R.V. Patel et al. / European Journal of Medicinal Chemistry 53 (2012) 41e51
49
1534 (2C]N, oxadiazole), 1479 (eNeCH2), 1141 (CeN, benzimid-
azole), 1058 (CeOeC, oxadiazole). 1H NMR (400 MHz, DMSOed6):
(eNeCH2), 1133 (CeN, benzimidazole), 1070 (CeOeC, oxadiazole).
1H NMR (400 MHz, DMSOed6):
d
8.59 (s, 1H, eN ¼ CH), 8.26 (s, 1H,
d
8.66 (s, 1H, eN ¼ CH), 8.37 (s, 1H, eNH), 7.61e7.17 (m, 12H, AreH),
4.28 (s, 2H, SeCH2), 3.80 (s, 2H, eNeCH2). 13C NMR (100 MHz,
DMSOe d6): 169.90(1C,C-2,oxadiazole),166.89(1C,CO),165.66(1C,
eNH), 7.91 (d, J ¼ 2.2 Hz, 1H), 7.67 (d, J ¼ 7.6 Hz, 1H), 7.44 (dd,
J ¼ 8.4, 1.9 Hz, 1H), 7.33e7.17 (m, 4H, AreH), 4.30 (s, 2H, SeCH2),
d
3.68 (s, 2H, eNeCH2). 13C NMR (100 MHz, DMSOe d6):
d 170.11
C-5, oxadiazole), 155.98 (1C, C-2, benzothiazole), 153.11 (1C, C-2,
benzimidazole), 144.90, 142.17, 139.80, 136.78, 134.77, 133.43, 130.15,
126.89,125.05,123.55, 121.90, 117.13 (12C, AreC), 44.68 (1C, NeCH2),
34.88 (1C, SeCH2). Anal Calcd. for C19H14N6O2S2: C, 54.01; H, 3.34; N,
19.89; Found: C, 53.92; H, 3.48; N, 20.02.
(1C, C-2, oxadiazole), 167.90 (1C, CO), 164.87 (1C, C-5, oxadiazole),
155.47 (1C, C-2, benzothiazole), 150.50 (1C, C-2, benzimidazole),
143.13, 141.19, 137.89, 134.12, 132.10, 129.80, 125.99, 124.67, 121.96,
119.20, 117.26, 116.53, 113.46 (12C, AreC), 45.07 (1C, NeCH2), 35.76
(1C, SeCH2). Anal Calcd. for C19H13IN6O2S2: C, 41.61; H, 2.39; N,
15.33; Found: C, 41.46; H, 2.56; N, 15.21.
5.1.9.2. 2e(5e((1Hebenzo[d]imidazole1eyl)methyl)e1,3,4eoxadia-
zole2eylthio)eNe(6echlorobenzo[d]thiazole2eyl)acetamide
(7b). Yellow solid, Yield 75%, mp.: 267e268 ꢀC. IR (KBr, cmꢁ1):
3299 (NH), 1681 (C]O), 1655 (C]N, benzimidazole), 1650 (C]N,
benzothiazole), 1622, 1554 (2C]N, oxadiazole), 1488 (eNeCH2),
1134 (CeN, benzimidazole), 1087 (CeOeC, oxadiazole). 1H NMR
5.1.9.6. 2e(5e((1Hebenzo[d]imidazole1eyl)methyl)e1,3,4eoxadia-
zole2eylthio)eNe(6enitrobenzo[d]thiazole2eyl)acetamide
(7f). Yellow solid, Yield 64%, mp.: 289e290 ꢀC. IR (KBr, cmꢁ1):
3313 (NH), 1674 (C]O), 1667 (C]N, benzimidazole), 1656 (C]N,
benzothiazole), 1637, 1546 (2C]N, oxadiazole), 1487 (eNeCH2),
1140 (CeN, benzimidazole), 1054 (CeOeC, oxadiazole). 1H NMR
(400 MHz, DMSOed6):
d
8.59 (s, 1H, eN ¼ CH), 8.28 (s, 1H, eNH),
7.75 (d, J ¼ 1.6 Hz, 1H), 7.48 (d, J ¼ 7.5 Hz, 1H), 7.37 (dd, J ¼ 7.7,
1.8 Hz, 1H), 7.29e7.14 (m, 4H, AreH), 4.35 (s, 2H, SeCH2), 3.66 (s,
(400 MHz, DMSOed6):
d
8.59 (s, 1H, eN ¼ CH), 8.26 (s, 1H, eNH),
8.02 (d, J ¼ 1.8 Hz, 1H), 7.77 (dd, J ¼ 7.3, 1.8 Hz, 1H), 7.60 (d,
J ¼ 7.1 Hz,1H), 7.46 (dd, J ¼ 7.5, 1.7 Hz, 2H), 7.31e7.22 (m, 2H, AreH),
4.18 (s, 2H, SeCH2), 3.55 (s, 2H, eNeCH2). 13C NMR (100 MHz,
2H, eNeCH2). 13C NMR (100 MHz, DMSOe d6):
d 171.13 (1C, C-2,
oxadiazole), 168.19 (1C, CO), 164.38 (1C, C-5, oxadiazole), 157.09
(1C, C-2, benzothiazole), 151.92 (1C, C-2, benzimidazole), 146.35,
143.78, 141.12, 136.89, 133.90, 131.11, 128.08, 126.82, 124.56, 121.86,
119.84, 117.10, 115.72 (12C, AreC), 41.90 (1C, NeCH2), 35.09 (1C,
SeCH2). Anal Calcd. for C19H13ClN6O2S2: C, 49.94; H, 2.87; N, 18.39;
Found: C, 50.11; H, 2.76; N, 18.21.
