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W. Zhao et al. / Bioorg. Med. Chem. 19 (2011) 3192–3203
3422, 2918, 2849, 1754, 1698, 1650, 1592, 1524, 1467, 1267, 1142,
804; 1H NMR (CDCl3, 300 MHz): d 7.51 (m, 3H, H-7, H-4, H-6), 7.34
(m, 2H, H-20, H-60), 6.95 (d, 1H, J = 8.13 Hz, H-50), 6.89 (s, 1H, H-10),
3.98 (s, 3H, –OCH3), 3.96 (s, 3H, –OCH3), 2.58 (t, 2H, J = 7.41 Hz, –
CH2CO–), 1.75 (m, 2H, –CH2–CH2CO–), 0.88 (m, 3H, –CH3); MS
(EI): m/z = 564. Anal. Calcd for C35H48O6: C, 74.44; H, 8.57. Found:
C, 74.16; H, 8.87.
4.1.8.23. Z-2-(3-Methoxybenzylidene)-3-oxo-2,3-dihydrobenzo-
furan-5-yl 10-undecylenate (ZWD1-2). Recrystallization from
acetone afforded yellow crystals. Yield: 540 mg (64.4%). Mp 95–
97 °C; IR (cmꢀ1): 3340, 2926, 2850, 1760, 1707, 1651, 1603,
1479, 1267, 1135, 1111, 786; 1H NMR (CDCl3, 300 MHz): d 7.50
(m, 3H, H-7, H-4, H-50), 7.36 (m, 3H, H-6, H-20, H-60), 6.98 (d, 1H,
J = 8.1 Hz, H-40), 6.88 (s, 1H, H-10), 5.81 (m, 1H, @CH–), 4.96 (m,
2H, @CH2), 3.88 (s, 3H, –OCH3), 2.58 (t, 2H, J = 7.2 Hz, –CH2CO–),
2.05 (m, 2H, @CH–CH2–), 1.76 (m, 2H, –CH2–CH2CO–); MS (EI):
m/z = 434. Anal. Calcd for C27H30O5: C, 74.63; H, 6.96. Found: C,
74.30; H, 6.92.
4.1.8.18. Z-2-(4-Fluorobenzylidene)-3-oxo-2,3-dihydrobenzofu-
ran-5-yl stearate (ZWC1-4). Purified by flash column chromatog-
raphy (petroleum ether/ethyl acetate 15:1) afforded yellow solid.
Yield: 680 mg (70.0%). Mp 91–93 °C; IR (cmꢀ1): 3415, 2922,
2851, 1762, 1705, 1648, 1509, 1471, 1134, 838; 1H NMR (CDCl3,
300 MHz): d 7.92 (m, 2H, H-20, H-60), 7.51 (d, 1H, J = 2.01 Hz, H-
4), 7.35 (m, 2H, H-6, H-7), 7.16 (t, 2H, J = 8.7 Hz, H-30, H-50), 6.88
(s, 1H, H-10), 2.58 (t, 2H, J = 7.53 Hz, –CH2CO–), 1.76 (m, 2H, –
CH2–CH2CO–), 0.88 (m, 3H, –CH3); MS (EI): m/z = 522. Anal. Calcd
for C33H43FO4: C, 75.83; H, 8.29. Found: C, 75.62; H, 8.14.
4.1.8.24. Z-2-(3,4-Dimethoxybenzylidene)-3-oxo-2,3-dihydro-
benzofuran-5-yl 10-undecylenate (ZWD1-3). Recrystallization
from acetone afforded yellow crystals. Yield: 680 mg (78.8%). Mp
110–112 °C; IR (cmꢀ1): 3493, 2923, 2852, 1754, 1698, 1650,
1592, 1524, 1482, 1267, 1143, 804; 1H NMR (CDCl3, 300 MHz): d
7.51 (m, 3H, H-7, H-4, H-6), 7.36 (m, 2H, H-20, H-60), 6.95 (d, 1H,
J = 8.16 Hz, H-50), 6.89 (s, 1H, H-10), 5.82 (m, 1H, @CH–), 4.96 (m,
2H, @CH2), 3.98 (s, 3H, –OCH3), 3.96 (s, 3H, –OCH3), 2.58 (t, 2H,
J = 7.47 Hz, –CH2CO–), 2.05 (m, 2H, @CH–CH2–), 1.76 (m, 2H, –
CH2–CH2CO–); MS (EI): m/z = 464. Anal. Calcd for C28H32O6ꢁ0.5H2O:
C, 71.02; H, 7.02. Found: C, 70.73; H, 7.11.
