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Arch. Pharm. Chem. Life Sci. 2008, 341, 99–112
(m, 4H, piperazine, SO2-N-(CH2)2); 4.94 (s, 2H, imidazole-CH2-CO);
6.91 (s, 1H, Ar-H); 7.17 (s, 1H, Ar-H); 7.43 (d, 1H, Ar-H, J = 8.0 Hz);
7.63 (m, 2H, Ar-H); 7.81 (d, 1H, Ar-H, J = 8.0 Hz); 8.10 (s, 1H, Ar-H);
10.71 (s, 1H, CO-NH). 13C-NMR (100 MHz, DMSO): d 21.5, 45.3,
46.2, 46.4, 49.6, 118.0, 121.3, 122.8, 123.9, 128.4, 130.7, 135.8,
138.8, 139.9, 166.9, and 168.9.
2-Imidazol-1-yl-N-[3-(pyrrolidinyl-1-
sulfonyl)phenyl]acetamide 5c
Method A: Yield was 53% from ethanol. Mp. 229–2308C; IR (KBr):
3229, 1699, 1608, 1112 cm– 1; LC-MS (APCI) m/z: 335 [M+] (100);
1H-NMR (400 MHz, DMSO): d 1.65 (m, 4H, pyrrolidine N-C-CH2-
CH2-C); 3.13 (m, 4H, pyrrolidine CH2-N-CH2); 4.94 (s, 2H, imida-
zole-CH2-CO); 6.91 (s, 1H, Ar-H); 7.18 (s, 1H, Ar-H); 7.49 (d, 1H, Ar-
H, J = 8.0 Hz); 7.59 (t, 1H, Ar-H, J = 8.0 Hz); 7.64 (s, 1H, Ar-H); 7.81
(d, 1H, Ar-H, J = 8.0 Hz); 8.14 (s, 1H, Ar-H); 10.69 (s,1H, CO-NH). 13C-
NMR (100 MHz, DMSO): d 25.2, 48.3, 49.6, 117.9, 121.2, 122.5,
123.4, 128.4, 130.6, 137.1, 138.8, 139.7, and 166.8.
2-Imidazol-1-yl-N-[3-(4-piperonylpiperazinyl-1-
sulfonyl)phenyl]acetamide 5h
Method A: Yield was 40% from ethanol. Mp. 222–2238C; IR (KBr):
1706, 1608, 1365, 1157 cm– 1; LC-MS (APCI) m/z: 483 [M+] (100);1H-
NMR (400 MHz, DMSO): d 2.39 (s, 4H, piperazine, CH2-N-(CH2)2);
2.87 (s, 4H, piperazine, SO2-N-(CH2)2); 3.36 (m, 2H, Ar-CH2-N); 4.95
(s, 2H, imidazole-CH2-CO); 5.96 (s, 2H, -O-CH2-O-); 6.80 (m, 4H, Ar-
H); 7.18 (s, 1H, Ar-H); 7.41 (d, 1H, Ar-H, J = 8.0 Hz); 7.62 (m, 2H, Ar-
H); 7.82 (d,1H, Ar-H, J = 8.0 Hz); 8.08 (s, 1H, Ar-H); 10.72 (s, 1H, CO-
NH-Ar). 13C-NMR (100 MHz, DMSO): d 46.5, 49.5, 51.7, 61.5, 101.2,
108.3, 109.4, 118.1, 121.3, 122.4, 122.8, 123.7, 128.4, 130.6,
131.9, 135.7, 138.9, 139.8, 146.7, 147.7, and 166.9.
