Design, synthesis, anticancer activities of novel 2-amino-4-phenylthiazole scaffold containing amide moieties Zhi-Hua Zhang, a Hong-Mei Wu, a Sai-Nan Deng, b Xiao-Yu Cai, b Yu Yao, b Muriira Cyrus Mwenda, b Jin-Yin Wang, b Dong Cai, *,c Yu Chen, *,d a School of Chemical and Environmental Engineering, Liaoning University of Technology, Jinzhou,121001, China; b College of Pharmacy, Jinzhou Medical University, Jinzhou, 121001, China ; c College of Public Basic Sciences , Jinzhou Medical University, Jinzhou, 121001, China; and d School of Life Science and Biopharmaceutics, Shenyang Pharmaceutical University, Shenyang, 110016, China.
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Design, synthesis, anticancer activities of novel 2-amino-4-
phenylthiazole scaffold containing amide moieties
Zhi-Hua Zhang,a Hong-Mei Wu,a Sai-Nan Deng,b Xiao-Yu Cai,b Yu Yao,b Muriira Cyrus Mwenda,b Jin-Yin Wang, b Dong Cai, *,c Yu Chen, *,d
a School of Chemical and Environmental Engineering, Liaoning University of Technology, Jinzhou,121001, China; bCollege of Pharmacy, Jinzhou Medical University, Jinzhou, 121001, China ; cCollege of Public Basic Sciences , Jinzhou Medical University, Jinzhou, 121001, China; and d School of Life Science and Biopharmaceutics, Shenyang Pharmaceutical University, Shenyang, 110016, China.
3-methyl-N-(3-(2-(2-morpholinoacetamido)thiazol-4-yl)phenyl)benzamide 5a:
3,4-dichloro-N-(3-(2-(2-morpholinoacetamido)thiazol-4-yl)phenyl)benzamide 5b:
0.00.51.01.52.02.53.03.54.04.55.05.56.06.57.07.58.08.59.09.510.010.511.011.512.012.513.0f1 (ppm)
3.81
1.91
4.31
0.97
3.08
1.03
1.09
1.02
0.88
0.94
0.96
2.47
dm
so2.
48 d
mso
2.49
2.50
2.51
3.28
3.29
3.33
HD
O3.
563.
573.
583.
59
7.37
7.37
7.39
7.39
7.41
7.41
7.55
7.56
7.56
7.60
7.62
7.64
7.64
7.79
7.80
7.82
7.82
7.92
7.92
7.93
7.94
7.95
7.96
8.21
8.22
8.22
8.23
8.38
10.4
510
.46
12.0
7
0102030405060708090100110120130140150160170180f1 (ppm)
39.2
8 dm
so39
.49
dmso
39.7
0 dm
so39
.91
dmso
40.1
2 dm
so40
.32
dmso
40.5
3 dm
so
53.3
9
60.8
0
66.5
8
108.
85
118.
4912
0.41
121.
94
128.
5212
9.48
130.
0413
1.23
131.
7313
4.85
135.
1413
5.53
139.
55
149.
11
157.
90
163.
56
168.
98
2,4-dichloro-N-(3-(2-(2-morpholinoacetamido)thiazol-4-yl)phenyl)benzamide 5c:
-0.50.00.51.01.52.02.53.03.54.04.55.05.56.06.57.07.58.08.59.09.510.010.511.011.512.012.513.0f1 (ppm)
3.89
2.16
4.10
1.07
1.03
2.19
2.07
0.82
0.63
0.99
1.05
2.52
dm
so2.
52 d
mso
2.53
dm
so2.
53 d
mso
2.54
2.55
2.56
3.34
3.41
HD
O3.
623.
633.
64
7.41
7.43
7.45
7.52
7.53
7.54
7.55
7.58
7.59
7.60
7.61
7.66
7.67
7.68
7.69
7.81
7.81
8.42
8.43
8.43
10.6
6
12.1
6
0102030405060708090100110120130140150160170180f1 (ppm)
39.2
5 dm
so39
.46
dmso
39.6
7 dm
so39
.88
dmso
40.0
9 dm
so40
.30
dmso
40.5
0 dm
so
53.3
7
60.7
7
66.5
7
108.
94
117.
5911
9.60
121.
90
127.
9212
9.60
129.
6413
0.77
131.
6513
5.28
136.
1513
9.53
149.
06
157.
92
164.
49
168.
