126 A. Zubriene_ et al.
J Enzyme Inhib Med Chem, 2014; 29(1): 124–131
(2H, s, CH2CO), 7.14–7.21 (2H, m, C5 ,6 –H), 7.47–7.51 (1H, J ¼ 7.8 Hz, C6–H), 8.41 (1H, s, C2–H). 13C NMR ꢁ ppm: 33.45,
0
0
0
0
m, C7 –H), 7.57–7.60 (1H, m, C4 –H), 7.63 (2H, s, NH2), 7.89 50.76, 111.01, 119.22, 122.14, 122.22, 125.67, 127.18, 129.06,
(1H, t, J ¼ 7.8 Hz, C5–H), 8.20 (1H, d, J ¼ 8.1 Hz, C4–H), 8.44 129.63, 130.43, 131.16, 132.37, 135.63, 136.67, 137.44, 142.98,
(1H, d, J ¼ 7.8 Hz, C6–H), 8.51 (1H, s, C2–H). 13C NMR ꢁ ppm: 145.55, 154.87, 193.01. HRMS Calcd for C22H19N3O3S
14.03, 50.78, 110.62, 118.83, 122.03, 122.21, 125.70, 130.57, ([M þ H]þ): 406.1220, Found: 406.1223.
131.31, 132.51, 135.66, 136.58, 142.96, 145.66, 153.33, 193.59.
4-[(2-Ethyl-1H-benzimidazol-1-yl)acetyl]benzenesulfona-
HRMS Calcd for C16H15N3O3S ([M þ H]þ): 330.0907, Found: mide (1e). Yield 71%, m.p. 236–238 ꢀC. IR (ꢀ, cmꢁ1): 3334
330.0903.
(NH2), 1699 (CO). 1H NMR ꢁ ppm: 1.31 (3H, t, J ¼ 7.5 Hz, CH3),
4-{[2-(Hydroxymethyl)-1H-benzimidazol-1-yl]acetyl}ben- 2.79 (2H, q, J ¼ 7.5 Hz, CH2), 6.07 (2H, s, CH2CO), 7.17–7.20
zenesulfonamide (1c). Yield 57%, m.p. 200–202 ꢀC. IR (2H, m, C5 ,6 –H), 7.47–7.50 (1H, m, C7 –H), 7.61–7.64 (1H, m,
0
0
0
1
(ꢀ, cmꢁ1): 3375, 3314 (NH2, OH), 1702 (CO). H NMR ꢁ ppm: C4 –H), 7.67 (2H, s, NH2), 8.07 (2H, d, J ¼ 8.1 Hz, C2,6–H), 8.33
0
4.70 (2H, s, CH2OH), 5.64 (2H, br s, OH), 6.09 (2H, s, CH2CO), (2H, d, J ¼ 8.1 Hz, C3,5–H). 13C NMR ꢁ ppm: 12.16, 20.50, 50.63,
0
7.20–7.26 (2H, m, C5 ,6 –H), 7.53–7.56 (1H, m, C7 –H), 7.64–7.68 110.70, 118.91, 122.12, 122.37, 126.73, 129.82, 136.49, 137.44,
0
0
0
(3H, m, C4 –H, NH2), 8.06 (2H, d, J ¼ 8.4 Hz, C2,6–H), 8.31 142.62, 149.21, 157.44, 193.89. HRMS Calcd for C17H17N3O3S
(2H, d, J ¼ 8.4 Hz, C3,5–H). 13C NMR ꢁ ppm: 51.04, 57.59, ([M þ H]þ): 344.1063, Found: 344.1062.
111.02, 119.59, 122.31, 123.01, 126.76, 129.72, 137.00, 137.54,
2-Chloro-4-[(2-ethyl-1H-benzimidazol-1-yl)acetyl]benzene-
142.33, 149.04, 154.76, 193.49. HRMS Calcd for sulfonamide (2e). Yield 66%, m.p. 236–238 ꢀC. IR (ꢀ, cmꢁ1):
C16H15N3O4S([M þ H]þ): 346.0856, Found: 346.0859.