4.1.8.19. Z-2-(4-Bromobenzylidene)-3-oxo-2,3-dihydrobenzofu-
ran-5-yl stearate (ZWC1-5). Purified by flash column chromatog-
raphy (petroleum ether/ethyl acetate 15:1) afforded yellow solid.
Yield: 890 mg (82.1%). Mp 114–116 °C; IR (cmꢀ1): 3414, 2918,
2849, 1760, 1705, 1649, 1601, 1478, 1274, 1141, 1111, 819; 1H
NMR (CDCl3, 300 MHz): d 7.77 (d, 2H, J = 8.52 Hz, H-20, H-60),
7.59 (d, 2H, J = 8.52 Hz, H-30, H-50), 7.51 (d, 1H, J = 2.07 Hz, H-4),
7.36 (m, 2H, H-6, H-7), 6.83 (s, 1H, H-10), 2.58 (t, 2H, J = 7.47 Hz,
–CH2CO–), 1.75 (m, 2H, –CH2–CH2CO–), 0.88 (m, 3H, –CH3); MS
(EI): m/z = 582. Anal. Calcd for C33H43BrO4: C, 67.92; H, 7.43.
Found: C, 67.79; H, 7.58.
4.1.8.25. Z-2-(4-Fluorobenzylidene)-3-oxo-2,3-dihydrobenzofu-
ran-5-yl 10-undecylenate (ZWD1-4). Recrystallization from ace-
tone afforded yellow crystals. Yield: 560 mg (71.3%). Mp 82–84 °C;
IR (cmꢀ1): 3410, 2926, 2852, 1752, 1707, 1655, 1509, 1478, 1241,
1
1147, 838; H NMR (CDCl3, 300 MHz): d 7.92 (m, 2H, H-20, H-60),
7.51 (d, 1H, J = 2.4 Hz, H-4), 7.36 (m, 2H, H-6, H-7), 7.16 (t, 2H,
J = 8.4 Hz, H-30, H-50), 6.87 (s, 1H, H-10), 5.82 (m, 1H, @CH–),
4.96 (m, 2H, @CH2), 2.58 (t, 2H, J = 7.5 Hz, –CH2CO–), 2.05 (m,
2H, @CH–CH2–), 1.76 (m, 2H, –CH2–CH2CO–); MS (EI): m/z = 422.
Anal. Calcd for C26H27FO4ꢁ0.75H2O: C, 71.62; H, 6.59. Found: C,
71.52; H, 6.65.
4.1.8.20. Z-2-(3-Chlorobenzylidene)-3-oxo-2,3-dihydrobenzofu-
ran-5-yl stearate (ZWC1-6). Purified by flash column chromatog-
raphy (petroleum ether/ethyl acetate 15:1) afforded yellow solid.
Yield: 690 mg (68.9%). Mp 88–90 °C; IR (cmꢀ1): 3422, 2917,
2850, 1764, 1708, 1655, 1605, 1481, 1142, 833; 1H NMR (CDCl3,
300 MHz): d 7.95 (s, 1H, H-4), 7.74 (m, 1H, H-50), 7.52 (m, 1H, H-
20), 7.39 (m, 4H, Ar-H), 6.82 (s, 1H, H-10), 2.58 (t, 2H, J = 7.5 Hz, –
CH2CO–), 1.76 (m, 2H, –CH2–CH2CO–), 0.88 (m, 3H, –CH3); MS
4.1.8.26. Z-2-(4-Bromobenzylidene)-3-oxo-2,3-dihydrobenzofu-
ran-5-yl 10-undecylenate (ZWD1-5). Recrystallization from ace-
tone afforded yellow crystals. Yield: 550 mg (61.2%). Mp 122–
124 °C; IR (cmꢀ1): 3416, 2924, 2851, 1761, 1705, 1649, 1602,
1478, 1274, 1140, 1111, 819; 1H NMR (CDCl3, 300 MHz): d 7.77
(d, 2H, J = 8.4 Hz, H-20, H-60), 7.59 (d, 2H, J = 8.4 Hz, H-30, H-50),
7.51 (d, 1H, J = 2.1 Hz, H-4), 7.36 (m, 2H, H-6, H-7), 6.83 (s, 1H,
H-10), 5.82 (m, 1H, @CH–), 4.96 (m, 2H, @CH2), 2.58 (t, 2H,
J = 7.2 Hz, –CH2CO–), 2.05 (m, 2H, @CH–CH2–), 1.76 (m, 2H, –
(EI): m/z = 538. Anal. Calcd for
72.93; H, 8.16. Found: C, 73.29; H, 8.62.
C
33H43ClO4ꢁ0.5CH3COCH3: C,
4.1.8.21. Z-2-(3-Nitrobenzylidene)-3-oxo-2,3-dihydrobenzofu-
ran-5-yl stearate (ZWC1-7). Purified by flash column chromatog-
raphy (petroleum ether/ethyl acetate 15:1) afforded yellow solid.
