M. Abid et al. / European Journal of Medicinal Chemistry 43 (2008) 2035e2039
2039
(s, 1H, imidazole ring proton), 7.82 (s, 1H, CH]N), 8.08 (s, 1H, NH),
7.85 (s, 1H, NH), 7.68 (d, J ¼ 15.23, 1H, CH), 7.57 (d, J ¼ 15.23, 1H,
CH), 7.11e7.32 (m, 4H, AreH), 4.62 (t, 2H, CH2), 3.57 (t, 2H, CH2),
4.25 (m, 1H, CH), 1.12e2.57 (m, 10H, CH2); 13C NMR (CDCl3): (d,
ppm) 174.5 (C]S), 163.0 (C]N), 158.8, 149.4, 140.2 (imidazoleeC),
137.3 (CH), 135.5 (CH), 122.4e133.1 (aryleC), 76.6 (CH2), 46.4
(CH), 39.1 (CH2), 26.7 (2CH2), 23.4 (CH2), 13.4 (CH2). Compound 2:
lmax (cmꢁ1): 388.5, 383, 237.3; IR: nmax (cmꢁ1) 3415 (OeH), 3314
(NH), 1630 (C]N), 1590 (C]N), 1182 (CeN), 1092 (C]S); 1H
NMR (CDCl3): (d, ppm) 9.19 (s, 1H, OeH), 8.01 (s, 1H, imidazole
ring proton), 7.94 (s, 1H, CH]N), 8.87 (s, 1H, NH), 8.10 (s, 1H,
NH), 7.87 (d, J ¼ 15.73, 1H, CH), 7.23 (d, J ¼ 15.73, 1H, CH), 7.28e
7.65 (m, 4H, AreH), 4.53 (t, 2H, CH2), 3.93 (t, 2H, CH2), 4.63 (m,
1H, CH), 1.24e2.84 (m, 14H, CH2); 13C NMR (CDCl3): (d, ppm)
175.6 (C]S), 166.2 (C]N), 157.4, 148.3, 142.2 (imidazoleeC), 138.6
(CH), 136.1 (CH), 122.8e133.1 (aryleC), 76.5 (CH2), 51.08 (CH),
39.1 (CH2), 31.06 (2CH2), 25.6 (CH2), 21.7 (2CH2), 13.4 (CH2). Com-
pound 3: lmax (cmꢁ1): 389, 383, 204.5; IR: nmax (cmꢁ1) 3408 (OeH),
3232 (NH), 1629 (C]N), 1588 (C]N), 1181 (CeN), 1095 (C]S);
1H NMR (CDCl3): (d, ppm) 9.61 (s, 1H, OeH), 8.25 (s, 1H, imidazole
ring proton), 7.96 (s, 1H, CH]N), 8.64 (s, 1H, NH), 8.42 (s, 1H,
NH), 7.71 (d, J ¼ 16.50, 1H, CH), 7.63 (d, J ¼ 16.50, 1H, CH), 7.06e
7.55 (m, 8H, AreH), 4.46 (t, 2H, CH2), 3.41 (t, 2H, CH2), 2.36 (s, 3H,
CH3); 13C NMR (CDCl3): (d, ppm) 175.5 (C]S), 164.2 (C]N),
157.4, 147.2, 144.2 (imidazoleeC), 139.1 (CH), 133.2 (CH), 120.4e
131.6 (aryleC), 78.2 (CH2), 36.5 (CH2), 19.9 (CH2). Compound 4:
lmax (cmꢁ1): 390.7, 383, 240, 203.3; IR: nmax (cmꢁ1) 3431 (OeH),
3275 (NH), 1663 (C]N), 1584 (C]N), 1262 (CeN), 1187 (C]S);
1H NMR (CDCl3): (d, ppm) 9.39 (s, 1H, OeH), 8.10 (s, 1H, imidazole
ring proton), 7.87 (s, 1H, CH]N), 8.43 (s, 1H, NH), 8.13 (s, 1H,
NH), 7.63 (d, J ¼ 16.10, 1H, CH), 7.49 (d, J ¼ 16.10, 1H, CH), 7.17e
7.29 (m, 4H, AreH), 4.86 (t, 2H, CH2), 3.91 (t, 2H, CH2), 2.32 (s, 3H,
CH3); 13C NMR (CDCl3): (d, ppm) 177.3 (C]S), 163.7 (C]N),
158.1, 149.2, 140.9 (imidazoleeC), 136.3 (CH), 134.5 (CH), 121.4e
133.6 (aryleC), 76.0 (CH2), 41.3 (CH2), 18.6 (CH2). Compound 5:
