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Table 2 Spectral data of synthesized benzimidazole derivatives

From: Design, synthesis and biological profile of heterocyclic benzimidazole analogues as prospective antimicrobial and antiproliferative agents

Comp. IR (ATR cm−1) 13C-NMR (DMSO-d6, δ ppm) 1H-NMR (DMSO-d6, δ ppm) C, H, N analyses calculated (found); MS ES + (ToF): m/z—[M++1]
Z1 {3074 (C–H str.), 1461 (C=C str.) of phenyl nucleus (pn)}, 1337 (C=N str.), 1258 (C–N str.), 706 (C–S str.), 2840 (C–H str., –CH2–), 1512 (C–NO2 str.), 1698 (C=O str.) 109.33, 119.56, 122.12, 123.10, 128.46, 132.16, 134.99, 149.64, 168.06 7.03–8.66 (m, 7H, Ar–H), 7.03 (s, 1H, NH of imidazole), 3.51 (s, 2H, CH2), 2.01 (s, 1H, NH) C, 48.26; H, 2.97; N, 18.76; (C, 48.22; H, 2.93; N, 18.72); 374
Z2 {3076 (C–H str.), 1459 (C=C str.) pn}, 1347 (C=N str.), 1254 (C–N str.), 695 (C–S str.), 2916 (C–H str., –CH2–), 1508 (C–NO2 str.), 1705 (C=O str.) 30.61, 109.41, 115.41, 119.11, 122.23, 125.31, 130.29, 132.20, 135.60, 146.12, 168.10, 206.31 6.62–7.99 (m, 8H, Ar–H), 6.62 (s, 1H, NH of imidazole), 3.49 (s, 2H, CH2), 2.10 (s, 1H, NH) C, 54.87; H, 3.68; N, 17.06; (C, 54.83; H, 3.64; N, 17.02); 329
Z3 {3070 (C–H str.), 1457 (C=C str.) pn}, 1351 (C=N str.), 1334 (C–N str.), 696 (C–S str.), 2835 (C–H str., –CH2–), 1507 (C–NO2 str.), 1716 (C=O str.) 30.59, 107.01, 109.41, 109.75, 119.90, 122.23, 129.82, 132.20, 148.69, 150.01 168.10 6.99–7.44 (m, 8H, Ar–H), 6.99 (s, 1H, NH of imidazole), 3.49 (s, 2H, CH2), 2.10 (s, 1H, NH) C, 54.87; H, 3.68; N, 17.06; (C, 54.91; H, 3.72; N, 17.10); 329
Z4 {3078 (C–H str.), 1461 (C=C str.) pn}, 1351 (C=N str.), 1333 (C–N str.), 698 (C–S str.), 2915 (C–H str., –CH2–), 654 (C–Br str.), 1719 (C=O str.) 109.40, 119.56, 122.22, 128.46, 132.16, 149.64, 168.06 6.82–7.11 (m, 8H, Ar–H), 6.82 (s, 1H, NH of imidazole), 3.63 (s, 2H, CH2), 1.05 (s, 1H, NH) C, 49.73; H, 3.34; N, 11.60; (C, 49.77; H, 3.38; N, 11.64); 363
Z5 {3092 (C–H str.), 1462 (C=C str.) pn}, 1353 (C=N str.), 1335 (C–N str.), 701 (C–S str.), 2850 (C–H str., –CH2–), 656 (C–Br str.), 1714 (C=O str.) 109.40, 119.32, 122.22, 128.34, 132.18, 134.99, 149.64, 168.06 6.65–7.25 (m, 8H, Ar–H), 6.65 (s, 1H, NH of imidazole), 3.77 (s, 2H, CH2), 2.12 (s, 1H, NH) C, 49.73; H, 3.34; N, 11.60; (C, 49.77; H, 3.38; N, 11.64); 363
Z6 {3083 (C–H str.), 1602 (C=C str.) pn}, 1356 (C=N str.), 1340 (C–N str.), 704 (C–S str.), 2850 (C–H str., –CH2–), 763 (C–Cl str.), 1503 (C–NO2 str.), 1716 (C=O str.) 109.37, 118.37, 121.02, 122.15, 123.94, 132.20, 135.41, 144.95, 168.10 7.06–7.22 (m, 8H, Ar–H), 7.06 (s, 1H, NH of imidazole), 3.51 (s, 2H, CH2), 2.12 (s, 1H, NH) C, 49.66; H, 3.06; N, 15.44; (C, 49.70; H, 3.10; N, 15.48); 363