DMSOe d6):
d 170.92 (1C, C-2, oxadiazole), 167.58 (1C, CO), 165.32
(1C, C-5, oxadiazole), 156.71 (1C, C-2, benzothiazole), 152.91 (1C, C-
2, benzimidazole), 147.10, 145.25, 143.19, 140.93, 138.76, 135.95,
132.19, 128.99, 127.11, 125.60, 122.38, 120.56 (12C, AreC), 45.19 (1C,
NeCH2), 36.72 (1C, SeCH2). Anal Calcd. for C19H13N7O4S2: C, 48.82;
H, 2.80; N, 20.97; Found: C, 48.93; H, 2.77; N, 21.11.
5.1.9.3. 2e(5e((1Hebenzo[d]imidazole1eyl)methyl)e1,3,4eoxadia-
zole2eylthio)eNe(6ebromobenzo[d]thiazole2eyl)acetamide
(7c). Light brown solid, Yield 78%, mp.: 258e259 ꢀC. IR (KBr,
cmꢁ1): 3307 (NH), 1672 (C]O), 1664 (C]N, benzimidazole), 1656
(C]N, benzothiazole), 1636, 1533 (2C]N, oxadiazole), 1472
(eNeCH2), 1134 (CeN, benzimidazole), 1060 (CeOeC, oxadiazole).
5.1.9.7. 2e(5e((1Hebenzo[d]imidazole1eyl)methyl)e1,3,4eoxadia-
zole2eylthio)eNe(6ecyanobenzo[d]thiazole2eyl)acetamide
(7g). Yellow solid, Yield 69%, mp.: 267e269 ꢀC. IR (KBr, cmꢁ1):
3283 (NH), 1681 (C]O), 1653 (C]N, benzimidazole), 1649 (C]N,
benzothiazole), 1631, 1540 (2C]N, oxadiazole), 1479 (eNeCH2),
1142 (CeN, benzimidazole), 1081 (CeOeC, oxadiazole). 1H NMR
1H NMR (400 MHz, DMSOed6):
d
8.62 (s, 1H, eN ¼ CH), 8.38 (s, 1H,
eNH), 7.68 (d, J ¼ 1.4 Hz, 1H), 7.55e7.21 (m, 11H, AreH), 4.41 (s, 2H,
(400 MHz, DMSOed6):
d
8.60 (s, 1H, eN ¼ CH), 8.24 (s, 1H, eNH),
SeCH2), 3.77 (s, 2H, eNeCH2). 13C NMR (100 MHz, DMSOe d6):
7.96 (d, J ¼ 1.9 Hz, 1H), 7.71 (d, J ¼ 7.6 Hz, 1H), 7.49 (dd, J ¼ 8.6,
d
168.79 (1C, C-2, oxadiazole), 166.18 (1C, CO), 165.52 (1C, C-5,
1.8 Hz, 1H), 7.39e7.26 (m, 4H, AreH), 4.29 (s, 2H, SeCH2), 3.67 (s,
oxadiazole), 154.80 (1C, C-2, benzothiazole), 153.01 (1C, C-2,
benzimidazole), 141.38, 138.93, 136.70, 134.21, 132.10, 129.97,
125.79, 124.56, 122.47, 121.09, 119.29, 117.11 (12C, AreC), 44.20 (1C,
NeCH2), 33.93 (1C, SeCH2). Anal Calcd. for C19H13BrN6O2S2: C,
45.52; H, 2.61; N, 16.76; Found: C, 45.33; H, 2.74; N, 16.53.
2H, eNeCH2). 13C NMR (100 MHz, DMSOe d6):
d 168.25 (1C, C-2,
oxadiazole), 167.11 (1C, CO), 164.69 (1C, C-5, oxadiazole), 155.14
(1C, C-2, benzothiazole), 150.96 (1C, C-2, benzimidazole), 141.19,
137.88, 134.90, 132.11, 130.09, 129.15, 126.79, 124.99, 123.10, 122.97,
118.60 (11C, AreC), 105.87 (1C, C^N), 96.91 (1C, eCeChN), 43.87
(1C, NeCH2), 35.10 (1C, SeCH2). Anal Calcd. for C20H13N7O2S2: C,
53.68; H, 2.93; N, 21.91; Found: C, 53.55; H, 2.76; N, 22.04.
