Med Chem Res
2H, CH2–Ar), 6.64–7.86 (m,9H, Ar–H), 7.04–7.36 (m, 4H,
Bz–H), 8.24 (s, 1H, NH, D2O exchangeable), 8.95 (s, 1H,
NH, D2O exchangeable), 10.24 (s, 1H, NH–Ar, D2O
exchangeable); 13C NMR (DMSO-d6) d (ppm): 43.44,
45.53, 110.28, 118.22, 119.82, 122.82, 123.63, 125.25,
126.19, 127.28, 127.39, 127.84, 128.81, 129.28, 130.10,
130.92, 133.43, 135.27, 137.34, 148.28, 152.16, 163.82.
126.92, 127.17, 127.82, 127.44, 128.21, 129.34, 130.28,
131.83, 132.23, 134.35, 138.32, 147.45, 152.39, 160.91; MS:
m/z 402 (M?1).
2-[(1-Benzyl-1H-benzo[d]imidazol-2-yl)methyl]-N-(2-
methoxyphenyl)hydrazinecarbothioamide (4f)
Yield: 63 %; m.p. 170 °C; IR (KBr) t cm-1: 3424 (NHstr.),
3299 (NHstr.), 3117 (NHstr.-thioamide), 2961 (Ar–CHstr.),
2901 (CHstr.), 1601 (C=N, cyclic), 1536 (C=Sstr.), 1169
2-[(1-Benzyl-1H-benzo[d]imidazol-2-yl) methyl]-N-o-
tolylhydrazinecarbothioamide (4c)
1
(OCH3); H NMR (DMSO-d6) d(ppm): 3.17 (s, 2H, CH2),
Yield: 51 %; m.p. 175 °C; IR (KBr) t cm-1: 3371 (NHstr.),
3194 (NHstr.), 3091 (NHstr.-thioamide), 2990 (Ar–CHstr.),
2943 (CHstr.), 1685 (C=N, cyclic), 1540 (C=Sstr.); 1H NMR
(CDCl3) d (ppm): 2.48 (s, 3H, CH3) 3.89 (s, 2H, CH2), 4.09
(s, 2H, CH2–Ar), 7.07–7.97 (m, 9H, Ar–H), 7.22–7.91 (m,
4H, Bz–H), 8.00 (s, 1H, NH, D2O exchangeable), 9.25 (s,
1H, NH, D2O exchangeable), 10.01 (s, 1H, NH–Ar, D2O
exchangeable); 13C NMR (DMSO-d6) d (ppm): 18.24,
41.27, 43.48, 110.17, 118.29, 119.83, 121.29, 124.10,
125.53, 126.82, 127.16, 127.23, 127.72, 128.73, 129.18,
130.28, 130.96, 133.14, 134.47, 136.17, 149.27, 151.92,
164.92; MS: m/z 403 (M?2).
3.40 (s, 3H, OCH3) 4.15 (s, 2H, CH2–Ar), 6.58–8.15 (m,
9H, Ar–H), 7.22–8.76 (m, 4H, Bz–H), 8.82 (s, 1H, NH,
D2O exchangeable), 9.19 (s, 1H, NH, D2O exchangeable),
11.11 (s, 1H, NH–Ar, D2O exchangeable); 13C NMR
(DMSO-d6) d (ppm): 39.24, 42.84, 55.25, 114.26, 119.28,
120.27, 121.38, 124.84, 125.28, 126.94, 127.21, 127.23,
127.49, 128.48, 129.28, 130.47, 131.23, 133.40, 134.35,
138.24, 147.36, 150.58, 163.41; MS: m/z 419 (M?2).