3333 (NH2), 1706 (CO). H NMR ꢁ ppm: 1.30 (3H, t, J ¼ 7.5 Hz,
1
2-Chloro-4-{[2-(hydroxymethyl)-1H-benzimidazol-1-yl]ace- CH3), 2.78 (2H, q, J ¼ 7.5 Hz, CH2), 6.09 (2H, s, CH2CO),
tyl}benzenesulfonamide (2c). Yield 52%, m.p. 195–197 ꢀC. IR 7.14–7.21 (2H, m, C5 ,6 –H), 7.47–7.50 (1H, m, C7 –H), 7.60–7.63
0
0
0
1
(ꢀ, cmꢁ1): 3370, 3267 (NH2, OH), 1707 (CO). H NMR ꢁ ppm: (1H, m, C4 –H), 7.93 (2H, s, NH2), 8.17–8.23 (2H, m, C5,6–H),
0
4.69 (2H, d, J ¼ 4.8 Hz, CH2OH), 5.60 (1H, br s, OH), 6.08 (2H, s, 8.38 (1H, s, C3–H). 13C NMR ꢁ ppm: 12.19, 20.46, 50.76,
0
0
0
CH2CO), 7.20–7.25 (2H, m, C5 ,6 –H), 7.50–7.57 (1H, m, C7 –H), 110.76, 118.90, 122.14, 122.36, 127.79, 130.06, 131.71,
0
7.60–7.65 (1H, m, C4 –H), 7.92 (2H, s, NH2), 8.19 (2H, s, C5,6
–
132.10, 136.44, 138.70, 142.59, 145.78, 157.41, 193.16. HRMS
H), 8.33 (1H, s, C3–H). 13C NMR ꢁ ppm: 51.11, 57.54, 110.97, Calcd for C17H16ClN3O3S ([M þ H]þ): 378.0674, Found:
119.66, 122.27, 122.33, 127.74, 130.15, 131.05, 131.81, 137.01, 378.0670.
138.88, 142.50, 145.63, 154.71, 192.80. HRMS Calcd for
3-[(2-Ethyl-1H-benzimidazol-1-yl)acetyl]benzenesulfona-
mide (3e). Yield 66%, m.p. 292–294 ꢀC. IR (ꢀ, cmꢁ1): 3288
C16H14ClN3O4S ([M þ H]þ): 380.0466, Found: 380.0463.
3-{[2-(Hydroxymethyl)-1H-benzimidazol-1-yl]acetyl}ben- (NH2), 1699 (CO). 1H NMR ꢁ ppm: 1.31 (3H, t, J ¼ 7.5 Hz, CH3),
zenesulfonamide (3c). Yield 60%, m.p. 220–222 ꢀC. IR 2.79 (2H, q, J ¼ 7.5 Hz, CH2), 6.09 (2H, s, CH2CO), 7.14–7.21
(ꢀ, cmꢁ1): 3364, 3272 (NH2, OH), 1703 (CO). H NMR ꢁ ppm: (2H, m, C5 ,6 –H), 7.47–7.50 (1H, m, C7 –H), 7.62–7.69 (1H, m,
1
0
0
0
0
4.69 (2H, d, J ¼ 3.3 Hz, CH2OH), 5.63 (1H, br s, OH), 6.12 (2H, s, NH2, C4 –H), 7.89 (1H, t, J ¼ 7.8 Hz, C5–H), 8.20 (1H, d,
0
0
0
CH2CO), 7.21–7.24 (2H, m, C5 ,6 –H), 7.54–7.57 (1H, m, C7 –H), J ¼ 8.1 Hz, C4–H), 8.45 (1H, d, J ¼ 7.8 Hz, C6–H), 8.51 (1H, s,
7.62–7.67 (3H, m, C4 –H, NH2), 7.87 (1H, t, J ¼ 7.8 Hz, C5–H), C2–H). 13C NMR ꢁ ppm: 12.20, 20.53, 50.53, 110.65, 119.01,
0
8.18 (1H, d, J ¼ 7.5 Hz, C4–H), 8.40 (1H, d, J ¼ 7.8 Hz, C6–H), 121.99, 122.27, 125.71, 130.56, 131.31, 132.54, 135.66, 136.60,
8.49 (1H, s, C2–H). 13C NMR ꢁ ppm: 50.98, 57.64, 111.02, 142.92, 145.66, 157.46, 193.72. HRMS Calcd for C17H17N3O3S
119.63, 122.26, 122.97, 125.65, 130.59, 131.16, 132.33, 135.74, ([M þ H]þ): 344.1063, Found: 344.1065.
