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CO-NH); 10.35 (s, 2H, -SO2-NH). Anal. Calcd CHNS: C:
57.27, H: 4.55, N: 14.06, S: 8.05. Found: C: 57.12, H: 4.25,
N: 13.99, S: 7.85.
5.1.9. Synthesis of 2-ethoxy-N-[4-(thiazol-2-yl-sulfamoyl)-
phenyl]-benzamide 3bII
It was obtained from the reaction of 4-amino-N- thiazol-2-
yl-benzenesulfonamide 2II (0.25 g, 0.979 mmol), 2-ethoxy-
benzoyl chloride (0.216 g, 1.176 mmol) and triethylamine
(0.594 g, 5.87 mmol). The product obtained was pure white
solid. m.p. = 205–210 °C. IR (cm–1 nujol): 3320.8, 1632.5,
5.1.5. Synthesis of 2-methoxy-N-[4-(pyrimidin-2-yl-sulfamoyl)-
phenyl]-benzamide 3aIV
It was obtained from the reaction of 4-amino-N-pyrimidin-
2-yl-benzenesulfonamide 2IV (0.25 g, 0.998 mmol), 2-methox-
ybenzoyl chloride (0.203 g, 1.194 mmol) and triethylamine
(0.605 g, 5.988 mmol). The product obtained was oily. IR
(cm–1 nujol): 3260, 1620, 1428, 1534.5. 1H NMR (CDCl3,
400 MHz) δ: 3.16 (s, 3H, -O-CH3); 6.76 (d, 1H, Py-H);
6.95–7.05 (m, 2H, Ar-H); 7.45–7.95 (m, 6H, Ar-H); 8.12 (t,
2H, Py-H); 10.05 (s, 2H, -CO-NH); 10.29 (s, 2H, -SO2-NH).
Anal. Calcd CHNS: C: 56.24, H: 4.20, N: 14.57, S: 8.34.
Found: C: 56.12, H: 4.17, N: 14.92, S: 8.31.
1
1455.6, 1457.8. H NMR (CDCl3, 400 MHz) δ: 1.42 (t, 3H, -
CH3); 3.19 (q, 2H, -O-CH2-); 6.66 (d, 1H, Th-H); 6.94–7.16
(m, 4H, Ar-H); 7.38–7.75 (m, 5H, Ar-H), 10.16 (s, 2H, -CO-
NH); 10.53 (s, 2H, -SO2-NH). Anal. Calcd CHNS: C: 53.58,
H: 4.25, N: 10.41, S: 15.89. Found: C: 53.46, H: 4.17, N:
10.33, S: 15.72.
5.1.10. Synthesis of 2-ethoxy-N-[4-(4-methyl-pyrimidin-2-yl-
sulfamoyl)-phenyl]-benzamide 3bIII
It was obtained from the reaction of 4-amino-N-(4-methyl-
pyrimidin-2-yl)-benzenesulfonamide 2III (0.25 g, 0.946
mmol), 2-ethoxybenzoyl chloride (0.209 g, 1.132 mmol) and
triethylamine (0.574 g, 5.672 mmol). The product obtained
was pure white solid. m.p. = 215–217 °C. IR (cm–1 nujol):
5.1.6. Synthesis of 2-(2-(2-methoxybenzoylamino) phenethyl)-
N-(2-methoxybenzoyl) benzenamine 3aV
It was obtained from the reaction of diamino dibenzyl 2V
(0.25 g, 1.179 mmol), 2-methoxybenzoyl chloride (0.4 g, 2.353
mmol) and triethylamine (0.713 g, 7.075 mmol). The product
obtained was oily. IR (cm–1 nujol): 3340, 1620, 1432, 1512.6.
1H NMR (CDCl3, 400 MHz) δ: 2.71 (s, 6H, -O-CH3); 3.06 (s,
4H, -CH2-Ar); 6.92–7.10 (m, 10H, Ar-H); 7.38 (t, 2H, Ar-H);
7.51 (d, 2H, Ar-H), 7.79 (d, 2H, Ar-H); 10.15 (s, 2H, -CO-
NH). Anal. Calcd CHNS: C: 74.50, H: 5.82, N: 5.99. Found:
C: 74.425, H: 5.801, N: 5.899.
1
3365, 1620, 1425, 1523. H NMR (CDCl3, 400 MHz) δ: 1.39
(t, 3H, -CH3); 2.51 (s, 3H, Ar-CH3); 3.09 (q, 2H, -O-CH2-);
6.69 (d, 1H, Py-H); 6.96–7.04 (m, 2H, Ar-H); 7.44–7.91 (m,
6H, Ar-H); 8.05 (d, 1H, Py-H); 10.05 (s, 1H, -CO-NH); 10.56
(s, 1H, -SO2-NH). Anal. Calcd CHNS: C: 58.24, H: 4.89, N:
13.58, S: 7.77. Found: C: 58.14, H: 4.75, N: 13.42, S: 7.65.
