Med Chem Res
CH2), 3.86 (CH3, s, N–CH3), 4.12 (CH2, t, J = 6.2 Hz, N–
CH2), 4.27 (CH2, t, J = 7.0 Hz, O–CH2), 6.69 (1H, d, J =
3.4 Hz, H-2), 7.03–7.12 (3H, m, H-3, H-11, H-12), 7.54
(2H, s, H-16, H-16), 7.73 (1H, sapparent, H-6), 7.82 (1H,
d, J = 1.4 Hz, H-1), 8.06 (2H, d, J = 8.9 Hz, H-9, H-10),
9.14 (1H, s, H-14). 13C-NMR (DMSO-d6, 75 MHz): δ 25.56
(CH2, CH2–CH2–CH2), 25.73 (CH2, CH2–CH2–CH2),
28.42 (CH2, CH2–CH2–CH2), 28.58 (CH2, CH2–CH2–
CH2), 28.76 (CH2, CH2–CH2–CH2), 29.68 (CH2, CH2–
CH2–CH2), 35.09 (CH3, N–CH3), 49.40 (CH2, N–CH2),
68.03 (CH2, O–CH2), 112.42 (CH, C-16), 114.13 (CH, C-
11, C-12), 116.01 (CH, C-2), 118.51 (CH, C-3), 122.27
(CH, C-6), 123.57 (CH, C-15), 130.01 (CH, C-14), 130.44
(C, C-8), 130.55 (CH, C-9, C-10), 136.46 (CH, C-5),
145.34 (CH, C-1), 151.71 (C, C-4), 163.48 (C, C-13),
188.74 (C=O, C-7). ESI-MS: m/z [M − Br]+ = 407.2335,
calcd for C25H31BrN2O3: 407.2339.
s
apparent, H-5), 7.91 (1H, d, J = 1.4 Hz, H-1), 8.07 (2H, d, J
= 8.9 Hz, H-9, H-10), 9.20 (1H, s, H-10). 13C-NMR
(DMSO-d6, 75 MHz): δ 25.66 (CH2, CH2–CH2–CH2),
26.73 (CH2, CH2–CH2–CH2), 36.24 (CH3, N–CH3), 48.90
(CH2, N–CH2), 67.66 (CH2, O–CH2), 113.55 (CH, C-16),
114.99 (CH, C-11,C-12), 117.11 (CH, C-2), 119.11 (CH, C-
3), 122.72 (CH, C-6), 124.12 (CH, C-15), 130.25 (CH, C-
14), 130.78 (C, C-8), 131.16 (CH, C-9, C-10), 137.06 (CH,
C-5), 146.23 (CH, C-1), 151.67 (C, C-4), 162.89 (C, C-13),
187.01 (C=O, C-7). ESI-MS: m/z [M − Br]+ = 351.1709,
calcd for C21H23BrN2O3: 351.1708.
3-(8-{4-[(2E)-3-(furan-2-yl)prop-2-enoyl]phenoxy}nonyl)-
1-methyl-1H-imidazol-3-ium bromide (8e) It was obtained
as a brown solid, 98% yield (0.49 mmol, 246 mg); M.p.
135–138 °C. IR (KBr): νmax (cm−1) 1654 (C=O), 1608
(C=C), 1608 (C=N), 1469 (C=CAr), 1276 (C–O–C), 831
(C–HAr). 1H-NMR (DMSO-d6, 300 MHz): δ 1.07–1.47
(5CH2, m, CH2–CH2–CH2), 1.61–1.87 (2CH2, m,
CH2–CH2–CH2), 3.85 (CH3, s, N–CH3), 4.07 (CH2, t, J =
6.5 Hz, N–CH2), 4.15 (CH2, t, J = 7.0 Hz, O–CH2), 6.69
(1H, d, J = 3.5 Hz, H-2), 6.98–7.12 (3H, m, H-3, H-11, H-
12), 7.53–7.58 (2H, m, H-15, H-16), 7.70 (1H, sapparent, H-
6), 7.77 (1H, sapparent, H-5), 7.91 (1H, d, J = 1.4 Hz, H-1),
8.06 (2H, d, J = 8.9 Hz, H-9, H-10), 9.14 (1H, s, H-14).
13C-NMR (DMSO-d6, 75 MHz): δ 25.87 (CH2, CH2–CH2–
CH2), 25.93 (CH2, CH2–CH2–CH2), 28.77 (CH2, CH2–
CH2–CH2), 28.96 (CH2, CH2–CH2–CH2), 29.10 (CH2,
CH2–CH2–CH2), 29.20 (CH2, CH2–CH2–CH2), 29.83
(CH2, CH2–CH2–CH2), 36.21 (CH3, N–CH3), 49.20 (CH2,
N–CH2), 68.04 (CH2, O–CH2), 113.54 (CH, C-16), 114.95
(CH, C-11, C-12), 117.06 (CH, C-2), 119.13 (CH, C-3),
122.72 (CH, C-6), 124.06 (CH, C-15), 130.21 (CH, C-14),
130.65 (C, C-8), 131.17 (CH, C-9, C-10), 136.96 (CH, C-
5), 146.64 (CH, C-1), 151.73 (C, C-4), 163.11 (C, C-13),
187.61 (C=O, C-7). ESI-MS: m/z [M − Br]+ = 421.2491,
calcd for C26H33BrN2O3: 421.2492.