2-Imidazol-1-yl-N-[3-(morpholine-1-
sulfonyl)phenyl]acetamide 5d
Method A: Yield was 40% from ethanol. Mp. 234–2358C; IR (KBr):
3239, 1708, 1607, 1319, 1116 cm– 1; LC-MS (APCI) m/z: 335 [M+]
(100); 1H-NMR (400 MHz, DMSO): d 2.86 (t, 4H, morpholine CH2-N-
CH2, J = 4.7 Hz); 3.63 (t, 4H, morpholine CH2-O-CH2, J = 4.7 Hz);
4.95 (s, 2H, imidazole-CH2-CO); 6.91 (s, 1H, Ar-H); 7.18 (s, 1H, Ar-
H); 7.43 (d, 1H, Ar-H, J = 8.0 Hz); 7.63 (m, 2H, Ar-H); 7.83 (d, 1H, Ar-
H, J = 8.0 Hz); 8.11 (m, 1H,Ar-H); 10.72 (s, 1H, CO-NH). 13C-NMR
(100 MHz, DMSO): d 46.4, 49.7, 65.9, 118.0, 121.1, 122.8, 123.8,
128.4, 130.7, 135.3, 138.8, 139.8, and 166.8.
2-Imidazol-1-yl-N-[3-(phenylpiperazinyl-1-
sulfonyl)phenyl]acetamide 5i
Method A: Yield was 85% from methanol. Mp. 230–2318C; IR
(KBr): 1698, 1618, 1270, 1158 cm– 1; LC-MS (APCI) m/z: 426 [M+]
(100); 1H-NMR (400 MHz, DMSO): d 3.01 (s, 4H, piperazine, phe-
nyl-N(CH2)2); 3.19 (m, 4H, piperazine, S-N(CH2)2); 4.95 (s, 2H, imi-
dazole-CH2-CO); 6.79 (t, 1H, Ar-H, J = 8.0 Hz); 6.89 (m, 3H, Ar-H);
7.19 (m, 3H, Ar-H); 7.47 (d, 1H, Ar-H, J = 8.0 Hz); 7.63 (m, 2H, Ar-H);
7.82 (d, 1H, Ar-H, J = 8.0 Hz); 8.16 (s, 1H, Ar-H); 10.72 (s, 1H, CO-
NH). 13C-NMR (100 MHz, DMSO): d 46.3, 48.4, 49.6, 116.6, 118.0,
120.2, 121.2, 122.9, 123.8, 128.4, 129.5, 130.7, 135.7, 138.9,
139.9, 150.8, and 166.8.
2-Imidazol-1-yl-N-[3-(benzylpiperidinyl-1-
sulfonyl)phenyl]acetamide 5e
Method A: Yield was 96% from methanol. Mp. 211–2128C; IR
(KBr): 3235, 1706, 1595, 1082 cm– 1; LC-MS (APCI) m/z: 439 [M+]
(100);1H-NMR (400 MHz, DMSO): d 1.18 (m, 2H, piperidine, N-CH2-
CH2-CH); 1.48 (broad s, 1H, piperidine, N-CH2-CH2-CH); 1.59 (d, 2H,
piperidine, N-CH2-CH2, J = 12.0 Hz); 2.18 (t, 2H, piperidine, N-CH2-,
J = 12.0 Hz); 2.45 (d, 2H, piperidine, N-CH2, J = 8.0 Hz); 3.59 (d, 2H,
phenyl-CH2-N-, J = 12.0 Hz); 4.93 (s, 2H, imidazole-CH2-CO); 6.90 (s,
1H, Ar-H); 7.14 (m, 4H, Ar-H); 7.24 (m, 2H, Ar-H); 7.39 (d, 1H, Ar-H,
J = 8.0 Hz); 7.59 (m, 2H, Ar-H); 7.81 (d, 1H, Ar-H, J = 8.0 Hz); 8.05 (s,
1H, Ar-H); 10.68 (s, 1H, CO-NH).13C-NMR (100 MHz, DMSO): d 31.1,
36.6, 42.1, 46.5, 49.6, 118.0, 121.2, 122.7, 123.5, 126.3, 128.5,
128.6, 129.4, 130.5, 136.6, 138.8, 140.0, 140.2, and 167.0.