5.1.9.4. 2e(5e((1Hebenzo[d]imidazole1eyl)methyl)e1,3,4eoxadia-
zole2eylthio)eNe(6efluorobenzo[d]thiazole2eyl)acetamide
(7d). Yellow solid, Yield 65%, mp.: 276e278 ꢀC. IR (KBr, cmꢁ1): 3293
(NH), 1684 (C]O), 1660 (C]N, benzimidazole), 1653 (C]N, benzo-
thiazole),1640,1528 (2C]N, oxadiazole),1491 (eNeCH2), 1151 (CeN,
benzimidazole), 1066 (CeOeC, oxadiazole). 1H NMR (400 MHz,
5.1.9.8. 2e(5e((1Hebenzo[d]imidazole1eyl)methyl)e1,3,4eoxadia-
zole2eylthio)eNe(6emethylbenzo[d]thiazole2eyl)acetamide
(7h). Yellow solid, Yield 79%, mp.: 254e255 ꢀC. IR (KBr, cmꢁ1): 3275
(NH), 1687 (C]O), 1657 (C]N, benzimidazole), 1651 (C]N, benzo-
thiazole), 1631, 1548 (2C]N, oxadiazole), 1485 (eNeCH2), 1147
(CeN, benzimidazole), 1059 (CeOeC, oxadiazole). 1H NMR
DMSOed6):
1.5 Hz, 1H), 7.68 (dd, J ¼ 2.2, 8.6 Hz, 1H), 7.40 (dd, J ¼ 5.1, 8.3 Hz, 1H),
7.29e7.14(m, 4H, AreH), 4.35(s,2H, SeCH2), 3.61 (s, 2H, eNeCH2).13
NMR (100 MHz, DMSOe d6): 169.05 (1C, C-2, oxadiazole),167.70 (1C,
d
8.70 (s,1H, eN ¼ CH), 8.31 (s,1H, eNH), 7.81 (dd, J ¼ 8.1,
C
(400 MHz, DMSOed6):
d
8.60 (s,1H, eN ¼ CH), 8.21 (s,1H, eNH), 7.83
d
(d, J ¼ 7.7 Hz, 1H), 7.60e7.17 (m, 6H, AreH), 4.37 (s, 2H, SeCH2), 3.58
CO), 166.17 (1C, C-5, oxadiazole), 156.72 (1C, C-2, benzothiazole),
151.91 (1C, C-2, benzimidazole), 144.19,143.10,140.92,137.25, 134.79,
132.13,128.97,126.77,125.90,123.16,120.99,117.64, (12C, AreC), 46.01
(1C, NeCH2), 37.67 (1C, SeCH2). Anal Calcd. for C19H13FN6O2S2: C,
51.81; H, 2.97; N, 19.08; Found: C, 51.70; H, 3.14; N, 18.99.
(s, 2H, eNeCH2), 2.28 (s, 3H, CH3). 13C NMR (100 MHz, DMSOe d6):
d
168.16 (1C, C-2, oxadiazole), 166.71 (1C, CO), 165.13 (1C, C-5, oxa-
diazole), 158.60 (1C, C-2, benzothiazole), 151.36 (1C, C-2, benzimid-
azole), 148.00, 141.67, 137.89, 134.60, 133.21, 130.91, 127.89, 126.10,
123.57, 122.10, 119.90, 115.45 (12C, AreC), 42.92 (1C, NeCH2), 34.59
(1C, SeCH2), 17.90 (1C, CH3). Anal Calcd. for C20H16N6O2S2: C, 55.03;
H, 3.69; N, 19.25; Found: C, 54.91; H, 3.73; N, 19.05.
5.1.9.5. 2e(5e((1Hebenzo[d]imidazole1eyl)methyl)e1,3,4eoxadia-
zole2eylthio)eNe(6eiodobenzo[d]thiazole2eyl)acetamide
(7e). Light Yellow solid, Yield 67%, mp.: 262e265 ꢀC. IR (KBr,
cmꢁ1): 3301 (NH), 1672 (C]O), 1654 (C]N, benzimidazole), 1651
(C]N, benzothiazole), 1627, 1552 (2C]N, oxadiazole), 1461
5.1.9.9. 2e(5e((1Hebenzo[d]imidazole1eyl)methyl)e1,3,4eoxadia-
zole2eylthio)eNe(6emethoxybenzo[d]thiazole2eyl)acetamide
(7i). Yellow solid, Yield 61%, mp.: 260e262 ꢀC. IR (KBr, cmꢁ1): 3295