Z7 {3071 (C–H str.), 1454 (C=C str.) pn}, 1352 (C=N str.), 1334 (C–N str.), 691 (C–S str.), 2924 (C–H str., –CH2–), 739 (C–Cl str.), 1715 (C=O str.) 109.41, 119.65, 122.23, 128.56, 132.19, 134.99, 149.46, 168.09 7.16–7.22 (m, 8H, Ar–H), 7.16 (s, 1H, NH of imidazole), 3.61 (s, 2H, CH2), 2.12 (s, 1H, NH) C, 56.69; H, 3.81; N, 13.22; (C, 56.65; H, 3.85; N, 13.18); 318
Z8 {3082 (C–H str.), 1459 (C=C str.) pn}, 1352 (C=N str.), 1334 (C–N str.), 695 (C–S str.), 2842 (C–H str., –CH2–), 738 (C–Cl str.), 1714 (C=O str) 109.40, 119.85, 122.21, 128.56, 132.18, 134.79, 149.46, 168.08 7.03–7.70 (m, 8H, Ar–H), 7.03 (s, 1H, NH of imidazole), 3.68 (s, 2H, CH2), 1.04 (s, 1H, NH) C, 56.69; H, 3.81; N, 13.22; (C, 56.65; H, 3.77; N, 13.126); 318
Z9 {3091 (C–H str.), 1454 (C=C str.) pn}, 1352 (C=N str., N=CH), 1334 (C–N str.), 691 (C–S str., CH2–S), 2844 (C–H str., –CH2–), 2948 (C–H str., CH3), 1714 (C=O str., ketone) 30.59, 109.41, 119.56, 122.23, 128.41, 132.19, 134.52, 149.27, 168.10, 206.30 7.15–7.22 (m, 7H, Ar–H), 7.15 (s, 1H, NH of imidazole), 3.63 (s, 6H, (CH3)2), 2.11 (s, 1H, NH) C, 65.57; H, 5.50; N, 13.49; (C, 65.53; H, 5.54; N, 13.45); 312
Z10 {3099 (C–H str.), 1623 (C=C str.) pn}, 1317 (C=N str.), 1305 (C–N str.), 704 (C–S str.), 2918 (C–H str., –CH2–), 744 (C–Cl str.), 1484 (C–NO2 str.), 1715 (C=O str.) 109.39, 113.46, 115.53, 122.18, 124.47, 125.51, 132.20, 135.92, 151.91, 168.10 6.91–7.99 (m, 7H, Ar–H), 6.91 (s, 1H, NH of imidazole), 3.59 (s, 2H, CH2), 2.12 (s, 1H, NH) C, 49.66; H, 3.06; N, 15.44; (C, 49.62; H, 3.02; N, 15.40); 363
Z11 {3070 (C–H str.), 1454 (C=C str.) pn}, 1352 (C=N str.), 1335 (C–N str.), 693 (C–S str.), 2835 (C–H str., –CH2–), 1012 (C–F str.), 1716 (C=O str.) 30.60, 109.41, 115.21, 122.24, 132.19, 145.42, 150.32, 168.10; 7.14–7.20 (m, 8H, Ar–H), 7.14 (s, 1H, NH of imidazole), 3.53 (s, 2H, CH2), 2.10 (s, 1H, NH); C, 59.79; H, 4.01; N, 13.94; (C, 59.75; H, 4.05; N, 13.90); 302
Z12 {3068 (C–H str.), 1454 (C=C str.) pn}, 1351 (C=N str.), 1332 (C–N str.), 691 (C–S str.), 2933 (C–H str., –CH2–), 1007 (C–F str.), 1714 (C=O str.) 109.40, 112.47, 122.23, 125.27, 132.19, 137.90, 146.32, 168.09 7.10–7.24 (m, 8H, Ar–H), 7.10 (s, 1H, NH of imidazole), 3.69 (s, 2H, CH2), 2.11 (s, 1H, NH) C, 59.79; H, 4.01; N, 13.94; (C, 59.83; H, 4.04; N, 13.98); 302