5.1.11. Synthesis of 2-ethoxy-N-[4-(pyrimidin-2-yl-sulfamoyl)-
phenyl]-benzamide 3bIV
5.1.7. Synthesis of 2-(2-(2-methoxybenzoylamino)-4-
It was obtained from the reaction of 4-amino-N-pyrimidin-
2-yl-benzenesulfonamide 2IV (0.25 g, 0.998 mmol), 2-ethoxy-
benzoyl chloride (0.221 g, 1.197 mmol) and triethylamine
(0.605 g, 5.988 mmol). The product obtained was pure white
crystalline solid. m.p. = 224–228 °C. IR (cm–1 nujol): 3300,
chlorophenoxy)-N-(2-methoxybenzoyl)benzamine 3aVI
It was obtained from the reaction of 2-(2-amino-4-chloro-
phenoxy) benzenamine 2VI (0.25 g, 1.21 mmol), 2-methoxy-
benzoyl chloride (0.288 g, 1.694 mmol) and triethylamine
(0.734 g, 7.26 mmol). The product obtained was oily. IR
(cm–1 nujol): 3320, 1645, 1422, 1499.5. 1H NMR (CDCl3,
400 MHz) δ: 3.06 (s, 6H, -O-CH3); 6.86–6.96 (m, 5H, Ar-H);
7.05–7.24 (m, 4H, Ar-H); 7.39 (t, 2H, Ar-H); 7.79–7.88 (d,
4H, Ar-H); 10.44 (s, 2H, -NH). Anal. Calcd CHNS: C:
66.87, H: 4.61, N: 5.57. Found: C: 66.77, H: 4.55, N: 5.32.
1
1640, 1456, 1546. H NMR (CDCl3, 400 MHz) δ: 1.39 (t,
3H, -CH3); 2.29 (q, 2H, -O-CH2-); 6.74 (t, 1H, Py-H), 6.98–
7.10 (m, 2H, Ar-H); 7.34 (t, 1H, Ar-H); 7.88–7.94 (m, 5H, Ar-
H); 8.23 (dd, 2H, Py-H), 10.16 (s, 2H, -CO-NH); 10.48 (s, 2H,
-SO2-NH). Anal. Calcd CHNS: C: 57.27, H: 4.55, N: 14.06, S:
8.05. Found: C: 57.22, H: 4.47, N: 14.00, S: 7.95.
5.1.8. Synthesis of N-(10,11-dihydro-5H-dibenzo[b,f]azepin-3-
5.1.12. Synthesis of 2-(2-(2-ethoxybenzoylamino)phenethyl)-N-
yl)-2-ethoxy-benzamide 3bI
(2-ethoxybenzoyl) benzenamine 3bV
It was obtained from the reaction of 10, 11-dihydro-5H-
dibenzo[b,f]azepin-3-yl-amine 2I (0.25 g, 1.190 mmol), 2-
ethoxybenzoyl chloride (0.263 g, 1.424 mmol) and triethyla-
mine (0.722 g, 7.14 mmol). The product obtained was pale
brown solid. m.p. = 130–133 °C. IR (cm–1 nujol): 3410,
It was obtained from the reaction of diamino dibenzyl 2V
(0.25 g, 1.179 mmol), 2-ethoxybenzoyl chloride (0.435 g,
2.358 mmol) and triethylamine (0.713 g, 7.075 mmol). The
product obtained was pale brown crystalline solid. m.p. =
1
117–120 °C. IR (cm–1 nujol): 3384, 1645, 1475, 1532. H
1
1650.4, 1455.9, 1489.5. H NMR (CDCl3, 400 MHz) δ: 1.28
NMR (CDCl3, 400 MHz) δ: 1.24 (t, 6H, -CH3); 3.15 (s, 4H, -
CH2-Ar); 3.55 (q, 4H, -O-CH2); 6.95–7.14 (m, 10H, Ar-H);
7.42 (t, 2H, Ar-H); 7.54 (d, 2H, Ar-H), 7.76 (d, 2H, Ar-H);
10.45 (s, 2H, -CO-NH). Anal. Calcd CHNS: C: 75.57, H:
6.34, N: 5.51. Found: C: 75.54, H: 6.72, N: 5.42.
(t, 3H, -CH3); 2.79 (s, 4H, -CH2); 3.08 (q, 2H, -O-CH2-); 3.82
(s, 1H, NH-IDB); 6.82–7.06 (m, 9H, Ar-H); 7.44 (t, 1H, Ar-H);
7.75 (d, 1H, Ar-H), 10.02 (s, 1H, -NH). Anal. Calcd CHNS: C:
77.07, H: 6.19, N: 7.82. Found: C: 76.86, H: 6.11, N: 7.71.