137.07, 142.45, 145.63, 154.75, 193.20. HRMS Calcd for
4-[(2-Propyl-1H-benzimidazol-1-yl)acetyl]benzenesulfona-
mide (1f). Yield 65%, m.p. 245–247 ꢀC. IR (ꢀ, cmꢁ1): 3300
C16H15N3O4S ([M þ H]þ): 346.0856, Found: 346.0857.
4-[(2-Benzyl-1H-benzimidazol-1-yl)acetyl]benzenesulfo- (NH2), 1700 (CO). 1H NMR ꢁ ppm: 0.97 (3H t, J ¼ 7.5 Hz, CH3),
namide (1d). Yield 62%, m.p. 241–243 ꢀC. IR (ꢀ, cmꢁ1): 3284 1.78 (2H, sextet, J ¼ 7,5 Hz, CH2), 2.75 (2H, t, J ¼ 7.2 Hz, CH2),
1
(NH2), 1703 (CO). H NMR ꢁ ppm: 4.26 (2H, s, CH2Ph), 6.06 6.08 (2H, s, CH2CO), 7.14–7.22 (2H, m, C5 ,6 –H), 7.45–7.48 (1H,
0
0
0
0
0
0
(2H, s, CH2CO), 7.15–7.28 (7H, m, C5 ,6 –H, Ph–H), 7.44–7.47 m, C7 –H), 7.60–7.63 (1H, m, C4 –H), 7.69 (2H, s, NH2), 8.07
(1H, m, C7 –H), 7.62–7.65 (1H, m, C4 –H), 7.68 (2H, s, NH2), (2H, d, J ¼ 8.4 Hz, C2,6–H), 8.33 (2H, d, J ¼ 8.7 Hz, C3,5–H). 13C
8.04 (2H, d, J ¼ 8.4 Hz, C2,6–H), 8.22 (2H, d, J ¼ 8.7 Hz, C3,5–H). NMR ꢁ ppm: 14.47, 20.95, 28.84, 50.66, 110.75, 118.88, 122.12,
13C NMR ꢁ ppm: 33.42, 50.83, 111.03, 119.17, 122.28, 122.59, 122.32, 126.71, 129.85, 136.38, 137.38, 142.66, 149.19, 156.32,
126.63, 127.19, 129.06, 129.60 (2C), 129.70, 136.60, 137.36, 193.85. HRMS Calcdfor C18H19N3O3S([M þ H]þ): 358.1220,
142.80, 149.03, 154.83, 193.15. HRMS Calcd for C22H19N3O3S Found: 358.1222.
0
0
([M þ H]þ): 406.1220, Found: 406.1217.
