高等学校化学学报 ›› 2014, Vol. 35 ›› Issue (7): 1445.doi: 10.7503/cjcu20131194
张成路(), 孙丽杰, 武飞宇, 曲瑞峰, 朱长安, 王雪, 柴金华, 国阳, 胡雪
收稿日期:
2013-12-06
出版日期:
2014-07-10
发布日期:
2014-04-21
作者简介:
联系人简介: 张成路, 男, 博士, 教授, 主要从事有机合成研究. E-mail: 基金资助:
ZHANG Chenglu*(), SUN Lijie, WU Feiyu, QU Ruifeng, ZHU Chang’an, WANG Xue, CHAI Jinhua, GUO Yang, HU Xue
Received:
2013-12-06
Online:
2014-07-10
Published:
2014-04-21
Contact:
ZHANG Chenglu
E-mail:zhangchenglu@lnnu.edu.cn
Supported by:
摘要:
在三氯氧磷催化下, 6种3-脂肪基-1,2,4-三唑(1a~1f)和3-苯基-1,2,4-三唑(1g)分别与对苯二甲酸和2-氨基-1,4-对苯二甲酸发生环化反应, 高产率合成了14种双枝三唑并噻二唑稠环衍生物(2和3), 并对其进行了结构表征及药物活性测试. 目标化合物对Cdc25B和PTP1B抑制活性筛选结果表明, 化合物2f, 3a和3g对Cdc25B有较高的抑制活性, IC50值分别为(3.45±0.60), (0.69±0.10)和(1.52±0.19) μg/mL; 化合物3a和3b对PTP1B表现出较高的抑制活性, IC50值分别为(0.98±0.13)和(2.00±0.16) μg/mL.
中图分类号:
TrendMD:
张成路, 孙丽杰, 武飞宇, 曲瑞峰, 朱长安, 王雪, 柴金华, 国阳, 胡雪. 1,4-双[3-脂肪基/苯基-1,2,4-三唑并[3,4-b]-1,3,4-噻二唑-6-基]芳基衍生物的合成与生物活性. 高等学校化学学报, 2014, 35(7): 1445.
ZHANG Chenglu, SUN Lijie, WU Feiyu, QU Ruifeng, ZHU Chang’an, WANG Xue, CHAI Jinhua, GUO Yang, HU Xue. Synthesis and Bioactivity of 1,4-Bis[3-aliphatic/aryl -1,2,4-triazole[3,4-b]-1,3,4-thiatriazole-6-yl] Aryl Derivatives†. Chem. J. Chinese Universities, 2014, 35(7): 1445.
Compd. | Appearance | Yield(%) | m. p./℃ | 1 H NMR(500 MHz, DMSO-d6), δ | IR(KBr), |
---|---|---|---|---|---|
1a | White solid | 85.0 | 112.1—113.7 | 13.39(s, 1H), 5.50(s, 2H), 2.62(t, J=7.5 Hz, 2H), 1.65—1.60(m, 2H), 1.30—1.25(m, 8H), 0.87(t, J=6.8 Hz, 3H) | 3292, 2915, 2750, 1921, 1605, 1562, 1384, 1234, 1138, 1016, 942, 769, 532 |
1b | White solid | 83.7 | 121.6—122.9 | 13.40(s, 1H), 5.50(s, 2H), 2.60(t, J=7.5 Hz, 2H), 1.65—1.61(m, 2H), 1.29—1.25(m, 12H), 0.85(t, J=6.7 Hz, 3H) | 3448, 2932, 2824, 1679, 1583, 1434, 1248, 1227, 1185, 1057, 954, 778, 524 |
1c | White solid | 79.3 | 120.2—122.0 | 13.39(s, 1H), 5.42(s, 2H), 2.60(t, J=7.5 Hz, 2H), 1.65—1.59(m, 2H), 1.28—1.24(m, 16H), 0.79(t, J=6.6 Hz, 3H) | 3386, 2901, 2846, 2587, 1621, 1578, 1447, 1368, 1304, 1215, 1131, 1076, 815 |
1d | White solid | 81.8 | 118.3—119.5 | 13.38(s, 1H), 5.48(s, 2H), 2.60(t, J=7.5 Hz, 2H), 1.65—1.60(m, 2H), 1.29—1.24(m, 20H), 0.86(t, J=6.5 Hz, 3H) | 3401, 2935, 2825, 2446, 1624, 1427, 1325, 1247, 1164, 1025, 964, 805, 653 |
1e | White solid | 78.0 | 108.8—110.0 | 13.40(s, 1H), 5.46(s, 2H), 2.56(t, J=7.5 Hz, 2H), 1.63—1.60(m, 2H), 1.28—1.23(m, 24H), 0.86(t, J=6.5 Hz, 3H) | 3378, 2834, 2815, 2545, 1621, 1454, 1425, 1326, 1314, 1224, 1152, 1034, 852 |
1f | White solid | 75.3 | 110.2—112.1 | 13.32(s, 1H), 5.45(s, 2H), 2.56(t, J=7.4 Hz, 2H), 1.65—1.60(m, 2H), 1.29—1.23(m, 28H), 0.85(t, J=6.8 Hz, 3H) | 3443, 2852, 2625, 1615, 1545, 1434, 1326, 1232, 1215, 1105, 946, 775 |