3-(5-{4-[(2E)-3-(furan-2-yl)prop-2-enoyl]phenoxy}pentyl)-
1-methyl-1H-imidazol-3-ium bromide (8c) It was obtained
as a brown solid, 61% yield (0.31 mmol, 138 mg); M.p.
138–139 °C. IR (KBr): νmax (cm−1) 1654 (C=O), 1595
(C=C), 1595 (C=N), 1471 (C=CAr), 1259 (C–O–C), 819
(C–HAr). 1H-NMR (DMSO-d6, 300 MHz): δ 1.32–1.48
(CH2, m, CH2–CH2–CH2), 1.71–1.93 (2CH2, m, CH2–
CH2–CH2), 3.85 (CH3, s, N–CH3), 4.09 (CH2, t, J = 6.0 Hz,
N–CH2), 4.20 (CH2, t, J = 6.8 Hz, O–CH2), 6.69 (1H, d, J
= 3.7 Hz, H-2), 7.06 (2H, d, J = 8.39 Hz, H-11, H-12), 7.09
(1H, d, J = 3.7 Hz, H-3), 7.53–7.57 (2H, m, H-15, H-16),
7.72 (1H, sapparent, H-6), 7.79 (1H, sapparent, H-5), 7.91 (1H,
d, J = 1.4 Hz, H-1), 8.07 (2H, d, J = 8.9 Hz, H-9, H-10),
9.14 (1H, s, H-14). 13C-NMR (DMSO-d6, 75 MHz): δ 22.53
(CH2, CH2–CH2–CH2), 28.29 (CH2, CH2–CH2–CH2),
29.52 (CH2, CH2–CH2–CH2), 36.23 (CH3, N–CH3), 49.08
(CH2, N–CH2), 68.01 (CH2, O–CH2), 113.56 (CH, C-16),
114.95 (CH, C-11, C-12), 117.12 (CH, C-2), 119.11 (CH,
C-3), 122.76 (CH, C-6), 124.10 (CH, C-15), 130.24 (CH,
C-14), 130.73 (C, C-8), 131.18 (CH, C-9, C-10), 137.01
(CH, C-5), 146.49 (CH, C-1), 151.69 (C, C-4), 162.96 (C,
C-13), 187.15 (C=O, C-7). 188.74 (C=O). ESI-MS: m/z
[M
−
Br]+ = 365.1865, calcd for C22H25BrN2O3:
365.1865.
3-(8-{4-[(2E)-3-(furan-2-yl)prop-2-enoyl]phenoxy}dode-
cyl)-1-methyl-1H-imidazol-3-ium bromide (8f) It was
obtained as a dark brown solid. 88% yield (0.44 mmol, 239
mg); M.p. 124–127 °C. IR (KBr): νmax (cm−1) 1654 (C=O),
1600 (C=C), 1600 (C=N), 1467 (C=CAr), 1259 (C–O–C),
3-(8-{4-[(2E)-3-(furan-2-yl)prop-2-enoyl]phenoxy}octyl)-
1-methyl-1H-imidazol-3-ium bromide (8d) It was
obtained as a brown solid, 60% yield (0.30 mmol, 146 mg);
M.p. 126–128 °C. IR (KBr): νmax (cm−1) 1654 (C=O),
1602 (C=C), 1602 (C=N), 1467 (C=CAr), 1274 (C–O–C),
833 (C–HAr). 1H-NMR (DMSO-d6, 300 MHz): δ 1.11–1.47
(4CH2, m, CH2–CH2–CH2), 1.62–1.84 (2CH2, m,
CH2–CH2–CH2), 3.85 (CH3, s, N–CH3), 4.07 (CH2, t, J =
6.5 Hz, N–CH2), 4.15 (CH2, t, J = 6.8 Hz, O–CH2), 6.70
(1H, dd, J = 1.8, 3.5 Hz, H-2), 6.90 (1H, d, J = 3.4, H-3),
7.05 (2H, d, H-11, H-12), 7.50–7.57 (2H, m, H-15, H-16),
7.71 (1H, sapparent, H-6), 7.78 (1H, sapparent, H-5), 7.91 (1H,
821 (C–HAr). 1H-NMR (DMSO-d6, 300 MHz):
δ
1.08–1.487 (8CH2, m, CH2–CH2–CH2), 1.62–1.83 (2CH2,
m, CH2–CH2–CH2), 3.84 (CH3, s, N–CH3), 4.06 (CH2, t, J
= 6.5 Hz, N–CH2), 4.14 (CH2, t, J = 7.2 Hz, O–CH2), 6.68
(1H, d, J = 3.5 Hz, H-2), 7.05 (2H, d, J = 8.9 Hz, H-11, H-
12), 7.08 (1H, d, J = 3.5 Hz, H-3), 7.51–7.57 (2H, m, H-15,
H-16), 7.70 (1H, sapparent, H-6), 7.77 (1H, sapparent, H-5),
7.90 (1H, d, J = 1.4 Hz, H-1), 8.05 (2H, d, J = 8.8 Hz, H-9,