Medicinal Chemistry Research
5.4 Hz, H-17, H-19), 7.81 (2H, d, J = 2.2 Hz, H-10, H-14),
7.68 (1H, s, H-5), 7.43-7.32 (3H, m, H-11, H-12, H-13),
7.26 (2H, d, J = 1.3 Hz, H-22, H-25), 6.33 (2H, d, J =
2.2 Hz, H-23, H-24). 13C NMR (75 MHz, DMSO-d6) δ
ppm: 165.32 (CO, C-8), 162.77 (C-2), 150.32 (C-4), 144.83
(C-15), 131.70 (C-9), 130.51(C-18), 128.98 (CH, C-11,C-
13), 128.73 (CH, C-16, C-20), 126.41 (CH, C-17, C-19),
126.26 (CH, C-10, C-14), 120.45 (CH, C-12), 118.02 (CH,
C-23, C-24), 111.20 (CH, C-22, C-25), 101.22 (CH, C-5);
MS (ESI): m/z = found 345.01 [M+] (calcd. 345.42); Anal.
Calcd. For C20H15N3OS: C, 69.54; H, 4.38; N, 12.17;
Found: C, 69.78; H, 4.62; N, 12.46.
N-[4-(4-nitrophenyl)-1,3-thiazol-2-yl]-4-(1H-pyrrol-1-yl)
benzamide (3d)
Compound 3d was obtained as yellow solid (yield 52%). m.
p. 194–196 °C; FTIR (KBr): 3398, 3147, 1603, 1513 cm−1
;
1H NMR (400 MHz, DMSO-d6) δ ppm: 12.62 (1H, s, NH),
8.22 (2H, d, J = 8.9 Hz, H-16, H-20), 8.09 (2H, d, J =
8.7 Hz, H-17, H-20), 7.67 (1H, s, H-5), 7.55 (2H, d, J =
2.4 Hz, H-10, H-14), 7.46 (2H, d, J = 1.8 Hz, H-11, H-13),
7.42 (2H, d, J = 2.1 Hz, H-24, H-25) 6.32 (2H, d, J =
2.0 Hz, H-23, H-26); 13C NMR (75 MHz, DMSO-d6) δ
ppm: 168.73 (CO, C-8), 149.93 (C-2), 146.50 (C-4), 143.32
(C-15), 141.23 (C-12), 139.92 (C-9), 131.09 (C-18), 129.59
(C-11, C-13), 126.94 (C-20, C-16), 125.22 (C-10, C-14),
124.76 (C-19, C-17), 118.10 (C-24, C-25), 110.33 (C-23, C-
26), 105.65 (C-5); MS (ESI): m/z = found 390.62 [M+]
(calcd. 390.42); anal. calcd. For C20H14N4O3S: C, 61.53; H,
3.61; N, 14.35; Found: C, 61.73; H, 3.91; N, 14.65.
N-[4-(4-bromophenyl)-1,3-thiazol-2-yl]-4-(1H-pyrrol-1-yl)
benzamide (3b)
Compound 3b was obtained as yellow solid (yield 70%).
m.p. 166–168 °C; FTIR (KBr): 3418, 3114, 1612,
1527 cm−1; 1H NMR (400 MHz, DMSO-d6) δ ppm: 12.81
(1H, s, NH), 8.24 (2H, d, J = 8.7 Hz, H-16, H-20), 7.91
(2H, d, J = 1.8 Hz, H-17, H-19), 7.76 (2H, d, J = 2.4 Hz,
H-10, H-16), 7.62 (1H, s, H-5), 7.54 (2H, d, J = 1.8 Hz,
H-11, H-13), 7.13 (2H, d, J = 35.4 Hz, H-23, H-26), 6.33
(2H, d, J = 2.2 Hz, H-24, H-25); 13C NMR (75 MHz,
DMSO-d6) δ ppm: 168.39 (CO, C-8), 164.33 (C-2),
148.55 (C-4), 142.81(C-15), 140.23 (C-12), 133.51 (C-9),
131.63 (C-18), 130.84 (CH, C-11, C-13), 129.99 (CH, C-
16, C-20), 127.96 (CH, C-10, C-14), 127.74 (CH, C-17,
C-19), 118.94 (CH, C-24, C-25), 109.23 (CH, C-23, C-
26), 102.34 (CH, C-5); MS (ESI): m/z = found 424.36 [M
+], 426.20 [M + 2] (calcd. 424.32); Anal. Calcd. For
C20H14BrN3OS: C, 56.61; H, 3.33; N, 9.90; Found: C,
57.01; H, 3.73; N, 10.10.