1g | White solid | 84.5 | 204.0—205.3* | 14.61(s, 1H), 7.89(d, J=7.4 Hz, 2H), 7.66—7.58(m, 3H), 5.51(s, 2H) | 3425, 3320, 3114, 1659, 1598, 1460, 1356, 1425, 1108, 956, 855, 767, 700 |
Table 1 Appearance, yields, melting points, 1H NMR and IR data for compounds 1
Compd. | Appearance | Yield(%) | m. p./℃ | 1 H NMR(500 MHz, DMSO-d6), δ | IR(KBr), |
---|---|---|---|---|---|
1a | White solid | 85.0 | 112.1—113.7 | 13.39(s, 1H), 5.50(s, 2H), 2.62(t, J=7.5 Hz, 2H), 1.65—1.60(m, 2H), 1.30—1.25(m, 8H), 0.87(t, J=6.8 Hz, 3H) | 3292, 2915, 2750, 1921, 1605, 1562, 1384, 1234, 1138, 1016, 942, 769, 532 |
1b | White solid | 83.7 | 121.6—122.9 | 13.40(s, 1H), 5.50(s, 2H), 2.60(t, J=7.5 Hz, 2H), 1.65—1.61(m, 2H), 1.29—1.25(m, 12H), 0.85(t, J=6.7 Hz, 3H) | 3448, 2932, 2824, 1679, 1583, 1434, 1248, 1227, 1185, 1057, 954, 778, 524 |
1c | White solid | 79.3 | 120.2—122.0 | 13.39(s, 1H), 5.42(s, 2H), 2.60(t, J=7.5 Hz, 2H), 1.65—1.59(m, 2H), 1.28—1.24(m, 16H), 0.79(t, J=6.6 Hz, 3H) | 3386, 2901, 2846, 2587, 1621, 1578, 1447, 1368, 1304, 1215, 1131, 1076, 815 |
1d | White solid | 81.8 | 118.3—119.5 | 13.38(s, 1H), 5.48(s, 2H), 2.60(t, J=7.5 Hz, 2H), 1.65—1.60(m, 2H), 1.29—1.24(m, 20H), 0.86(t, J=6.5 Hz, 3H) | 3401, 2935, 2825, 2446, 1624, 1427, 1325, 1247, 1164, 1025, 964, 805, 653 |
1e | White solid | 78.0 | 108.8—110.0 | 13.40(s, 1H), 5.46(s, 2H), 2.56(t, J=7.5 Hz, 2H), 1.63—1.60(m, 2H), 1.28—1.23(m, 24H), 0.86(t, J=6.5 Hz, 3H) | 3378, 2834, 2815, 2545, 1621, 1454, 1425, 1326, 1314, 1224, 1152, 1034, 852 |
1f | White solid | 75.3 | 110.2—112.1 | 13.32(s, 1H), 5.45(s, 2H), 2.56(t, J=7.4 Hz, 2H), 1.65—1.60(m, 2H), 1.29—1.23(m, 28H), 0.85(t, J=6.8 Hz, 3H) | 3443, 2852, 2625, 1615, 1545, 1434, 1326, 1232, 1215, 1105, 946, 775 |
1g | White solid | 84.5 | 204.0—205.3* | 14.61(s, 1H), 7.89(d, J=7.4 Hz, 2H), 7.66—7.58(m, 3H), 5.51(s, 2H) | 3425, 3320, 3114, 1659, 1598, 1460, 1356, 1425, 1108, 956, 855, 767, 700 |
Compd. | Appearance | Yield(%) | m. p. /℃ | HRMS(positive-SIMS)[M+H]+, m/z(calcd.) |
---|---|---|---|---|
2a | Yellow solid | 68.9 | 160.0—161.5 | 523.2421(523.2426) |
2b | Yellow solid | 82.1 | 159.4—161.1 | 579.3058(579.3052) |
2c | Yellow solid | 74.2 | 156.3—158.2 | 635.3674(635.3678) |
2d | Yellow solid | 64.6 | 157.4—160.0 | 691.4300(691.4304) |
2e | Yellow solid | 68.7 | 161.6—163.1 | 747.4933(747.4930) |
2f | Yellow solid | 70.8 | 162.7—164.5 | 803.5559(803.5556) |
2g | Yellow solid | 70.3 | 240.2—242.0 | 479.0852(479.0860) |
3a | Yellow solid | 63.4 | 210.3—212.0 | 538.2538(538.2535) |
3b | Yellow solid | 65.3 | 208.6—210.8 | 594.3158(594.3161) |
