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5.1.31. (
L
)-2-(5-Nitrofuran-2-yl)-N-(2-(4-nitrophenyl)pentan-3-
13.23 (s, 1H), 13.51 (s, 1H). Anal. Calcd for C20H16ClN5O3: C,
yl)-1H-benzimidazole-4-carboxamide (35)
Compound 35 was synthesized from (
58.61; H, 3.94; N, 17.09. Found: C, 58.74; H, 3.88; N, 17.15.
L)-2-amino-1-(4-nitro-
phenyl)propane-1,3-diol and compound 11 using general proce-
dure B as a white solid. Yield = 92%. 1H NMR (DMSO, 400 MHz) d:
3.60 (q, J = 5.2 Hz, 1H), 3.66 (q, J = 5.2 Hz, 1H), 4.18 (q, J = 5.2 Hz,
1H), 5.07 (s, 1H), 5.27 (d, J = 2.4 Hz, 1H), 6.16 (d, J = 3.6 Hz, 1H),
7.37 (t, J = 8 Hz, 1H), 7.53 (d, J = 4.4 Hz, 1H), 7.72–7.78 (m, 4H),
8.00 (d, J = 4.4 Hz, 1H), 8.06 (d, J = 9.6 Hz, 3H), 10.05 (d, J = 8.4 Hz,
2H), 14.05 (s, 1H). Anal. Calcd for C21H17N5O8: C, 53.96; H, 3.67;
N, 14.98. Found: C, 54.17; H, 3.56; N, 14.85.
5.1.37. 2-(2,3,4-Trimethoxyphenyl)-N-(2-fluorophenyl)-1H-
benzimidazole-4-carboxamide (41)
Compound 41 was synthesized from 2-fluoroaniline and com-
pound 13 using general procedure B as a slightly yellow solid.
Yield = 75%. 1H NMR (DMSO, 400 MHz) d: 3.85 (s, 3H), 3.91 (s,
3H), 3.99 (s, 3H), 7.09–7.17 (m, 2H), 7.25 (t, J = 7.6 Hz, 1H), 7.36–
7.42 (m, 2H), 7.87 (d, J = 8 Hz, 1H), 7.97 (d, J = 7.6 Hz, 1H), 8.22
(d, J = 8.8 Hz, 1H), 8.66 (t, J = 8 Hz, 1H), 12.58 (s, 1H), 12.59 (s,
1H). Anal. Calcd for C23H20FN3O4: C, 65.55; H, 4.78; N, 9.97. Found:
C, 65.67; H, 4.82; N, 9.85.
5.1.32. (Erythro)-2-(5-nitrofuran-2-yl)-N-(1-amino-2-hydroxy-
2-(4-nitrophenyl)ethyl)-1H-benzimidazole-4-carboxamide (36)
Compound 36 was synthesized from (erythro)-2-amino-1-(4-
nitrophenyl)propan-1-ol and compound 11 using general proce-
dure B as a slightly yellow solid. Yield = 90%. 1H NMR (DMSO,
400 MHz) d: 1.06–1.08 (d, J = 6.4 Hz, 3H), 4.29 (q, J = 4 Hz, 1H),
4.85 (d, J = 3.2 Hz, 1H), 5.73 (d, J = 5.2 Hz, 1H), 7.29 (d, J = 8.4 Hz,
2H), 7.37 (t, J = 8 Hz, 1H), 7.45 (d, J = 8.4 Hz, 2H), 7.52 (d, J = 8 Hz,
1H), 7.72 (d, J = 7.6 Hz, 1H), 7.85 (d, J = 4 Hz, 1H), 7.92 (d, J = 8 Hz,
1H), 9.90 (d, J = 2 Hz, 1H), 13.93 (s, 1H). Anal. Calcd for
5.1.38. (
pentan-3-yl)-1H-benzimidazole-4-carboxamide (42)
Compound 42 was synthesized from ( )-2-amino-1-(4-nitro-
L)-2-(2,3,4-Trimethoxyphenyl)-N-(2-(4-nitrophenyl)-
L
phenyl)propane-1,3-diol and compound 13 using general proce-
dure B as a white solid. Yield = 80%. 1H NMR (DMSO, 400 MHz) d:
3.55 (q, J = 6.8 Hz, 1H), 3.67 (q, J = 7.6 Hz, 1H), 3.85 (s, 3H), 3.90
(s, 3H), 4.00 (s, 3H), 4.23 (q, J = 3.6 Hz, 1H), 5.04 (q, J = 2 Hz, 1H),
5.25 (d, J = 4 Hz, 1H), 6.20 (d, J = 4 Hz, 1H), 6.97 (d, J = 8.4 Hz, 1H),
7.22 (t, J = 8 Hz, 1H), 7.66–7.74 (m, 4H), 8.05 (d, J = 9.2 Hz, 2H),
8.34 (d, J = 8.8 Hz, 1H), 10.50 (d, J = 8.8 Hz, 1H), 12.40 (s, 1H). Anal.