lmax (cmꢁ1): 384, 235, 204.9; IR: nmax (cmꢁ1) 3412 (OeH), 3224
(NH), 1630 (C]N), 1586 (C]N), 1181 (CeN), 1092 (C]S); 1H
NMR (CDCl3): (d, ppm) 9.96 (s, 1H, OeH), 8.03 (s, 1H, imidazole
ring proton), 7.99 (s, 1H, CH]N), 8.79 (s, 1H, NH), 8.62 (s, 1H,
NH), 7.92 (d, J ¼ 16.21, 1H, CH), 7.82 (d, J ¼ 16.21, 1H, CH), 7.27e
7.77 (m, 8H, AreH), 4.36 (t, 2H, CH2), 3.84 (t, 2H, CH2), 4.25 (d,
2H, CH2); 13C NMR (CDCl3): (d, ppm) 175.3 (C]S), 161.8 (C]N),
157.8, 147.2, 142.2 (imidazoleeC), 137.3 (CH), 134.3 (CH), 122.6e
132.1 (aryleC), 74.3 (CH2), 53.4 (CH2), 39.4 (CH2). Compound 6:
lmax (cmꢁ1): 386, 382, 341, 240, 208; IR: nmax (cmꢁ1) 3434 (OeH),
3217 (NH), 1663 (C]N), 1565 (C]N), 1270 (CeN), 1183 (C]S);
1H NMR (CDCl3): (d, ppm) 8.15 (s, 1H, OeH), 8.07 (s, 1H, imidazole
ring proton), 7.74 (s, 1H, CH]N), 7.97 (s, 1H, NH), 7.85 (s, 1H,
NH), 7.68 (d, J ¼ 15.38, 1H, CH), 7.55 (d, J ¼ 15.38, 1H, CH), 6.96e
7.38 (m, 4H, AreH), 4.37 (t, 2H, CH2), 3.65 (t, 2H, CH2), 1.29e3.36
(m, 8H, CH2); 13C NMR (CDCl3): (d, ppm) 178.5 (C]S), 166.2
(C]N), 159.6, 151.4, 142.2 (imidazoleeC), 139.6 (CH), 133.5 (CH),
120.2e131.4 (aryleC), 72.5 (CH2), 37.1 (CH2), 34.7 (2CH2), 25.8
22.4 (2CH2), 14.4 (2CH2). Compound 8: lmax (cmꢁ1): 395.7, 326.9,
205.6; IR: nmax (cmꢁ1) 3429 (OeH), 3312 (NH), 1659 (C]N), 1529
(C]N), 1183 (CeN), 1082 (C]S); 1H NMR (CDCl3): (d, ppm) 8.69
(s, 1H, OeH), 8.10 (s, 1H, imidazole ring proton), 7.93 (s, 1H,
CH]N), 8.32 (s, 1H, NH), 8.19 (s, 1H, NH), 7.89 (d, J ¼ 15.75, 1H,
CH), 7.77 (d, J ¼ 15.75, 1H, CH), 7.21e7.56 (m, 4H, AreH), 4.66 (t,
2H, CH2), 3.84 (t, 2H, CH2), 1.13e3.28 (m, 9H, CH2), 0.98 (d, 3H,
CH3); 13C NMR (CDCl3): (d, ppm) 176.8 (C]S), 165.3 (C]N),
153.8, 148.9, 142.4 (imidazoleeC), 139.1 (CH), 135.1 (CH), 121.2e
134.6 (aryleC), 74.2 (CH2), 38.6 (CH2), 42.6 (2CH2), 27.4 (2CH2),
29.4 (CH), 11.2 (CH3). Compound 9: lmax (cmꢁ1): 389.1, 384, 242;
IR: nmax (cmꢁ1) 3433 (OeH), 3265 (NH), 1641 (C]N), 1584 (C]N),
1267 (CeN), 1184 (C]S); 1H NMR (CDCl3): (d, ppm) 8.68 (s, 1H,
OeH), 8.28 (s, 1H, imidazole ring proton), 7.88 (s, 1H, CH]N), 8.11
(s, 1H, NH), 7.90 (s, 1H, NH), 7.84 (d, J ¼ 15.44, 1H, CH), 7.74 (d,
J ¼ 15.44, 1H, CH), 7.31e7.65 (m, 9H, AreH), 4.94 (t, 2H, CH2),
3.93 (t, 2H, CH2), 3.14e3.73 (m, 8H, CH2); 13C NMR (CDCl3): (d,
ppm) 174.5 (C]S), 162.2 (C]N), 157.3, 148.3, 140.1 (imidazoleeC),