Z13 {3073 (C–H str.), 1455 (C=C str.) pn}, 1351 (C=N str.), 1333 (C–N str.), 693 (C–S str.), 2844 (C–H str., –CH2–), 2870 (C–H str., CH3), 1713 (C=O str.) 30.62, 109.41, 114.34, 122.24, 125.86, 127.89, 132.20, 144.56, 149.64, 168.10 7.13–7.19 (m, 8H, Ar–H), 7.13 (s, 1H, NH of imidazole), 3.47 (s, 3H, CH3), 2.10 (s, 1H, NH) C, 64.62; H, 5.08; N, 14.13; (C, 64.66; H, 5.04; N, 14.10); 298
Z14 {3069 (C–H str.), 1454 (C=C str.) pn}, 1352 (C=N str.), 1335 (C–N str.), 691 (C–S str.), 2914 (C–H str., –CH2–), 2850 (C–H str., N–CH3), 1714 (C=O str.) 30.96, 109.42, 114.37, 122.25, 128.79, 132.21, 145.64, 168.11 7.14–7.20 (m, 9H, Ar–H), 7.14 (s, 1H, NH of imidazole), 3.51 (q, 2H, –CH2), 2.10 (t, 3H, CH3) C, 65.57; H, 5.50; N, 13.49; (C, 65.53; H, 5.54; N, 13.45); 312
Z15 {3079 (C–H str.), 1458 (C=C str.) pn}, 1344 (C=N str.), 1327 (C–N str.), 693 (C–S str.), 2844 (C–H str., –CH2–), 2857 (C–H str., N–CH3), 1706 (C=O str.) 30.59, 109.41, 114.33, 122.23, 127.89, 132.19, 139.27, 144.75, 168.10 7.08–7.22 (m, 9H, Ar–H), 7.08 (s, 1H, NH of imidazole), 3.61 (s, 31H, CH2), 2.11 (s, 3H, CH3) C, 64.62; H, 5.08; N, 14.13; (C, 64.58; H, 5.12; N, 14.17); 298
Z16 {3105 (C–H str.), 1455 (C=C str.) pn}, 1701 (–CO str.), 1386 (C=N str.), 1343 (C–N str.), 1165 (N–N str., hydrazide), 694 (C–S str.), 2915 (C–H str., –CH2–), 1510 (C–NO2 str.) 109.41, 114.33, 119.17, 122.23, 126.32, 132.19, 137.42, 144.27, 168.09 7.04–7.35 (m, 8H, Ar–H), 7.04 (s, 1H, NH of imidazole), 2.11 (s, 1H, NH), 12.62 (s, 1H, N=CH) C, 54.08; H, 3.69; N, 19.71; (C, 54.04; H, 3.65; N, 19.75); 356
Z17 {3112 (C–H str.), 1600 (C=C str.) pn}, 1701 (–CO str.), 1355 (C=N str.), 1337 (C–N str.), 1178 (N–N str., hydrazide), 702 (C–S str.), 2844 (C–H str., –CH2–), 1512 (C–NO2 str.) 109.39, 122.21, 130.92, 132.18, 139.87, 141.50, 145.71, 150.72, 168.08 7.18–8.26 (m, 8H, Ar–H), 6.84 (s, 1H, NH of imidazole), 3.55 (s, 2H, CH2), 2.12 (s, 1H, NH), 12.66 (s, 1H, N=CH) C, 54.08; H, 3.69; N, 19.71; (C, 54.03; H, 3.73; N, 19.67); 356
Z18 {3106 (C–H str.), 1604 (C=C str.) pn}, 1703 (–CO str.), 1337 (C=N str.), 1270 (C–N str.), 1174 (N–N str., hydrazide), 697 (C–S str.), 2843 (C–H str., –CH2–), 1509 (C–NO2 str.) 61.89, 111.30, 122.91, 123.16, 130.29, 132.18, 139.78, 146.17, 146.54, 150.27, 191.68 7.23–8.38 (m, 8H, Ar–H), 5.61 (s, 1H, NH of imidazole), 3.57 (s, 2H, CH2), 2.12 (s, 1H, NH), 12.63 (s, 1H, N=CH) C, 54.08; H, 3.69; N, 19.71; (C, 54.12; H, 3.64; N, 19.68); 356
Z19 {3081 (C–H str.), 1449 (C=C str.) pn}, 1716 (–CO str.), 1351 (C=N str.), 1331 (C–N str.), 1163 (N–N str., hydrazide), 689 (C–S str.), 2924 (C–H str., –CH2–), 3648 (O–H str.), 2839 (C–H str., –OCH3), 1256 (C–O–C str., phenyl ether) 30.60, 109.41, 111.19, 122.23, 127.89, 130.92, 132.19, 138.79, 145.92, 168.09 7.15–7.21 (m, 7H, Ar–H), 7.15 (s, 1H, NH of imidazole), 3.58 (s, 2H, CH2), 2.11 (s, 1H, NH), 12.60 (s, 1H, N=CH) C, 57.29; H, 4.52; N, 15.72; (C, 57.25; H, 4.56; N, 15.76); 357
