Table 1
Physical and spectral data of compounds 4e32.
Compounds Yield (%) Mp (ꢀC)
MS (Mþ) m/z 1H NMR (DMSO-d6)
d
13C NMR (DMSO-d6)
d
4
5
6
66
65
69
249e250 222
7.47e7.62 (4H, m, H-6, H-20, H-30, H-50), 7.70e7.87 (2H, m, H-7, H-8), 8.12e8.19
(3H, m, H-5, H-20, H-60), 12.54 (1H, s, NH)
7.37e7.63 (3H, m, H-6, H-40, H-50), 7.70e7.86 (2H, m, H-7, H-8), 7.95e8.05 (2H,
m, H-20, H-60), 8.13 (1H, dd, J ¼ 1.2, 8.0 Hz, H-5), 12.58 (1H, s, NH)
7.48e7.56 (3H, m, H-30, H-40, H-50), 7.61e7.83 (3H, m, H-20, H-60, H-8), 8.12e8.16
(2H, m, H-5, H-7), 12.64 (1H, s, NH)
120.95, 125.84, 126.57, 127.46, 127.75, 128.59, 131.38, 132.70, 134.59, 148.69,
152.33, 162.26
279e280 240
114.29, 114.77, 118.04, 118.46, 121.11, 123.93, 125.87, 126.90, 127.60, 130.65,
130.81, 134.67, 134.92, 135.08, 148.44, 151.01, 159.66, 162.13, 164.51
110.31, 110.77, 114.17, 122.11, 122.28, 122.86, 123.34, 127.78, 128.65, 130.21,
130.37, 131.46, 132.58, 145.58, 151.92, 151.95, 157.57, 161.72, 161.79, 162.25,
162.44, 168.23
110.78, 111.24, 114.72, 115.19, 118.52, 118.94, 122.72, 122.88, 123.34, 123.82,
124.32, 130.75, 130.91, 131.12, 131.29, 135.20, 135.36, 145.73, 151.04, 158.16,
160.09, 162.02, 163.04, 164.93
>280
>300
240
258
7
44
72
79
54
45
7.37e7.46 (1H, m, H-40), 7.52e7.60 (1H, m, H-50), 7.69e7.84 (3H, m, H-8, H-20, H-60),
7.93e8.03 (2H, m, H-5, H-7), 12.72 (1H, s, NH)
8
163ꢂ164 296
152e153 314
177e178 314
169e170 332
7.12e7.19 (1H, m, H-400), 7.42e7.61 (6H, m, H-6, H-30, H-40, H-50, H-300, H-500),
7.79e7.90 (2H, m, H-7, H-8), 7.97e8.01 (2H, m, H-200, H-600), 8.46e8.49 (2H, m,
H-20, H-60), 8.58 (1H, dd, J ¼ 1.2, 8.0 Hz, H-5), 9.88 (1H, s, NH)
114.03, 122.23, 123.02, 123.62, 125.86, 127.91, 128.12, 128.37, 128.47, 130.23,
133.13, 138.36, 139.32, 150.51, 157.92, 159.04
9
7.09e7.29 (2H, m, H-50, H-400), 7.37e7.58 (4H, m, H-6, H-40, H-300, H-500), 7.74e7.81
(2H, m, H-7, H-8), 7.86e7.90(2H, m, H-200, H-600), 8.05 (1H, d, J ¼ 10.6 Hz, H-20),
8.21 (1H, d, J ¼ 7.6 Hz, H-60), 8.50 (1H, dd, J ¼ 1.2, 8.0 Hz, H-5), 9.87 (1H, s, NH)
7.11e7.18 (1H, m, H-400), 7.41e7.48 (5H, m, H-6, H-30, H-50, H-300, H-500), 7.62e7.71
(1H, m, H-7), 7.83e7.98 (3H, m, H-8, H-200, H-600), 8.37e8.42 (3H, m, H-5, H-20, H-60),
9.73 (1H, s, NH)
114.01, 114.17, 114.47, 116.81, 117.23, 122.53, 123.08, 123.91, 126.26, 128.20,
128.52, 130.33, 130.49, 133.31, 139.16, 140.99, 141.14, 150.35, 157.85, 158.03,
160.03, 164.85
107.25, 107.72, 114.34, 114.52, 122.11, 122.60, 123.67, 127.86, 128.34, 128.48,
130.19, 130.69, 130.85, 138.17, 139.18, 147.60, 156.91, 157.54, 157.62,
158.71, 161.77
107.74, 108.21, 114.30, 114.75, 114.91, 115.10, 117.21, 117.64, 122.78, 123.27,
