C.-C. Hung et al. / Bioorg. Med. Chem. 13 (2005) 1791–1797
1795
1481, 1444, 1424, 1350, 1283, 1183, 1114, 1077, 1004,
4.1.9.
N-(4-Bromo-phenyl)-3-(3,4-dihydroxy-phenyl)-
1
975, 906, 880, 850, 811, 778, 680, 668 cmÀ1; H NMR
acrylamide (14). Light yellow solid (247.8 mg, 74%);
mp 230–232 ꢁC; IR (film) 3266, 1661, 1596, 1528,
1487, 1444, 1395, 1352, 1298, 1283, 1242, 1181, 1114,
(acetone-d6) d 6.60 (1H, d, J = 15.5 Hz), 6.85 (1H, d,
J = 7.9 Hz), 6.95–7.13 (3H, m), 7.28 (1H, t,
J = 7.9 Hz), 7.58 (1H, d, J = 15.5 Hz), 7.60 (1H, d,
J = 15.5 Hz), 8.00–8.02 (1H, m), 9.47 (1H, br s); 13C
NMR 115.0, 116.3, 118.3, 119.0, 119.9, 122.0, 123.8,
127.9, 130.9, 134.6, 141.7, 142.8, 146.2, 148.2, 165.4;
EIMS (relative intensity) m/z 291 (8), 289 (M+,
23), 164 (10), 163 (100), 162 (35), 135 (17), 134
(29), 127 (18), 117 (11), 89 (22), 77 (7); exact mass
calcd for C15H12ClNO3 m/z 289.0506, EI-HRMS m/z
289.0497.
1072, 1007, 974, 812, 504 cmÀ1; H NMR (acetone-d6)
1
d 6.59 (1H, d, J = 15.3 Hz), 6.84 (1H, d, J = 8.0 Hz),
6.96 (1H, d, J = 8.0 Hz), 7.11 (1H, s), 7.43 (2H, dd,
J = 8.6, 1.3 Hz), 7.57 (1H, d, J = 15.3 Hz), 7.71 (2H,
dd, J = 8.6, 1.3 Hz), 8.28 (1H, br s), 9.41 (1H, br s);
13C NMR d 115.0, 116.0, 116.3, 119.1, 121.9, 122.0,
127.9, 132.3, 139.6, 142.6, 146.1, 148.1, 165.3; EIMS
(relative intensity) m/z 333 (M+, 20), 173 (27), 171
(26), 164 (14), 163 (100), 162 (67), 145 (11), 135
(25), 134 (44), 117 (16), 89 (28); exact mass calcd
for C15H12BrNO3 m/z 333.0001, EI-HRMS m/z
333.0006.
4.1.6.
N-(4-Chloro-phenyl)-3-(3,4-dihydroxy-phenyl)-
acrylamide (11). Light yellow solid (282 mg, 97%); mp
198–200 ꢁC; IR (film) 3249, 1655, 1648, 1596, 1560,
1522, 1491, 1399, 1283, 1242, 1185, 1174, 1116, 1091,
4.1.10.
N-(3-Cyano-phenyl)-3-(3,4-dihydroxy-phenyl)-
975, 811 cmÀ1
;
1H NMR (acetone-d6) d 6.57 (1H, d,
acrylamide (15). Light yellow solid (97 mg, 35%); mp
279–280 ꢁC; IR (film) 3317, 2927, 2856, 2233, 1698,
1668, 1587, 1549, 1484, 1430, 1362, 1284, 1256, 1192,
J = 15.4 Hz), 6.85 (1H, d, J = 8.2 Hz), 6.98 (1H, dd,
J = 8.2, 1.9 Hz), 7.31 (1H, dt, J = 9.0, 2.5 Hz), 7.55
(1H, d, J = 15.4 Hz), 7.77 (1H, dd, J = 9.0, 2.5 Hz),
9.35 (1H, br s); 13C NMR d 115.0, 116.3, 119.2, 121.5,
121.9, 128.1, 128.3, 129.4, 139.4, 142.4, 146.2, 148.2,
165.0; EIMS (relative intensity) m/z 291 (8), 289 (M+,
22), 164 (10), 163 (100), 162 (20), 135 (19), 134 (24),
129 (11), 127 (35), 117 (12), 89 (26), 78 (6), 77 (9); exact
mass calcd for C15H12ClNO3 m/z 289.0506, EI-HRMS
m/z 289.0504.
1169, 1116, 976, 791, 668, 680 cmÀ1 1H NMR (ace-
;
tone-d6) d 6.52 (1H, d, J = 15.5 Hz), 6.78 (1H, d,
J = 8.1 Hz), 6.96 (1H, dd, J = 8.1, 1.4 Hz), 7.06 (1H, d,
J = 1.8 Hz), 7.40–7.51 (2H, m), 7.55 (1H, d,
J = 15.5 Hz), 7.84 (1H, d, J = 7.9 Hz), 8.14 (1H, s); 13C
NMR d 113.7, 115.2, 116.5, 118.0, 119.5, 122.5, 123.8,
125.1, 128.0, 128.2, 131.0, 141.3, 144.3, 146.8, 149.2,
167.5; EIMS (relative intensity) m/z 280 (M+, 16), 164
(10), 163 (100), 162 (27), 135 (16), 134 (18), 117 (12),
89 (21); exact mass calcd for C16H12N2O3 m/z
280.0848, EI-HRMS m/z 280.0842.
4.1.7.
