L.-X. Liu et al. / European Journal of Medicinal Chemistry 66 (2013) 423e437
433
4.1. 5. 5. 1-(1-(Dibenzo[b, d]furan-2-yl)ethyl)-3-(2-(4-
1522, 1438, 1343, 1196, 1105, 1030, 960, 816, 768, 671. 1H NMR
(DMSO): 8.39 (1H, s), 8.23e8.19 (4H, m), 7.79 (1H, s), 7.71e7.54
(6H, m), 7.42 (1H, s), 6.09e6.07 (1H, m), 5.67 (2H, s), 2.76 (3H, s),
1.99 (3H, s). 13C NMR (DMSO):
155.9, 155.1, 147.3, 144.5, 141.7,
methoxyphenyl)-2-oxoethyl)-1H-imidazol-3-ium
bromide
(16).
d
Yield 70%, white powder, mp 213e214 ꢂC. IR nmax (cmꢃ1): 3416,
3039, 2837, 1689, 1600, 1438, 1321, 1245, 1172, 1026, 828, 751, 630.
d
1H NMR (DMSO):
d
9.48 (1H, s), 8.43 (1H, s), 8.19 (1H, d, J ¼ 7.5), 8.11
134.0, 129.2, 128.0, 126.5, 123.9, 123.2, 122.4, 121.4, 119.9, 119.4,
(1H, s), 8.03 (2H, d, J ¼ 8.7), 7.82e7.80 (2H, m), 7.77e7.65 (2H, m),
7.54 (1H, t, J ¼ 8.1), 7.45 (1H, t, J ¼ 7.5), 7.14 (2H, d, J ¼ 8.7), 6.16e6.14
(1H, m), 6.06 (2H, s), 3.86 (3H, s), 2.04 (3H, d, J ¼ 6.9). 13C NMR
112.0, 111.7, 57.0, 49.9, 21.0, 10.3. HRMS (ESI-TOF) m/z Calcd for
C
25H22N3O3 [M ꢃ Br]þ 412.1656, found 412.1669.
(DMSO):
d
189.5, 164.1, 155.9, 155.3, 136.7, 134.2, 130.6, 128.1, 126.6,
4.1.5.11. 1-(1-(Dibenzo[b,d]furan-2-yl)ethyl)-3-(2-oxo-2-
phenylethyl)-2-methyl-1H-imidazol-3-ium bromide (22). Yield 70%,
white powder, mp 246e247 ꢂC. IR nmax (cmꢃ1): 3420, 3125, 3013,
2925, 2353, 1696, 1604, 1561, 1481, 1441, 1345, 1204, 1131, 1069, 990,
126.4, 124.5, 124.1, 123.3, 123.2, 121.3, 120.8, 119.9, 114.3, 112.2, 111.8,
58.7, 55.7, 55.2, 20.9. HRMS (ESI-TOF) m/z Calcd for C26H23N2O3
[M ꢃ Br]þ 411.1703, found 411.1698.
831, 754, 687. 1H NMR (MeOD):
d 8.13e8.09 (4H, m), 7.92 (1H, s),
4.1.5.6. 1-(1-(Dibenzo[b,d]furan-2-yl)ethyl)-3-(2-(4-bromophenyl)-
2-oxoethyl)-1H-imidazol-3-ium bromide (17). Yield 70%, white
powder, mp 239e241 ꢂC. IR nmax (cmꢃ1): 3397, 3125, 3041, 2962,
1701, 1580, 1482, 1441, 1395, 1198, 1161, 991, 818, 754, 625. 1H NMR
7.72e7.59 (6H, m), 7.56e7.50 (2H, m), 7.40 (1H, t, J ¼ 7.2), 6.11e6.07
(1H, m), 6.06 (2H, m), 2.61 (3H, s), 2.09 (3H, d, J ¼ 6.9). 13C NMR
(MeOD):
d 191.9, 158.1, 157.4, 147.3, 135.8, 135.1, 130.2, 129.6, 129.1,
126.9, 126.3, 124.9, 124.4, 122.2, 120.1, 120.1, 113.4, 112.7, 59.5, 55.9,
21.8, 10.6. HRMS (ESI-TOF) m/z Calcd for C26H23N2O2 [M ꢃ Br]þ
395.1754, found 395.1758.
(DMSO):
d
9.37 (1H, s), 8.39 (1H, s), 8.17 (1H, d, J ¼ 6.0), 8.08 (1H, s),
7.97 (2H, d, J ¼ 9.0), 7.86e7.76 (4H, m), 7.73 (1H, d, J ¼ 8.1), 7.65 (1H,
d, J ¼ 8.1), 7.56 (1H, t, J ¼ 6.9), 7.44 (1H, t, J ¼ 6.9), 6.14e6.12 (1H, m),
6.05 (2H, s), 2.04 (3H, d, J ¼ 6.0). 13C NMR (DMSO):
d
190.7, 155.9,
4.1.5.12. 1-(1-(Dibenzo[b,d]furan-2-yl)ethyl)-3-(2-(4-
hydroxyphenyl)-2-oxoethyl)-2-methyl-1H-imidazol-3-ium bromide
(23). Yield 70%, white powder, mp 252e253 ꢂC. IR nmax (cmꢃ1):
3129, 2930, 2582, 2430, 1680, 1590, 1510, 1442, 1351, 1223, 1170,
155.3, 136.7, 134.1, 132.6, 132.2, 130.0, 128.6, 128.1, 126.6, 124.5,
124.1, 123.4, 123.1, 121.3, 120.8, 119.8, 112.2, 111.8, 58.7, 55.5, 20.8.
