd, J=8.2, 1.4 Hz, 1H), 6.57-6.61 (m, 1H), 5.10 (d, J=4.1 Hz, 2H), 4.02 (s, 2H), 3.61 (d, J=3.2 Hz, 3H), 2.31 (d, J=2.3 Hz, 3H). MS (ESI): m/z 463 (M+1).

2-(2-((3,4-dimethoxyphenyl)amino)-2-oxoethoxy)-N-(2-oxo-2-phenylethyl)benzamide (DKC1125h16) ¹H-NMR (400 MHz, CDCl₃) δ 8.20 (s, 2H), 8.17 (q, J=2.3 Hz, 2H), 8.14 (dd, J=7.8, 1.8 Hz, 2H), 7.90-7.92 (m, 2H), 7.60-7.64 (m, 1H), 7.15-7.19 (m, 1H), 7.03 (d, J=8.2 Hz, 2H), 6.82 (dd, J=8.2, 1.4 Hz, 1H), 6.57-6.61 (m, 1H), 5.34 (d, J=4.1 Hz, 2H), 4.33 (s, 2H), 3.61 (d, J=3.2 Hz, 3H), 2.31 (d, J=2.3 Hz, 3H). MS (ESI): m/z 449 (M+1).

2-(2-(benzo [d] [1,3]dioxol-5-ylamino)-2-oxoethoxy)-N-(2-oxo-2-phenylethyl)benzamide (DKC1125h17) ¹H-NMR (400 MHz, CDCl₃) δ 8.90 (s, 1H), 8.71 (s, 1H), 8.17 (q, J=2.3 Hz, 1H), 8.14 (dd, J=7.8, 1.8 Hz, 1H), 7.90-7.92 (m, 2H), 7.60-7.64 (m, 1H), 7.46-7.53 (m, 3H), 7.15-7.19 (m, 1H), 7.03 (d, J=8.2 Hz, 1H), 6.82 (dd, J=8.2, 1.4 Hz, 1H), 6.57-6.61 (m, 1H), 6.0 (s, 2H), 5.01 (d, J=4.1 Hz, 2H), 4.68 (s, 2H). MS (ESI): m/z 433 (M+1).

2-(2-((2, 3-dihydrobenzo[b] [1, 4]dioxin-6-yl)amino)-2-oxoethoxy)-N-(2-oxo-2-phenylethyl)benzamide (DKC1125h18) ¹H-NMR (400 MHz, CDCl₃) δ 9.01 (s, 1H), 8.71 (s, 1H), 8.17 (q, J=2.3 Hz, 1H), 8.14 (dd J=7.8, 1.8 Hz, 1H), 7.90-7.92 (m, 2H), 7.60-7.64 (m, 1H), 7.46-7.53 (m, 3H), 7.15-7.19 (m, 1H), 7.03 (d, J=8.2 Hz, 1H), 6.82 (dd, J=8.2, 1.4 Hz, 1H), 6.57-6.61 (m, 1H), 6.34-6.45 (m, 2H), 6.12-6.23 (m, 2H), 5.43 (d, J=4.1 Hz, 2H), 4.90 (s, 2H). MS (ESI): m/z 447 (M+1).

2-(2-((2,3-dihydro-1H-inden-5-yl)amino)-2-oxoethoxy)-N-(2-oxo-2-phenylethyl)benzamide (DKC1125h19) ¹H-NMR (400 MHz, CDCl₃) δ 8.71 (s, 2H), 8.17 (q, J=2.3 Hz, 1H), 8.14 (dd, J=7.8, 1.8 Hz, 1H), 7.90-7.92 (m, 2H), 7.60-7.64 (m, 1H), 7.46-7.53 (m, 3H), 7.15-7.19 (m, 1H), 7.03 (d, J=8.2 Hz, 1H), 6.82 (dd, J=8.2, 1.4 Hz, 1H), 6.57-6.61 (m, 1H), 5.15 (d, J=4.1 Hz, 2H), 4.78 (s, 2H), 3.60-3.62 (d, J=3.1 Hz, 2H), 3.64-3.66 (d, J=3.4 Hz, 2H), 2.31-2.34 (d, J=2.32 Hz, 2H). MS (ESI): m/z 429 (M+1).

2-(2-((3-isopropoxyphenyl)amino)-2-oxoethoxy)-N-(2-oxo-2-phenylethyl)benzamide (DKC1125h20) ¹H-NMR (400 MHz, CDCl₃) δ 9.12 (s, 1H), 8.43 (s, 1H), 8.01-8.03 (m, 2H), 7.81-7.84 (m, 1H), 7.74-7.77 (m, 1H), 7.49-7.56 (m, 3H), 7.20 (dd, J=7.4, 1.8 Hz, 3H), 7.10-7.15 (m, 2H), 7.05-7.08 (m, 2H), 5.03 (t, J=3.9 Hz, 2H), 4.83 (s, 2H), 4.76-4.80 (m, 3H), 4.32-4.40 (m, 3H). MS (ESI): m/z 447 (M+1).

2-(2-oxo-2-((4-phenoxyphenyl)amino)ethoxy)-N-(2-oxo-2-phenylethyl)benzamide (DKC1125h21) ¹H-NMR (400 MHz, CDCl₃) δ 8.31 (s, 1H), 8.17 (q, J=2.3 Hz, 1H), 8.14 (dd, J=7.8, 1.8 Hz, 2H), 7.90-7.92 (m, 2H), 7.80 (dd, J=8.0, 1.8 Hz, 2H), 7.61-7.64 (m, 2H), 7.56 (s, 2H), 7.46-7.53 (m, 3H), 7.32 (d, J=8.2 Hz, 1H), 7.24 (dd, J=6.7, 1.4 Hz, 1H), 6.82 (dd, J=8.2, 1.4 Hz, 1H), 6.57-6.61 (m, 1H), 5.03 (d, J=4.1 Hz, 2H), 4.89 (s, 2H). MS (ESI): m/z 481 (M+1).

2-(2-((2-fluoro-5-(trifluoromethyl) phenyl)amino)-2-oxoethoxy)-N-(2-oxo-2-phenylethyl)benzamide (DKC1125h22) ¹H-NMR (400 MHz, CDCl₃) δ 8.71 (s, 2H), 8.37 (q, J=2.3 Hz, 2H), 8.12-8.18 (dd, J=7.8, 1H), 7.90-7.92 (m, 2H), 7.46-7.53 (m, 3H), 7.15-7.19 (m, 1H), 7.03 (d, J=8.2 Hz, 1H), 6.82 (dd, J=8.2, 1.4 Hz, 1H), 6.57-6.61 (m, 1H), 5.13 (d, J=4.1 Hz, 2H), 4.89 (s, 2H). MS (ESI): m/z 475 (M+1).

2-(2-((3-hydroxyphenyl)amino)-2-oxoethoxy)-N-(2-oxo-2-phenylethyl)benzamide (DKC1125h23) ¹H-NMR (400 MHz, CDCl₃) 9.56 (s, 1H), 8.43 (s, 1H), 8.01-8.03 (dd, J=8.0, 1.4 Hz, 2H), 7.81-7.84 (m, 1H), 7.74-7.77 (m, 1H), 7.49-7.56 (m, 3H), 7.20-7.24 (m, 3H), 7.10-7.15 (m, 2H), 7.05-7.08 (m, 1H), 5.40 (m, 1H), 5.03 (t, J=3.9 Hz, 2H), 4.83 (s, 2H). MS (ESI): m/z 405 (M+1).

2-(2-((2-chlorophenyl)amino)-2-oxoethoxy)-N-(2-oxo-2-phenylethyl)benzamide (DKC1125h24) ¹H-NMR (400 MHz, CDCl₃) δ 9.66 (s, 1H), 8.20 (s, 1H), 8.11-8.13 (m, 2H), 7.81-7.84 (m, 1H), 7.74-7.77 (m, 1H), 7.49-7.56 (m, 3H), 7.29 (dd, J=6.7, 1.8 Hz, 3H), 7.10-7.15 (m, 2H), 7.05-7.08 (m, 1H), 5.24 (t, J=3.9 Hz, 2H), 4.40 (s, 2H). MS (ESI): m/z 423 (M+1).

2-(2-((3-bromophenyl)amino)-2-oxoethoxy)-N-(2-oxo-2-phenylethyl)benzamide (DKC1125h25) ¹H-NMR (400 MHz, CDCl₃) δ 9.76 (s, 1H), 8.39 (s, 1H), 8.01-8.03 (m, 2H), 7.81-7.84 (m, 1H), 7.74-7.77 (m, 2H), 7.49-7.56 (m, 3H), 7.24 (dd, J=6.7, 1.4 Hz, 2H), 7.10-7.15 (m, 2H), 7.05-7.08 (m, 1H), 5.12 (t, J=3.9 Hz, 2H), 4.90 (s, 2H). MS (ESI): m/z 467 (M+1).

2-(2-(isopropylamino)-2-oxoethoxy)-N-(2-oxo-2-phenylethyl)benzamide (DKC1125h26) ¹H-NMR (400 MHz, CDCl₃) δ 9.76 (s, 1H), 8.01-8.03 (s, 1H), 7.81-7.84 (m, 1H), 7.74-7.77 (m, 2H), 7.30-7.34 (m, 2H), 7.10-7.15 (m, 2H), 7.05-7.08 (m, 1H), 6.01-6.1 (m, 1H), 5.03 (t, J=3.9 Hz, 2H), 4.83 (s, 2H), 4.9 (s, 3H), 4.3 (s, 3H). MS (ESI): m/z 355 (M+1).

2-(2-(3,4-dihydroisoquinolin-2 (1H)-yl)-2-oxoethoxy)-N-(2-oxo-2-phenylethyl)benzamide (DKC1125h27) ¹H-NMR (400 MHz, CDCl₃) δ 8.71 (s, 1H), 8.17 (d, J=2.3 Hz, 1H), 8.14 (dd, J=7.8, 1.8 Hz, 1H), 7.90-7.92 (m, 2H), 7.60-7.64 (m, 1H), 7.46-7.53 (m, 3H), 7.15-7.19 (m, 1H), 7.03 (d, J=8.2 Hz, 1H), 6.82 (dd, J=8.2, 1.4 Hz, 2H), 6.57-6.61 (m, 1H), 5.03 (d, J=4.1 Hz, 2H), 4.89 (s, 2H), 3.60-3.62 (d, J=3.1 Hz, 2H), 3.64-3.66 (d, J=3.4 Hz, 2H), 2.31-2.34 (d, J=2.3 Hz, 2H). MS (ESI): m/z 429 (M+1).

2-(2-oxo-2-propylamino)ethoxy)-N-(2-oxo-2-phenylethyl)benzamide (DKC1125h28) ¹H-NMR (400 MHz, CDCl₃) δ 8.39 (s, 1H), 8.02 (d, J=7.3 Hz, 1H), 7.80 (dd, J=7.8, 1.4 Hz, 2H), 7.62 (d, J=3.2 Hz, 3H), 7.56-7.58 (m, 3H), 6.89-6.96 (m, 1H), 5.03 (t, J=3.9 Hz, 2H), 4.83 (s, 2H), 4.04-4.10 (m, 2H), 3.95 (t, J=5.7 Hz, 2H), 3.7 (s, 3H) MS (ESI): m/z 355 (M+1).

2-(2-(isopentylamino)-2-oxoethoxy)-N-(2-oxo-2-phenylethyl)benzamide (DKC1125h29) ¹H-NMR (400 MHz, CDCl₃) δ 8.96 (s, 1H) 8.02 (d, J=7.3 Hz, 1H), 7.72 (dd, J=7.8, 1.4 Hz, 2H), 7.71 (d, J=3.2 Hz, 3H), 7.52-7.56 (m, 3H), 6.89-6.94 (m, 1H), 5.03 (t, J=3.9 Hz, 2H), 4.83 (s, 2H), 4.66 (s, 1H), 4.04-4.10 (m, 2H), 3.95 (t, J=5.7 Hz, 2H), 3.8 (s, 3H), 3.3 (s, 3H). MS (ESI): m/z 383(M+1).

2-(2-(cyclohexylamino)-2-oxoethoxy)-N-(2-oxo-2-phenylethyl)benzamide (DKC1125h30) ¹H-NMR (400 MHz, CDCl₃) δ 8.02 (d, J=7.3 Hz, 1H), 7.79 (dd, J=7.8, 1.4 Hz, 1H), 7.71 (d, J=3.2 Hz, 3H), 7.52-7.56 (m, 3H), 6.89-6.94 (m, 1H), 5.03 (t, J=3.9 Hz, 2H), 4.83 (s, 2H), 4.42-4.48 (m, 1H), 3.26 (td, J=8.7, 4.3 Hz, 2H), 2.4 (m, 2H), 2.17-2.25 (m, 4H), 2.06-2.14 (m, 2H). MS (ESI): m/z 395 (M+1).

Examples 231 to 305. Preparation of Compounds 231 to 305 (DKC1125i01 to 75) According to the Present Invention

Synthesis of Compounds 231 to 305 (DKC1125i01 to 75)

Compounds 231 to 305 (DKC1125i01-75) of the present invention were synthesized according to the following Reaction Scheme 8.

Preparation Method for Bromomethylbenzoyl Chloride (1)

SOCl₂ (2 mL, 27.91 mmol) was added dropwise to bromomethylbenzoic acid (1 g, 4.651 mmol) under an anhydrous atmosphere at room temperature. The reaction mixture was stirred under reflux for 4.5 hrs. After completion of the reaction, excess of SOCl₂ was removed by evaporation to obtain bromomethylbenzoyl chloride (1) (1.62 g, 6.95 mmol, 73%) which was used in the next step without any purification.

Preparation Method for 3-(bromomethyl)-N-(2-oxo-2-phenylethyl)benzamide (R₁=CH₂Br, R₂=H) (3)

To 3-(bromomethyl)benzoyl chloride (1) (1 g, 4.29 mmol) in DCM (100 mL) was added 2-amino-1-phenylethan-1-one (2) (737 mg, 4.29 mmol) and added NaHCO₃ (50 mL). The reaction mixture was stirred at room temperature for 1 hr. The stirred mixture was extracted with DCM, washed with brine, and then dried over anhydrous Na₂SO₄. Purification using an EA/HEX system column afforded 3-(bromomethyl)-N-(2-oxo-2-phenylethyl)benzamide (R₁=CH₂Br, R₂=H) (3) (883 mg, 62%).

¹H-NMR (400 MHz, CDCl₃) δ 8.03-8.05 (m, 2H), 7.86-7.88 (m, 2H), 7.65 (d, J=7.3 Hz, 1H), 7.49-7.56 (m, 4H), 7.30 (s, 1H), 4.97 (d, J=4.1 Hz, 2H), 4.52 (s, 2H).

Preparation Method for 4-(bromomethyl)-N-(2-oxo-2-phenylethyl)benzamide (R₁=CH₂Br, R₂=H) (3)

To 4-(bromomethyl)benzoyl chloride (1) (1 g, 4.29 mmol) in DCM (100 mL) was added 2-amino-1-phenylethan-1-one (2) (736 mg, 4.29 mmol) and added NaHCO₃ (50 mL). The reaction mixture was stirred at room temperature for 1 hr. The stirred mixture was extracted with DCM, washed brine and then dried over anhydrous Na₂SO₄. Purification using an EA/HEX system column afforded 4-(bromomethyl)-N-(2-oxo-2-phenylethyl)benzamide (R₁=CH₂Br, R₂=H) (3) (1.18 g, 3.56 mmol, 83%).

¹H-NMR (400 MHz, CDCl₃) δ 8.05 (dd, J=8.5, 1.1 Hz, 2H), 7.91-7.92 (m, 1H), 7.81 (dd, J=6.2, 1.6 Hz, 1H), 7.64-7.68 (m, 1H), 7.52-7.59 (m, 3H), 7.47 (t, J=7.8 Hz, 1H), 7.31 (s, 1H), 4.98 (d, J=4.1 Hz, 2H), 4.55 (s, 2H)

Preparation Method for 3-(bromomethyl)-N-(2-(3-methoxyphenyl)-2-oxoethyl)benzamide (R₁=CH₂Br, R₂=OCH₃) (3)

To 3-(bromomethyl)benzoyl chloride (1) (1 g, 4.29 mmol) in DCM (100 mL) was added 1-amino-3-(3-methoxyphenyl)propan-2-one (2) (736 mg, 4.29 mmol) and added NaHCO₃ (50 mL). The reaction mixture was stirred at room temperature for 1 hr. The stirred mixture was extracted with DCM, washed brine and then dried over anhydrous Na₂SO₄. Purification using an r EA/HEX system column afforded 3-(bromomethyl)-N-(2-(3-methoxyphenyl)-2-oxoethyl)benzamide (R₁=CH₂Br, R₂=OCH₃) (3) (1.01 g, 65%).

¹H-NMR (400 MHz, CDCl₃) δ 7.91-7.92 (m, 1H), 7.81 (dt, J=7.8, 1.4 Hz, 1H), 7.61-7.64 (m, 1H), 7.54-7.59 (m, 2H), 7.46 (q, J=8.1 Hz, 2H), 7.18-7.21 (m, 1H), 4.96 (d, J=4.1 Hz, 2H), 4.55 (s, 2H), 3.89 (s, 3H).

Preparation Method for 2-(bromomethyl)-N-(2-oxo-2-phenylethyl)benzamide (R₁=CH₂Br, R₂=H) (3)

To 2-(bromomethyl)benzoyl chloride (1) (1 g, 4.29 mmol) in DCM (100 mL) was added 2-amino-1-phenylethan-1-one (2) (736 mg, 4.29 mmol) and added NaHCO₃ (50 mL). The reaction mixture was stirred at room temperature for 1 hr. The stirred mixture was extracted with DCM, washed brine and then dried over anhydrous Na₂SO₄. The resulting crude product was purified by column chromatography to obtain the title compound (3) (955 mg, 67%).