2-Imidazol-1-yl-N-[3-(N-methylanilinyl-1-
sulfonyl)phenyl]acetamide 5j
ethod B: Yield was 53% from ethanol/water. Mp. 216–2178C; IR
(KBr): 3235, 1700, 1609, 1174 cm– 1; LC-MS (APCI) m/z: 371 [M+]
(100); 1H-NMR (400 MHz, DMSO): d 3.15 (s, 3H, N-CH3); 4.91 (s, 2H,
imidazole-CH2-CO); 6.89 (s, 1H, Ar-H); 7.12 (m, 4H, Ar-H); 7.30 (m,
3H, Ar-H); 7.51 (t, 1H, Ar-H, J = 8.0 Hz); 7.63 (s, 1H, Ar-H); 7.89 (m,
2H, Ar-H); 10.68 (s, 1H, CO-NH). 13C-NMR (100 MHz, DMSO): d 38.5,
49.6, 118.0, 121.2, 122.6, 123.6, 126.7, 127.8, 128.4, 129.4, 130.4,
137.2, 138.8, 139.6, 141.4, and 166.8.
2-Imidazol-1-yl-N-[3-(benzylpiperazinyl-1-
sulfonyl)phenyl]acetamide 5f
Method A: Yield was 64% from ethanol. Mp. 228–2298C; IR (KBr):
3233, 1701, 1609, 1368, 1161 cm– 1; LC-MS (APCI) m/z: 440 [M+]
(100); 1H-NMR (400 MHz, DMSO): d 2.42 (s, 4H, piperazine CH2-N-
(CH2)2); 2.88 (s, 4H, piperazine S-N-(CH2)2); 3.45 (s, 2H, Ar-CH2-N);
4.94 (s, 2H, imidazole-CH2-CO); 6.90 (s, 1H, Ar-H); 7.17 (s, 1H, Ar-
H); 7.22 (m, 3H, Ar-H); 7.28 (m, 2H, Ar-H); 7.41 (d, 1H, Ar-H, J =
8.0 Hz); 7.62 (m, 2H, Ar-H); 7.83 (d, 1H, Ar-H, J = 8.0 Hz); 8.08
(s,1H,Ar-H); 10.71 (s,1H, CO-NH). 13C-NMR (100 MHz, DMSO): d
46.5, 49.6, 51.9, 61.8, 118.1, 121.2, 122.9, 123.7, 127.5, 128.4,
128.7, 129.2, 130.6, 135.7, 138.1, 138.8, 139.8, and 166.9.
2-Imidazol-1-yl-N-[3-(diphenylaminyl-1-
sulfonyl)phenyl]acetamide 5k
Method A: Yield was 71% from ethanol. Mp. 207–2088C; IR (KBr):
3437, 1702, 1594, 1109 cm– 1; LC-MS (APCI) m/z: 433 [M+] (100);
1H-NMR (400 MHz, DMSO): d 4.95 (s, 2H, imidazole-CH2-CO); 6.92
(s, 1H, Ar-H); 7.18 (s, 1H, Ar-H); 7.35 (m, 11H, Ar-H); 7.56 (t, 1H, Ar-
H, J = 8.0 Hz); 7.66 (s, 1H, Ar-H); 7.92 (d, 1H, Ar-H, J = 8.0 Hz); 8.09
(s, 1H, Ar-H); 10.71 (s, 1H, CO-NH). 13C-NMR (100 MHz, DMSO): d
49.7, 117.9, 121.2, 122.7, 123.8, 128.3, 128.5, 128.8, 130.0, 130.6,
138.9, 139.9, 140.8, 141.4, and 166.8.
2-Imidazol-1-yl-N-[3-(acetylpiperazinyl-1-
sulfonyl)phenyl]acetamide 5g
Method A: Yield after column chromatography (5% methanol/
dichloromethane followed by 10% methanol/dichloromethane)
2-Imidazol-1-yl-N-[3-(benzylaminyl-1-
sulfonyl)phenyl]acetamide 5l
was 43%. Mp. 180–1818C; IR (KBr): 3405, 1707, 1654, 1154 cm– 1
;
LC-MS (APCI) m/z: 440 [M+] (100); 1H-NMR (400 MHz, DMSO): d
1.93 (s, 3H, CO-CH3); 2.87 (m, 4H, piperazine, CO-N-(CH2)2); 3.50
Method A: Yield was 48% from ethanol. Mp. 216–2178C; IR (KBr):
1707, 1593, 1153 cm– 1; LC-MS (APCI) m/z: 371 [M+] (100); 1H-NMR
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