HRMS (ESI-TOF) m/z Calcd for C25H20BrN2O2 [M ꢃ Br]þ 459.0708,
found 459.0678.
1112, 1040, 990, 838, 748, 677. 1H NMR (DMSO):
d 10.68 (1H, s), 8.39
(1H, s), 8.20 (1H, d, J ¼ 7.5), 8.14 (1H, s), 7.94 (2H, d, J ¼ 8.7), 7.79 (2H,
s), 7.76e7.70 (1H, m), 7.62e7.52 (2H, m), 7.43 (1H, t, J ¼ 7.5), 6.98
(2H, d, J ¼ 8.7), 6.17e6.14 (1H, m), 6.06 (2H, s), 2.65 (3H, s), 2.01 (3H,
4.1.5.7. 1-(1-(Dibenzo[b,d]furan-2-yl)ethyl)-3-(2-(4-fluorophenyl)-2-
oxoethyl)-1H-imidazol-3-ium bromide (18). Yield 70%, white pow-
der, mp 209e210 ꢂC. IR nmax (cmꢃ1): 3419, 3116, 3049, 2966, 1695,
1598, 1485, 1441, 1333, 1235, 1195, 1157, 995, 836, 756, 631. 1H NMR
d, J ¼ 6.6). 13C NMR (DMSO):
d 188.9, 163.3, 155.9, 155.1, 145.3, 134.1,
131.1, 128.0, 126.2, 125.1, 124.1, 123.2, 121.4, 119.7, 118.6, 115.6, 112.1,
(DMSO):
d
9.46 (1H, s), 8.43 (1H, s), 8.20e8.12 (4H, m), 7.83e7.78
111.8, 56.9, 54.1, 21.0, 10.0. HRMS (ESI-TOF) m/z Calcd for
C
(2H, m), 7.73 (1H, d, J ¼ 7.8), 7.67 (1H, d, J ¼ 7.8), 7.56 (1H, t, J ¼ 7.5),
26H23N2O3 [M ꢃ Br]þ 411.1703, found 411.1689.
7.50e7.42 (3H, m), 6.18e6.12 (1H, m), 6.12 (2H, s), 2.05 (3H, d,
J ¼ 6.9). 13C NMR (DMSO):
d
190.0, 155.9, 155.3, 136.7, 134.1, 131.3,
4.1.5.13. 1-(1-(Dibenzo[b,d]furan-2-yl)ethyl)-3-(2-(4-
methoxyphenyl)-2-oxoethyl)-2-methyl-1H-imidazol-3-ium bromide
(24). Yield 70%, white powder, mp 231e232 ꢂC. IR nmax (cmꢃ1):
3401, 3051, 2927, 2835, 1686, 1597, 1511, 1433, 1318, 1239, 1175,
131.2,130.4,128.1,126.6,124.5,124.1,123.3,123.2,121.3,120.8,119.9,
116.4, 116.1, 112.2, 111.8, 58.7, 55.5, 20.9. HRMS (ESI-TOF) m/z Calcd
for C25H20FN2O2 [M ꢃ Br]þ 399.1503, found 399.1480.
1030, 821, 745, 590. 1H NMR (MeOD):
d
8.12e8.07 (4H, m), 7.89 (1H,
s), 7.63e7.52 (5H, m), 7.40e7.38 (1H, m), 7.09e7.06 (2H, m), 6.07e
6.00 (1H, m), 5.99 (2H, m), 3.89 (3H, s), 2.59 (3H, s), 2.08 (3H, s). 13
NMR (MeOD): 190.2, 166.4, 158.1, 157.3, 147.3, 135.0, 132.1, 129.1,
4.1.5.8. 1-(1-(Dibenzo[b,d]furan-2-yl)ethyl)-3-(2-(naphthalen-2-yl)-
2-oxoethyl)-1H-imidazol-3-ium bromide (19). Yield 70%, white
powder, mp 261e262 ꢂC. IR nmax (cmꢃ1): 3370, 3122, 3041, 2918,
C
d
1687, 1445, 1360, 1266, 1165, 814, 714, 696. 1H NMR (DMSO):
d
9.44
127.8, 126.9, 126.3, 124.9, 124.4, 122.3, 120.1, 120.0, 115.4, 113.4,
(1H, s), 8.83 (1H, s), 8.41 (1H, s), 8.19 (1H, d, J ¼ 7.5), 8.13e8.11 (2H,
m), 8.07e8.01 (2H, m), 7.85e7.80 (2H, m), 7.75e7.66 (4H, m), 7.60e
7.57 (1H, m), 7.47 (1H, t, J ¼ 7.5), 6.22 (2H, s), 6.17e6.15 (1H, m), 2.06
112.8, 59.4, 56.3, 55.5, 21.8, 10.7. HRMS (ESI-TOF) m/z Calcd for
C
27H25N2O3 [M ꢃ Br]þ 425.1865, found 425.1865.