Yield: 705 mg (68.6%). Mp 104–106 °C; IR (cmꢀ1): 3449, 2915,
2851, 1760, 1707, 1654, 1614, 1531, 1478, 1350, 1136, 1108,
CH2–CH2CO–);
MS
(EI):
m/z = 484.
Anal.
Calcd
for
C26H27BrO4ꢁ0.5H2O: C, 63.42; H, 5.73. Found: C, 63.47; H, 5.83.
1
833; H NMR (CDCl3, 300 MHz): d 8.82 (s, 1H, H-20), 8.25 (d, 1H,
J = 7.53 Hz, H-40), 8.15 (d, 1H, J = 7.95 Hz, H-60), 7.64 (t, 1H,
J = 7.95 Hz, H-50), 7.54 (s, 1H, H-4), 7.41 (m, 2H, H-6, H-7), 6.90
(s, 1H, H-10), 2.58 (t, 2H, J = 7.44 Hz, –CH2CO–), 1.76 (m, 2H, –
CH2–CH2CO–), 0.88 (m, 3H, –CH3); MS (EI): m/z = 549. Anal. Calcd
for C33H43NO6: C, 72.10; H, 7.88; N, 2.55. Found: C, 71.69; H,
7.79; N, 2.69.
4.1.8.27. Z-2-(3-Chlorobenzylidene)-3-oxo-2,3-dihydrobenzofu-
ran-5-yl 10-undecylenate (ZWD1-6). Recrystallization from ace-
tone afforded yellow crystals. Yield: 430 mg (65.0%). Mp 94–96 °C;
IR (cmꢀ1): 3457, 2925, 2853, 1758, 1710, 1653, 1606, 1477, 1140,
1108, 821; 1H NMR (CDCl3, 300 MHz): d 7.95 (s, 1H, H-4), 7.74
(m, 1H, H-50), 7.52 (m, 1H, H-20), 7.38 (m, 4H, Ar-H), 6.82 (s, 1H,
H-10), 5.82 (m, 1H, @CH–), 4.96 (m, 2H, @CH2), 2.58 (t, 2H,
J = 7.41 Hz, –CH2CO–), 2.05 (m, 2H, @CH–CH2–), 1.76 (m, 2H, –
4.1.8.22. Z-2-(4-Methoxybenzylidene)-3-oxo-2,3-dihydrobenzo-
furan-5-yl 10-undecylenate (ZWD1-1). Recrystallization from
acetone afforded yellow crystals. Yield: 650 mg (80.5%). Mp 129–
131 °C; IR (cmꢀ1): 3451, 2925, 2851, 1756, 1703, 1646, 1596,
1511, 1450, 1254, 1191, 1140, 838; 1H NMR (CDCl3, 300 MHz): d
7.89 (d, 2H, J = 8.7 Hz, H-20, H-60), 7.50 (d, 1H, J = 1.5 Hz, H-4),
7.35 (m, 2H, H-6, H-7), 6.99 (d, 2H, J = 8.7 Hz, H-30, H-50), 6.90 (s,
1H, H-10), 5.82 (m, 1H, @CH–), 5.04 (m, 2H, @CH2), 3.88 (s, 3H, –
OCH3), 2.58 (t, 2H, J = 7.47 Hz, –CH2CO–), 2.05 (m, 2H, @CH–CH2–
), 1.77 (m, 2H, –CH2–CH2CO–); MS (EI): m/z = 434. Anal. Calcd for
CH2–CH2CO–);
MS
(EI):
m/z = 438.
Anal.
Calcd
for
C26H27ClO4ꢁ1.5H2O: C, 67.02; H, 6.49. Found: C, 66.76; H, 6.22.
4.1.8.28. Z-2-(3-Nitrobenzylidene)-3-oxo-2,3-dihydrobenzofu-
ran-5-yl 10-undecylenate (ZWD1-7). Recrystallization from
acetone afforded yellow crystals. Yield: 620 mg (74.2%). Mp 108–
110 °C; IR (cmꢀ1): 3416, 2922, 2852, 1758, 1704, 1651, 1614,
1529, 1477, 1349, 1135, 1105, 834; 1H NMR (CDCl3, 300 MHz): d
8.82 (s, 1H, H-20), 8.25 (d, 1H, J = 7.8 Hz, H-40), 8.15 (d, 1H,
J = 7.8 Hz, H-60), 7.64 (t, 1H, J = 8.1 Hz, H-50), 7.54 (s, 1H, H-4),
C27H30O5ꢁ0.5H2O: C, 73.12; H, 7.04. Found: C, 73.08; H, 7.09.