N-[4-(4-methoxyphenyl)-1,3-thiazol-2-yl]-4-(1H-pyrrol-1-yl)
benzamide (3e)
Compound 3e was obtained as yellow solid (yield 80%). m.
p. 186–188 °C; FTIR (KBr): 3415, 3114, 1652, 1526 cm−1
;
1H NMR (400 MHz, DMSO-d6) δ ppm: 12.76 (1H, s, NH),
8.26 (2H, d, J = 8.8 Hz, H-11, H-13), 7.91 (2H, d, J =
8.8 Hz, H-10, H-14), 7.80 (2H, d, J = 8.8 Hz, H-19, H-17),
7.56 (1H, s, H-5), 7.55 (2H, d, J = 2.2 Hz, H-20, H-16),
7.00 (2H, d, J = 27.0 Hz, H-23, H-26), 6.33 (2H, d, J =
2.1 Hz, H-24, H-25), 3.80 (3H, s, H-21, OCH3). 13C NMR
(75 MHz, DMSO-d6) δ ppm: 168.73 (CO, C-8), 165.25 (C-
2), 149.93 (C-4), 147.90 (C-15), 143.32 (C-9), 140.92
(C-18), 131.16 (C-12), 129.59 (C-11, C-13), 127.94 (C-16,
C-20), 126.22 (C-10, C-14), 119.10 (C-17, C-19), 118.87
(C-24, C-25), 111.33 (C-23, C-26), 106.65 (C-5), 60.80 (C-
21); MS (ESI): m/z = found 374.98 [M-1] (calcd. 375.45);
Anal. Calcd. For C21H17N3O2S: C, 67.18; H, 4.56; N,
11.19; Found: C, 67.46; H, 4.78; N, 11.35.
N-[4-(4-chlorophenyl)-1,3-thiazol-2-yl]-4-(1H-pyrrol-1-yl)
benzamide (3c)
Compound 3c was obtained as yellow solid (yield 69%). m.
p. 190–192 °C; FTIR (KBr): 3436, 3113, 1607, 1528 cm−1
;
1H NMR (400 MHz, DMSO-d6) δ ppm: 12.81 (1H, s, NH),
8.24 (2H, d, J = 8.7 Hz, H-16, H-20), 8.01 (2H, d, J =
8.4 Hz, H-10, H-14), 7.94 (2H, d, J = 2.6 Hz, H-17, H-19),
7.61 (1H, s, H-5), 7.55 (2H, d, J = 2.0 Hz, H-11, H-13),
7.36 (2H, d, J = 2.0 Hz, H-23, H-26), 6.33 (2H, d, J =
2.0 Hz, H-24, H-25); 13C NMR (75 MHz, DMSO-d6) δ
ppm: 168.33 (CO, C-8), 164.32 (C-2), 158.77 (C-4), 142.83
(C-15), 140.86 (C-12), 133.70 (C-9), 131.51 (C-18), 129.98
(CH, C-11, C-13), 128.73 (CH, C-16, C-20), 128.41 (CH,
C-10, C-14), 127.45 (CH, C-17, C-19), 119.00 (CH, C-24,
C-25), 111.39 (CH, C-23, C-26), 102.24 (C-5); MS (ESI):
m/z = found 380.02 [M+], 381.20 [M + 2] (calcd. 379.86);
anal. calcd. For C20H14ClN3OS: C, 63.24; H, 3.72;
N, 11.06; Found: C, 63.61; H, 4.02; N, 11.44.
4-(2,5-dimethyl-1H-pyrrol-1-yl)-N-(4-phenyl-1,3-thiazol-2-yl)
benzamide (4a)
Compound 4a was obtained as brown solid (yield 62%). m.
p. 154–156 °C; FTIR (KBr): 3320, 2920, 1606, 1516 cm−1
;
1H NMR (400 MHz, DMSO-d6) δ ppm: 12.89 (1H, s, NH),
8.07 (2H, d, J = 16.0 Hz, H-16, H-20), 7.98 (2H, d, J =
7.6 Hz, H-17, H-20), 7.80 (2H, d, J = 8.0 Hz,H-10, H-14),
7.70 (1H, s, H-5), 7.40–7.22 (3H, m, H-11, H-12, H-13),
5.85 (2H, d, J = 7.6 Hz, H-23, H-24), 2.02 (6H, s, H-26, H-
27-diCH3); 13C NMR (75 MHz, DMSO-d6) δ ppm: 168.73
(CO, C-8), 164.25 (C-2), 146.83 (C-4), 143.90 (C-15),
143.12 (C-12), 138.92 (C-9), 131.99 (C-18), 128.59 (CH,
C-11, C-14), 125.94 (CH, C-16, C-20), 124.29 (CH, C-10,