¹H-NMR (400 MHz, CDCl₃) δ 8.02-8.05 (m, 2H), 7.66 (tt, J=7.5, 1.4 Hz, 1H), 7.37-7.59 (m, 6H), 7.10 (s, 1H), 4.99 (d, J=4.6 Hz, 2H), 4.84 (s, 2H)

General Preparation Method for Compounds 231 to 253 (DKC1125i01 to 23)

The title compounds were prepared. Specifically, to 3-(bromomethyl)-N-(2-oxo-2-phenylethyl)benzamide (R₁=CH₂Br, R₂=H) (3) (50 mg, 0.15 mmol) in DCM (1 mL) was added secondary amine described in Table 10 below. Then, DIEA (39 mg, 0.30 mmol) was added thereto. The reaction mixture was stirred at 35° C. for 3 hrs. Purification using an EA/HEX system column afforded the final compound (yield: 50 to 60%).

TABLE 10
Secondary amines used in preparation
of compounds 231 to 253
(DKC1125i01 to 23)
Compounds  Secondary amine
DKC1125i01 Dimethylamine hydrochloride
DKC1125i02 1,2,3,4-tetrahydroisoquinoline
DKC1125i03 N-methylisopropylamine
DKC1125i04 1-(2-fluorophenyl)piperazine
DKC1125i05 2-(1-Piperazinyl)pyrimidine
DKC1125i06 1-(2-methoxyphenyl)piperazine
DKC1125i07 4-Piperidinopiperidine
DKC1125i08 1-(4-nitrophenyl)piperazine
DKC1125i09 N-Ethylaniline
DKC1125i10 1-(2-pyridyl)piperazine, HCl
DKC1125i11 Diallylamine
DKC1125i12 N-Benzylmethylamine
DKC1125i13 2-(Methylamino)ethanol
DKC1125i14 2-(Butylamino)ethanol
DKC1125i15 1-Boc-piperazine
DKC1125i16 N-methyl-1-butylamine
DKC1125i17 Diethylamine
DKC1125i18 Di-n-propylamine
DKC1125i19 N-ethylbutylamine
DKC1125i20 Dipentylamine
DKC1125i21 N-Methylpropargylamine
DKC1125i22 Morpholine
DKC1125i23 1-methylpiperazine

General Preparation Method for Compounds 254 to 278 (DKC1125i24 to 48)

To 4-(bromomethyl)-N-(2-oxo-2-phenylethyl)benzamide (R₁=CH₂Br, R₂=H) (3) (50 mg, 0.15 mmol) in DCM (1 mL) was added secondary amine shown in Table 11 below. Then, DIEA (39 mg, 0.30 mmol) was added thereto. The reaction mixture was stirred at 35° C. for 3 hrs. Purification using an EA/HEX system column afforded to the final compound (50 to 60% yield).

TABLE 11
Secondary amines used in preparation
of compounds 254 to 278
(DKC1125i24 to 48)
Compounds  Secondary amine
DKC1125i24 1,2,3,4-tetrahydroisoquinoline
DKC1125i25 N-methylcyclohexylamine
DKC1125i26 N-methylisopropylamine
DKC1125i27 1-(2-fluorophenyl)piperazine
DKC1125i28 2-(1-Piperazinyl)pyrimidine
DKC1125i29 1-(2-methoxyphenyl)piperazine
DKC1125i30 4-Piperidinopiperidine
DKC1125i31 1-(4-nitrophenyl)piperazine
DKC1125i32 N-Methylaniline
DKC1125i33 N-Ethylaniline
DKC1125i34 1-(2-pyridyl)piperazine, HCl
DKC1125i35 Diallylamine
DKC1125i36 N-Benzylmethylamine
DKC1125i37 2-(Methylamino)ethanol
DKC1125i38 2-(Butylamino)ethanol
DKC1125i39 1-Boc-piperazine
DKC1125i40 dicyclohexylamine
DKC1125i41 N-methyl-1-butylamine
DKC1125i42 Di-n-propylamine
DKC1125i43 N-ethylbutylamine
DKC1125i44 2-(Ethylamino)ethanol
DKC1125i45 N-Methylpropargylamine
DKC1125i46 N-ethylpropan-1-amine
DKC1125i47 Ethyl piperazine-1-carboxylate
DKC1125i48 2,6-dimethylmorpholine

General Preparation Method for Compounds 279 to 295 (DKC1125i49 to 65)

To 3-(bromomethyl)-N-(2-(3-methoxyphenyl)-2-oxoethyl)benzamide (R₁=CH₂Br, R₂=OCH₃) (3) (50 mg, 0.15 mmol) in DCM (1 mL) was added secondary amine shown in Table 12 below. Then, DIEA (39 mg, 0.30 mmol) was added thereto. The reaction mixture was stirred at 35° C. for 3 hrs. Purification using an EA/HEX system column afforded the final compound (50 to 60% yield).

TABLE 12
Secondary amines used in preparation
of compounds 279 to 295
(DKC1125i49 to 65)
Compounds  Secondary amine
DKC1125i49 1,2,3,4-tetrahydroisoquinoline
DKC1125i50 N-methylcyclohexylamine
DKC1125i51 1-(2-fluorophenyl)piperazine
DKC1125i52 1-(2-methoxyphenyl)piperazine
DKC1125i53 4-Piperidinopiperidine
DKC1125i54 1-(2-pyridyl)piperazine, HCl
DKC1125i55 Diallylamine
DKC1125i56 N-Benzylmethylamine
DKC1125i57 N-Ethylmethylamine
DKC1125i58 2-(Butylamino)ethanol
DKC1125i59 1-Boc-piperazine
DKC1125i60 N-ethylbutylamine
DKC1125i61 Dipentylamine
DKC1125i62 1-Piperazineethanol
DKC1125i63 morpholine
DKC1125i64 N-ethylpropan-1-amine
DKC1125i65 2,6-dimethylmorpholine

General Preparation Method for Compounds 296 to 305 (DKC1125i66 to 75)

To 2-(bromomethyl)-N-(2-oxo-2-phenylethyl)benzamide (R₁=CH₂Br, R₂=H) (3) (50 mg, 0.15 mmol) in DCM (1 mL) was added secondary amine shown in Table 13 below. Then, DIEA (39 mg, 0.30 mmol) was added thereto. The reaction mixture was stirred at 35° C. for 3 hrs. Purification using an EA/HEX system column afforded the final compound (50 to 60% yield).

TABLE 13
Secondary amines used in preparation
of compounds 296 to 305
(DKC1125i66 to 75)
Compounds  Secondary amine
DKC1125i66 Dimethylamine hydrochloride
DKC1125i67 1,2,3,4-tetrahydroisoquinoline
DKC1125i68 N-methylcyclohexylamine
DKC1125i69 1-(2-fluorophenyl)piperazine
DKC1125i70 2-(1-Piperazinyl)pyrimidine
DKC1125i71 4-Piperidinopiperidine
DKC1125i72 1-(2-pyridyl)piperazine, HCl
DKC1125i73 Diallylamine
DKC1125i74 Morpholine
DKC1125i75 Ethyl piperazine-1-carboxylate

Confirmation of Preparation of Compounds 231 to 305 (DKC1125i01 to 75)

3-((dimethylamino)methyl)-N-(2-oxo-2-phenylethyl)benzamide (DKC1125i01) ¹H-NMR (400 MHz, CDCl₃) δ 8.02-7.29 (m, 10H), 4.94 (d, J=4.0 Hz, 2H), 3.62 (s, 2H), 2.34 (s, 6H). MS(ESI): m/z 297 (M+1).

3-((3,4-dihydroisoquinolin-2 (1H)-yl)methyl)-N-(2-oxo-2-phenylethyl)benzamide (DKC1125i02) ¹H-NMR (400 MHz, CDCl₃) δ 8.01-7.44 (m, 10H), 7.10 (s, 3H), 6.97 (d, 8.0 Hz, 1H), 4.96 (d, J=4 Hz 2H), 3.75 (s, 2H), 3.65 (s, 2H), 2.79 (t, J=6.0 Hz, 2H), 1.26 (t, J=6.8 Hz, 2H). MS(ESI): m/z 385 (M+1).

3-((isopropyl(methyl)amino)methyl)-N-(2-oxo-2-phenylethyl)benzamide (DKC1125i03) ¹H-NMR (400 MHz, CDCl₃) δ 8.03-7.40 (m, 10H), 4.95 (d, J=4.0 Hz, 2H), 3.69 (s, 2H), 3.05 (q, J=6.4 Hz, 1H), 2.24 (s, 3H), 1.16 (d, J=6.4 Hz, 6H). MS(ESI): m/z 325 (M+1).

3-((4-(2-fluorophenyl)piperazin-1-yl)methyl)-N-(2-oxo-2-phenylethyl)benzamide (DKC1125i04) ¹H-NMR (400 MHz, CDCl₃) δ 8.04-8.06 (m, 2H), 7.89 (s, 1H), 7.79 (d, J=7.8 Hz, 1H), 7.66 (t, J=7.5 Hz, 1H), 7.52-7.56 (m, 3H), 7.44 (t, J=7.8 Hz, 1H), 7.33 (s, 1H), 6.90-7.07 (m, 4H), 4.98 (d, J=4.6 Hz, 2H), 3.65 (s, 2H), 3.13 (t, J=4.6 Hz, 4H), 2.67 (t, J=4.3 Hz, 4H). MS(ESI): m/z 432 (M+1).

N-(2-oxo-2-phenylethyl)-3-((4-(pyrimidin-2-yl)piperazin-1-yl)methyl)benzamide (DKC1125i05) ¹H-NMR (400 MHz, CDCl₃) δ 8.27 (d, J=4.8 Hz, 2H), 8.02-7.39 (m, 10H), 6.45 (t, J=4.8 Hz, 1H), 4.95 (d, J=4.4 Hz, 2H), 3.83 (t, J=4.8 Hz, 4H), 3.60 (s, 2H), 2.52 (t, J=4.8 Hz, 4H). MS (ESI): m/z 417 (M+1).

3-((4-(2-methoxyphenyl)piperazin-1-yl)methyl)-N-(2-oxo-2-phenylethyl)benzamide (DKC1125i06) ¹H-NMR (400 MHz, CDCl₃) δ 8.09-7.33 (m, 10H), 7.01-6.84 (m, 4H), 4.98 (d, J=4.0 Hz, 2H), 3.85 (s, 3H), 3.65 (s, 2H), 3.10 (s, 4H), 2.68 (s, 4H). MS(ESI): m/z 445 (M+1).

3-([1,4′-bipiperidin]-1′-ylmethyl)-N-(2-oxo-2-phenylethyl)benzamide (DKC1125i07) ¹H-NMR (400 MHz, CDCl₃) δ 8.01 (d, J=8.7 Hz, 2H), 7.80 (s, 1H), 7.76 (d, J=7.3 Hz, 1H), 7.63 (dd, J=8.0, 6.6 Hz, 1H), 7.49-7.53 (m, 2H), 7.34-7.45 (m, 3H), 4.94 (d, J=4.1 Hz, 2H), 3.52 (s, 2H), 2.95-3.10 (m, 6H), 2.01-2.13 (m, 5H), 1.75-1.84 (m, 2H), 1.44-1.58 (m, 4H), 1.16-1.30 (m, 2H). MS(ESI): m/z 421 (M+1).

3-((4-(4-nitrophenyl)piperazin-1-yl)methyl)-N-(2-oxo-2-phenylethyl)benzamide (DKC1125i08) ¹H-NMR (400 MHz, CDCl₃) δ 8.02-8.14 (m, 4H), 7.88 (s, 1H), 7.79 (d, J=7.8 Hz, 1H), 7.63-7.67 (m, 1H), 7.51-7.54 (m, 3H), 7.41-7.46 (m, 1H), 7.34 (s, 1H), 6.79 (d, J=9.6 Hz, 2H), 4.97 (d, J=4.1 Hz, 2H), 3.62 (s, 2H), 3.42 (t, J=5.0 Hz, 4H), 2.60 (t, J=5.0 Hz, 4H). MS(ESI): m/z 460 (M+1).

3-((ethyl(phenyl)amino)methyl)-N-(2-oxo-2-phenylethyl)benzamide (DKC1125i09) ¹H-NMR (400 MHz, CDCl₃) δ 8.01-8.04 (m, 5H), 7.50-7.81 (m, 7H), 6.69 (s, 3H), 4.94 (d, J=4.1 Hz, 2H), 4.53 (s, 2H), 3.49 (brs, 2H), 1.67 (brs, 3H). MS(ESI): m/z 373 (M+1).

N-(2-oxo-2-phenylethyl)-3-((4-(pyridin-2-yl)piperazin-1-yl)methyl)benzamide (DKC1125i10) ¹H-NMR (400 MHz, CDCl₃) δ 7.98-8.17 (m, 4H), 7.82 (d, J=7.8 Hz, 1H), 7.43-7.65 (m, 7H), 6.61-6.67 (m, 2H), 4.95 (d, J=4.4 Hz, 2H), 3.75 (s, 2H), 3.67 (t, J=4.8 Hz, 4H), 2.70 (brs, 4H). MS (ESI): m/z 416 (M+1).

3-((diallylamino)methyl)-N-(2-oxo-2-phenylethyl)benzamide (DKC1125i11) ¹H-NMR (400 MHz, CDCl₃) δ 8.03-8.06 (m, 2H), 7.30-7.84 (m, 8H), 5.85-5.95 (m, 2H), 5.15-5.24 (m, 4H), 4.97 (d, J=4.1 Hz, 2H), 3.64 (s, 2H), 3.10 (d, J=6.4 Hz, 4H). MS(ESI): m/z 349 (M+1).

3-((benzyl(methyl)amino)methyl)-N-(2-oxo-2-phenylethyl)benzamide (DKC1125i12) ¹H-NMR (400 MHz, CDCl₃) δ 8.04-8.07 (m, 2H), 7.88 (s, 1H), 7.27-7.78 (m, 12H), 4.98 (d, J=4.1 Hz, 2H), 3.59 (s, 2H), 3.55 (s, 2H), 2.20 (s, 3H). MS(ESI): m/z 373 (M+1).

3-(((2-hydroxyethyl) (methyl)amino)methyl)-N-(2-oxo-2-phenylethyl)benzamide (DKC1125i13) ¹H-NMR (400 MHz, CDCl₃) δ 8.03 (dd, J=8.5, 1.1 Hz, 2H), 7.92 (s, 1H), 7.79-7.82 (m, 1H), 7.62-7.64 (m, 1H), 7.42-7.54 (m, 5H), 4.95 (d, J=4.1 Hz, 2H), 3.76 (s, 2H), 3.71 (t, J=5.2 Hz, 2H), 3.13 (q, J=7.3 Hz, 1H), 2.72 (t, J=5.3 Hz, 2H), 2.35 (s, 3H). MS(ESI): m/z 327 (M+1).

3-((butyl (2-hydroxyethyl)amino)methyl)-N-(2-oxo-2-phenylethyl)benzamide (DKC1125i14) ¹H-NMR (400 MHz, CDCl₃) δ 8.16 (s, 1H), 8.00-8.02 (m, 2H), 7.88 (d, J=7.8 Hz, 1H), 7.61-7.69 (m, 3H), 7.45-7.53 (m, 3H), 4.94 (d, J=4.6 Hz, 2H), 4.11 (s, 2H), 3.83 (t, J=5.0 Hz, 2H), 3.13 (q, J=7.5 Hz, 2H), 3.00 (t, J=4.8 Hz, 2H), 2.86 (t, J=7.8 Hz, 2H), 1.58 (t, J=7.3 Hz, 2H), 0.90 (t, J=7.5 Hz, 3H). MS (ESI): m/z 369 (M+1).

tert-butyl 4-(3-((2-oxo-2-phenylethyl) carbamoyl)benzyl) piperazine-1-carboxylate (DKC1125i15) ¹H-NMR (400 MHz, CDCl₃) δ 8.02-8.04 (m, 2H), 7.84 (s, 1H), 7.77 (d, J=7.8 Hz, 1H), 7.65 (t, J=7.5 Hz, 1H), 7.40-7.55 (m, 4H), 7.32 (s, 1H), 4.97 (d, J=4.1 Hz, 2H), 3.56 (s, 2H), 3.43 (t, J=4.8 Hz, 4H), 2.40 (brt, 4H), 1.45 (s, 9H). MS(ESI): m/z 439 (M+1).

3-((butyl (methyl)amino)methyl)-N-(2-oxo-2-phenylethyl)benzamide (DKC1125i16) ¹H-NMR (400 MHz, CDCl₃) δ 8.17 (s, 1H), 7.99-8.04 (m, 3H), 7.90 (d, J=7.8 Hz, 1H), 7.60-7.69 (m, 2H), 7.47-7.52 (m, 3H), 4.92 (d, J=5.0 Hz, 2H), 4.03 (s, 2H), 2.81 (t, J=8.0 Hz, 2H), 2.54 (s, 3H), 1.73-1.77 (m, 2H), 1.48-1.58 (m, 2H), 1.32-1.40 (m, 3H) MS(ESI): m/z 339 (M+1).

3-((diethylamino)methyl)-N-(2-oxo-2-phenylethyl)benzamide (DKC1125i17) ¹H-NMR (400 MHz, CDCl₃) δ 8.32 (s, 1H), 7.98-8.00 (m, 2H), 7.92 (d, J=7.8 Hz, 1H), 7.84 (s, 1H), 7.71 (d, J=7.8 Hz, 1H), 7.59-7.63 (m, 1H), 7.46-7.51 (m, 3H), 4.91 (d, J=4.6 Hz, 2H), 4.12 (s, 2H), 3.02 (q, J=7.3 Hz, 4H), 1.35 (t, J=7.1 Hz, 6H). MS(ESI): m/z 325 (M+1).

