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Med Chem Res (2012) 21:459–467
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7.66-7.41 (m, 9H, Ar–H), 7.19 (s,1H, CH=C), 6.85-6.82
(d, 2H, Ar–H), 3.79 (s, 3H, OCH3), Mass spectra: M?
(369), M-77 (292), M-105 (264).
1654 (C=O), 1602 (C=N), H NMR(DMSO-d6) (d, ppm):
13.30 (bs, 1H, CONH), 10.33 (s, 1H, NH), 8.52 (s, 1H,
Ar–H), 8.14-8.11 (d, 1H, Ar–H), 7.99-7.97 (d, 2H, Ar–H),
7.77(s, 1H, CH=C), 7.73-7.70 (d, 2H, Ar–H), 7.64-7.58
(m, 4H, Ar–H), 7.37-7.32 (t, 2H, Ar–H).
N-[(E)-1-(1H-Benzimidazol-2-yl)-2-(2-chlorophenyl)vinyl]
benzamide (3e) IR: vmax (cm-1); 3271 (NH), 1654
1
(C=O), 1602 (C=N), H NMR(DMSO-d6) (d, ppm): 12.04
N-[(E)-2-(4-Dimethylaminophenyl)-1-(6-nitro-1H-benzimid-
azol-2-yl)vinyl]benzamide (3l) IR: vmax (cm-1); 3310
(bs, 1H, CONH), 9.41 (s, 1H, NH), 8.05-8.03 (d, 2H,
Ar–H), 7.76-7.43 (m, 7H, Ar–H), 7.42 (s, 1H, CH=C),
7.22-7.04 (m, 4H, Ar–H).
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(NH), 1645 (C=O), 1611 (C=N), H NMR(DMSO-d6) (d,
ppm): 13.38 (bs, 1H, CONH), 10.24 (s, 1H, NH), 8.50 (s,
1H, Ar–H), 8.24-8.22 (d, 1H, Ar–H), 8.13-8.11 (d, 2H,
Ar–H), 7.71-7.68 (d, 2H, Ar–H), 7.64-7.58 (m, 4H, Ar–H),
7.26 (s, 1H, CH=C), 6.86-6.83 (d, 2H, Ar–H), 3.07 (s, 6H,
N(CH3)2).
N-[(E)-1-(1H-Benzimidazol-2-yl)-2-(4-dimethylaminophenyl)
vinyl]benzamide (3f) IR: vmax (cm-1); 3273 (NH), 1656
1
(C=O), 1603 (C=N), H NMR(DMSO-d6) (d, ppm): 12.01
(bs, 1H, CONH), 9.42 (s, 1H, NH), 8.05-8.03 (d, 2H, 20,60
Ar–H), 7.78-7.41 (m, 9H, Ar–H), 7.28 (s, 1H, CH=C),
6.85-6.83 (d, 2H, Ar–H), 3.04 (s, 6H, CH3).
N-[(E)-1-(6-Methyl-1H-benzimidazol-2-yl)-2-phenylvinyl]-
benzamide (3m) IR: vmax (cm-1); 3305 (NH), 1648
1
(C=O), 1602 (C=N), H NMR(DMSO-d6) (d, ppm): 12.41
N-[(E)-1-(6-Nitro-1H-benzimidazol-2-yl)-2-phenylvinyl]ben-
zamide (3g) IR: vmax (cm-1); 3298 (NH), 1644 (C=O),
1605 (C=N), 1H NMR(DMSO-d6) (d, ppm): 13.21 (bs, 1H,
CONH), 10.38 (s, 1H, NH), 8.49 (s, 1H, Ar–H), 8.18-8.16
(d, 1H, Ar–H), 8.03-8.01 (d, 2H, Ar–H), 7.73-7.70 (d, 2H,
Ar–H), 7.64-7.58 (m, 5H, Ar–H), 7.42 (s, 1H, CH=C),
7.37-7.32 (t, 2H, Ar–H).
(bs, 1H, CONH), 10.15 (s, 1H, NH), 8.03-8.01 (d, 2H,
Ar–H), 7.81 (s, 1H, Ar–H), 7.68-7.44 (m, 8H, Ar–H), 7.34
(s, 1H, CH=C), 7.14-7.12 (d, 2H, Ar–H), 2.37 (s, 3H, CH3).
N-[(E)-2-(4-Methylphenyl)-1-(6-methyl-1H-benzimidazol-2-
yl)vinyl]benzamide (3n) IR: vmax (cm-1); 3310 (NH),
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1647 (C=O), 1602 (C=N), H NMR(DMSO-d6) (d, ppm):
12.33 (bs,1H, CONH), 10.13 (s,1H, NH), 8.06-8.04 (d, 2H,
Ar–H), 7.82 (s, 1H, Ar–H), 7.76-7.37 (m, 6H, Ar–H), 7.36
(s, 1H, CH=C), 7.20-7.13 (m, 3H, Ar–H), 2.39 (s, 3H,
CH3), 2.26 (s, 3H, CH3).