98
3-chloro-N-(3-(2-(2-morpholinoacetamido)thiazol-4-yl)phenyl)benzamide 5d:
0.00.51.01.52.02.53.03.54.04.55.05.56.06.57.07.58.08.59.09.510.010.511.011.512.012.513.0f1 (ppm)
4.06
2.06
4.21
0.99
5.10
1.02
0.89
0.83
0.90
0.94
2.47
dm
so2.
48 d
mso
2.49
2.50
3.29
3.35
HD
O3.
563.
573.
583.
59
7.36
7.38
7.39
7.40
7.41
7.53
7.55
7.56
7.61
7.63
7.66
7.90
7.92
7.93
8.01
8.39
10.4
110
.42
12.0
7
3-bromo-N-(3-(2-(2-morpholinoacetamido)thiazol-4-yl)phenyl)benzamide 5e:
-0.50.00.51.01.52.02.53.03.54.04.55.05.56.06.57.07.58.08.59.09.510.010.511.011.512.012.513.0f1 (ppm)
3.41
2.20
3.72
1.09
1.48
3.12
1.97
1.04
0.91
0.91
1.15
2.53
dm
so2.
56
3.34
3.35
3.41
HD
O3.
63
7.42
7.43
7.45
7.47
7.61
7.67
7.69
7.92
7.95
7.97
7.98
8.07
8.45
10.4
7
12.1
3
0102030405060708090100110120130140150160170180f1 (ppm)
39.2
6 dm
so39
.47
dmso
39.6
8 dm
so39
.89
dmso
40.1
0 dm
so40
.31
dmso
40.5
2 dm
so
53.3
9
60.7
9
66.5
7
108.
81
118.
4712
0.41
121.
83
126.
9512
7.84
129.
4413
0.89
131.
8913
3.64
135.
1113
7.22
139.
68
149.
15
157.
89
164.
47
168.
98
4-fluoro-N-(3-(2-(2-morpholinoacetamido)thiazol-4-yl)phenyl)benzamide 5g：
0.00.51.01.52.02.53.03.54.04.55.05.56.06.57.07.58.08.59.09.510.010.511.011.512.0f1 (ppm)
4.17
1.89
4.25
3.04
0.78
2.21
1.92
0.85
0.92
0.97
2.47
dm
so2.
47 d
mso
2.48
dm
so2.
492.
503.
283.
293.
35 H
DO
3.56
3.57
3.58
3.59
7.33
7.33
7.34
7.35
7.35
7.36
7.37
7.38
7.39
7.40
7.55
7.55
7.60
7.62
8.01
8.02
8.03
8.04
8.05
8.06
8.38
8.39
10.3
310
.34
12.0
7
0102030405060708090100110120130140150160170180f1 (ppm)
39.2
6 dm
so39
.47
dmso
39.6
8 dm
so39
.89
dmso
40.1
0 dm
so40
.31
dmso
40.5
2 dm
so
53.3
9
60.8
0
66.5
8
108.
77
115.
6911
5.91
118.
4712
0.40
121.
66
129.
4113
0.80
130.
8913
1.67
131.
7013
5.09
139.
86
149.
20
157.
88
163.
2816
4.84
165.
7616
8.98
3-fluoro-N-(3-(2-(2-morpholinoacetamido)thiazol-4-yl)phenyl)benzamide 5h:
N-(3-(2-(2-morpholinoacetamido)thiazol-4-yl)phenyl)-3-(trifluoromethyl)benzamide
5i:
0102030405060708090100110120130140150160170180f1 (ppm)
39.2
6 dm
so39
.47
dmso
39.6
8 dm
so39
.89
dmso
40.1
0 dm
so40
.31
dmso
40.5
2 dm
so
53.3
9
60.8
0
66.5
7
108.
84
118.
5912
0.50
121.
9212
4.64
124.
6812
8.65
129.
4812
9.75
130.
2213
0.50
132.
3413
3.65
135.
1413
6.10
139.
61
149.
11
157.
90
164.
43
168.
98
N-(3-(2-(2-morpholinoacetamido)thiazol-4-yl)phenyl)-4-(trifluoromethyl)benzamide
5j:
0102030405060708090100110120130140150160170180f1 (ppm)
39.2
6 dm
so39
.46
dmso
39.6
7 dm
so39
.88
dmso
40.0
9 dm
so40
.30
dmso
40.5
1 dm
so
53.3
9
60.8
4
66.5
8
108.
80
118.
5212
0.46
121.
9212
3.00
124.
5212
5.71
125.
7912
5.83
125.
8712
5.90
129.
0712
9.46
129.
9413
1.64
131.
9513
5.16
139.
0813
9.64
149.
