Medicinal Chemistry Research
After completion of the reaction, the precipitates were fil-
tered and recrystallized from ethanol to obtain the desired
benzothiophene-diaryl urea compounds 17a–g.
Calcd for C22H14ClN3O5S (%), C, 56.48; H, 3.02; N, 8.98;
S, 6.85; Found, C, 56.98; H, 3.05; N, 9.04; S, 6.07. MS (EI,
70 eV) m/z: 467.3 [35M]+, 469.4 [37M]+. Purity: 98.43% (by
HPTLC).
4-(3-phenylureido)phenyl 5-nitrobenzo[b]
thiophene-2-carboxylate (17a)
4-(3-(4-chlorophenyl)ureido)phenyl3-methyl-5-
nitrobenzo[b]thiophene-2-carboxylate (17d)
White solid; m.p: 325–327 °C was decomposed. Time: 7 h,
Yield: 90%. IR (KBr, cm−1): 3305, 3095, 2933, 1743, 1629,
1564, 1509. H NMR (DMSO-d6, 400 MHz) δ: 6.95–6.99
White solid; m.p: 227–229 °C was decomposed. Time: 7 h,
Yield: 87%. IR (KBr, cm−1): 3281, 3082, 1708, 1646, 1564,
1507. 1H-NMR (DMSO-d6, 400 MHz) δ: 2.84 (s, 3H, CH3),
7.24 (d, 2H, J = 8.7 Hz, ArH), 7.31 (d, 2H, J = 8.7 Hz,
ArH), 7.48 (d, 2H, J = 8.8 Hz, ArH), 7.53 (d, 2H, J =
8.9 Hz, ArH), 8.34 (s, 2H, ArH), 8.82–8.85 (m, 3H,
NHCONH, ArH). 13C-NMR (DMSO-d6,400 MHz) δ:13.13,
119.17, 119.75, 119.84, 121.55, 122.02, 124.49, 125.39,
128.59, 137.69, 138.62, 139.37, 143.21, 144.42, 145.39,
152.43, 160.77. Anal. Calcd for C23H16ClN3O5S(%) C,
57.32; H, 3.35; N, 8.72; S, 6.65; Found; C, 56.06; H, 3.25;
N, 10.24; S, 7.11. MS (EI, 70 eV) m/z: 481.3 [35M]+, 483.0
[37M]+. Purity: 99.33% (byHPTLC).
1
(m, 1H, ArH), 7.26–7.30 (m, 4H, ArH), 7.46 (d, 2H, J =
7.75 Hz, ArH), 7.54 (d, 2H, J = 8.9Hz, ArH), 8.35 (dd, 1H,
J = 9Hz, J = 2.2Hz, ArH), 8.41 (d, 1H, J = 9Hz, ArH), 8.65
(s, 1H, ArH), 8.74 (s, 1H NHCONH), 8.84 (s, 1H
NHCONH), 9.04 (d, 1H J = 2.2 Hz). 13C NMR (DMSO-d6,
400 MHz) δ: 118.23, 119.06, 121.26, 121.82, 121.86,
121.95, 124.63, 128.77, 132.83, 135.59, 137.95, 138.34,
139.61, 144.42, 145.57, 147.08, 152.54, 160.40. Anal.
Calcd. for C22H15N3O5S (%), C, 60.96; H, 3.49; N, 9.69; S,
7.40; Found; C, 60.30; H, 3.14; N, 10.33; S, 8.64. MS (EI,
70 eV) m/z: 433.1 [M]+, Purity: 91.96% (by HPTLC).
4-(3-phenylureido)phenyl 3-methyl-5-nitrobenzo[b]
thiophene-2-carboxylate (17b)
4-(3-cyclohexylureido)phenyl 5-nitrobenzo[b]
thiophene-2-carboxylate (17e)
White solid; m.p: 308–309 °C was decomposed. Time:
6.5 h, Yield: 85%. IR (KBr, cm−1): 3308, 3099, 2928, 1727,
1633, 1570, 1508.1H NMR (DMSO-d6, 400 MHz) δ: 2.84
(s, 3H, CH3), 6.96–6.98 (m, 1H, ArH), 7.22–7.27 (m, 4H,
ArH), 7.46 (d, 2H, J = 7.3 Hz, ArH), 7.54 (d, 2H, J =
8.3 Hz, ArH), 8.33 (s, 2H, ArH), 8.74 (s, 1H, NHCONH),
8.81 (s, 1H, NHCONH), 8.85 (s, 1H, ArH). 13C NMR
(DMSO-d6, 400 MHz) δ:13.16, 118.27, 119.05, 119.84,
121.57, 121.90, 122.02, 124.50, 128.79, 137.93, 139.39,
139.64, 143.22, 144.32, 145.41, 152.58, 160.81. Anal.