N-(2-Bromo-phenyl)-3-(3,4-dihydroxy-phenyl)-
acrylamide (12). Yellow solid (275.9 mg, 83%); mp
166–168 ꢁC; IR (film) 3259, 2931, 2854, 1660, 1593,
1521, 1435, 1365, 1284, 1181, 1114, 975, 849, 811, 752,
4.1.11. 2-[3-(3,4-Dihydroxy-phenyl)-acryloylamino]-ben-
zoic acid ethyl ester (16). Yellow solid (273.6 mg, 84%);
mp 186–188 ꢁC; IR (film) 3261, 2981, 1680, 1604,
1588, 1525, 1447, 1368, 1258, 1163, 1113, 1090, 1003,
1
733, 661, 563, 522 cmÀ1; H NMR (acetone-d6) d 6.86
(1H, d, J = 15.2 Hz), 6.86 (1H, d, J = 8.2 Hz), 7.00–
7.07 (2H, m), 7.16 (1H, d, J = 2.0 Hz), 7.32–7.38 (1H,
m), 7.59 (1H, d, J = 15.4 Hz), 7.59–7.61 (1H, m), 8.24–
8.27 (1H, m), 8.58 (1H, br s); 13C NMR d 114.7,
115.0, 115.8, 118.5, 121.7, 124.3, 125.9, 127.5, 128.3,
132.8, 137.1, 142.7, 145.7, 147.8, 164.8; EIMS (relative
intensity) m/z 335 (19), 333 (M+, 20), 254 (10), 173
(27), 171 (26), 164 (14), 163 (100), 162 (67), 145 (11),
135 (25), 134 (44), 127 (10), 117 (16), 89 (28), 77 (10); ex-
act mass calcd for C15H12BrNO3 m/z 333.0001, EI-
HRMS m/z 333.0006.
972, 811, 755, 668 cmÀ1; H NMR (acetone-d6) d 1.40
1
(3H, t, J = 7.2 Hz), 4.41 (2H, q, J = 7.2 Hz), 6.57 (1H,
d, J = 15.4 Hz), 6.88 (1H, d, J = 8.1 Hz), 7.07–7.15
(2H, m), 7.22 (1H, d, J = 2.0 Hz), 7.55–7.62 (2H, m),
8.04–8.07 (1H, m), 8.83 (1H, d, J = 8.1 Hz), 11.18 (1H,
s); 13C NMR d 14.3, 62.1, 115.2, 116.1, 116.3, 119.8,
121.0, 122.3, 123.0, 127.8, 131.6, 135.0, 142.8, 143.0,
146.2, 148.4, 165.1, 168.8; EIMS (relative intensity)
m/z 327 (M+, 39), 166 (18), 165 (100), 163 (75), 162
(15), 135 (21), 134 (35), 120 (13), 119 (29), 117 (15), 92
(11), 89 (26); exact mass calcd for C18H17NO5 m/z
327.1107, EI-HRMS m/z 327.1111.
4.1.8.
N-(3-Bromo-phenyl)-3-(3,4-dihydroxy-phenyl)-
acrylamide (13). Light yellow solid (330 mg, 99%); mp
160–162 ꢁC; IR (film) 3259, 2931, 2853, 1662, 1588,
1525, 1477, 1444, 1420, 1374, 1282, 1181, 1113, 1070,
4.1.12. 3-(3,4-Dihydroxy-phenyl)-N-(3,4-dimethoxy-phe-
nyl)-acrylamide (17). Light yellow solid (229.6 mg,
73%); mp 200–202 ꢁC; IR (film) 3334, 1693, 1656,
1605, 1513, 1443, 1406, 1259, 1233, 1213, 1154, 1134,
1115, 1023, 976, 851, 810, 770, 668 cmÀ1; 1H NMR (ace-
tone-d6) d 3.75 (3H, s), 3.76 (3H, s), 6.60 (1H, d,
J = 15.5 Hz), 6.84 (1H, d, J = 8.1 Hz), 6.86 (1H, d,
J = 8.7 Hz), 6.95 (1H, dd, J = 8.1, 1.8 Hz), 7.10 (1H, d,
J = 1.8 Hz), 7.21 (1H, d, J = 8.7 Hz), 7.52 (1H, s), 7.54
(1H, d, J = 15.5 Hz), 9.22 (1H, br s); 13C NMR d 55.9,
56.4, 105.8, 112.3, 113.2, 114.9, 116.3, 119.6, 121.8,
128.2, 134.1, 141.8, 146.2, 146.6, 148.0, 150.2, 164.9;
EIMS (relative intensity) m/z 315 (M+, 88), 300 (10),
1
1044, 974, 849, 810, 775, 679, 590, 563, 521 cmÀ1; H
NMR (acetone-d6) d 6.57 (1H, d, J = 15.5 Hz), 6.85
(1H, d, J = 8.2 Hz), 6.98 (1H, dd, J = 8.2, 1.8 Hz), 7.10
(1H, d, J = 1.8 Hz), 7.21–7.26 (2H, m), 7.56 (1H, d,
J = 15.5 Hz), 7.60–7.63 (1H, m), 8.15 (1H, d,
J = 1.9 Hz), 9.43 (1H, br s); 13C NMR d 115.0, 116.3,
118.7, 119.0, 122.0, 122.7 (·2), 126.7, 128.0, 131.2,
142.0, 142.7, 146.2, 148.3, 165.2; EIMS (relative inten-
sity) m/z 335 (20), 333 (M+, 21), 173 (13), 171 (13),
164 (13), 163 (100), 162 (60), 145 (10), 135 (21), 134
(33), 117 (13), 89 (23); exact mass calcd for
C15H12BrNO3 m/z 333.0001, EI-HRMS m/z 332.9998.