124.15, 124.20, 124.41, 128.94, 130.73, 130.89, 131.22, 131.40, 134.83, 139.35,
141.11, 141.27, 147.81, 147.83, 157.53, 157.81, 157.85, 157.92, 158.05, 158.13,
160.40, 162.40, 165.22
10
11
7.13e7.33 (2H, m, H-40, H-400), 7.41e7.56 (3H, m, H-50, H-300, H-500), 7.68e7.78
(1H, m, H-7), 7.85e7.91 (3H, m, H-8, H-200, H-600), 8.03 (1H, d, J ¼ 10.6 Hz, H-20),
8.20 (1H, d, J ¼ 7.6 Hz, H-60), 8.39 (1H, dd, J ¼ 2.5, 9.8 Hz, H-5), 9.80 (1H, s, NH)
12
13
14
18
12
17
>270
363
3.79 (3H, s, OCH3), 7.02 (2H, d, J ¼ 9.0 Hz, H-300, H-500), 7.27e7.33 (1H, m, H-400),
7.45e7.56 (1H, m, H-50), 7.65e7.71 (1H, m, H-7), 7.73e7.79 (1H, m, H-200, H-600),
7.86e7.90 (1H, m, H-8), 8.02 (1H, d, J ¼ 10.6 Hz, H-20), 8.18 (1H, d, J ¼ 7.6 Hz, H-60),
8.34 (1H, dd, J ¼ 2.5, 9.8 Hz, H-5), 9.72 (1H, s, NH)
55.63, 107.60, 108.08, 114.04, 114.26, 114.72, 114.81, 114.99, 117.05, 117.47,
122.45, 122.94, 124.14, 124.42, 130.58, 130.73, 131.06, 131.23, 132.21, 141.21,
141.36, 147.65, 156.28, 157.43, 157.96, 158.04, 160.34, 162.28, 165.16
144e145 362
166e167 332
3.82 (3H, s, OCH3), 6.76 (1H, dd, J ¼ 2.4, 8.0 Hz, H-400), 7.28e7.39 (2H, m, H-40, H-500),
7.47e7.60 (2H, m, H-200, H-50), 7.70e7.82 (2H, m, H-7, H-600), 7.89e7.97 (1H, m, H-8),
8.11 (1H, d, J ¼ 10.6 Hz, H-20), 8.25 (1H, d, J ¼ 7.6 Hz, H-60), 8.42 (1H, dd, J ¼ 2.5,
9.8 Hz, H-5), 9.80 (1H, s, NH)
55.33, 70.96, 107.53, 107.70, 108.00, 110.12, 114.12, 114.54, 114.75, 114.93,
117.18, 117.60, 122.78, 123.27, 123.97, 129.56, 130.68, 130.83, 131.10, 131.27,
140.39, 140.85, 141.01, 147.58, 157.40, 157.79, 157.87, 159.63, 160.22,
162.27, 165.04
3.80 (3H, s, OCH3), 6.99e7.32 (4H, m, H-40, H-300, H-400, H-500), 7.39e7.50 (1H, m, H-50), 55.99, 107.59, 108.06, 112.11, 114.24, 114.69, 114.75, 114.92, 117.03, 117.46,
7.65e7.76 (2H, m, H-7, H-600), 7.84e7.96 (2H, m, H-8, H-20), 8.10 (1H, d, J ¼ 7.6 Hz,
120.51, 122.63, 123.13, 124.03, 124.07, 126.46, 127.00, 127.08, 127.25, 130.53,
130.69, 131.13, 131.30, 141.19, 141.35, 147.73, 153.55, 157.46, 157.90, 157.95,
158.01, 158.74, 158.82, 162.33, 165.14
109.27, 109.76, 114.58, 114.77, 115.36, 115.64, 115.83, 116.09, 119.33, 119.75,
124.39, 124.89, 125.26, 126.20, 126.36, 126.65, 131.37, 131.53, 134.19, 136.74,
141.56, 156.77, 157.61, 158.06, 158.83, 160.17, 162.45, 162.96, 165.02
107.54, 108.02, 109.25, 110.15, 110.57, 114.23, 114.92, 117.15, 117.57, 117.81,
122.72, 123.22, 124.01, 130.16, 130.35, 130.56, 130.72, 131.17, 131.34, 140.87,
141.03, 141.13, 141.36, 147.67, 157.62, 160.01, 162.35, 162.37, 164.81, 165.17
107.37, 107.83, 113.74, 114.19, 115.77, 116.16, 116.84, 117.25, 122.68, 123.18,
H-60), 8.34 (1H, dd, J ¼ 2.5, 9.8 Hz, H-5), 9.43 (1H, s, NH)