3-((dipropylamino)methyl)-N-(2-oxo-2-phenylethyl)benzamide (DKC1125i18) ¹H-NMR (400 MHz, CDCl₃) δ 8.04 (d, J=7.3 Hz, 2H), 7.84 (s, 1H), 7.75 (d, J=7.8 Hz, 1H), 7.64 (t, J=7.3 Hz, 1H), 7.33-7.54 (m, 5H), 4.96 (d, J=4.6 Hz, 2H), 3.62 (s, 2H), 2.35-2.41 (m, 4H), 1.45-1.54 (m, 4H), 0.87 (t, J=7.3 Hz, 6H). MS(ESI): m/z 353 (M+1).

3-((butyl(ethyl)amino)methyl)-N-(2-oxo-2-phenylethyl)benzamide (DKC1125i19) ¹H-NMR (400 MHz, CDCl₃) δ 7.37-8.18 (m, 10H), 4.94 (d, J=4.1 Hz, 2H), 3.96 (s, 2H), 2.75-3.05 (m, 4H), 1.25-1.84 (m, 10H). MS(ESI): m/z 353 (M+1).

3-((dipentylamino)methyl)-N-(2-oxo-2-phenylethyl)benzamide (DKC1125i20) ¹H-NMR (400 MHz, CDCl₃) δ 7.31-8.05 (m, 10H), 4.97 (d, J=4.1 Hz, 2H), 3.50-3.63 (m, 2H), 2.09-2.40 (m, 8H), 1.01-1.57 (m, 14H). MS(ESI): m/z 410 (M+1).

3-((ethynyl(methyl)amino)methyl)-N-(2-oxo-2-phenylethyl)benzamide (DKC1125i21) ¹H-NMR (400 MHz, CDCl₃) δ 8.04 (d, J=7.3 Hz, 2H), 7.79-7.85 (m, 2H), 7.63-7.67 (m, 1H), 7.32-7.55 (m, 5H), 4.97 (d, J=4.1 Hz, 2H), 3.64 (s, 2H), 3.33 (d, J=2.3 Hz, 1H), 2.35 (s, 3H). MS(ESI): m/z 307 (M+1).

3-(morpholinomethyl)-N-(2-oxo-2-phenylethyl)benzamide (DKC1125i22) ¹H-NMR (400 MHz, CDCl₃) δ 8.04 (d, J=7.3 Hz, 2H), 7.85 (s, 1H), 7.77 (d, J=7.3 Hz, 1H), 7.62-7.67 (m, 1H), 7.33-7.55 (m, 5H), 4.96 (d, J=4.6 Hz, 2H), 3.71 (t, J=4.6 Hz, 4H), 3.56 (s, 2H), 2.46 (t, J=4.3 Hz, 4H). MS (ESI): m/z 339 (M+1).

3-((4-methylpiperazin-1-yl)methyl)-N-(2-oxo-2-phenylethyl)benzamide (DKC1125i23) ¹H-NMR (400 MHz, CDCl₃) δ 7.34-8.04 (m, 10H), 4.96 (d, J=4.1 Hz, 2H), 3.56 (s, 2H), 2.52 (s, 11H). MS(ESI): m/z 352 (M+1).

4-((3,4-dihydroisoquinolin-2(1H)-yl)methyl)-N-(2-oxo-2-phenylethyl)benzamide (DKC1125i24) ¹H-NMR (400 MHz, CDCl₃) δ 8.03-8.08 (m, 2H), 7.86 (d, J=8.2 Hz, 2H), 7.63-7.67 (m, 1H), 7.50-7.55 (m, 4H), 7.31 (brs, 1H), 7.08-7.13 (m, 3H), 6.98-7.00 (m, 1H), 4.97 (d, J=4.1 Hz, 2H), 3.75 (s, 2H), 3.65 (s, 2H), 2.92 (t, J=5.7 Hz, 2H), 2.76 (t, J=5.9 Hz, 2H). MS(ESI): m/z 385 (M+1).

4-((cyclohexyl(methyl)amino)methyl)-N-(2-oxo-2-phenylethyl)benzamide (DKC1125i25) ¹H-NMR (400 MHz, CDCl₃) δ 8.08 (d, J=7.3 Hz, 2H), 7.92 (d, J=7.8 Hz, 2H), 7.55-7.71 (m, 5H), 7.38 (s, 1H), 5.01 (d, J=4.6 Hz, 2H), 3.91 (s, 2H), 3.72-3.79 (m, 1H), 2.43 (s, 3H), 2.09 (d, J=11.4 Hz, 2H), 1.89 (d, J=12.8 Hz, 2H), 1.61-1.72 (m, 2H), 1.43 (dd, J=12.1, 2.5 Hz, 2H), 1.21-1.33 (m, 2H). MS(ESI): m/z 365 (M+1).

4-((isopropyl(methyl)amino)methyl)-N-(2-oxo-2-phenylethyl)benzamide (DKC1125i26) ¹H-NMR (400 MHz, CDCl₃) δ 8.02-8.04 (m, 2H), 7.85-7.87 (m, 2H), 7.63-7.66 (m, 1H), 7.48-7.54 (m, 4H), 7.29 (s, 1H), 4.95 (d, J=4.1 Hz, 2H), 4.50 (s, 2H), 1.60 (s, 3H), 1.24 (s, 6H), 0.81-0.88 (m, 1H). MS (ESI): m/z 325 (M+1).

4-((4-(2-fluorophenyl)piperazin-1-yl)methyl)-N-(2-oxo-2-phenylethyl)benzamide (DKC1125i27) ¹H-NMR (400 MHz, CDCl₃) δ 8.03-8.06 (m, 2H), 7.85-7.87 (m, 2H), 7.63-7.68 (m, 1H), 7.47-7.56 (m, 4H), 7.30 (t, J=4.1 Hz, 1H), 6.91-7.08 (m, 4H), 4.98 (d, J=4.6 Hz, 2H), 3.64 (s, 2H), 3.12 (t, J=4.8 Hz, 4H), 2.65 (t, J=4.8 Hz, 4H). MS (ESI): m/z 433 (M+1).

N-(2-oxo-2-phenylethyl)-4-((4-(pyrimidin-2-yl)piperazin-1-yl)methyl)benzamide (DKC1125i28) ¹H-NMR (400 MHz, CDCl₃) δ 8.30 (d, J=4.6 Hz, 2H), 8.03-8.05 (m, 2H), 7.86 (d, J=8.2 Hz, 2H), 7.65 (tt, J=7.4, 1.4 Hz, 1H), 7.46-7.55 (m, 4H), 7.30 (t, J=3.9 Hz, 1H), 6.47 (t, J=4.6 Hz, 1H), 4.97 (d, J=4.6 Hz, 2H), 3.84 (t, J=5.0 Hz, 4H), 3.60 (s, 2H), 2.51 (t, J=5.0 Hz, 4H). MS(ESI): m/z 417 (M+1).

4-((4-(2-methoxyphenyl)piperazin-1-yl)methyl)-N-(2-oxo-2-phenylethyl)benzamide (DKC1125i29) ¹H-NMR (400 MHz, CDCl₃) δ 8.03-8.05 (m, 2H), 7.86 (d, J=8.2 Hz, 2H), 7.63-7.67 (m, 1H), 7.47-7.55 (m, 4H), 7.30 (t, J=4.1 Hz, 1H), 6.84-7.02 (m, 4H), 4.97 (d=4.1 Hz, 2H), 3.86 (s, 3H), 3.64 (s, 2H), 3.10 (brs, 4H), 2.67 (brs, 4H). MS(ESI): m/z 445 (M+1).

4-([1,4′-bipiperidin]-1′-ylmethyl)-N-(2-oxo-2-phenylethyl)benzamide (DKC1125i30) ¹H-NMR (400 MHz, CDCl₃) δ 7.99-8.02 (m, 2H), 7.82 (d, J=8.2 Hz, 2H), 7.60-7.62 (m, 1H), 7.50 (t, J=7.8 Hz, 2H), 7.34-7.38 (m, 3H), 4.93 (d, J=4.1 Hz, 2H), 3.65-3.72 (m, 3H), 3.54 (s, 2H), 3.11 (q, J=7.5 Hz, 4H), 2.98 (d, J=12.3 Hz, 2H), 2.21 (d, J=11.9 Hz, 2H), 2.09 (t, J=11.2 Hz, 2H), 1.86 (dd, J=11.9, 3.7 Hz, 2H), 1.55 (t, J=7.5 Hz, 4H). MS(ESI): m/z 421 (M+1).

4-((4-(4-nitrophenyl)piperazin-1-yl)methyl)-N-(2-oxo-2-phenylethyl)benzamide (DKC1125i31) ¹H-NMR (400 MHz, CDCl₃) 8.10-8.14 (m, 2H), 8.03-8.06 (m, 2H), 7.87 (d, J=8.2 Hz, 2H), 7.64-7.68 (m, 1H), 7.43-7.56 (m, 4H), 7.29 (t, J=4.1 Hz, 1H), 6.80-6.84 (m, 2H), 4.98 (d, J=4.6 Hz, 2H), 3.63 (s, 2H), 3.44 (t, J=5.0 Hz, 4H), 2.61 (t, J=5.3 Hz, 4H). MS(ESI): m/z 460 (M+1).

4-((methyl (phenyl)amino)methyl)-N-(2-oxo-2-phenylethyl)benzamide (DKC1125i32) ¹H-NMR (400 MHz, CDCl₃) δ 8.04 (d, J=7.8 Hz, 2H), 7.82-7.87 (m, 2H), 7.51-7.67 (m, 3H), 7.33-7.40 (m, 2H), 7.22-7.24 (m, 1H), 6.73-6.91 (m, 5H), 4.96 (d, J=4.1 Hz, 2H), 4.59 (s, 2H), 3.05 (s, 3H). MS (ESI): m/z 359 (M+1).

4-((ethyl(phenyl)amino)methyl)-N-(2-oxo-2-phenylethyl)benzamide (DKC1125i33) ¹H-NMR (400 MHz, CDCl₃) δ 8.02-8.05 (m, 3H), 7.82-7.88 (m, 3H), 7.49-7.68 (m, 6H), 7.30-7.36 (m, 1H), 7.19 (dd, J=8.9, 7.1 Hz, 1H), 6.69 (t, J=8.0 Hz, 1H), 4.97 (d, J=4.1 Hz, 2H), 4.52 (s, 2H), 3.50 (q, J=7.0 Hz, 2H), 1.22 (t, J=7.1 Hz, 3H). MS(ESI): m/z 373 (M+1).

N-(2-oxo-2-phenylethyl)-4-((4-(pyridin-2-yl)piperazin-1-yl)methyl)benzamide (DKC1125i34) ¹H-NMR (400 MHz, CDCl₃) δ 8.18-8.19 (m, 1H), 8.03-8.06 (m, 2H), 7.86 (d, J=8.2 Hz, 2H), 7.63-7.68 (m, 1H), 7.45-7.56 (m, 5H), 7.29 (s, 1H), 6.60-6.65 (m, 2H), 4.98 (d, J=4.1 Hz, 2H), 3.61 (s, 2H), 3.56 (t, J=5.0 Hz, 4H), 2.57 (t, J=5.0 Hz, 4H). MS (ESI): m/z 416 (M+1).

4-((diallylamino)methyl)-N-(2-oxo-2-phenylethyl)benzamide (DKC1125i35) ¹H-NMR (400 MHz, CDCl₃) δ 8.04 (d, J=8.2 Hz, 2H), 7.83 (d, J=8.2 Hz, 2H), 7.63-7.67 (m, 1H), 7.53 (t, J=7.5 Hz, 2H), 7.28-7.45 (m, 3H), 5.83-5.93 (m, 2H), 5.13-5.22 (m, 4H), 4.97 (d, J=4.1 Hz, 2H), 3.62 (s, 2H), 3.08 (d, J=6.4 Hz, 4H). MS(ESI): m/z 349 (M+1).

4-((benzyl(methyl)amino)methyl)-N-(2-oxo-2-phenylethyl)benzamide (DKC1125i36) ¹H-NMR (400 MHz, CDCl₃) δ 8.04 (d, J=7.3 Hz, 2H), 7.85 (d, J=8.2 Hz, 2H), 7.65 (t, J=7.5 Hz, 1H), 7.47-7.55 (m, 4H), 7.27-7.38 (m, 6H), 4.97 (d, J=4.1 Hz, 2H), 3.57 (s, 2H), 3.54 (s, 2H), 2.20 (s, 3H). MS(ESI): m/z 373 (M+1).

4-(((2-hydroxyethyl) (methyl)amino)methyl)-N-(2-oxo-2-phenylethyl)benzamide (DKC1125i37) ¹H-NMR (400 MHz, CDCl₃) δ 8.02 (d, J=7.3 Hz, 2H), 7.86 (d, J=8.2 Hz, 2H), 7.63 (t, J=7.3 Hz, 1H), 7.47-7.53 (m, 4H), 7.36 (s, 1H), 4.95 (d, J=4.6 Hz, 2H), 3.80 (s, 2H), 3.72 (t, J=5.9 Hz, 2H), 2.75 (t, J=5.3 Hz, 2H), 2.37 (s, 3H). MS(ESI): m/z 327 (M+1).

4-((butyl(2-hydroxyethyl)amino)methyl)-N-(2-oxo-2-phenylethyl)benzamide (DKC1125i38) ¹H-NMR (400 MHz, CDCl₃) δ 8.02-8.04 (m, 2H), 7.86 (d, J=8.2 Hz, 2H), 7.64 (t, J=7.5 Hz, 1H), 7.46-7.54 (m, 4H), 7.34 (d, J=3.7 Hz, 1H), 4.96 (d, J=4.1 Hz, 2H), 3.80 (s, 2H), 3.65 (t, J=5.0 Hz, 2H), 3.13 (q, J=7.5 Hz, 1H), 2.75 (t, J=5.3 Hz, 2H), 2.59 (t, J=7.5 Hz, 2H), 1.54-1.60 (m, 2H), 1.24-1.34 (m, 2H), 0.89 (q, J=7.3 Hz, 3H). MS(ESI): m/z 369 (M+1).

tert-butyl 4-(4-((2-oxo-2-phenylethyl)carbamoyl)benzyl) piperazine-1-carboxylate (DKC1125i39) ¹H-NMR (400 MHz, CDCl₃) δ 8.03 (d, J=7.3 Hz, 2H), 7.83 (d, J=8.2 Hz, 2H), 7.41-7.66 (m, 5H), 7.30 (d, J=3.7 Hz, 1H), 4.96 (d, J=4.1 Hz, 2H), 3.55 (s, 2H), 3.43 (t, J=4.6 Hz, 4H), 2.38 (brs, 4H), 1.44 (s, 9H). MS(ESI): m/z 439 (M+1).

4-((dicyclohexylamino)methyl)-N-(2-oxo-2-phenylethyl)benzamide (DKC1125i40) ¹H-NMR (400 MHz, CDCl₃) δ 8.03-8.05 (m, 2H), 7.80 (d, J=8.2 Hz, 2H), 7.47-7.67 (m, 6H), 4.97 (d, J=4.6 Hz, 2H), 3.80 (s, 2H), 2.49-2.55 (m, 2H), 1.56-1.78 (m, 10H), 1.01-1.30 (m, 10H). MS(ESI): m/z 434 (M+1).

4-((butyl (methyl)amino)methyl)-N-(2-oxo-2-phenylethyl)benzamide (DKC1125i41) ¹H-NMR (400 MHz, CDCl₃) δ 7.98-8.00 (m, 2H), 7.85 (d, J=8.2 Hz, 2H), 7.47-7.62 (m, 5H), 7.40 (t, J=4.1 Hz, 1H), 4.92 (d, J=4.1 Hz, 2H), 3.80 (s, 2H), 2.58 (t, J=8.0 Hz, 2H), 2.36 (s, 3H), 1.58-1.64 (m, 2H), 1.26-1.33 (m, 2H), 0.88 (t, J=7.3 Hz, 3H). MS (ESI): m/z 339 (M+1).

4-((dipropylamino)methyl)-N-(2-oxo-2-phenylethyl)benzamide (DKC1125i42) ¹H-NMR (400 MHz, CDCl₃) δ 8.01-8.03 (m, 2H), 7.82-7.84 (m, 2H), 7.61-7.65 (m, 1H), 7.40-7.53 (m, 4H), 7.29-7.32 (m, 1H), 4.95 (d, J=4.6 Hz, 2H), 3.66 (s, 2H), 2.42 (t, J=7.5 Hz, 4H), 1.47-1.56 (m, 4H), 0.86 (t, J=7.3 Hz, 6H). MS(ESI): m/z 353 (M+1).

4-((butyl(ethyl)amino)methyl)-N-(2-oxo-2-phenylethyl)benzamide (DKC1125i43) ¹H-NMR (400 MHz, CDCl₃) δ 8.01-8.03 (m, 2H), 7.82-7.84 (m, 2H), 7.61-7.65 (m, 1H), 7.40-7.53 (m, 4H), 7.29-7.32 (m, 1H), 4.95 (d, J=4.6 Hz, 2H), 3.66 (s, 2H), 2.42 (t, J=7.5 Hz, 4H), 1.47-1.56 (m, 4H), 0.86 (t, J=7.3 Hz, 6H). MS(ESI): m/z 353 (M+1).

4-((ethyl(2-hydroxyethyl)amino)methyl)-N-(2-oxo-2-phenylethyl)benzamide (DKC1125i44) ¹H-NMR (400 MHz, CDCl₃) δ 8.03 (d, J=7.3 Hz, 2H), 7.81-7.84 (m, 2H), 7.64 (t, J=7.5 Hz, 1H), 7.28-7.54 (m, 5H), 4.96 (d, J=4.6 Hz, 2H), 3.47-3.61 (m, 4H), 2.08-2.43 (m, 4H), 1.43-1.48 (m, 3H) MS(ESI): m/z 341 (M+1).

4-((ethynyl(methyl)amino)methyl)-N-(2-oxo-2-phenylethyl)benzamide (DKC1125i45) ¹H-NMR (400 MHz, CDCl₃) δ 8.03 (d, J=7.8 Hz, 2H), 7.84 (d, J=8.2 Hz, 2H), 7.30-7.66 (m, 6H), 4.96 (d, J=4.1 Hz, 2H), 3.63 (s, 2H), 3.32 (s, 1H), 2.34 (s, 3H). MS(ESI): m/z 307 (M+1).