Z20 {3085 (C–H str.), 1454 (C=C str.) pn}, 1714 (–CO str.), 1352 (C=N str.), 1334 (C–N str.), 1166 (N–N str., hydrazide), 688 (C–S str.), 2852 (C–H str., –CH2–), 3645 (O–H str.), 2822 (C–H str., –OCH3), 1255 (C–O–C str., phenyl ether), 2901 (C–H str., CH3) 30.59, 109.41, 122.23, 125.21, 132.19, 130.18, 137.13, 144.65, 168.09 7.03–7.86 (m, 7H, Ar–H), 7.03 (s, 1H, NH of imidazole), 3.63 (s, 1H, OH), 2.11 (s, 1H, NH), 1.21 (t, 3H, CH3), 12.61 (s, 1H, N=CH) C, 58.36; H, 4.90; N, 15.12; (C, 58.40; H, 4.94; N, 15.16); 371
Z21 {3109 (C–H str.), 1466 (C=C str.) pn}, phenyl nucleus), 1732 (–CO str.), 1356 (C=N str.), 1338 (C–N str.), 1178 (N–N str., hydrazide), 703 (C–S str.), 2842 (C–H str., –CH2–), 658 (C–Br str.) 30.59, 109.41, 122.23, 128.61, 131.05, 132.13, 132.19, 134.95, 192.01 7.17–7.22 (m, 8H, Ar–H), 7.17 (s, 1H, NH of imidazole), 3.66 (s, 2H, CH2), 2.11 (s, 1H, NH), 12.62 (s, 1H, N=CH) C, 49.37; H, 3.37; N, 14.39; (C, 49.33; H, 3.33; N, 14.35); 390
Z22 {3091 (C–H str.), 1603 (C=C str.) pn}, 1703 (–CO str.), 1346 (C=N str.), 1294 (C–N str.), 1168 (N–N str., hydrazide), 690 (C–S str.), 2841 (C–H str., –CH2–), 3648 (O–H str.) 109.40, 122.22, 129.51, 131.03, 134.59, 146.32, 149.66, 168.08 7.18–7.24 (m, 8H, Ar–H), 7.18 (s, 1H, NH of imidazole), 3.74 (s, 1H, OH), 2.11 (s, 1H, NH), 12.64 (s, 1H, N=CH) C, 58.88; H, 4.32; N, 17.17; (C, 58.84; H, 4.36; N, 17.13); 327
Z23 {3075 (C–H str.), 1452 (C=C str.) pn}, 1730 (–CO str.), 1380 (C=N str.), 1345 (C–N str.), 1170 (N–N str., hydrazide), 695 (C–S str.), 2876 (C–H str., –CH2–), 2835 (C–H str., –OCH3), 1253 (C–O–C str., phenyl ether) 109.40, 119.38, 122.22, 123.45, 128.67, 131.55, 132.18, 147.82, 168.08 7.18–7.24 (m, 7H, Ar–H), 7.18 (s, 1H, NH of imidazole), 375 (s, 6H, (OCH3)2), 2.12 (s, 1H, NH), 12.64 (s, 1H, N=CH) C, 58.36; H, 4.90; N, 15.12; (C, 58.40; H, 4.94; N, 15.16); 371
Z24 {3087 (C–H str.), 1601 (C=C str.) pn}, 1713 (–CO str.), 1354 (C=N str.), 1337 (C–N str.), 1176 (N–N str., hydrazide), 694 (C–S str.), 2843 (C–H str., –CH2–), 684 (C–Br str.), 1623 (conjugated C=C and phenyl subst. C=C) 109.42, 122.21, 123.89, 128.66, 128.90, 130.55, 131.36, 132.23, 132.82, 150.14, 187.80 7.13–7.94 (m, 9H, Ar–H), 7.06 (s, 1H, NH of imidazole), 2.00 (s, 2H, CH2), 7.06 (s, 1H, NH), 12.55 (s, 1H, N=CH), 7.19 (s, 1H, Br–C=CH) C, 52.06; H, 3.64; N, 13.49; (C, 52.02; H, 3.68; N, 13.45); 416