138.1 (CH), 134.5 (CH), 121.5e132.1 (aryleC), 75.6 (CH2), 46.4
(2CH2), 49.7 (2CH2), 36.4 (CH2). Compound 10: lmax (cmꢁ1): 387,
383, 237, 205.8; IR: nmax (cmꢁ1) 3432 (OeH), 3221 (NH), 1642
(C]N), 1583 (C]N), 1206 (CeN), 1185 (C]S); 1H NMR (CDCl3):
(d, ppm) 8.28 (s, 1H, OeH), 8.15 (s, 1H, imidazole ring proton), 8.08
(s, 1H, CH]N), 7.85 (s, 1H, NH), 7.82 (s, 1H, NH), 7.68 (d,
J ¼ 16.05, 1H, CH), 7.57 (d, J ¼ 16.05, 1H, CH), 7.11e7.32 (m, 4H,
AreH), 4.62 (t, 2H, CH2), 3.57 (t, 2H, CH2), 4.25 (m, 1H, CH), 1.12e
2.57 (m, 10H, CH2); 13C NMR (CDCl3): (d, ppm) 174.5 (C]S), 163.0
(C]N), 158.8, 149.4, 140.2 (imidazoleeC), 137.3 (CH), 135.5 (CH),
122.4e133.1 (aryleC), 76.6 (CH2), 46.4 (CH), 39.1 (CH2), 26.7
(2CH2), 23.4 (CH2), 13.4 (CH2). Compound 11: lmax (cmꢁ1): 387.9,
382, 203; IR: nmax (cmꢁ1) 3492 (OeH), 3210 (NH), 1642 (C]N),
1584 (C]N), 1265 (CeN), 1129 (C]S); 1H NMR (CDCl3): (d, ppm)
8.76 (s, 1H, OeH), 8.11 (s, 1H, imidazole ring proton), 7.69 (s, 1H,
CH]N), 8.47 (s, 1H, NH), 8.34 (s, 1H, NH), 7.77 (d, J ¼ 15.87, 1H,
CH), 7.57 (d, J ¼ 15.87, 1H, CH), 7.13e7.45 (m, 8H, AreH), 4.66 (t,
2H, CH2), 3.58 (t, 2H, CH2), 2.27e3.29 (m, 6H, CH2); 13C NMR
(CDCl3): (d, ppm) 174.5 (C]S), 163.0 (C]N), 158.8, 149.4, 140.2 (imi-
dazoleeC), 137.3 (CH), 135.5 (CH), 122.4e133.1 (aryleC), 76.6 (CH2),
46.4 (CH), 39.1 (CH2), 26.7 (2CH2), 23.4 (CH2), 13.4 (CH2).
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M.T.G. Garza, D.E. Cruz-Vega, B.D. Mata-Cardenas, F. Naqvi,
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(2CH2). Compound 7: lmax (cmꢁ1): 395.6, 327, 208; IR: nmax (cmꢁ1
)
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3431 (OeH), 3265 (NH), 1630 (C]N), 1583 (C]N), 1183 (CeN),
1061 (C]S); 1H NMR (CDCl3): (d, ppm) 8.56 (s, 1H, OeH), 8.32 (s,
1H, imidazole ring proton), 7.88 (s, 1H, CH]N), 8.07 (s, 1H, NH),
7.93 (s, 1H, NH), 7.61 (d, J ¼ 15.81, 1H, CH), 7.52 (d, J ¼ 15.81, 1H,
CH), 7.15e7.46 (m, 4H, AreH), 4.62 (t, 2H, CH2), 3.76 (t, 2H, CH2),
1.25e2.57 (m, 12H, CH2); 13C NMR (CDCl3): (d, ppm) 177.1 (C]S),
165.4 (C]N), 157.4, 149.1, 141.7 (imidazoleeC), 139.3 (CH), 134.2
(CH), 122.2e133.8 (aryleC), 74.3 (CH2), 41.7 (CH2), 36.6 (2CH2),
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Antimicrob. Agents Chemother. 50 (2006) 344e347.
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145e149.