Calcd for C26H26N4O8: C, 59.77; H, 5.02; N, 10.72. Found: C, 59.92;
H, 5.09; N, 10.61.
C21H17ClN4O5: C, 57.22; H, 3.89; N, 12.71. Found: C, 57.44; H,
3.76; N, 12.65.
5.1.33. 2-(3,4-Dimethoxyphenyl)-N-(2-fluorophenyl)-1H-
benzimidazole-4-carboxamide (37)
Compound 37 was synthesized from 2-fluoroaniline and com-
pound 12 using general procedure B as a slightly yellow solid.
Yield = 76%. 1H NMR (DMSO, 400 MHz) d: 3.86 (s, 3H), 3.93 (s,
3H), 7.14 (t, J = 5.2 Hz, 1H), 7.20–7.27 (m, 2H), 7.37–7.41 (m, 2H),
7.78 (d, J = 7.6 Hz, 1H), 7.90 (d, J = 8.4 Hz, 1H), 7.95–7.98 (m, 2H),
8.69 (t, J = 8 Hz, 1H), 12.68 (s, 1H), 13.42 (s, 1H). Anal. Calcd for
5.1.39. 2-(2,3,4-Trimethoxyphenyl)-N-(3-hydroxypropyl)-1H-
benzimidazole-4-carboxamide (43)
Compound 43 was synthesized from 3-aminopropan-1-ol and
compound 13 using general procedure
B as a white solid.
Yield = 80%. 1H NMR (DMSO, 400 MHz) d: 1.76 (q, J = 6.8 Hz, 2H),
3.51 (q, J = 6.4 Hz, 1H), 3.58 (q, J = 5.2 Hz, 1H), 3.83 (s, 3H), 3.89
(s, 3H), 3.94 (s, 3H), 4.58 (t, J = 5.2 Hz, 1H), 7.04 (d, J = 8.8 Hz,
1H), 7.28 (t, J = 8 Hz, 1H), 7.75 (d, J = 8 Hz, 1H), 7.84 (d, J = 6.8 Hz,
1H), 8.04 (d, J = 8.8 Hz, 1H), 10.00 (t, J = 5.6 Hz, 1H), 12.49 (s, 1H).
Anal. Calcd for C20H23N3O5: C, 62.33; H, 6.01; N, 10.90. Found: C,
62.12; H, 6.11; N, 10.85.
C22H18FN3O3: C, 67.51; H, 4.64; N, 10.74. Found: C, 67.40; H,
4.69; N, 10.82.
5.1.34. 2-(3,4-Dimethoxyphenyl)-N-(3-hydroxypropyl)-1H-
benzimidazole-4-carboxamide (38)
Compound 38 was synthesized from 3-aminopropan-1-ol and
compound 12 using general procedure
B
as
a
white solid.
5.1.40. 2-(2,3,4-Trimethoxyphenyl)-N-(pentan-3-yl)-1H-
benzimidazole-4-carboxamide (44)
Yield = 80%. 1H NMR (DMSO, 400 MHz) d: 1.78 (q, J = 6.4 Hz, 2H),
3.53 (q, J = 5.2 Hz, 2H), 3.63 (q, J = 5.2 Hz, 2H), 3.84 (s, 3H), 3.89
(s, 3H), 4.60 (t, J = 6 Hz, 1H), 7.16 (d, J = 8 Hz, 1H), 7.279 (t,
J = 8 Hz, 1H), 7.67 (d, J = 8 Hz, 1H), 7.81–7.83 (m, 3H), 10.02 (t,
J = 5.2 Hz, 1H), 13.22 (s, 1H). Anal. Calcd for C19H21N3O4: C,
64.21; H, 5.96; N, 11.82. Found: C, 64.38; H, 5.84; N, 11.74.