4-(morpholinomethyl)-N-(2-oxo-2-phenylethyl)benzamide (DKC1125i46) ¹H-NMR (400 MHz, CDCl₃) δ 8.04 (d, J=7.3 Hz, 2H), 7.84 (d, J=8.2 Hz, 2H), 7.65 (t, J=7.3 Hz, 1H), 7.43-7.55 (m, 4H), 7.29 (s, 1H), 4.96 (d, J=4.1 Hz, 2H), 3.72 (t, J=4.8 Hz, 4H), 3.55 (s, 2H), 2.45 (t, J=4.6 Hz, 4H). MS(ESI): m/z 339 (M+1).

ethyl 4-(4-((2-oxo-2-phenylethyl)carbamoyl)benzyl)piperazine-1-carboxylate (DKC1125i47) ¹H-NMR (400 MHz, CDCl₃) δ 8.01 (d, J=8.5 Hz, 2H), 7.81-7.83 (m, 2H), 7.60-7.64 (m, 1H), 7.48-7.52 (m, 2H), 7.31-7.42 (m, 3H), 4.94 (d, J=4.1 Hz, 2H), 4.08-4.17 (m, 4H), 3.46 (t, J=5.2 Hz, 4H), 2.38 (s, 4H), 1.23 (t, J=6.8 Hz, 3H). MS(ESI): m/z 410 (M+1).

4-((2,6-dimethylmorpholino)methyl)-N-(2-oxo-2-phenylethyl)benzamide (DKC1125i48) ¹H-NMR (400 MHz, CDCl₃) δ 8.03 (d, J=7.8 Hz, 2H), 7.84 (d, J=7.8 Hz, 2H), 7.63-7.66 (m, 1H), 7.29-7.54 (m, 5H), 4.96 (d, J=4.1 Hz, 2H), 3.66-3.72 (m, 2H), 3.52 (s, 2H), 2.66-2.69 (m, 2H), 1.74-1.79 (m, 2H), 1.13 (d, J=5.9 Hz, 6H). MS(ESI): m/z 367 (M+1).

3-((3,4-dihydroisoquinolin-2(1H)-yl)methyl)-N-(2-(3-methoxyphenyl)-2-oxoethyl)benzamide (DKC1125i49)¹H-NMR (400 MHz, CDCl₃) δ 7.79-7.90 (m, 2H), 7.53-7.63 (m, 3H), 7.32-7.46 (m, 3H), 7.17-7.20 (m, 1H), 7.09-7.12 (m, 3H), 6.98 (d, J=7.8 Hz, 1H), 4.95 (d, J=4.1 Hz, 2H), 3.88 (d, J=3.2 Hz, 3H), 3.75 (s, 2H), 3.65 (s, 2H), 2.92 (t, J=5.7 Hz, 2H), 2.77 (t, J=5.9 Hz, 2H). MS(ESI): m/z 416 (M+1).

3-((cyclohexyl(methyl)amino)methyl)-N-(2-(3-methoxyphenyl)-2-oxoethyl)benzamide (DKC1125i50)¹H-NMR (400 MHz, CDCl₃) δ 7.97 (s, 1H), 7.78 (d, J=7.8 Hz, 1H), 7.37-7.59 (m, 6H), 7.13-7.16 (m, 1H), 4.91 (d, J=4.6 Hz, 2H), 3.84 (s, 3H), 3.75 (s, 2H), 2.61 (s, 1H), 2.28 (s, 3H), 1.99 (d, J=11.0 Hz, 2H), 1.82 (d, J=12.8 Hz, 2H), 1.63 (d, J=12.8 Hz, 2H), 1.19-1.36 (m, 4H). MS(ESI): m/z 396 (M+1).

3-((1-(2-fluorophenyl)piperidin-4-yl)methyl)-N-(2-(3-methoxyphenyl)-2-oxoethyl)benzamide (DKC1125i51)¹H-NMR (400 MHz, CDCl₃) δ 7.77-7.88 (m, 2H), 7.33-7.63 (m, 6H), 6.91-7.19 (m, 5H), 4.95 (d, J=4.1 Hz, 2H), 3.87 (s, 3H), 3.12 (t, J=4.8 Hz, 4H), 2.94 (s, 1H), 2.87 (s, 1H), 2.65 (t, J=4.8 Hz, 5H). MS(ESI): m/z 462 (M+1).

N-(2-(3-methoxyphenyl)-2-oxoethyl)-3-((4-(2-methoxyphenyl)piperazin-1-yl)methyl)benzamide (DKC1125i52) ¹H-NMR (400 MHz, CDCl₃) δ 7.88 (s, 1H), 7.77-7.80 (m, 1H), 7.61-7.63 (m, 1H), 7.54-7.56 (m, 2H), 7.41-7.45 (m, 2H), 7.33 (t, J=3.9 Hz, 1H), 7.17-7.20 (m, 1H), 6.88-7.01 (m, 3H), 6.85 (dd, J=8.0, 1.1 Hz, 1H), 4.95 (d, J=4.6 Hz, 2H), 3.88 (s, 3H), 3.85 (s, 3H), 3.65 (s, 2H), 3.10 (brs, 4H), 2.69 (brs, 4H). MS(ESI): m/z 475 (M+1).

3-([1,4′-bipiperidin]-1′-ylmethyl)-N-(2-(3-methoxyphenyl)-2-oxoethyl)benzamide (DKC1125i53)¹H-NMR (400 MHz, CDCl₃) δ 7.75-7.82 (m, 2H), 7.34-7.62 (m, 6H), 7.18 (d, J=8.2 Hz, 1H), 4.94 (d, J=4.1 Hz, 2H), 3.87 (s, 3H), 3.53 (s, 2H), 2.94 (d, J=10.1 Hz, 1H), 2.61 (s, 8H), 1.99 (t, J=11.7 Hz, 2H), 1.83 (d, J=11.0 Hz, 2H), 1.66 (s, 4H), 1.46 (s, 2H). MS(ESI): m/z 451 (M+1).

N-(2-(3-methoxyphenyl)-2-oxoethyl)-3-((4-(pyridin-2-yl)piperazin-1-yl)methyl)benzamide (DKC1125i54) ¹H-NMR (400 MHz, CDCl₃) δ 8.17-8.20 (m, 1H), 7.87 (s, 1H), 7.78 (d, J=7.8 Hz, 1H), 7.61-7.63 (m, 1H), 7.41-7.55 (m, 5H), 7.33 (t, J=4.3 Hz, 1H), 7.18 (dd, J=8.0, 3.0 Hz, 1H), 6.59-6.64 (m, 2H), 4.95 (d, J=4.1 Hz, 2H), 3.87 (s, 3H), 3.61 (s, 2H), 3.55 (t, J=5.0 Hz, 4H), 2.57 (t, J=5.0 Hz, 4H). MS (ESI): m/z 446 (M+1).

3-((diallylamino)methyl)-N-(2-(3-methoxyphenyl)-2-oxoethyl)benzamide (DKC1125i55) ¹H-NMR (400 MHz, CDCl₃) δ 7.84 (s, 1H), 7.75 (d, J=7.8 Hz, 1H), 7.61-7.63 (m, 1H), 7.51-7.54 (m, 2H), 7.42 (q, J=7.9 Hz, 2H), 7.30 (d, J=4.6 Hz, 1H), 7.18 (dd, J=8.0, 3.0 Hz, 1H), 5.84-5.94 (m, 2H), 5.16-5.24 (m, 4H), 4.95 (d, J=4.6 Hz, 2H), 3.88 (s, 3H), 3.64 (s, 2H), 3.10 (d, J=6.4 Hz, 4H). MS(ESI): m/z 379 (M+1).

3-((benzyl (methyl)amino)methyl)-N-(2-(3-methoxyphenyl)-2-oxoethyl)benzamide (DKC1125i56)¹H-NMR (400 MHz, CDCl₃) δ 7.98 (s, 1H), 7.81 (d, J=7.8 Hz, 1H), 7.29-7.62 (m, 11H), 7.16-7.19 (m, 1H), 4.94 (d, J=4.6 Hz, 2H), 3.87 (s, 4H), 3.73 (s, 3H), 2.29 (s, 3H). MS(ESI): m/z 403 (M+1).

3-((ethyl (methyl)amino)methyl)-N-(2-(3-methoxyphenyl)-2-oxoethyl)benzamide (DKC1125i57)¹H-NMR (400 MHz, CDCl₃) δ 7.30-7.91 (m, 8H), 7.18-7.21 (m, 1H), 4.96 (d, J=4.1 Hz, 2H), 4.65 (s, 1H), 4.54 (s, 1H), 3.85-3.89 (m, 5H), 1.61 (s, 3H), 1.25 (s, 3H). MS(ESI): m/z 341 (M+1).

3-((butyl (2-hydroxyethyl)amino)methyl)-N-(2-(3-methoxyphenyl)-2-oxoethyl)benzamide (DKC1125i58)¹H-NMR (400 MHz, CDCl₃) δ 8.13 (s, 1H), 7.87 (d, J=7.8 Hz, 1H), 7.40-7.63 (m, 6H), 7.15-7.18 (m, 1H), 4.93 (d, J=4.6 Hz, 2H), 4.06 (s, 2H), 3.87 (s, 3H), 3.80 (t, J=5.0 Hz, 2H), 2.96 (t, J=4.8 Hz, 2H), 2.82 (t, J=8.0 Hz, 2H), 1.58 (t, J=7.5 Hz, 3H), 1.30-1.35 (m, 4H). MS (ESI): m/z 400 (M+1).

tert-butyl 4-(3-((2-(3-methoxyphenyl)-2-oxoethyl)carbamoyl)benzyl)piperazine-1-carboxylate (DKC1125i59) ¹H-NMR (400 MHz, CDCl₃) δ 7.84 (s, 1H), 7.77 (dd, J=7.8, 1.4 Hz, 1H), 7.62 (dd, J=7.8, 0.9 Hz, 1H), 7.29-7.54 (m, 5H), 7.17-7.20 (m, 1H), 4.95 (d, J=4.1 Hz, 2H), 3.88 (s, 3H), 3.57 (s, 2H), 3.44 (t, J=4.6 Hz, 4H), 2.41 (brs, 4H), 1.45 (s, 9H). MS(ESI): m/z 469 (M+1).

3-((butyl (ethyl)amino)methyl)-N-(2-(3-methoxyphenyl)-2-oxoethyl)benzamide (DKC1125i60) ¹H-NMR (400 MHz, CDCl₃) δ 8.04 (s, 1H), 7.82 (d, J=7.8 Hz, 1H), 7.61 (d, J=7.8 Hz, 2H), 7.40-7.53 (m, 4H), 7.15-7.18 (m, 1H), 4.93 (d, J=4.6 Hz, 2H), 3.87 (s, 3H), 3.82 (s, 2H), 2.72 (q, J=7.0 Hz, 2H), 2.62 (t, J=7.8 Hz, 2H), 1.50 (d, J=6.9 Hz, 3H), 1.27-1.37 (m, 2H), 1.18 (t, J=7.1 Hz, 2H), 0.90 (t, J=7.3 Hz, 3H). MS(ESI): m/z 384 (M+1).

3-((dipentylamino)methyl)-N-(2-(3-methoxyphenyl)-2-oxoethyl)benzamide (DKC1125i61) ¹H-NMR (400 MHz, CDCl₃) δ 7.82 (s, 1H), 7.72-7.76 (m, 1H), 7.62 (d, J=7.8 Hz, 1H), 7.52-7.57 (m, 2H), 7.35-7.46 (m, 2H), 7.30 (d, J=3.2 Hz, 1H), 7.17-7.21 (m, 1H), 4.95 (d, J=4.1 Hz, 2H), 3.88 (s, 3H), 3.55 (s, 2H), 2.02-2.43 (m, 8H), 1.39-1.58 (m, 6H), 1.22-1.32 (m, 8H). MS(ESI): m/z 371 (M+1).

3-((4-(2-hydroxyethyl)piperazin-1-yl)methyl)-N-(2-(3-methoxyphenyl)-2-oxoethyl)benzamide (DKC1125i62)¹H-NMR (400 MHz, CDCl₃) δ 7.88 (s, 1H), 7.78 (d, J=7.8 Hz, 1H), 7.69 (s, 1H), 7.60 (d, J=7.8 Hz, 1H), 7.34-7.52 (m, 4H), 7.16-7.19 (m, 1H), 4.93 (d, J=4.6 Hz, 2H), 3.88 (s, 3H), 3.66 (s, 2H), 3.12 (t, J=7.5 Hz, 2H), 2.95 (t, J=4.8 Hz, 2H), 2.83 (brs, 4H), 1.50 (brs, 4H). MS(ESI): m/z 440 (M+1).

N-(2-(3-methoxyphenyl)-2-oxoethyl)-3-(morpholinomethyl)benzamide (DKC1125i63) ¹H-NMR (400 MHz, CDCl₃) δ 7.91 (s, 1H), 7.77 (d, J=7.8 Hz, 1H), 7.49-7.59 (m, 3H), 7.37-7.42 (m, 3H), 7.13-7.16 (m, 1H), 4.91 (d, J=4.1 Hz, 2H), 3.84 (s, 3H), 3.74 (t, J=4.6 Hz, 4H), 3.64 (s, 2H), 3.11 (q, J=7.3 Hz, 2H), 1.53 (q, J=7.0 Hz, 2H). MS (ESI): m/z 369 (M+1).

3-((ethyl(propyl)amino)methyl)-N-(2-(3-methoxyphenyl)-2-oxoethyl)benzamide (DKC1125i64)¹H-NMR (400 MHz, CDCl₃) δ 8.15 (s, 1H), 7.76-7.79 (m, 1H), 7.48-7.66 (m, 3H), 7.33-7.42 (m, 3H), 7.14-7.18 (m, 1H), 4.90 (d, J=5.0 Hz, 2H), 3.99 (s, 2H), 3.85 (s, 3H), 3.61-3.70 (m, 2H), 1.47 (d, J=6.9 Hz, 2H), 0.94-0.99 (m, 8H). MS(ESI): m/z 369 (M+1).

3-((2,6-dimethylmorpholino)methyl)-N-(2-(3-methoxyphenyl)-2-oxoethyl)benzamide (DKC1125i65)¹H-NMR (400 MHz, CDCl₃) δ 7.84 (s, 1H), 7.77 (d, J=7.8 Hz, 1H), 7.62 (d, J=7.8 Hz, 1H), 7.50-7.54 (m, 2H), 7.43 (td, J=7.8, 4.1 Hz, 2H), 7.30 (d, J=4.1 Hz, 1H), 7.17-7.20 (m, 1H), 4.95 (d, J=4.1 Hz, 2H), 3.88 (s, 3H), 3.67-3.73 (m, 2H), 3.53 (s, 2H), 2.67 (t, J=10.6 Hz, 2H), 1.78 (t, J=10.7 Hz, 2H), 1.14 (d, J=6.4 Hz, 6H). MS(ESI): m/z 397 (M+1).

2-((dimethylamino)methyl)-N-(2-oxo-2-phenylethyl)benzamide (DKC1125i66) ¹H-NMR (400 MHz, CDCl₃) δ 7.42-8.05 (m, 10H), 3.67 (d, J=4.1 Hz, 2H), 3.10 (s, 2H), 1.47 (s, 6H). MS(ESI): m/z 297 (M+1).

2-((3,4-dihydroquinolin-1(2H)-yl)methyl)-N-(2-oxo-2-phenylethyl)benzamide (DKC1125i67) ¹H-NMR (400 MHz, CDCl₃) δ 7.93-8.08 (m, 4H), 7.38-7.60 (m, 8H), 7.04-7.10 (m, 1H), 6.92 (d, J=6.9 Hz, 1H), 4.85 (d, J=3.7 Hz, 2H), 3.93 (s, 2H), 2.97-3.09 (m, 2H), 2.90 (t, J=5.7 Hz, 2H), 2.83 (t, J=5.7 Hz, 2H). MS(ESI): m/z 385 (M+1).

2-((cyclohexyl(methyl)amino)methyl)-N-(2-oxo-2-phenylethyl)benzamide (DKC1125i68) ¹H-NMR (400 MHz, CDCl₃) δ 7.97-8.01 (m, 3H), 7.83 (d, J=7.3 Hz, 1H), 7.47-7.65 (m, 6H), 4.92 (s, 2H), 4.35 (s, 2H), 3.66-3.72 (m, 1H), 2.63 (s, 3H), 2.23 (d, J=11.0 Hz, 2H), 1.89 (d, J=13.3 Hz, 2H), 1.67 (d, J=13.3 Hz, 2H), 1.28 (m, 4H). MS(ESI): m/z 365 (M+1).

2-((4-(2-fluorophenyl)piperazin-1-yl)methyl)-N-(2-oxo-2-phenylethyl)benzamide (DKC1125i69) ¹H-NMR (400 MHz, CDCl₃) δ 7.99-8.07 (m, 3H), 7.42-7.66 (m, 7H), 7.00-7.10 (m, 2H), 6.91-6.97 (m, 2H), 5.02 (d, J=5.5 Hz, 2H), 3.81 (s, 2H), 3.12 (brs, 4H), 2.76 (brs, 4H). MS(ESI): m/z 433 (M+1).

N-(2-oxo-2-phenylethyl)-2-((4-(pyrimidin-2-yl)piperazin-1-yl)methyl)benzamide (DKC1125i70) ¹H-NMR (400 MHz, CDCl₃) δ 8.28 (d, J=4.4 Hz, 2H), 7.96-8.03 (m, 3H), 7.41-7.63 (m, 6H), 7.20 (d, J=6.8 Hz, 1H), 6.48 (t, J=4.4 Hz, 1H), 5.02 (d, J=5.0 Hz, 2H), 3.84 (brs, 4H), 3.74 (s, 2H), 2.60 (t, J=5.0 Hz, 4H). MS(ESI): m/z 417 (M+1).