2-[(1-Benzyl-1H-benzo[d]imidazol-2-yl)methyl]-N-(3-
methoxyphenyl)hydrazinecarbothioamide (4g)
Yield: 61 %; m.p. 151 °C; IR (KBr) t cm-1: 3458 (NHstr.),
3273 (NHstr.), 3123 (NHstr.-thioamide), 2984 (Ar–CHstr.),
2928 (CHstr.), 1648 (C=N, cyclic), 1521 (C=Sstr.), 1114
2-[(1-Benzyl-1H-benzo[d]imidazol-2-yl)methyl]-N-m-
tolylhydrazinecarbothioamide (4d)
1
Yield: 44 %; m.p. 210 °C; IR (KBr) t cm-1: 3345 (NHstr.),
3173 (NHstr.), 3065 (NHstr.-thioamide), 2985 (Ar–CHstr.),
2932 (CHstr.), 1647 (C=N, cyclic), 1564 (C=Sstr.); 1H NMR
(CDCl3) d (ppm): 2.45(s, 3H, CH3) 3.58 (s, 2H, CH2), 4.05
(s, 2H, CH2–Ar), 7.04–7.85 (m, 9H, Ar–H), 7.12–7.99 (m,
4H, Bz–H), 8.05 (s, 1H, NH, D2O exchangeable), 9.29 (s,
1H, NH, D2O exchangeable), 10.17 (s, 1H, NH–Ar, D2O
exchangeable); 13C NMR (DMSO-d6) d (ppm): 17.26,
42.47, 44.29, 112.21, 117.13, 120.15, 121.72, 124.27,
125.17, 126.73, 127.33, 127.74, 127.85, 128.83, 129.92,
130.12, 130.83, 133.26, 134.18, 136.92, 147.22, 153.12,
162.61; MS: m/z 401 (M?1).
(OCH3); H NMR (CDCl3) d (ppm): 3.25 (s, 2H, CH2),
3.63 (s, 3H, OCH3), 4.27 (s, 2H, CH2–Ar), 6.24–8.56
(m,9H, Ar–H), 7.02–8.21 (m, 4H, Bz–H), 8.15 (s, 1H, NH,
D2O exchangeable), 9.01 (s, 1H, NH, D2O exchangeable),
11.23 (s, 1H, NH–Ar, D2O exchangeable); 13C NMR
(DMSO-d6) d (ppm): 41.25, 43.95, 57.28, 111.37, 119.83,
120.73, 121.49, 122.39, 125.25, 126.29, 127.35, 127.57,
127.21, 128.24, 129.35, 130.64, 131.24, 133.87, 137.25,
141.23, 148.26, 150.35, 165.45.
2-[(1-Benzyl-1H-benzo[d]imidazol-2-yl)methyl]-N-(4-
methoxyphenyl)hydrazinecarbothioamide (4h)
Yield: 59 %; m.p. 200 °C; IR (KBr) t cm-1: 3445 (NHstr.),
3273 (NHstr.), 3154 (NHstr.-thioamide), 2921 (Ar–CHstr.),
2958 (CHstr.), 1625 (C=N, cyclic), 1556 (C=Sstr.), 1147
2-[(1-Benzyl-1H-benzo[d]imidazol-2-yl)methyl]-N-p-
tolylhydrazinecarbothioamide (4e)
Yield: 65 %; m.p. 215 °C; IR (KBr) t cm-1: 3321 (NHstr.),
3173 (NHstr.), 3054 (NHstr.-thioamide), 2974 (Ar–CHstr.),
2965 (CHstr.), 1627 (C=N, cyclic), 1538 (C=Sstr.); 1H NMR
(CDCl3) d (ppm): 2.44(s, 3H, CH3), 3.48 (s, 2H, CH2), 4.04
(s, 2H, CH2–Ar), 7.06–7.84 (m, 9H, Ar–H), 7.14–7.47 (m,
4H, Bz–H), 8.45 (s, 1H, NH, D2O exchangeable), 9.04 (s, 1H,
NH, D2O exchangeable), 10.14 (s, 1H, NH–Ar, D2O
exchangeable); 13C NMR (DMSO-d6) d (ppm): 18.25, 40.23,
43.18, 113.41, 118.92, 120.62, 121.16, 124.68, 125.15,
1
(OCH3); H NMR (CDCl3) d (ppm): 3.26 (s, 2H, CH2),
3.58 (s, 3H, OCH3), 4.15 (s, 2H, CH2–Ar), 6.14–8.56
(m,9H, Ar–H), 7.05–8.12 (m, 4H, Bz–H), 8.17 (s, 1H, NH,
D2O exchangeable), 9.06 (s, 1H, NH, D2O exchangeable),
11.31 (s, 1H, NH–Ar, D2O exchangeable); 13C NMR
(DMSO-d6) d (ppm): 40.34, 45.24, 53.26, 114.26, 118.26,
120.23, 121.24, 123.34, 125.36, 126.45, 127.56, 127.68,
127.48, 128.23, 129.42, 129.62, 132.54, 133.35, 139.24,
140.24, 146.36, 149.85, 164.43.
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