Compound 44 was synthesized from pentan-3-amine and com-
pound 13 using general procedure B as a yellow solid. Yield = 80%.
1H NMR (DMSO, 400 MHz) d: 0.95 (t, J = 8 Hz, 6H), 1.53–1.69 (m,
4H), 3.83 (s, 3H), 3.88 (s, 3H), 3.94–4.00 (m, 4H), 7.08 (d,
J = 8.8 Hz, 1H), 7.29 (t, J = 7.6 Hz, 1H), 7.75 (d, J = 8 Hz, 1H), 7.813
(d, J = 7.6 Hz, 1H), 7.93 (d, J = 8.8 Hz, 1H), 9.88 (d, J = 8.4 Hz, 1H),
12.50 (s, 1H). Anal. Calcd for C22H27N3O4: C, 66.48; H, 6.85; N,
10.57. Found: C, 66.54; H, 6.78; N, 10.68.
5.1.35. 2-(3,4-Dimethoxyphenyl)-N-(pentan-3-yl)-1H-
benzimidazole-4-carboxamide (39)
Compound 39 was synthesized from pentan-3-amine and com-
pound 12 using general procedure B as a yellow solid. Yield = 83%.
1H NMR (DMSO, 400 MHz) d: 0.97 (t, J = 8 Hz, 6H), 1.58–1.66 (m,
4H), 3.84 (s, 3H), 3.86 (s, 3H), 3.96 (q, J = 6 Hz, 1H), 7.18 (d,
J = 9.2 Hz, 1H), 7.30 (t, J = 7.6 Hz, 1H), 7.67 (d, J = 8 Hz, 1H), 7.76–
7.83 (m, 3H), 9.93 (d, J = 8.4 Hz, 1H), 13.24 (s, 1H). Anal. Calcd for
5.1.41. 2-(2,3,4-Trimethoxyphenyl)-N-(5-chloropyrazin-2-yl)-
1H-benzimidazole-4-carboxamide (45)
Compound 45 was synthesized from 5-chloropyrazin-2-amine
and compound 13 using general procedure B as a yellow solid.
Yield = 75%. 1H NMR (DMSO, 400 MHz) d: 3.85 (s, 3H), 3.91 (s,
3H), 3.98 (s, 3H), 7.11 (d, J = 9.2 Hz, 1H), 7.41 (t, J = 8 Hz, 1H),
7.90 (d, J = 8 Hz, 1H), 7.99–8.05 (m, 2H), 8.63 (s, 1H), 9.46 (s, 1H),
12.74 (s, 1H), 12.96 (s, 1H). Anal. Calcd for C21H18ClN5O4: C,
57.34; H, 4.12; N, 15.92. Found: C, 57.16; H, 4.08; N, 16.13.
C21H25N3O3: C, 68.64; H, 6.86; N, 11.44. Found: C, 68.80; H, 6.94;
N, 11.27.
5.1.36. 2-(3,4-Dimethoxyphenyl)-N-(5-chloropyrazin-2-yl)-1H-
benzimidazole-4-carboxamide (40)
Compound 40 was synthesized from 5-chloropyrazin-2-amine
and compound 12 using general procedure B as a yellow solid.
Yield = 75%. 1H NMR (DMSO, 400 MHz) d: 3.86 (s, 3H), 3.93 (s,
3H), 7.21 (d, J = 8 Hz, 1H), 7.41 (t, J = 7.6 Hz, 1H), 7.82–7.87 (m,
2H), 7.92 (s, 1H), 7.99 (d, J = 7.6 Hz, 1H), 8.64 (s, 1H), 9.45 (s, 1H),
5.1.42. 2-(2,3,4-Trimethoxyphenyl)-N-(1H-benzimidazol-2-yl)-
1H-benzimidazole-4-carboxamide (46)
Compound 46 was synthesized from 1H-benzimidazol-2-amine
and compound 13 using general procedure B as a slightly yellow
solid. Yield = 69%. 1H NMR (DMSO, 400 MHz) d: 3.84 (s, 3H), 3.88
(s, 3H), 4.02 (s, 3H), 7.05 (d, J = 9.2 Hz, 1H), 7.31–7.37 (m, 3H),