2-([1,4′-bipiperidin]-1′-ylmethyl)-N-(2-oxo-2-phenylethyl)benzamide (DKC1125i71) ¹H-NMR (400 MHz, CDCl₃) δ 7.89-7.99 (m, 3H), 7.37-7.64 (m, 5H), 7.20 (d, J=5.9 Hz, 1H), 5.06 (d, J=4.6 Hz, 2H), 3.66-3.73 (m, 3H), 3.06-3.15 (m, 4H), 2.02-2.25 (m, 4H), 1.49-1.58 (m, 10H). MS(ESI): m/z 421 (M+1).

N-(2-oxo-2-phenylethyl)-2-((4-(pyridin-2-yl)piperazin-1-yl)methyl)benzamide (DKC1125i72) ¹H-NMR (400 MHz, CDCl₃) δ 8.16-8.17 (m, 1H), 7.97-8.03 (m, 3H), 7.59-7.63 (m, 1H), 7.39-7.54 (m, 6H), 7.22-7.24 (m, 1H), 6.60-6.67 (m, 2H), 5.00 (d, J=5.0 Hz, 2H), 3.77 (s, 2H), 3.54 (t, J=4.8 Hz, 4H), 2.66 (t, J=5.0 Hz, 4H). MS(ESI): m/z 415 (M+1).

2-((diallylamino)methyl)-N-(2-oxo-2-phenylethyl)benzamide (DKC1125i73) ¹H-NMR (400 MHz, CDCl₃) δ 8.02-8.04 (m, 2H), 7.92-7.95 (m, 1H), 7.37-7.63 (m, 7H), 5.81-5.92 (m, 2H), 5.14-5.21 (m, 4H), 4.97 (s, 2H), 3.81 (s, 2H), 3.18 (d, J=6.9 Hz, 4H). MS(ESI): m/z 349 (M+1).

2-(morpholinomethyl)-N-(2-oxo-2-phenylethyl)benzamide (DKC1125i74) ¹H-NMR (400 MHz, CDCl₃) δ 7.92-8.05 (m, 3H), 7.37-7.69 (m, 6H), 7.20-7.23 (m, 1H), 5.01 (d, J=5.0 Hz, 2H), 3.67-3.73 (m, 6H), 2.55 (brs, 4H). MS(ESI): m/z 339 (M+1).

ethyl 4-(2-((2-oxo-2-phenylethyl)carbamoyl)benzyl)piperazine-1-carboxylate (DKC1125i75) ¹H-NMR (400 MHz, CDCl₃) δ 8.01-8.03 (m, 2H), 7.91-7.96 (m, 1H), 7.60-7.64 (m, 1H), 7.37-7.55 (m, 6H), 7.19 (dd, J=6.9, 1.8 Hz, 1H), 5.01 (d, J=4.6 Hz, 2H), 4.12 (q, J=7.2 Hz, 2H), 3.70 (s, 2H), 3.50 (t, J=4.6 Hz, 4H), 2.50 (t, J=5.0 Hz, 4H), 1.24 (t, J=7.1 Hz, 3H). MS(ESI): m/z 410 (M+1).

Experimental Example 1: Measurement of Cancer Metastasis-Related Promoter Activity-Increasing Effects of Compounds by Luciferase Assay

Experiments were conducted to evaluate the metastasis-related promoter activity-increasing effects of the compounds according to the present invention. Specifically, the KAI1 promoter reporter vector was used. In this case, the pRL-TK vector, a vector expressing renilla luciferase, was used as an internal control indicating the transfection efficiency in each transfected well.

First, 24 hours before transfection, 2×10⁶ human colon cancer cell line, Caco2) cells were cultured in 10 ml of DMEM containing 10% FBS and 1% penicillin/streptomycin on a 100-mm-diameter plate, and then transformed with 5 μg of a pRL-TK vector mixture containing a transfection reagent and the KAI1 promoter, and then cultured in a 5% CO₂ incubator at 37° C. for 48 hours. Thereafter, the adherent cells were detached using trypsin and counted using a hemacytometer, and then 5×10³ transfected Caco2 cells in 100 μl of DMEM containing 10% FBS and 1% penicillin/streptomycin were seeded into each well of a 96-well plate and cultured in a 5% CO₂ incubator at 37° C. for 24 hours. Next, 1 μM of each of the 305 compounds prepared in Examples 1 to 305 was added to each well, and after 16 hours, 100 μl of a lysis buffer for analysis containing a luciferase substrate was added, and the cells were lysed with stirring for 20 minutes. After completion of lysis, the cells were measured for luciferase activity using a luciferase reporter assay system (Promega, USA). In the experiment, DMSO was used as a control, and PHA-665752 known to increase the KAI1 promoter activity was used as a negative control. In addition, data were analyzed at a significance level of p<0.05 by one-way ANOVA (Tukey's HSD), and SPSS 17.0 (Chicago, USA) statistical program was used. The results are shown in Tables 14 to 20 below. In Table 14 to 20, PHA is the PHA-665752, and KIT is KITENIN.

As a result of the experiment, it was confirmed that compounds 1 to 305 of Examples 1 to 305 had more significant effects on the KAI1 promoter reporter activity than the control DMSO.

TABLE 14
	Relative
	KAI		In vivo
	promoter		relative
	activity	SD	invation
cont	1.00	0.02
PHA	1.43	0.27
Example 1 (DKC1125a1)	1.70	0.12	0.967212071
Example 2 (DKC1125a2)	1.14	0.08	0.865139296
Example 3 (DKC1125a3)	2.12	0.13	1.0000975
Example 4 (DKC1125a4)	1.88	0.11	1.083507938
Example 5 (DKC1125a5)	1.98	0.14	0.812007649
Example 6 (DKC1125a6)	1.91	0.12	1.143814805
Example 7 (DKC1125a7)	1.20	0.08	1.091112955
Example 8 (DKC1125a8)	1.15	0.09	1.0773117
Example 9 (DKC1125a9)	1.14	0.09	0.84188251
Example 10 (DKC1125a10)	1.08	0.06	0.909895874
Example 11 (DKC1125a11)	1.82	0.12	1.036035283
Example 12 (DKC1125a12)	1.75	0.12	1.357212927
Example 13 (DKC1125a13)	1.73	0.14	0.856537389
Example 14 (DKC1125a14)	1.02	0.08	0.91063011
Example 15 (DKC1125a15)	1.74	0.16	1.170012516
Example 16 (DKC1125a16)	0.92	0.08	0.964495994
Example 17 (DKC1125a17)	0.98	0.03	0.928830813
Example 18 (DKC1125a18)	2.18	0.06	1.099903893
Example 19 (DKC1125a19)	0.98	0.06	1.201337942
Example 20 (DKC1125a20)	0.99	0.05	1.217248385
Example 21 (DKC1125a21)	0.99	0.11	1.098839349
Example 22 (DKC1125a22)	1.56	0.07	1.16319745
Example 23 (DKC1125a23)	1.00	0.05	1.103863595
Example 24 (DKC1125a24)	0.84	0.05	1.127960077
Example 25 (DKC1125a25)	1.49	0.06	1.215411799
Example 26 (DKC1125a26)	1.26	0.16	1.062762281
Example 27 (DKC1125a27)	1.31	0.13	1.043524891
Example 28 (DKC1125a28)	1.02	0.07	1.057274411
Example 29 (DKC1125a29)	0.90	0.03	1.026118119
Example 30 (DKC1125a30)	1.41	0.13	0.763132184
Example 31 (DKC1125a31)	1.18	0.11	0.821148791
Example 32 (DKC1125a32)	1.02	0.08	1.383289259
Example 33 (DKC1125a33)	1.78	0.12	0.751253077
Example 34 (DKC1125a34)	1.34	0.13	1.10271548
Example 35 (DKC1125a35)	1.28	0.09	0.881117392
Example 36 (DKC1125a36)	1.16	0.08	1.055670632
Example 37 (DKC1125a37)	1.17	0.06	0.964820331
Example 38 (DKC1125a38)	1.57	0.18	1.118590107
Example 39 (DKC1125a39)	1.21	0.13	0.598418507
Example 40 (DKC1125a40)	1.00	0.03	1.173484717
Example 41 (DKC1125a41)	1.19	0.14	0.756462374
Example 42 (DKC1125a42)	1.12	0.07	1.525309265
Example 43 (DKC1125a43)	1.91	0.17	0.977360052
EV			1
KIT			1.418701735

TABLE 15
	Relative
	KAI		In vivo
	promoter		relative
	activity	SD	invation
cont	1.00	0.02
PHA	1.43	0.27
Example 44 (DKC1125b1)	0.98	0.06	0.975231046
Example 45 (DKC1125b2)	0.84	0.03	1.475976967
Example 46 (DKC1125b3)	0.98	0.06	1.181352768
Example 47 (DKC1125b4)	0.76	0.02	0.903801892
Example 48 (DKC1125b5)	0.85	0.05	1.189692419
Example 49 (DKC1125b6)	0.70	0.06	1.196722292
Example 50 (DKC1125b7)	0.94	0.03	1.089160084
Example 51 (DKC1125b8)	1.81	0.07	1.512528499
Example 52 (DKC1125b9)	1.36	0.13	1.157600115
Example 53 (DKC1125b10)	2.02	0.12	0.941084399
Example 54 (DKC1125b11)	0.70	0.04	1.082513363
Example 55 (DKC1125b12)	0.67	0.02	1.178638102
Example 56 (DKC1125b13)	0.92	0.08	1.248572694
Example 57 (DKC1125b14)	0.94	0.08	1.216616259
Example 58 (DKC1125b15)	0.91	0.08	1.243673251
Example 59 (DKC1125b16)	1.56	0.04	1.007369545
Example 60 (DKC1125b17)	0.81	0.04	0.9712691
Example 61 (DKC1125b18)	0.72	0.03	1.000434781
Example 62 (DKC1125b19)	1.03	0.05	1.122415428
Example 63 (DKC1125b20)	0.70	0.02	1.102301352
Example 64 (DKC1125b21)	1.35	0.09	1.083225317
Example 65 (DKC1125b22)	0.84	0.03	1.191339154
Example 66 (DKC1125b23)	0.87	0.08	1.167665305
Example 67 (DKC1125b24)	0.87	0.07	1.174738656
Example 68 (DKC1125b25)	0.88	0.05	1.124828465
Example 69 (DKC1125b26)	0.84	0.04	1.095461697
Example 70 (DKC1125b27)	0.81	0.03	1.273966647
Example 71 (DKC1125b28)	0.85	0.06	1.134844742
Example 72 (DKC1125b29)	0.80	0.05	1.04378249
Example 73 (DKC1125b30)	0.99	0.06	1.115749685
Example 74 (DKC1125b31)	0.78	0.05	1.169583778
Example 75 (DKC1125b32)	0.71	0.07	1.283061731
Example 76 (DKC1125b33)	0.83	0.06	1.120344782
Example 77 (DKC1125b34)	0.92	0.05	1.273648713
Example 78 (DKC1125b35)	0.90	0.05	1.170409863
Example 79 (DKC1125b36)	1.03	0.05	1.101727984
Example 80 (DKC1125b37)	0.86	0.07	1.182643525
Example 81 (DKC1125b38)	0.80	0.04	1.142382765
Example 82 (DKC1125b39)	0.80	0.02	1.189048399
Example 83 (DKC1125b40)	0.80	0.05	1.170551167
Example 84 (DKC1125b41)	0.94	0.04	1.181249507
Example 85 (DKC1125b42)	0.96	0.07	1.206282048
Example 86 (DKC1125b43)	1.01	0.07	1.192621759
Example 87 (DKC1125b44)	0.91	0.07	1.218137994
EV			1

TABLE 16
	Relative
	KAI		In vivo
	promoter		relative
	activity	SD	invation
con	1	0.055867817
PHA	1.20	0.043393675
Example 88 (DKC1125C1)	1.35	0.081249856	0.921644707
Example 89 (DKC1125C2)	1.27	0.059512199	1.07388343
Example 90 (DKC1125C3)	1.88	0.219588912	1.124246315
Example 91 (DKC1125C4)	2.44	0.221626597	1.0580728
Example 92 (DKC1125C5)	2.29	0.179681535	1.064202769
Example 93 (DKC1125C6)	2.48	0.140226867	1.090545444
Example 94 (DKC1125C7)	1.81	0.090850801	1.095687249
Example 95 (DKC1125C8)	1.21	0.046088014	1.160261277
Example 96 (DKC1125C9)	2.23	0.129624575	1.140757593
Example 97 (DKC1125C10)	1.80	0.087958979	1.02382481
Example 98 (DKC1125C11)	2.64	0.112880624	1.120653752
Example 99 (DKC1125C12)	1.71	0.049767964	1.133689705
Example 100 (DKC1125C13)	1.62	0.051742572	1.093844908
Example 101 (DKC1125C14)	3.04	0.146269026	0.881467731
Example 102 (DKC1125C15)	2.53	0.156923386	1.120589549
Example 103 (DKC1125C16)	1.70	0.050962298	1.171655873
Example 104 (DKC1125C17)	1.78	0.055249295	1.115470076
Example 105 (DKC1125C18)	1.25	0.039978414	1.0791341
Example 106 (DKC1125C19)	2.44	0.129482512	1.170731912
Example 107 (DKC1125C20)	2.07	0.147047337	0.986796561
Example 108 (DKC1125C21)	1.36	0.071134957	0.989004578
Example 109 (DKC1125C22)	2.89	0.287084408	0.905353953
Example 110 (DKC1125C23)	1.49	0.059141858	1.009342899
Example 111 (DKC1125C24)	1.44	0.058746042	1.065364002
Example 112 (DKC1125C25)	2.82	0.128566052	0.983474766
Example 113 (DKC1125C26)	1.40	0.044927755	1.166980237
Example 114 (DKC1125C27)	1.38	0.04051327	1.196784279
Example 115 (DKC1125C28)	2.04	0.133934593	1.209331733
Example 116 (DKC1125C29)	2.15	0.19730863	1.164258598
Example 117 (DKC1125C30)	1.32	0.062835904	1.075661568
Example 118 (DKC1125C31)	1.74	0.13810257	0.76806331
Example 119 (DKC1125C32)	1.35	0.041971277	1.202847253
Example 120 (DKC1125C33)	1.38	0.049104151	1.096641916
Example 121 (DKC1125C34)	0.96	0.186314456	1.202604399
EV			1
KIT			1.156487271

TABLE 17
	Relative
	KAI		In vivo
	promoter		relative
	activity	SD	invation
Cont	1.00	0.04
PHA	2.04	0.50
Example 122 (DKC1125D1)	1.65	0.08	1.373534212
Example 123 (DKC1125D2)	1.14	0.02	1.312034373
Example 124 (DKC1125D3)	1.04	0.04	1.266167671
Example 125 (DKC1125D4)	1.48	0.07	0.89653738
Example 126 (DKC1125D5)	1.08	0.02	1.351757201
Example 127 (DKC1125D6)	2.46	0.07	1.350506317
Example 128 (DKC1125D7)	1.10	0.04	1.179120716
Example 129 (DKC1125D8)	1.30	0.04	1.298274653
Example 130 (DKC1125E1)	1.32	0.05	0.987543526
Example 131 (DKC1125E2)	1.19	0.05	1.292834764
Example 132 (DKC1125E3)	1.18	0.02	1.226348845
Example 133 (DKC1125E4)	1.15	0.07	1.319848032
Example 134 (DKC1125E5)	1.09	0.04	1.296825956
Example 135 (DKC1125E6)	1.30	0.06	1.484699948
Example 136 (DKC1125E7)	1.17	0.03	1.296697958
Example 137 (DKC1125F1)	1.19	0.04	1.231017841
Example 138 (DKC1125F2)	1.15	0.04	1.258420919
Example 139 (DKC1125F3)	1.01	0.03	1.313526706
Example 140 (DKC1125F4)	1.15	0.03	1.552957467
Example 141 (DKC1125F5)	1.06	0.03	1.392812365
Example 142 (DKC1125F6)	1.12	0.03	1.800082616
Example 143 (DKC1125F7)	1.16	0.03	0.802837469
Example 144 (DKC1125F8)	1.08	0.02	1.284340392
Example 145 (DKC1125F9)	1.10	0.03	1.432724279
Example 146 (DKC1125F10)	1.16	0.05	0.747426234
Example 147 (DKC1125F11)	1.10	0.04	0.952431514
Example 148 (DKC1125F12)	1.44	0.04	1.84351155
Example 149 (DKC1125F13)	1.07	0.03	1.260689964
Example 150 (DKC1125F14)	1.14	0.03	1.071189823
EV			1
KIT			1.580081278