Calcd for C23H17N3O5S (%), C, 61.74; H, 3.83; N, 9.39; S,
7.16; Found; C, 61.32; H, 3.73; N, 9.66; S,8.57. MS (EI,
70 eV) m/z: 447.6 [M]+, Purity: 96.00% (by HPTLC).
White solid; m.p: 304–305 °C was decomposed. Time: 6 h,
Yield: 90%. IR (KBr, cm−1): 3372, 3282, 3094, 1732, 1653,
1554, 1508.1H NMR (DMSO-d6, 400 MHz) δ: 1.12–1.121
(m, 3H, CH2), 1.26–1.35 (m, 2H, CH2), 1.52–1.55 (m, 1H,
CH2), 1.64–1.67 (m, 2H, CH2), 1.73–1.81 (m, 2H, CH2),
3.34 (m, 1H, CH2), 6.14 (d, 1H, J = 7.8 Hz NHCONH),
7.19 (d, 2H, J = 9 Hz, ArH), 7.46 (d, 2H, J = 9 Hz, ArH),
8.35 (dd, 1H, J = 9 Hz, J = 2.2 Hz, ArH), 8.41 (d, 1H, J =
9 Hz, ArH), 8.48 (s, 1H, ArH), 8.63 (s, 1H, NHCONH),
9.03 (d, 1H, J = 2 Hz, ArH). 13C NMR (DMSO-d6,
400 MHz) δ: 24.32, 25.21, 32.92, 47.58, 118.20, 121.22,
121.74, 121.79, 124.61, 132.75, 135.65, 138.33, 138.84,
143.71, 145.55, 147.06, 154.37, 160.42. Anal. Calcd for
C22H21N3O5S (%); C, 60.13; H; 4.82; N, 9.56;S, 7.29;
Found; C, 60.49; H, 4.03; N, 9.77; S,7.43. MS (EI, 70 eV)
m/z: 439.6 [M]+. Purity: 100% (by HPTLC).
4-(3-(4-chlorophenyl)ureido)phenyl 5-nitrobenzo[b]
thiophene-2-carboxylate (17c)
Yellow solid; m.p: 328–330 °C was decomposed. Time:
8 h, Yield: 90%. IR (KBr, cm−1): 3290, 3086, 1731, 1634,
1564, 1506. 1H NMR (DMSO-d6, 500 MHz) δ: 7.28 (d, 2H,
J = 10 Hz, ArH), 7.33 (d, 2H, J = 10 Hz, ArH), 7.50 (d, 2H,
J = 10 Hz, J = 5 Hz ArH), 7.55 (d, 2H, J = 5 Hz, ArH),
8.35 (dd, 1H, J = 10 Hz, J = 5 Hz, ArH), 8.41 (d,1H, 1H, J
= 5 Hz, ArH), 8.65 (s, 1H, ArH), 8.65 (d,1H, 1H, J = 5 Hz,
ArH),9.04, (s, 2H, NHCONH)0.13CNMR (DMSO-d6,
400 MHz) δ:119.19, 119.73, 121.25, 121.82, 121.96,
124.62, 125.37, 128.60, 132.84, 135.56, 137.77, 138.33,
138.65, 144.53, 145.56, 147.06, 152.46, 160.38. Anal.
4-(3-cyclohexylureido)phenyl 3-methyl-5-nitrobenzo
[b]thiophene-2-carboxylate (17f)
White solid; m.p: 278–280 °C was decomposed. Time:
8.5 h, Yield: 85%. IR (KBr, cm−1): 3274, 3083, 1732, 1630,
1564, 1503. 1H NMR (DMSO-d6, 400 MHz) δ: 1.15–1.123
(m, 3H, CH2), 1.28–1.33 (m, 2H, CH2),1.54–1.56 (m, 1H,
CH2), 1.66–1.68 (m, 2H, CH2), 1.81–1.83 (m, 2H, CH2),
2.86 (s, 3H, CH3), 3.48 (d, 1H, J = 5 Hz,CH2), 6.08 (d, 1H,
J = 7.8 Hz NHCONH), 7.18 (d, 2H, J = 10 Hz, ArH), 7.46
(d, 2H, J = 10 Hz, ArH), 8.38 (s, 2H, ArH), 8.41 (s, 1H,