Z25 {3070 (C–H str.), 1453 (C=C str.) pn}, 1712 (–CO str.), 1352 (C=N str.), 1334 (C–N str.), 1167 (N–N str., hydrazide), 688 (C–S str.), 2846 (C–H str., –CH2–), 1728 (C–H str., CHO) 78.04, 111.42, 122.92, 129.61, 129.94, 135.88, 139.55, 145.74, 192.70 7.25–7.98 (m, 8H, Ar–H), 7.03 (s, 1H, NH of imidazole), 3.61 (s, 2H, CH2), 2.11 (s, 1H, NH), 12.60 (s, 1H, N=CH), 10.04 (s, 1H, CHO) C, 60.34; H, 4.17; N, 16.56; (C, 60.38; H, 4.13; N, 16.52); 384
Z26 {3105 (C–H str.), 1453 (C=C str.) pn}, 1713 (–CO str.), 1352 (C=N str.), 1332 (C–N str.), 1163 (N–N str., hydrazide), 686 (C–S str.), 2927 (C–H str., –CH2–), 2843 (C–H str., N–CH3) 30.55, 39.49, 109.40, 110.89, 122.24, 124.45, 132.22, 154.02, 189.66 7.17–7.86 (m, 8H, Ar–H), 7.11 (s, 1H, NH of imidazole), 3.78 (s, 2H, CH2), 2.12 (s, 1H, NH), 12.65 (s, 1H, N=CH), 2.64 (s, 6H, (CH3)2) C, 61.17; H, 5.42; N, 19.81; (C, 61.13; H, 5.46; N, 19.85); 354
Z27 {3092 (C–H str.), 1596 (C=C str.) pn}, 1710 (–CO str.), 1354 (C=N str.), 1336 (C–N str.), 1175 (N–N str., hydrazide), 700 (C–S str.), 2930 (C–H str., –CH2–), 739 (C–Cl str.) 61.91, 109.39, 122.20, 127.94, 130.66, 132.18, 133.65, 135.28, 137.04, 139.60, 188.40 6.74–7.72 (m, 7H, Ar–H), 6.74 (s, 1H, NH of imidazole), 3.02 (s, 2H, CH2), 2.11 (s, 1H, NH), 12.62 (s, 1H, N=CH) C, 50.67; H, 3.19; N, 14.77; (C, 50.63; H, 3.15; N, 14.73); 380
Z28 {3111 (C–H str.), 1598 (C=C str.) pn}, 1703 (–CO str.), 1355 (C=N str.), 1337 (C–N str.), 1177 (N–N str., hydrazide), 701 (C–S str.), 2845 (C–H str., –CH2–), 740 (C–Cl str.) 30.58, 109.41, 119.56, 122.23, 124.54, 131.23, 132.18, 147.12, 168.08 7.16–7.28 (m, 8H, Ar–H), 7.16 (s, 1H, NH of imidazole), 3.65 (s, 2H, CH2), 2.11 (s, 1H, NH), 12.62 (s, 1H, N=CH) C, 55.73; H, 3.80; N, 16.25; (C, 55.77; H, 3.84; N, 16.29); 345
Z29 {3110 (C–H str.), 1598 (C=C str.) pn}, 1712 (–CO str.), 1355 (C=N str.), 1337 (C–N str.), 1176 (N–N str., hydrazide), 700 (C–S str.), 2860 (C–H str., –CH2–), 1616 (phenyl conjugation) 109.40, 122.21, 128.72, 132.17, 134.54, 139.42, 141.72, 147.21, 168.07 7.18–7.27 (m, 9H, Ar–H), 7.18 (s, 1H, NH of imidazole), 3.82 (s, 2H, CH2), 2.12 (s, 1H, NH), 12.66 (s, 1H, N=CH) C, 64.26; H, 4.79; N, 16.65; (C, 64.22; H, 4.75; N, 16.69); 337
Z30 {3103 (C–H str.), 1599 (C=C str.) pn}, 1713 (–CO str.), 1352 (C=N str.), 1335 (C–N str.), 1168 (N–N str., hydrazide), 691 (C–S str., CH2–S), 2841 (C–H str., –CH2–), 2818 (C–H str., –OCH3), 1255 (C–O–C str., phenyl ether) 109.41, 115.26, 122.23, 124.30, 132.19, 141.50, 145.71, 168.09, 205.61 7.15–7.25 (m, 8H, Ar–H), 7.15 (s, 1H, NH of imidazole), 3.70 (s, 2H, CH2), 2.10 (s, 1H, NH), 12.60 (s, 1H, N=CH), 3.59 (s, 1H, OH) C, 59.98; H, 4.74; N, 16.46; (C, 59.94; H, 4.98; N, 16.42); 341