TABLE 18
	Relative
	KAI		In vivo
	promoter		relative
	activity	SD	invation
cont	1.00	0.035728039
#25	1.72	0.051949457
Example 151 (DKC1125g1)	1.05	0.015406669	1.212117692
Example 152 (DKC1125g2)	1.08	0.05020165	1.160090569
Example 153 (DKC1125g3)	1.05	0.022504904	1.095142017
Example 154 (DKC1125g4)	1.05	0.033408055	1.172964579
Example 155 (DKC1125g5)	0.99	0.036569054	1.150687562
Example 156 (DKC1125g6)	0.99	0.040959537	1.15752525
Example 157 (DKC1125g7)	1.05	0.059800725	1.088757172
Example 158 (DKC1125g8)	1.00	0.021721992	1.170875812
Example 159 (DKC1125g9)	0.99	0.05344675	1.059322396
Example 160 (DKC1125g10)	1.05	0.039047303	1.066565508
Example 161 (DKC1125g11)	0.95	0.11431494	1.121492247
Example 162 (DKC1125g12)	0.99	0.04776634	1.042903884
Example 163 (DKC1125g13)	1.10	0.046391673	1.162700934
Example 164 (DKC1125g14)	0.98	0.027883891	1.088399165
Example 165 (DKC1125g15)	1.07	0.031173347	1.133081227
Example 166 (DKC1125g16)	1.01	0.04132212	1.094224477
Example 167 (DKC1125g17)	1.04	0.034419555	1.159165916
Example 168 (DKC1125g18)	1.05	0.051934534	1.199229456
Example 169 (DKC1125g19)	0.99	0.034417249	1.186412348
Example 170 (DKC1125g20)	1.03	0.019980382	1.244191285
Example 171 (DKC1125g21)	1.07	0.030083522	1.190841197
Example 172 (DKC1125g22)	0.93	0.042731342	1.159585566
Example 173 (DKC1125g23)	1.07	0.048598895	1.120954052
Example 174 (DKC1125g24)	1.07	0.045490053	1.144233961
Example 175 (DKC1125g25)	0.97	0.030587107	1.148880933
Example 176 (DKC1125g26)	1.08	0.03777825	1.260190147
Example 177 (DKC1125g27)	0.95	0.025583177	1.158698848
Example 178 (DKC1125g28)	0.91	0.027068291	1.228353644
Example 179 (DKC1125g29)	0.97	0.028444174	1.081229551
Example 180 (DKC1125g30)	1.09	0.030961498	1.252928067
Example 181 (DKC1125g31)	1.06	0.047857709	1.193766893
Example 182 (DKC1125g32)	0.93	0.050219774	1.094710513
Example 183 (DKC1125g33)	0.96	0.034837465	1.193745555
Example 184 (DKC1125g34)	0.98	0.011433171	1.113907724
Example 185 (DKC1125g35)	1.12	0.020945265	1.113542605
Example 186 (DKC1125g36)	1.06	0.023271028	1.144717625
Example 187 (DKC1125g37)	1.03	0.045390634	1.23497558
Example 188 (DKC1125g38)	0.92	0.028776265	1.123381858
Example 189 (DKC1125g39)	0.90	0.024634724	1.18502774
Example 190 (DKC1125g40)	0.83	0.048934241	1.202513159
Example 191 (DKC1125g41)	0.84	0.025066468	1.105775523
Example 192 (DKC1125g42)	0.92	0.024830991	1.250301105
Example 193 (DKC1125g43)	0.82	0.019545606	1.214076059
Example 194 (DKC1125g44)	1.01	0.040004484	1.259054483
Example 195 (DKC1125g45)	1.08	0.037760393	1.139454218
Example 196 (DKC1125g46)	0.84	0.015353354	1.112954621
Example 197 (DKC1125g47)	0.92	0.025999083	1.213772583
Example 198 (DKC1125g48)	0.87	0.033098976	1.149841149
Example 199 (DKC1125g49)	0.97	0.030843205	1.105472047
Example 200 (DKC1125g50)	1.01	0.033825902	1.073633174
EV			1.047669401
KIT			1.287517189

TABLE 19
	Relative
	KAI		In vivo
	promoter		relative
	activity	SD	invation
cont	1	0.045599246
#25	2.657463873	0.063163146
Example 201 (DKC1125h1)	1.45738535	0.079462555	0.928329384
Example 202 (DKC1125h2)	1.312848554	0.057783663	1.13776894
Example 203 (DKC1125h3)	1.053432732	0.023471095	1.17750128
Example 204 (DKC1125h4)	1.304834442	0.036602658	1.095031374
Example 205 (DKC1125h5)	1.096349677	0.043106182	1.165632777
Example 206 (DKC1125h6)	1.050041236	0.030215636	1.10968126
Example 207 (DKC1125h7)	1.430985662	0.052532617	1.036274662
Example 208 (DKC1125h8)	1.141502143	0.042137772	1.18447855
Example 209 (DKC1125h9)	1.124707639	0.052152941	1.069956065
Example 210 (DKC1125h10)	1.02640633	0.023509915	0.927379237
Example 211 (DKC1125h11)	1.440195485	0.035947539	0.869891769
Example 212 (DKC1125h12)	1.012011355	0.015036199	1.218681463
Example 213 (DKC1125h13)	1.136015792	0.03074789	1.209439556
Example 214 (DKC1125h14)	1.085757281	0.034425293	1.244025861
Example 215 (DKC1125h15)	0.975093626	0.03535319	1.304068487
Example 216 (DKC1125h16)	1.202091224	0.03332846	1.254991844
Example 217 (DKC1125h17)	1.179071269	0.036269836	1.265776846
Example 218 (DKC1125h18)	1.333459412	0.057451894	1.169109505
Example 219 (DKC1125h19)	1.27302544	0.040484495	1.145489183
Example 220 (DKC1125h20)	1.14776276	0.03159924	0.932439544
Example 221 (DKC1125h21)	0.961286968	0.031480315	1.32159739
Example 222 (DKC1125h22)	1.196063971	0.044053472	1.275056854
Example 223 (DKC1125h23)	1.096834141	0.018382377	1.194515818
Example 224 (DKC1125h24)	1.133087247	0.025384233	1.249752938
Example 225 (DKC1125h25)	1.349029621	0.045429658	1.234879207
Example 226 (DKC1125h26)	1.088612385	0.05682518	1.348570612
Example 227 (DKC1125h27)	1.012540188	0.01932845	1.153121316
Example 228 (DKC1125h28)	0.982240102	0.013079669	1.277757272
Example 229 (DKC1125h29)	1.058902384	0.033688612	1.244864086
Example 230 (DKC1125h30)	1.075326759	0.032648818	1.266617453
EV			1
KIT			1.205379404

TABLE 20
	Relative
	KAI		In vivo
	promoter		relative
	activity	SD	invation
cont	1	0.129112624
Example 231 (DKC1125i1)	1.556398647	0.356950339	1.122056659
Example 232 (DKC1125i2)	1.231242745	0.088151665	1.125203154
Example 233 (DKC1125i3)	1.151771581	0.044393835	1.025831359
Example 234 (DKC1125i4)	1.549705281	0.215596374	1.119107161
Example 235 (DKC1125i5)	1.444493299	0.11360543	1.13306392
Example 236 (DKC1125i6)	1.301399979	0.118292539	1.111736154
Example 237 (DKC1125i7)	1.555303186	0.075592034	1.113930493
Example 238 (DKC1125i8)	1.603237137	0.192740023	1.119662586
Example 239 (DKC1125i9)	1.080807827	0.099370588	1.13515976
Example 240 (DKC1125i10)	1.304013005	0.126278512	1.1003048
Example 241 (DKC1125i11)	1.103382864	0.02639089	1.126095117
Example 242 (DKC1125i12)	1.17351246	0.217832762	1.146366755
Example 243 (DKC1125i13)	1.476648593	0.246946908	1.105040959
Example 244 (DKC1125i14)	1.514132953	0.093639982	1.100228189
Example 245 (DKC1125i15)	1.34532394	0.199290669	1.126305796
Example 246 (DKC1125i16)	1.876396336	0.278631225	1.147773102
Example 247 (DKC1125i17)	1.273772255	0.177238928	1.124489037
Example 248 (DKC1125i18)	1.300907524	0.166614644	1.115525629
Example 249 (DKC1125i19)	1.346344025	0.217908326	1.112617173
Example 250 (DKC1125i20)	1.250584162	0.122450664	0.978086712
Example 251 (DKC1125i21)	2.365102536	0.369710339	1.197359133
Example 252 (DKC1125i22)	1.560973955	0.242281458	1.165185534
Example 253 (DKC1125i23)	0.963357336	0.077755496	1.421250062
Example 254 (DKC1125i24)	2.076943564	0.156698532	0.914289467
Example 255 (DKC1125i25)	1.731617111	0.258660774	1.173719376
Example 256 (DKC1125i26)	2.249993719	0.25040892	1.266677793
Example 257 (DKC1125i27)	1.360595066	0.170128384	1.337561493
Example 258 (DKC1125i28)	2.308821978	0.32046683	1.223037271
Example 259 (DKC1125i29)	1.227092054	0.258824364	1.251473381
Example 260 (DKC1125i30)	1.328778963	0.078885596	1.092134856
Example 261 (DKC1125i31)	1.251468571	0.187588116	1.196759931
Example 262 (DKC1125i32)	1.541190334	0.238186218	1.089562938
Example 263 (DKC1125i33)	2.229416139	0.213378821	1.301160646
Example 264 (DKC1125i34)	1.905300423	0.18881145	1.199189572
Example 265 (DKC1125i35)	1.912227454	0.149517135	1.342792884
Example 266 (DKC1125i36)	2.212346045	0.113129725	1.400822467
Example 267 (DKC1125i37)	3.559546841	0.38015012	0.904641718
Example 268 (DKC1125i38)	1.599719602	0.127926085	1.220238582
Example 269 (DKC1125i39)	1.37605212	0.095531412	1.162686287
Example 270 (DKC1125i40)	1.468374849	0.151630778	1.237535549
Example 271 (DKC1125i41)	1.30625669	0.15116153	1.227526454
Example 272 (DKC1125i42)	1.589342874	0.11944405	1.230201962
Example 273 (DKC1125i43)	1.195039773	0.196597091	1.17105928
Example 274 (DKC1125i44)	5.269907991	0.405048334	1.21949993
Example 275 (DKC1125i45)	6.848650523	1.198566554	1.145663608
Example 276 (DKC1125i46)	3.393903609	0.21257212	1.224121918
Example 277 (DKC1125i47)	1.300399994	0.124870762	1.126237302
Example 278 (DKC1125i48)	1.380129948	0.265090603	1.217358561
Example 279 (DKC1125i49)	2.276031015	0.299057444	1.187429924
Example 280 (DKC1125i50)	1.628018171	0.189568898	1.19499449
Example 281 (DKC1125i51)	1.518168068	0.18664641	1.236428774
Example 282 (DKC1125i52)	1.470347181	0.166307965	1.213865002
Example 283 (DKC1125i53)	1.328550323	0.189829759	1.235314781
Example 284 (DKC1125i54)	1.443445576	0.142080934	1.275521989
Example 285 (DKC1125i55)	1.471193902	0.109249503	1.246500426
Example 286 (DKC1125i56)	1.429571413	0.231373226	1.232636867
Example 287 (DKC1125i57)	2.059948845	0.157138042	1.375947375
Example 288 (DKC1125i58)	1.730695015	0.22183601	1.221513779
Example 289 (DKC1125i59)	1.614154058	0.09440281	1.262830168
Example 290 (DKC1125i60)	1.231245258	0.244002014	0.92340877
Example 291 (DKC1125i61)	1.61539022	0.243489702	1.125527523
Example 292 (DKC1125i62)	1.448628915	0.252312759	1.238358412
Example 293 (DKC1125i63)	1.246390758	0.226601045	1.174329078
Example 294 (DKC1125i64)	1.565235197	0.14861702	1.033340391
Example 295 (DKC1125i65)	1.524549881	0.099988167	1.310621189
Example 296 (DKC1125i66)	1.531260835	0.185676483	1.026110264
Example 297 (DKC1125i67)	1.327040296	0.133929746	1.230702417
Example 298 (DKC1125i68)	1.341102898	0.081503164	1.213135975
Example 299 (DKC1125i69)	2.166005035	0.449875932	1.06790064
Example 300 (DKC1125i70)	1.911006367	0.368118524	0.986889529
Example 301 (DKC1125i71)	1.614450536	0.220205424	1.145603457
Example 302 (DKC1125i72)	1.412219916	0.242568691	1.175212092
Example 303 (DKC1125i73)	1.846492264	0.176562687	1.137812724
Example 304 (DKC1125i74)	1.236122069	0.047645221	1.193134627
Example 305 (DKC1125i75)	1.14356065	0.045375583	1.186202848
EV			1
KIT			1.369215237

Claims

1. A compound represented by the following Formula 1 or a pharmaceutically acceptable salt thereof:

2. The compound or pharmaceutically acceptable salt thereof according to claim 1, wherein, in the compound of Formula 1, X is C or N;L is C1 to C4 alkylene or a bond;R1 is hydrogen, F, Cl, Br, substituted or unsubstituted C1-C4 alkyl, methoxy, N(CH3)2, NH(CH3), amino, or a substituted or unsubstituted 5- to 12-membered heterocycle, wherein the substituent of the substituted alkyl is may be unsubstituted or substituted with dimethylamino, diethylamino, dipropylamino, dibutylamino, hydroxyethyl(ethyl)amino, ethyl(butyl)amino, dipentylamino, methyl(ethynyl)amino, ethyl(phenyl)amino, diallylamino, methyl(benzyl)amino, methyl(hydroxyethyl)amino, phenyl(methyl)amino, ethyl(phenyl)amino, butyl(hydroxyethyl)amino, butyl(methyl)amino, dicyclohexylamino, ethoxycarbonyl-piperazine, t-butoxycarbonyl-piperazine, fluorophenyl-piperidine, pyridinyl-piperazine, pyrimidinyl-piperazine, hydroxyethylpiperazine, methoxyphenyl-piperazine, nitrophenyl-piperazine, dimethylmorpholine, morpholine, methylpiperazine, dihydroxyisoquinoline, cyclohexyl(methyl)amino, isopropyl(methyl)amino, fluorophenyl-piperazine, or piperidinylpiperidine;R2 is