(3H, d, J ¼ 6.6). 13C NMR (DMSO):
d
191.2, 155.9, 155.2, 136.8, 135.5,
4.1.5.14. 1-(1-(Dibenzo[b,d]furan-2-yl)ethyl)-3-(2-(4-bromophenyl)-
2-oxoethyl)-2-methyl-1H-imidazol-3-ium bromide (25). Yield 70%,
white powder, mp 259e260 ꢂC. IR nmax (cmꢃ1): 3430, 3109, 3044,
2926, 1696, 1631, 1583, 1484, 1441, 1343, 1204, 1069, 989, 815, 755,
134.1, 132.0, 130.9, 130.5, 129.6, 129.3, 128.8, 128.1, 127.8, 127.4,
126.6, 124.6, 124.1, 123.4, 123.1, 121.2, 120.9, 119.9, 112.2, 111.8, 58.8,
55.5, 20.8. HRMS (ESI-TOF) m/z Calcd for C29H23N2O2 [M ꢃ Br]þ
431.1754, found 431.1736.
628. 1H NMR (DMSO):
d
8.18 (1H, s), 8.20 (1H, d, J ¼ 6.0), 8.14 (1H, s),
7.85 (2H, d, J ¼ 8.4), 7.78 (2H, d, J ¼ 8.7), 7.74e7.71 (3H, m), 7.62e
4.1.5.9. 1-(1-(Dibenzo[b,d]furan-2-yl)ethyl)-3-butyl-2-methyl-1H-
imidazol-3-ium iodide (20). Yield 70%, yellow oil. IR nmax (cmꢃ1):
3420, 3059, 2959, 2871,1582,1444,1376,1247,1197,1123, 1037, 882,
7.53 (2H, m), 7.44 (1H, t, J ¼ 7.5), 6.16e6.13 (3H, m), 2.68 (3H, s), 2.02
(3H, d, J ¼ 6.6). 13C NMR (DMSO):
d 190.5, 155.9, 155.1, 145.4, 134.1,
132.7, 132.0,130.3,128.6,128.1,126.3,124.1,123.3,123.2,121.4,119.7,
832, 747, 675. 1H NMR (CDCl3):
d
8.03e7.98 (2H, m), 7.56 (2H, s),
118.7, 112.2, 111.8, 57.0, 54.5, 21.0, 9.9. HRMS (ESI-TOF) m/z Calcd for
7.43e7.41 (2H, m), 7.36 (2H, s), 7.23e7.21 (1H, m), 6.11e6.08 (1H, m),
4.09 (2H, t, J ¼ 7.5), 2.72 (3H, s), 1.92 (3H, d, J ¼ 6.0), 1.69e1.66 (2H,
C
26H22BrN2O2 [M ꢃ Br]þ 473.0865, found 473.0843.
m), 1.26e1.12 (2H, m), 0.80 (3H, t, J ¼ 7.5). 13C NMR (CDCl3):
d
156.5,
4.1.5.15. 1-(1-(Dibenzo[b,d]furan-2-yl)ethyl)-3-(2-(4-fluorophenyl)-
2-oxoethyl)-2-methyl-1H-imidazol-3-ium bromide (26). Yield 70%,
white powder, mp 240e242 ꢂC. IR nmax (cmꢃ1): 3416, 3052, 2920,
1693, 1595, 1505, 1428, 1342, 1279, 1231, 1196, 1156, 990, 839, 758,
155.8,143.3,132.8,127.8, 125.6, 125.1,123.4,123.1, 121.9, 121.5, 119.5,
119.2, 112.4, 111.6, 58.4, 48.8, 31.6, 22.3, 19.5, 13.5, 12.3. HRMS (ESI-
TOF) m/z Calcd for C22H25N2O [M ꢃ I]þ 333.1961, found 333.1969.
681. 1H NMR (DMSO):
d 8.37 (1H, s), 8.21e8.13 (4H, m), 7.80e7.72
4.1.5.10. 1-(1-(Dibenzo[b,d]furan-2-yl)ethyl)-3-(4-nitrobenzyl)-2-
methyl-1H-imidazol-3-ium bromide (21). Yield 70%, white powder,
mp 244e245 ꢂC. IR nmax (cmꢃ1): 3415, 3159, 3060, 2982, 2925,1598,
(3H, m), 7.63e7.42 (5H, m), 6.15e6.13 (3H, m), 2.68 (3H, s), 2.02 (3H,
d 189.8, 155.9, 155.1, 145.4, 134.1, 131.6,
131.4, 130.5, 128.1, 126.3, 124.1, 123.3, 123.2, 121.3, 119.7, 118.7, 112.2,
d, J ¼ 6.6). 13C NMR (DMSO):