11
158.
03
164.
82
169.
05
N-(3-(2-(2-morpholinoacetamido)thiazol-4-yl)phenyl)furan-2-carboxamide 5k:
0.00.51.01.52.02.53.03.54.04.55.05.56.06.57.07.58.08.59.09.510.010.511.011.512.012.513.0f1 (ppm)
4.13
2.06
4.09
0.93
1.10
0.82
1.04
1.07
0.93
0.84
0.98
0.99
1.02
2.51
dm
so2.
51 d
mso
2.51
dm
so2.
52 d
mso
2.52
dm
so2.
532.
542.
553.
333.
37 H
DO
3.61
3.62
3.63
6.73
6.73
6.73
6.74
7.38
7.39
7.41
7.43
7.59
7.63
7.63
7.64
7.65
7.65
7.66
7.97
7.97
8.38
8.39
8.39
10.2
9
12.1
2
0102030405060708090100110120130140150160170180f1 (ppm)
34.6
8 dm
so34
.89
dmso
35.1
0 dm
so35
.31
dmso
35.5
2 dm
so35
.72
dmso
35.9
3 dm
so
48.7
9
56.2
0
61.9
8
104.
1910
8.01
110.
6111
3.84
115.
7711
7.05
124.
83
130.
50
134.
73
141.
6514
3.27
144.
56
152.
0515
3.28
164.
37
2-methoxy-N-(3-(2-(2-morpholinoacetamido)thiazol-4-yl)phenyl)acetamide 5l:
0.00.51.01.52.02.53.03.54.04.55.05.56.06.57.07.58.08.59.09.510.010.511.011.512.012.513.0f1 (ppm)
10.7
3
2.10
2.11
1.03
1.21
0.97
1.20
0.92
0.73
1.00
2.47
dm
so
3.35
3.35
3.36
HD
O3.
983.
994.
144.
14
7.30
7.30
7.32
7.32
7.34
7.35
7.48
7.50
7.52
7.53
7.55
7.57
8.27
9.79
12.2
2
0102030405060708090100110120130140150160170180f1 (ppm)
39.2
6 dm
so39
.47
dmso
39.6
8 dm
so39
.88
dmso
40.0
9 dm
so40
.30
dmso
40.5
1 dm
so
59.0
959
.18
70.8
672
.09
108.
80
117.
8111
9.78
121.
48
129.
42
135.
08
139.
21
149.
19
157.
75
168.
5516
9.04
N-(3-(2-(2-morpholinoacetamido)thiazol-4-yl)phenyl)cyclohexanecarboxamide 5m：
0102030405060708090100110120130140150160170180f1 (ppm)
21.0
721
.24
24.9
834
.68
dmso
34.8
9 dm
so35
.10
dmso
35.3
0 dm
so35
.51
dmso
35.7
2 dm
so35
.93
dmso
40.6
4
48.7
8
56.1
8
61.9
6
104.
01
112.
6111
4.42
114.
8811
6.20
121.
88
124.
76
130.
45
135.
67
144.
69
153.
20
164.
31
170.
16
N-(4-(3-acetamidophenyl)thiazol-2-yl)-2-morpholinoacetamide 5n:
0.00.51.01.52.02.53.03.54.04.55.05.56.06.57.07.58.08.59.09.510.010.511.011.512.012.513.0f1 (ppm)
2.95
3.98
2.11
4.13
0.96
1.05
1.96
0.97
0.89
1.01
2.02
2.02
2.03
2.46
dm
so2.
47 d
mso
2.47
dm
so2.
482.
482.
492.
492.
502.
503.
273.
283.
283.
33 H
DO
3.34
HD
O3.
34 H
DO
3.56
3.56
3.57
3.58
3.58
7.27
7.28
7.28
7.29
7.29
7.30
7.31
7.31
7.32
7.39
7.41
7.49
7.50
7.50
7.52
7.52
7.53
8.17
8.18
8.18
8.19
9.99
10.0
1
12.0
6
2-chloro-N-(3-(2-(2-morpholinoacetamido)thiazol-4-yl)phenyl)acetamide 5o:
0102030405060708090100110120130140150160170180f1 (ppm)
39.2
6 dm
so39
.47
dmso
39.5
539
.67
dmso
39.8
8 dm
so40
.09
dmso
40.3
0 dm
so40
.51
dmso
44.0
5
53.3
5
60.6
8
66.4
8
108.
96
117.
3911
9.30
121.
72
126.
66
129.
66
135.
25
139.
27
148.
98
157.
87
165.
12
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