3. The compound or pharmaceutically acceptable salt thereof according to claim 1, which is selected from the group consisting of the following compounds 1 to 305: 4-chloro-N-(2-oxo-2-phenylethyl)benzamide (DKC1125a01);N-(2-oxo-2-phenylethyl)-2-phenoxypropanamide (DKC1125a02);2-fluoro-N-(2-oxo-2-phenylethyl)benzamide (DKC1125a03);4-fluoro-N-(2-oxo-2-phenylethyl)benzamide (DKC1125a04);N-(2-oxo-2-phenylethyl)furan-2-carboxamide (DKC1125a05);2-chloro-N-(2-oxo-2-phenylethyl)benzamide (DKC1125a06);3-chloro-N-(2-oxo-2-phenylethyl)benzamide (DKC1125a07);(E)-N-(2-oxo-2-phenylethyl)but-2-enamide (DKC1125a08);N-(2-oxo-2-phenylethyl)-3-phenylpropanamide (DKC1125a09);N-(2-oxo-2-phenylethyl)acrylamide (DKC1125a10);2-methyl-N-(2-oxo-2-phenylethyl)benzamide (DKC1125a11);4-methoxy-N-(2-oxo-2-phenylethyl)benzamide (DKC1125a12);3-methyl-N-(2-oxo-2-phenylethyl)benzamide (DKC1125a13);N-(2-oxo-2-phenylethyl)propionamide (DKC1125a14);N-(2-oxo-2-phenylethyl)cyclohexanecarboxamide (DKC1125a15);N-(2-oxo-2-phenylethyl)cyclopropanecarboxamide (DKC1125a16);N-(2-oxo-2-phenylethyl)cyclobutanecarboxamide (DKC1125a17);N-(2-oxo-2-phenylethyl)thiophene-2-carboxamide (DKC1125a18);3,3-dimethyl-N-(2-oxo-2-phenylethyl)butanamide (DKC1125a19);N-(2-oxo-2-phenylethyl)pentanamide (DKC1125a20);3-nitro-N-(2-oxo-2-phenylethyl)benzenesulfonamide (DKC1125a21);2,4-difluoro-N-(2-oxo-2-phenylethyl)benzamide (DKC1125a22);2-methoxy-N-(2-oxo-2-phenylethyl)acetamide (DKC1125a23);N-(2-oxo-2-phenylethyl)pivalamide (DKC1125a24);N-(2-oxo-2-phenylethyl)methanesulfonamide (DKC1125a25);4-fluoro-N-(2-oxo-2-phenylethyl)benzenesulfonamide (DKC1125a26);4-methyl-N-(2-oxo-2-phenylethyl)benzenesulfonamide (DKC1125a27);N-(2-oxo-2-phenylethyl)-1-phenylmethanesulfonamide (DKC1125a28);N-(2-oxo-2-phenylethyl)-3,5-bis(trifluoromethyl)benzamide (DKC1125a29);N-(2-oxo-2-phenylethyl)-2-(trifluoromethyl)benzamide (DKC1125a30);N-(2-oxo-2-phenylethyl)-3-(trifluoromethyl)benzamide (DKC1125a31);N-(2-oxo-2-phenylethyl)-4-(trifluoromethyl)benzamide (DKC1125a32);2-chloro-4-fluoro-N-(2-oxo-2-phenylethyl)benzamide (DKC1125a33);3-nitro-N-(2-oxo-2-phenylethyl)benzamide (DKC1125a34);3,4-difluoro-N-(2-oxo-2-phenylethyl)benzamide (DKC1125a35);3,5-dichloro-N-(2-oxo-2-phenylethyl)benzamide (DKC1125a36);2,3-dichloro-N-(2-oxo-2-phenylethyl)benzamide (DKC1125a37);N-(2-oxo-2-phenylethyl)-4-(trifluoromethoxy)benzamide (DKC1125a38);N-(2-oxo-2-phenylethyl)-3-(trifluoromethoxy)benzamide (DKC1125a39);3,5=dimethyl-N-(2-oxo-2-phenylethyl)benzamide (DKC1125a40);N-(2-oxo-2-phenylethyl)-2-(trifluoromethoxy)benzamide (DKC1125a41);3,5-dimethoxy-N-(2-oxo-2-phenylethyl)benzamide (DKC1125a42);N-(2-oxo-2-phenylethyl)-[1,1′-biphenyl]-4-carboxamide (DKC1125a43);N-(2-(4-chlorophenyl)-2-oxoethyl)-2-fluorobenzamide (DKC1125b01);N-(2-(4-chlorophenyl)-2-oxoethyl)-4-fluorobenzamide (DKC1125b02);N-(2-(4-chlorophenyl)-2-oxoethyl)furan-2-carboxamide (DKC1125b03);3-chloro-N-(2-(4-chlorophenyl)-2-oxoethyl)benzamide (DKC1125b04);(E)-N-(2-(4-chlorophenyl)-2-oxoethyl)but-2-enamide (DKC1125b05);N-(2-(4-chlorophenyl)-2-oxoethyl)-3-phenylpropanamide (DKC1125b06);N-(2-(4-chlorophenyl)-2-oxoethyl)acrylamide (DKC1125b07);N-(2-(4-chlorophenyl)-2-oxoethyl)-2-methylbenzamide (DKC1125b08);N-(2-(4-chlorophenyl)-2-oxoethyl)-4-methoxybenzamide (DKC1125b09);N-(2-(4-chlorophenyl)-2-oxoethyl)-3-methylbenzamide (DKC1125b10);N-(2-(4-chlorophenyl)-2-oxoethyl)propionamide (DKC1125b11);N-(2-(4-chlorophenyl)-2-oxoethyl)cyclohexanecarboxamide (DKC1125b12);N-(2-(4-chlorophenyl)-2-oxoethyl)cyclopropanecarboxamide (DKC1125b13);N-(2-(4-chlorophenyl)-2-oxoethyl)cyclobutanecarboxamide (DKC1125b14);N-(2-(4-chlorophenyl)-2-oxoethyl)thiophene-2-carboxamide (DKC1125b15);N-(2-(4-chlorophenyl)-2-oxoethyl)-2-(methoxymethyl)benzamide (DKC1125b16);N-(2-(4-chlorophenyl)-2-oxoethyl)-3,3-dimethylbutanamide (DKC1125b17);N-(2-(4-chlorophenyl)-2-oxoethyl)pentanamide (DKC1125b18);N-(2-(4-chlorophenyl)-2-oxoethyl)-4-methoxybenzamide (DKC1125b19);N-(2-(4-chlorophenyl)-2-oxoethyl)-3-nitrobenzenesulfonamide (DKC1125b20);N-(2-(4-chlorophenyl)-2-oxoethyl)-2,4ifluorobenzamide (DKC1125b21);N-(2-(4-chlorophenyl)-2-oxoethyl)-2-methoxyacetamide (DKC1125b22);N-(2-(4-chlorophenyl)-2-oxoethyl)pivalamide (DKC1125b23);N-(2-(4-chlorophenyl)-2-oxoethyl)-4-fluorobenzenesulfonamide (DKC1125b24);N-(2-(4-chlorophenyl)-2-oxoethyl)-4-methylbenzenesulfonamide (DKC1125b25);4-chloro-N-(2-(4-chlorophenyl)-2-oxoethyl)benzenesulfonamide (DKC1125b26);N-(2-(4-chlorophenyl)-2-oxoethyl)-1-phenylmethanesulfonamide (DKC1125b27);N-(2-(4-chlorophenyl)-2-oxoethyl)-4-methoxybenzenesulfonamide (DKC1125b28);N-(2-(4-chlorophenyl)-2-oxoethyl)-3,5-bis(trifluoromethyl)benzamide (DKC1125b29);N-(2-(4-chlorophenyl)-2-oxoethyl)-2-(trifluoromethyl)benzamide (DKC1125b30);N-(2-(4-chlorophenyl)-2-oxoethyl)-3-(trifluoromethyl)benzamide (DKC1125b31);N-(2-(4-chlorophenyl)-2-oxoethyl)-4-(trifluoromethyl)benzamide (DKC1125b32);2-chloro-N-(2-(4-chlorophenyl)-2-oxoethyl)-4-fluorobenzamide (DKC1125b33);N-(2-(4-chlorophenyl)-2-oxoethyl)-3-nitrobenzamide (DKC1125b34);N-(2-(4-chlorophenyl)-2-oxoethyl)-3,4ifluorobenzamide (DKC1125b35);3,5-dichloro-N-(2-(4-chlorophenyl)-2-oxoethyl)benzamide (DKC1125b36);2,3-dichloro-N-(2-(4-chlorophenyl)-2-oxoethyl)benzamide (DKC1125b37);N-(2-(4-chlorophenyl)-2-oxoethyl)-4-(trifluoromethoxy)benzamide (DKC1125b38);N-(2-(4-chlorophenyl)-2-oxoethyl)-3-(trifluoromethoxy)benzamide (DKC1125b39);N-(2-(4-chlorophenyl)-2-oxoethyl)-3,5-dimethylbenzamide (DKC1125b40);N-(2-(4-chlorophenyl)-2-oxoethyl)-2-(trifluoromethoxy)benzamide (DKC1125b41);N-(2-(4-chlorophenyl)-2-oxoethyl)-3,5imethoxybenzamide (DKC1125b42);N-(2-(4-chlorophenyl)-2-oxoethyl)-[1,1′-biphenyl]-4-carboxamide (DKC1125b43);4-chloro-N-(2-(4-chlorophenyl)-2-oxoethyl)benzamide (DKC1125b44);4-chloro-N-(2-(4-(dimethylamino)phenyl)-2-oxoethyl)benzamide (DKC1125c01);N-(2-(4-(dimethylamino)phenyl)-2-oxoethyl)-2-phenoxypropanamide (DKC1125c02);N-(2-(4-(dimethylamino)phenyl)-2-oxoethyl)-2-fluorobenzamide (DKC1125c03);N-(2-(4-(dimethylamino)phenyl)-2-oxoethyl)-4-fluorobenzamide (DKC1125c04);N-(2-(4-(dimethylamino)phenyl)-2-oxoethyl)furan-2-carboxamide (DKC1125c05);2-chloro-N-(2-(4-(dimethylamino)phenyl)-2-oxoethyl)benzamide (DKC1125c06);3-chloro-N-(2-(4-(dimethylamino)phenyl)-2-oxoethyl)benzamide (DKC1125c07);N-(2-(4-(dimethylamino)phenyl)-2-oxoethyl)acrylamide (DKC1125c08);N-(2-(4-(dimethylamino)phenyl)-2-oxoethyl)-2-methylbenzamide (DKC1125c09);N-(2-(4-(dimethylamino)phenyl)-2-oxoethyl)-4-methoxybenzamide (DKC1125c10);N-(2-(4-(dimethylamino)phenyl)-2-oxoethyl)-3-methylbenzamide (DKC1125c11);N-(2-(4-(dimethylamino)phenyl)-2-oxoethyl)propionamide (DKC1125c12);N-(2-(4-(dimethylamino)phenyl)-2-oxoethyl)cyclopropanecarboxamide (DKC1125c13);N-(2-(4-(dimethylamino)phenyl)-2-oxoethyl)thiophene-2-carboxamide (DKC1125c14);N-(2-(4-(dimethylamino)phenyl)-2-oxoethyl)-3,3-dimethylbutanamide (DKC1125c15);N-(2-(4-(dimethylamino)phenyl)-2-oxoethyl)pentanamide (DKC1125c16);N-(2-(4-(dimethylamino)phenyl)-2-oxoethyl)-4-methoxybenzamide (DKC1125c17);N-(2-(4-(dimethylamino)phenyl)-2-oxoethyl)-2,4ifluorobenzamide (DKC1125c18);N-(2-(4-(dimethylamino)phenyl)-2-oxoethyl)-2-methoxyacetamide (DKC1125c19);N-(2-(4-(dimethylamino)phenyl)-2-oxoethyl)-4-fluorobenzenesulfonamide (DKC1125c20);4-chloro-N-(2-(4-(dimethylamino)phenyl)-2-oxoethyl)benzenesulfonamide (DKC1125c21);N-(2-(4-(dimethylamino)phenyl)-2-oxoethyl)benzenesulfonamide (DKC1125c22);N-(2-(4-(dimethylamino)phenyl)-2-oxoethyl)-1-phenylmethanesulfonamide (DKC1125c23);N-(2-(4-(dimethylamino)phenyl)-2-oxoethyl)-4-methoxybenzenesulfonamide (DKC1125c24);N-(2-(4-(dimethylamino)phenyl)-2-oxoethyl)-2-(trifluoromethyl)benzamide (DKC1125c25);N-(2-(4-(dimethylamino)phenyl)-2-oxoethyl)-3-(trifluoromethyl)benzamide (DKC1125c26);N-(2-(4-(dimethylamino)phenyl)-2-oxoethyl)-4-(trifluoromethyl)benzamide (DKC1125c27);2-chloro-N-(2-(4-(dimethylamino)phenyl)-2-oxoethyl)-4-fluorobenzamide (DKC1125c28);N-(2-(4-(dimethylamino)phenyl)-2-oxoethyl)-3,4ifluorobenzamide (DKC1125c29);3,5-dichloro-N-(2-(4-(dimethylamino)phenyl)-2-oxoethyl)benzamide (DKC1125c30);2,3-dichloro-N-(2-(4-(dimethylamino)phenyl)-2-oxoethyl)benzamide (DKC1125c31);N-(2-(4-(dimethylamino)phenyl)-2-oxoethyl)-4-(trifluoromethoxy)benzamide (DKC1125c32);N-(2-(4-(dimethylamino)phenyl)-2-oxoethyl)-3,5imethylbenzamide (DKC1125c33);N-(2-(4-(dimethylamino)phenyl)-2-oxoethyl)-3,5imethoxybenzamide (DKC1125c34);4-chloro-N-(2-(3-methoxyphenyl)-2-oxoethyl)benzamide (DKC1125d01);(E)-N-(2-(3-methoxyphenyl)-2-oxoethyl)but-2-enamide (DKC1125d02);N-(2-(3-methoxyphenyl)-2-oxoethyl)propionamide (DKC1125d03);N-(2-(3-methoxyphenyl)-2-oxoethyl)cyclopropanecarboxamide (DKC1125d04);N-(2-(3-methoxyphenyl)-2-oxoethyl)cyclobutanecarboxamide (DKC1125d05);N-(2-(3-methoxyphenyl)-2-oxoethyl)thiophene-2-carboxamide (DKC1125d06);N-(2-(3-methoxyphenyl)-2-oxoethyl)pentanamide (DKC1125d07);N-(2-(3-methoxyphenyl)-2-oxoethyl)benzenesulfonamide (DKC1125d08);4-chloro-N-(2-oxo-2-(pyridin-3-yl)ethyl)benzamide (DKC1125e01);N-(2-oxo-2-(pyridin-3-yl)ethyl)-2-phenoxypropanamide (DKC1125e02);2-fluoro-N-(2-oxo-2-(pyridin-3-yl)ethyl)benzamide (DKC1125e03);4-fluoro-N-(2-oxo-2-(pyridin-3-yl)ethyl)benzamide (DKC1125e04);(E)-N-(2-oxo-2-(pyridin-3-yl)ethyl)but-2-enamide (DKC1125e05);2-methyl-N-(2-oxo-2-(pyridin-3-yl)ethyl)benzamide (DKC1125e06);N-(2-oxo-2-(pyridin-3-yl)ethyl)propionamide (DKC1125e07);2-fluoro-N-(2-(4-morpholinophenyl)-2-oxoethyl)benzamide (DKC1125f01);2-chloro-N-(2-(4-morpholinophenyl)-2-oxoethyl)benzamide (DKC1125f02);(E)-N-(2-(4-morpholinophenyl)-2-oxoethyl)but-2-enamide (DKC1125f03);4-methoxy-N-(2-(4-morpholinophenyl)-2-oxoethyl)benzamide (DKC1125f04);3-methyl-N-(2-(4-morpholinophenyl)-2-oxoethyl)benzamide (DKC1125f05);N-(2-(4-morpholinophenyl)-2-oxoethyl)propionamide (DKC1125f06);N-(2-(4-morpholinophenyl)-2-oxoethyl)cyclopropanecarboxamide (DKC1125f07);N-(2-(4-morpholinophenyl)-2-oxoethyl)cyclobutanecarboxamide (DKC1125f08);N-(2-(4-morpholinophenyl)-2-oxoethyl)pentanamide (DKC1125f09);4-fluoro-N-(2-(4-morpholinophenyl)-2-oxoethyl)benzenesulfonamide (DKC1125f10);4-chloro-N-(2-(4-morpholinophenyl)-2-oxoethyl)benzenesulfonamide (DKC1125f11);N-(2-(4-morpholinophenyl)-2-oxoethyl)benzenesulfonamide (DKC1125f12);N-(2-(4-morpholinophenyl)-2-oxoethyl)-1-phenylmethanesulfonamide (DKC1125f13);4-methoxy-N-(2-(4-morpholinophenyl)-2-oxoethyl)benzenesulfonamide (DKC1125f14);2-((1-(4-chlorobenzoyl)piperidin-4-yl)oxy)-N-(2-oxo-2-phenylethyl)benzamide (DKC1125 g01);N-(2-oxo-2-phenylethyl)-2-((1-(2-phenoxypropanoyl)piperidin-4-yl)oxy)benzamide (DKC1125 g02);2-((1-(2-fluorobenzoyl)piperidin-4-yl)oxy)-N-(2-oxo-2-phenylethyl)benzamide (DKC1125 g03);2-((1-(4-fluorobenzoyl)piperidin-4-yl)oxy)-N-(2-oxo-2-phenylethyl)benzamide (DKC1125 g04);2-((1-(furan-2-carbonyl)piperidin-4-yl)oxy)-N-(2-oxo-2-phenylethyl)benzamide (DKC1125 g05);2-((1-(2-chlorobenzoyl)piperidin-4-yl)oxy)-N-(2-oxo-2-phenylethyl)benzamide (DKC1125 g06);2-((1-(3-chlorobenzoyl)piperidin-4-yl)oxy)-N-(2-oxo-2-phenylethyl)benzamide (DKC1125 g07);(E)-2-((1-(but-2-enoyl)piperidin-4-yl)oxy)-N-(2-oxo-2-phenylethyl)benzamide (DKC1125 g08);N-(2-oxo-2-phenylethyl)-2-((1-(3-phenylpropanoyl)piperidin-4-yl)oxy)benzamide (DKC1125 g09);2-((1-acryloylpiperidin-4-yl)oxy)-N-(2-oxo-2-phenylethyl)benzamide (DKC1125 g10);2-((1-(2-methylbenzoyl)piperidin-4-yl)oxy)-N-(2-oxo-2-phenylethyl)benzamide (DKC1125 g11);2-((1-(2-methoxybenzoyl)piperidin-4-yl)oxy)-N-(2-oxo-2-phenylethyl)benzamide (DKC1125 g12);2-((1-(3-methylbenzoyl)piperidin-4-yl)oxy)-N-(2-oxo-2-phenylethyl)benzamide (DKC1125 g13);N-(2-oxo-2-phenylethyl)-2-((1-propionylpiperidin-4-yl)oxy)benzamide (DKC1125 g14);2-((1-(cyclohexanecarbonyl)piperidin-4-yl)oxy)-N-(2-oxo-2-phenylethyl)benzamide (DKC1125 g15);2-((1-(cyclopropanecarbonyl)piperidin-4-yl)oxy)-N-(2-oxo-2-phenylethyl)benzamide (DKC1125 g16);2-((1-(cyclobutanecarbonyl)piperidin-4-yl)oxy)-N-(2-oxo-2-phenylethyl)benzamide (DKC1125 g17);N-(2-oxo-2-phenylethyl)-2-((1-(thiophene-2-carbonyl)piperidin-4-yl)oxy)benzamide (DKC1125 g18);2-((1-(2-(methoxymethyl)benzoyl)piperidin-4-yl)oxy)-N-(2-oxo-2-phenylethyl)benzamide (DKC1125 g19);2-((1-(3,3-dimethylbutanoyl)piperidin-4-yl)oxy)-N-(2-oxo-2-phenylethyl)benzamide (DKC1125 g20);2-((1-(morpholine-4-carbonyl)piperidin-4-yl)oxy)-N-(2-oxo-2-phenylethyl)benzamide (DKC1125 