2-Chloro-4-[(2-propyl-1H-benzimidazol-1-yl)acetyl]benze-
4-[(2-Benzyl-1H-benzimidazol-1-yl)acetyl]-2-chlorobenze- nesulfonamide (2f). Yield 71%, m.p. 240–242 ꢀC. IR (ꢀ, cmꢁ1):
1
nesulfonamide (2d). Yield 71%, m.p. 210–212 ꢀC. IR (ꢀ, cmꢁ1): 3354 (NH2), 1702 (CO). H NMR ꢁ ppm: 0.97 (3H, t, J ¼ 7.5 Hz,
3382, 3294 (NH2), 1705 (CO). 1H NMR ꢁ ppm: 4.27 (2H, s, CH3), 1.78 (2H, sextet, J ¼ 7.5 Hz, CH2), 2.74 (2H, t, J ¼ 7.5 Hz,
0
CH2Ph), 6.07 (2H, s, CH2CO), 7.19–7.26 (7H, m, C5 ,6 –H, Ph– CH2), 6.09 (2H, s, CH2CO), 7.13–7.20 (2H, m, C5 ,6 –H),
0
0
0
0
0
0
0
H), 7.45–7.49 (1H, m, C7 –H), 7.61–7.64 (1H, m, C4 –H), 7.93 7.45–7.48 (1H, m, C7 –H), 7.59–7.62 (1H, m, C4 –H), 7.93 (2H,
(2H, s, NH2), 8.07 (1H, d, J ¼ 8.1 Hz, C5–H), 8.18 (1H, d, s, NH2), 8.20 (2H, s, C5,6–H), 8.39 (1H, s, C3–H). 13C NMR
J ¼ 8.1 Hz, C6–H), 8.25 (1H, s, C3–H). 13C NMR ꢁ ppm: 33.40, ꢁ ppm: 14.49, 21.00, 28.87, 50.78, 110.74, 118.96, 122.05,
50.91, 111.01, 119.21, 122.25, 122.56, 127.15, 127.66, 129.03, 122.24, 127.79, 130.05, 131.71, 132.13, 136.41, 138.69, 142.90,
129.62, 129.98, 131.59, 131.87, 136.61, 137.41, 138.67, 142.91, 145.78, 156.31, 193.14. HRMS Calcd for C18H18ClN3O3S
145.63, 154.77, 192.46. HRMS Calcd for C22H18ClN3O3S ([M þ H]þ): 392.0830, Found: 392.0827.
([M þ H]þ): 440.0830, Found: 440.0836.
3-[(2-Propyl-1H-benzimidazol-1-yl)acetyl]benzenesulfona-
3-[(2-Benzyl-1H-benzimidazol-1-yl)acetyl]benzenesulfona- mide (3f). Yield 87%, m.p. 275–277 ꢀC. IR (ꢀ, cmꢁ1): 3314
mide (3d). Yield 88%, m.p. 146–148 ꢀC. IR (ꢀ, cmꢁ1): 3340 (NH2), 1701 (CO). 1H NMR ꢁ ppm: 0.97 (3H, t, J ¼ 7.5 Hz, CH3),
1
(NH2), 1702 (CO). H NMR ꢁ ppm: 4.27 (2H, s, CH2Ph), 6.08 1.79 (2H, sextet, J ¼ 7.5 Hz, CH2), 2.75 (2H, t, J ¼ 7.5 Hz, CH2),
0
(2H, s, CH2CO), 7.17–7.36 (7H, m, C5 ,6 –H, Ph–H), 7.45–7.52 6.09 (2H, s, CH2CO), 7.13–7.21 (2H, m, C5 ,6 –H), 7.46–7.49 (1H,
0
0
0
0
(1H, m, C7 –H), 7.64–7.69 (1H, m, C4 –H, NH2), 7.85 (1H, t, m, C7 –H), 7.60–7.62 (3H, m, C4 –H, NH2), 7.89 (1H, t,
0
0
0
J ¼ 7.8 Hz, C5–H), 8.18 (1H, d, J ¼ 7.8 Hz, C4–H), 8.34 (1H, d, J ¼ 7.8 Hz, C5–H), 8.20 (1H, d, J ¼ 8.1 Hz, C4–H), 8.45 (1H, d,