15
16
17
18
19
20
21
22
16
14
25
21
20
22
232e233 351
107e108 351
200e201 351
7.30e7.50 (3H, m, H-40, H-300, H-500), 7.56e7.67 (1H, m, H-50), 7.81e7.97 (3H, m,
H-7, H-200, H-600), 8.08e8.28 (3H, m, H-8, H-20, H-60), 8.71 (1H, dd, J ¼ 2.5,
9.8 Hz, H-5), 11.08 (1H, s, NH)
6.89e6.96 (1H, m, H-400), 7.20e7.27 (1H, m, H-40), 7.33e7.49(2H, m, H-50, H-500),
7.61e7.64 (2H, m, H-200, H-600), 7.73e7.94 (3H, m, H-7, H-8, H-20), 8.08
(1H, d, J ¼ 7.6 Hz, H-60), 8.22 (1H, dd, J ¼ 2.5, 9.8 Hz, H-5), 9.70 (1H, s, NH)
7.22e7.69 (5H, m, H-40, H-50, H-300, H-400, H-500), 7.74e7.98 (4H, m, H-20, H-7, H-8,
H-600), 8.08 (1H, d, J ¼ 7.6 Hz, H-60), 8.35 (1H, dd, J ¼ 2.5, 9.8 Hz, H-5), 9.98 (1H, s, NH) 123.63, 124.41, 125.91, 126.15, 127.58, 127.99, 130.47, 130.86, 131.02, 136.39,
137.62, 140.53, 147.43, 152.49, 154.26, 158.47, 159.17, 161.27, 161.96, 164.70
>300
367.5
7.21e7.28 (1H, m, H-40), 7.40e7.51 (3H, m, H-50, H-300, H-500), 7.62e7.97
(5H, m, H-7, H-8, H-20, H-200, H-600), 8.11 (1H, d, J ¼ 7.6 Hz, H-60), 8.26 (1H, dd,
J ¼ 2.5, 9.8 Hz, H-5), 9.75 (1H, s, NH)
107.22, 107.70, 113.80, 114.27, 114.38, 114.56, 115.28, 116.78, 117.20, 117.62,
122.39, 122.88, 123.62, 127.41, 128.31, 130.26, 130.42, 130.77, 130.94, 137.90,
140.47, 140.62, 147.30, 157.07, 157.33, 157.41, 159.92, 161.94, 164.74
170.10, 107.58, 113.84, 114.30, 114.48, 116.72, 117.14, 119.90, 121.37, 122.29,
122.78, 123.05, 123.60, 129.88, 130.08, 130.23, 130.75, 130.91, 132.76, 140.42,
147.53, 147.26, 157.12, 157.21, 159.93, 161.92, 164.76
107.71, 108.18, 114.22, 114.51, 114.68, 117.19, 117.61, 123.05, 123.55, 124.06,
128.01, 128.33, 129.81, 130.23, 130.64, 130.79, 131.11, 131.30, 131.48, 136.06,
140.99, 141.14, 147.90, 157.52, 157.86, 159.03, 159.11, 160.30, 162.39, 165.12
107.30, 107.78, 113.88, 114.36, 114.57, 115.58, 116.90, 117.32, 122.46, 122.96,
123.81, 124.01, 130.31, 130.47, 130.60, 130.77, 131.25, 138.32, 140.29, 140.43,
147.06, 157.28, 159.94, 161.99, 164.76
223e224 367.5
185e186 367.5
7.12e7.28 (2H, m, H-40, H-400), 7.34e7.49 (2H, m, H-50, H-500), 7.58e7.96 (4H, m,
H-7, H-8, H-200, H-600), 8.08e8.14 (2H, m, H-20, H-60), 8.22 (1H, dd, J ¼ 2.5,
9.8 Hz, H-5), 9.68 (1H, s, NH)
7.19e7.28 (1H, m, H-40), 7.35e7.51 (3H, m, H-300, H-400, H-500), 7.67e7.71 (2H,
m, H-50, H-600), 7.75e7.96 (3H, m, H-20, H-7, H-8), 8.03 (1H, d, J ¼ 7.6 Hz, H-60),
8.35 (1H, dd, J ¼ 2.5, 9.8 Hz, H-5), 9.96 (1H, s, NH)
231
412
7.22e7.31 (1H, m, H-40), 7.41e7.70 (4H, m, H-7, H-50, H-300, H-500), 7.79e7.83
(3H, m, H-8, H-200, H-600), 7.92 (1H, d, J ¼ 10.6 Hz, H-20), 8.09 (1H, d, J ¼ 7.6 Hz, H-60),
8.25 (1H, dd, J ¼ 2.5, 9.8 Hz, H-5), 9.78 (1H, s, NH)