N-[(E)-2-(4-Methylphenyl)-1-(6-nitro-1H-benzimidazol-2-
yl)vinyl]benzamide (3h) IR: vmax (cm-1); 3312 (NH),
1
1658 (C=O), 1607 (C=N), H NMR(DMSO-d6) (d, ppm):
13.37 (bs, 1H, CONH), 10.37 (s, 1H, NH), 8.51 (s, 1H,
Ar–H), 8.14-8.12 (d, 1H, Ar–H), 8.03-8.01 (d, 2H, Ar–H),
7.66-7.38 (m, 6H, Ar–H), 7.34 (s, 1H, CH=C), 7.12-7.10
(d, 2H, Ar–H), 2.38 (s, 3H, CH3).
N-[(E)-2-(4-Hydroxyphenyl)-1-(6-methyl-1H-benzimidazol-
2-yl)vinyl]benzamide (3o) IR: vmax (cm-1); 3296 (NH),
1
1656 (C=O), 1604 (C=N), H NMR(DMSO-d6) (d, ppm):
12.30 (bs, 1H, CONH, D2O exchangeable), 11.05 (s, 1H,
OH, D2O exchangeable), 10.11 (s, 1H, NH, D2O
exchangeable), 8.03-8.01 (d, 2H, Ar–H), 7.79 (s,1H,
Ar–H), 7.68-7.42 (m, 6H, Ar–H), 7.34 (s, 1H, CH=C),
7.14-7.12 (d, 1H, Ar–H), 7.03-7.01 (d, 2H, Ar–H), 2.37
(s, 3H, CH3).
N-[(E)-2-(4-Hydroxyphenyl)-1-(6-nitro-1H-benzimidazol-
2-yl)vinyl]benzamide (3i) IR: vmax (cm-1); 3296 (NH),
1
1647 (C=O), 1606 (C=N), H NMR(DMSO-d6) (d, ppm):
13.32 (bs, 1H, CONH), 10.49 (s, 1H, OH), 10.38 (s, 1H,
NH), 8.49 (s, 1H, Ar–H), 8.14-8.12 (d, 1H, Ar–H), 8.03-
8.01 (d, 2H, Ar–H), 7.76-7.32 (m, 6H, Ar–H), 7.29 (s, 1H,
CH=C), 6.91-6.89 (d, 2H, Ar–H).
N-[(E)-2-(4-Methoxyphenyl)-1-(6-methyl-1H-benzimidazol-
2-yl)vinyl]benzamide (3p) IR: vmax (cm-1); 3312 (NH),
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N-[(E)-2-(4-Methoxyphenyl)-1-(6-nitro-1H-benzimidazol-
2-yl)vinyl]benzamide (3j) IR: vmax (cm-1); 3308 (NH),
1648 (C=O), 1605 (C=N), H NMR(DMSO-d6) (d, ppm):
12.44 (bs, 1H, CONH), 10.12 (s, 1H, NH), 8.03-8.01
(d, 2H, Ar–H), 7.80 (s, 1H, Ar–H), 7.62-7.37 (m, 6H, Ar–H),
7.34 (s, 1H, CH=C), 7.14-7.12 (d, 1H, Ar–H), 6.85-6.82
(d, 2H, Ar–H), 3.79 (s, 3H, OCH3), 2.38 (s, 3H, CH3).
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1650 (C=O), 1604 (C=N), H NMR(DMSO-d6) (d, ppm):
13.34 (bs, 1H, CONH), 10.38 (s, 1H, NH), 8.49 (s, 1H,
Ar–H), 8.14-8.12 (d, 1H, Ar–H), 8.03-8.01 (d, 2H, Ar–H),
7.76-7.41 (m, 6H, Ar–H), 7.34 (s, 1H, CH=C), 6.86-6.84
(d, 2H, Ar–H), 3.84 (s, 3H, OCH3).
N-[(E)-2-(2-Chlorophenyl)-1-(6-methyl-1H-benzimidazol-
2-yl)vinyl]benzamide (3q) IR: vmax (cm-1); 3308 (NH),
1
N-[(E)-2-(2-Chlorophenyl)-1-(6-nitro-1H-benzimidazol-2-
yl)vinyl]benzamide (3k) IR: vmax (cm-1); 3306 (NH),
1654 (C=O), 1602 (C=N), H NMR(DMSO-d6) (d, ppm):
12.54 (bs, 1H, CONH), 10.14 (s, 1H, NH), 7.98-7.95
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