g21);N-(2-oxo-2-phenylethyl)-2-((1-pentanoylpiperidin-4-yl)oxy)benzamide (DKC1125 g22);2-((1-(4-methoxybenzoyl)piperidin-4-yl)oxy)-N-(2-oxo-2-phenylethyl)benzamide (DKC1125 g23);2-((1-(4-cyanobenzoyl)piperidin-4-yl)oxy)-N-(2-oxo-2-phenylethyl)benzamide (DKC1125 g24);2-((1-((3-(dioxo-15-sulfanyl)phenyl)sulfonyl)piperidin-4-yl)oxy)-N-(2-oxo-2-phenylethyl)benzamide (DKC1125 g25);2-(4-(2-((2-oxo-2-phenylethyl)carbamoyl)phenoxy)piperidine-1-carbonyl)phenylacetate (DKC1125 g26);2-((1-(2,4-difluorobenzoyl)piperidin-4-yl)oxy)-N-(2-oxo-2-phenylethyl)benzamide (DKC1125 g27);2-((1-(2-methoxyacetyl)piperidin-4-yl)oxy)-N-(2-oxo-2-phenylethyl)benzamide (DKC1125 g28);N-(2-oxo-2-phenylethyl)-2-((1-pivaloylpiperidin-4-yl)oxy)benzamide (DKC1125 g29);N,N-dimethyl-4-(2-((2-oxo-2-phenylethyl)carbamoyl)phenoxy)piperidine-1-carboxamide (DKC1125 g30);2-((1-(4-bromobenzoyl)piperidin-4-yl)oxy)-N-(2-oxo-2-phenylethyl)benzamide (DKC1125 g31);2-((1-acetylpiperidin-4-yl)oxy)-N-(2-oxo-2-phenylethyl)benzamide (DKC1125 g32);2-((1-(methylsulfonyl)piperidin-4-yl)oxy)-N-(2-oxo-2-phenylethyl)benzamide (DKC1125 g33);2-((1-((4-fluorophenyl)sulfonyl)piperidin-4-yl)oxy)-N-(2-oxo-2-phenylethyl)benzamide (DKC1125 g34);N-(2-oxo-2-phenylethyl)-2-((1-tosylpiperidin-4-yl)oxy)benzamide (DKC1125 g35);2-((1-((4-chlorophenyl)sulfonyl)piperidin-4-yl)oxy)-N-(2-oxo-2-phenylethyl)benzamide (DKC1125 g36);N-(2-oxo-2-phenylethyl)-2-((1-(phenylsulfonyl)piperidin-4-yl)oxy)benzamide (DKC1125 g37);2-((1-(benzylsulfonyl)piperidin-4-yl)oxy)-N-(2-oxo-2-phenylethyl)benzamide (DKC1125 g38);2-((1-((4-methoxyphenyl)sulfonyl)piperidin-4-yl)oxy)-N-(2-oxo-2-phenylethyl)benzamide (DKC1125 g39);2-((1-(3,5-bis(trifluoromethyl)benzoyl)piperidin-4-yl)oxy)-N-(2-oxo-2-phenylethyl)benzamide (DKC1125 g40);N-(2-oxo-2-phenylethyl)-2-((1-(2-(trifluoromethyl)benzoyl)piperidin-4-yl)oxy)benzamide (DKC1125 g41);N-(2-oxo-2-phenylethyl)-2-((1-(3-(trifluoromethyl)benzoyl)piperidin-4-yl)oxy)benzamide (DKC1125 g42);N-(2-oxo-2-phenylethyl)-2-((1-(4-(trifluoromethyl)benzoyl)piperidin-4-yl)oxy)benzamide (DKC1125 g43);2-((1-(2-chloro-4-fluorobenzoyl)piperidin-4-yl)oxy)-N-(2-oxo-2-phenylethyl)benzamide (DKC1125 g44);2-((1-(3-nitrobenzoyl)piperidin-4-yl)oxy)-N-(2-oxo-2-phenylethyl)benzamide (DKC1125 g45);2-((1-(3,4-difluorobenzoyl)piperidin-4-yl)oxy)-N-(2-oxo-2-phenylethyl)benzamide (DKC1125 g46);2-((1-(3,5-dichlorobenzoyl)piperidin-4-yl)oxy)-N-(2-oxo-2-phenylethyl)benzamide (DKC1125 g47);2-((1-(2,3-dichlorobenzoyl)piperidin-4-yl)oxy)-N-(2-oxo-2-phenylethyl)benzamide (DKC1125 g48);N-(2-oxo-2-phenylethyl)-2-((1-(4-(trifluoromethoxy)benzoyl)piperidin-4-yl)oxy)benzamide (DKC1125 g49);N-(2-oxo-2-phenylethyl)-2-((1-(3-(trifluoromethoxy)benzoyl)piperidin-4-yl)oxy)benzamide (DKC1125 g50);2-(2-oxo-2-(phenylamino) ethoxy)-N-(2-oxo-2-phenylethyl)benzamide (DKC1125h01);2-(2-oxo-2-(o-toylamino) ethoxy)-N-(2-oxo-2-phenylethyl)benzamide (DKC1125h02);2-(2-(allylamino)-2-oxoethoxy)-N-(2-oxo-2-phenylethyl)benzamide (DKC1125h03);2-(2-(benzylamino)-2-oxoethoxy)-N-(2-oxo-2-phenylethyl)benzamide (DKC1125h04);2-(2-((fluorobenzyl)amino)-2-oxoethoxy)-N-(2-oxo-2-phenylethyl)benzamide (DKC1125h05);2-(2-((2-methoxy-4-methylphenyl)amino)-2-oxoethoxy)-N-(2-oxo-2-phenylethyl)benzamide (DKC1125h06);2-(2-((3-fluoro-4-methoxyphenyl)amino)-2-oxoethoxy)-N-(2-oxo-2-phenylethyl)benzamide (DKC1125h07);2-(2-oxo-2-(pyridin-3-ylamino)ethoxy)-N-(2-oxo-2-phenylethyl)benzamide (DKC1125h08);2-(2-((3-methoxyphenyl)amino)-2-oxoethoxy)-N-(2-oxo-2-phenylethyl)benzamide (DKC1125h09);2-(2-oxo-2-((2-propylphenyl)amino)ethoxy)-N-(2-oxo-2-phenylethyl)benzamide (DKC1125h10);2-(2-((1-fluoro-3-nitrophenyl)amino)-2-oxoethoxy)-N-(2-oxo-2-phenylethylbenzamide (DKC1125h11);2-(2-((benzo [1,3]dioxol-5-ylmethyl)amino)-2-oxoethoxy)-N-(2-oxo-2-phenylethylbenzamide (DKC1125h12);2-(2-oxo-2-((4-propylphenyl)amino)ethoxy)-N-(2-oxo-2-phenylethyl)benzamide (DKC1125h13);2-(2-oxo-2-((3-phenoxyphenyl)amino)ethoxy)-N-(2-oxo-2-phenylethyl)benzamid (DKC1125h14);2-(2-((3,4-dimethoxybenzyl)amino)-2-oxoethoxy)-N-(2-oxo-2-phenylethyl)benzamide (DKC1125h15);2-(2-((3,4-dimethoxyphenyl)amino)-2-oxoethoxy)-N-(2-oxo-2-phenylethyl)benzamide (DKC1125h16);2-(2-(benzo[d] [1,3]dioxol-5-ylamino)-2-oxoethoxy)-N-(2-oxo-2-phenylethyl)benzamide (DKC1125h17);2-(2-((2, 3-dihydrobenzo[b] [1, 4]dioxin-6-yl)amino)-2-oxoethoxy)-N-(2-oxo-2-phenylethyl)benzamide (DKC1125h18);2-(2-((2,3-dihydro-1H-inden-5-yl)amino)-2-oxoethoxy)-N-(2-oxo-2-phenylethyl)benzamide (DKC1125h19);2-(2-((3-isopropoxyphenyl)amino)-2-oxoethoxy)-N-(2-oxo-2-phenylethyl)benzamide (DKC1125h20);2-(2-oxo-2-((4-phenoxyphenyl)amino)ethoxy)-N-(2-oxo-2-phenylethyl)benzamide (DKC1125h21);2-(2-((2-fluoro-5-(trifluoromethyl) phenyl)amino)-2-oxoethoxy)-N-(2-oxo-2-phenylethyl)benzamide (DKC1125h22);2-(2-((3-hydroxyphenyl)amino)-2-oxoethoxy)-N-(2-oxo-2-phenylethyl)benzamide (DKC1125h23);2-(2-((2-chlorophenyl)amino)-2-oxoethoxy)-N-(2-oxo-2-phenylethyl)benzamide (DKC1125h24);2-(2-((3-bromophenyl)amino)-2-oxoethoxy)-N-(2-oxo-2-phenylethyl)benzamide (DKC1125h25);2-(2-(isopropylamino)-2-oxoethoxy)-N-(2-oxo-2-phenylethyl)benzamide (DKC1125h26);2-(2-(3,4-dihydroisoquinolin-2 (1H)-yl)-2-oxoethoxy)-N-(2-oxo-2-phenylethyl)benzamide (DKC1125h27);2-(2-oxo-2-propylamino)ethoxy)-N-(2-oxo-2-phenylethyl)benzamide (DKC1125h28);2-(2-(isopentylamino)-2-oxoethoxy)-N-(2-oxo-2-phenylethyl)benzamide (DKC1125h29);2-(2-(cyclohexylamino)-2-oxoethoxy)-N-(2-oxo-2-phenylethyl)benzamide (DKC1125h30);3-((dimethylamino)methyl)-N-(2-oxo-2-phenylethyl)benzamide (DKC1125i01);3-((3,4-dihydroisoquinolin-2 (1H)-yl)methyl)-N-(2-oxo-2-phenylethyl)benzamide (DKC1125i02);3-((isopropyl(methyl)amino)methyl)-N-(2-oxo-2-phenylethyl)benzamide (DKC1125i03);3-((4-(2-fluorophenyl)piperazin-1-yl)methyl)-N-(2-oxo-2-phenylethyl)benzamide (DKC1125i04);N-(2-oxo-2-phenylethyl)-3-((4-(pyrimidin-2-yl)piperazin-1-yl)methyl)benzamide (DKC1125i05);3-((4-(2-methoxyphenyl)piperazin-1-yl)methyl)-N-(2-oxo-2-phenylethyl)benzamide (DKC1125i06);3-([1,4′-bipiperidin]-1′-ylmethyl)-N-(2-oxo-2-phenylethyl)benzamide (DKC1125i07);3-((4-(4-nitrophenyl)piperazin-1-yl)methyl)-N-(2-oxo-2-phenylethyl)benzamide (DKC1125i08);3-((ethyl(phenyl)amino)methyl)-N-(2-oxo-2-phenylethyl)benzamide (DKC1125i09);N-(2-oxo-2-phenylethyl)-3-((4-(pyridin-2-yl)piperazin-1-yl)methyl)benzamide (DKC1125i10);3-((diallylamino)methyl)-N-(2-oxo-2-phenylethyl)benzamide (DKC1125i11);3-((benzyl (methyl)amino)methyl)-N-(2-oxo-2-phenylethyl)benzamide (DKC1125i12);3-(((2-hydroxyethyl) (methyl)amino)methyl)-N-(2-oxo-2-phenylethyl)benzamide (DKC1125i13);3-((butyl(2-hydroxyethyl)amino)methyl)-N-(2-oxo-2-phenylethyl)benzamide (DKC1125i14);tert-butyl 4-(3-((2-oxo-2-phenylethyl)carbamoyl)benzyl)piperazine-1-carboxylate (DKC1125i15);3-((butyl(methyl)amino)methyl)-N-(2-oxo-2-phenylethyl)benzamide (DKC1125i16);3-((diethylamino)methyl)-N-(2-oxo-2-phenylethyl)benzamide (DKC1125i17);3-((dipropylamino)methyl)-N-(2-oxo-2-phenylethyl)benzamide (DKC1125i18);3-((butyl (ethyl)amino)methyl)-N-(2-oxo-2-phenylethyl)benzamide (DKC1125i19);3-((dipentylamino)methyl)-N-(2-oxo-2-phenylethyl)benzamide (DKC1125i20);3-((ethynyl(methyl)amino)methyl)-N-(2-oxo-2-phenylethyl)benzamide (DKC1125i21);3-(morpholinomethyl)-N-(2-oxo-2-phenylethyl)benzamide (DKC1125i22);3-((4-methylpiperazin-1-yl)methyl)-N-(2-oxo-2-phenylethyl)benzamide (DKC1125i23);4-((3,4-dihydroisoquinolin-2 (1H)-yl)methyl)-N-(2-oxo-2-phenylethyl)benzamide (DKC1125i24);4-((cyclohexyl(methyl)amino)methyl)-N-(2-oxo-2-phenylethyl)benzamide (DKC1125i25);4-((isopropyl(methyl)amino)methyl)-N-(2-oxo-2-phenylethyl)benzamide (DKC1125i26);4-((4-(2-fluorophenyl)piperazin-1-yl)methyl)-N-(2-oxo-2-phenylethyl)benzamide (DKC1125i27);N-(2-oxo-2-phenylethyl)-4-((4-(pyrimidin-2-yl)piperazin-1-yl)methyl)benzamide (DKC1125i28);4-((4-(2-methoxyphenyl)piperazin-1-yl)methyl)-N-(2-oxo-2-phenylethyl)benzamide (DKC1125i29);4-([1,4′-bipiperidin]-1′-ylmethyl)-N-(2-oxo-2-phenylethyl)benzamide (DKC1125i30);4-((4-(4-nitrophenyl)piperazin-1-yl)methyl)-N-(2-oxo-2-phenylethyl)benzamide (DKC1125i31);4-((methyl (phenyl)amino)methyl)-N-(2-oxo-2-phenylethyl)benzamide (DKC1125i32);4-((ethyl(phenyl)amino)methyl)-N-(2-oxo-2-phenylethyl)benzamide (DKC1125i33);N-(2-oxo-2-phenylethyl)-4-((4-(pyridin-2-yl)piperazin-1-yl)methyl)benzamide (DKC1125i34);4-((diallylamino)methyl)-N-(2-oxo-2-phenylethyl)benzamide (DKC1125i35);4-((benzyl (methyl)amino)methyl)-N-(2-oxo-2-phenylethyl)benzamide (DKC1125i36);4-(((2-hydroxyethyl) (methyl)amino)methyl)-N-(2-oxo-2-phenylethyl)benzamide (DKC1125i37);4-((butyl(2-hydroxyethyl)amino)methyl)-N-(2-oxo-2-phenylethyl)benzamide (DKC1125i38);tert-butyl 4-(4-((2-oxo-2-phenylethyl)carbamoyl)benzyl)piperazine-1-carboxylate (DKC1125i39);4-((dicyclohexylamino)methyl)-N-(2-oxo-2-phenylethyl)benzamide (DKC1125i40);4-((butyl(methyl)amino)methyl)-N-(2-oxo-2-phenylethyl)benzamide (DKC1125i41);4-((dipropylamino)methyl)-N-(2-oxo-2-phenylethyl)benzamide (DKC1125i42);4-((butyl (ethyl)amino)methyl)-N-(2-oxo-2-phenylethyl)benzamide (DKC1125i43);4-((ethyl(2-hydroxyethyl)amino)methyl)-N-(2-oxo-2-phenylethyl)benzamide (DKC1125i44);4-((ethynyl(methyl)amino)methyl)-N-(2-oxo-2-phenylethyl)benzamide (DKC1125i45);4-(morpholinomethyl)-N-(2-oxo-2-phenylethyl)benzamide (DKC1125i46);ethyl 4-(4-((2-oxo-2-phenylethyl)carbamoyl)benzyl)piperazine-1-carboxylate (DKC1125i47);4-((2,6-dimethylmorpholino)methyl)-N-(2-oxo-2-phenylethyl)benzamide (DKC1125i48);3-((3,4-dihydroisoquinolin-2 (1H)-yl)methyl)-N-(2-(3-methoxyphenyl)-2-oxoethyl)benzamide (DKC1125i49);3-((cyclohexyl (methyl)amino)methyl)-N-(2-(3-methoxyphenyl)-2-oxoethyl)benzamide (DKC1125i50);3-((1-(2-fluorophenyl)piperidin-4-yl)methyl)-N-(2-(3-methoxyphenyl)-2-oxoethyl)benzamide (DKC1125i51);N-(2-(3-methoxyphenyl)-2-oxoethyl)-3-((4-(2-methoxyphenyl)piperazin-1-yl)methyl)benzamide (DKC1125i52);3-([1,4′-bipiperidin]-1′-ylmethyl)-N-(2-(3-methoxyphenyl)-2-oxoethyl)benzamide (DKC1125i53);N-(2-(3-methoxyphenyl)-2-oxoethyl)-3-((4-(pyridin-2-yl)piperazin-1-yl)methyl)benzamide (DKC1125i54);3-((diallylamino)methyl)-N-(2-(3-methoxyphenyl)-2-oxoethyl)benzamide (DKC1125i55);3-((benzyl(methyl)amino)methyl)-N-(2-(3-methoxyphenyl)-2-oxoethyl)benzamide (DKC1125i56);3-((ethyl (methyl)amino)methyl)-N-(2-(3-methoxyphenyl)-2-oxoethyl)benzamide (DKC1125i57);3-((butyl (2-hydroxyethyl)amino)methyl)-N-(2-(3-methoxyphenyl)-2-oxoethyl)benzamide (DKC1125i58);tert-butyl 4-(3-((2-(3-methoxyphenyl)-2-oxoethyl)carbamoyl)benzyl)piperazine-1-carboxylate (DKC1125i59);3-((butyl (ethyl)amino)methyl)-N-(2-(3-methoxyphenyl)-2-oxoethyl)benzamide (DKC1125i60);3-((dipentylamino)methyl)-N-(2-(3-methoxyphenyl)-2-oxoethyl)benzamide (DKC1125i61);3-((4-(2-hydroxyethyl)piperazin-1-yl)methyl)-N-(2-(3-methoxyphenyl)-2-oxoethyl)benzamide (DKC1125i62);N-(2-(3-methoxyphenyl)-2-oxoethyl)-3-(morpholinomethyl)benzamide (DKC1125i63);3-((ethyl (propyl)amino)methyl)-N-(2-(3-methoxyphenyl)-2-oxoethyl)benzamide (DKC1125i64);3-((2,6-dimethylmorpholino)methyl)-N-(2-(3-methoxyphenyl)-2-oxoethyl)benzamide (DKC1125i65);2-((dimethylamino)methyl)-N-(2-oxo-2-phenylethyl)benzamide (DKC1125i66);2-((3,4-dihydroquinolin-1(2H)-yl)methyl)-N-(2-oxo-2-phenylethyl)benzamide (DKC1125i67);2-((cyclohexyl(methyl)amino)methyl)-N-(2-oxo-2-phenylethyl)benzamide (DKC1125i68);2-((4-(2-fluorophenyl)piperazin-1-yl)methyl)-N-(2-oxo-2-phenylethyl)benzamide (DKC1125i69);N-(2-oxo-2-phenylethyl)-2-((4-(pyrimidin-2-yl)piperazin-1-yl)methyl)benzamide (DKC1125i70);2-([1,4′-bipiperidin]-1′-ylmethyl)-N-(2-oxo-2-phenylethyl)benzamide (DKC1125i71);N-(2-oxo-2-phenylethyl)-2-((4-(pyridin-2-yl)piperazin-1-yl)methyl)benzamide (DKC1125i72);2-((diallylamino)methyl)-N-(2-oxo-2-phenylethyl)benzamide (DKC1125i73);2-(morpholinomethyl)-N-(2-oxo-2-phenylethyl)benzamide (DKC1125i74); andethyl 4-(2-((2-oxo-2-phenylethyl)carbamoyl)benzyl)piperazine-1-carboxylate (DKC1125i75).

4. A composition for inhibiting cancer metastasis and invasion containing the compound of claim 1.

5. The composition of claim 4, wherein the cancer is selected from the group consisting of colon cancer, laryngeal cancer, lung cancer, prostate cancer, breast cancer, gastric cancer, and hepatocellular carcinoma.

6. A composition for treating cancer containing the compound of claim 1.

7. The composition of claim 6, wherein the cancer is selected from the group consisting of colon