3c | Yellow solid | 67.9 | 205.5—207.0 | 650.3782(650.3787) |
3d | Yellow solid | 58.1 | 209.0—212.0 | 706.4410(706.4413) |
3e | Yellow solid | 55.0 | 210.1—211.5 | 762.5035(762.5039) |
3f | Yellow solid | 63.0 | 212.3—214.2 | 818.5669(818.5665) |
3g | Yellow solid | 60.3 | 250.3—251.7 | 494.0974(494.0970) |
Table 2 Appearance, yields, melting points and HRMS data for compounds 2 and 3
Compd. | Appearance | Yield(%) | m. p. /℃ | HRMS(positive-SIMS)[M+H]+, m/z(calcd.) |
---|---|---|---|---|
2a | Yellow solid | 68.9 | 160.0—161.5 | 523.2421(523.2426) |
2b | Yellow solid | 82.1 | 159.4—161.1 | 579.3058(579.3052) |
2c | Yellow solid | 74.2 | 156.3—158.2 | 635.3674(635.3678) |
2d | Yellow solid | 64.6 | 157.4—160.0 | 691.4300(691.4304) |
2e | Yellow solid | 68.7 | 161.6—163.1 | 747.4933(747.4930) |
2f | Yellow solid | 70.8 | 162.7—164.5 | 803.5559(803.5556) |
2g | Yellow solid | 70.3 | 240.2—242.0 | 479.0852(479.0860) |
3a | Yellow solid | 63.4 | 210.3—212.0 | 538.2538(538.2535) |
3b | Yellow solid | 65.3 | 208.6—210.8 | 594.3158(594.3161) |
3c | Yellow solid | 67.9 | 205.5—207.0 | 650.3782(650.3787) |
3d | Yellow solid | 58.1 | 209.0—212.0 | 706.4410(706.4413) |
3e | Yellow solid | 55.0 | 210.1—211.5 | 762.5035(762.5039) |
3f | Yellow solid | 63.0 | 212.3—214.2 | 818.5669(818.5665) |
3g | Yellow solid | 60.3 | 250.3—251.7 | 494.0974(494.0970) |
Compd. | 1 H NMR(500 MHz, DMSO-d6), δ | 13 C NMR(125 MHz, DMSO-d6 ), δ | IR(KBr), |
---|---|---|---|
2a | 8.06(s, 4H), 3.18(t, J=7.6 Hz, 4H), 1.98—1.92(m, 4H), 1.51—1.44(m, 4H), 1.38—1.35(m, 4H), 1.29—1.25(m, 8H), 0.88(t, J=7.1 Hz, 6H) | 161.32, 155.39, 145.31, 132.50, 127.02, 31.78, 29.20, 23.21, 22.66, 22.46, 14.05 | 3426, 3322, 3158, 2936, 2846, 1673, 1599, 1465, 1391, 1153, 1063, 959, 841 |
2b | 8.06(s, 4H), 3.15(t, J=7.6 Hz, 4H), 1.96—1.91(m, 4H), 1.50—1.44(m, 4H), 1.42—1.34(m, 4H), 1.27—1.22(m, 16H), 0.87(t, J=7.1 Hz, 6H) | 161.17, 155.38, 145.20, 132.28, 127.14, 31.77, 29.23, 23.19, 22.73, 22.28, 14.01 | 3420, 3322, 3138, 2924, 2835, 1646, 1578, 1452, 1401, 1156, 959, 852 |
2c | 8.06(s, 4H), 3.15(t, J=7.5 Hz, 4H), 1.96—1.91(m, 4H), 1.51—1.41(m, 4H), 1.32—1.26(m, 28H), 0.87(t, J=6.6 Hz, 6H) | 161.21, 155.36, 145.31, 132.03, 126.96, 31.78, 29.12, 23.23, 22.76, 22.51, 14.10 | 3423, 3330, 3117, 2920, 2856, 1647, 1569, 1456, 1415, 1148, 1067, 944, 827 |
2d | 8.06(s, 4H), 3.15(t, J=7.1 Hz, 4H), 1.94—1.90(m, 4H), 1.48—1.45(m, 4H), 1.36—1.35(m, 4H), 1.27—1.25(m, 32H), 0.87(t, J=6.5 Hz, 6H) | 161.28, 155.37, 145.29, 132.72, 127.79, 31.71, 29.23, 23.38, 22.68, 22.45, 14.17 | 3438, 3222, 3131, 2921, 2842, 1648, 1607, 1459, 1386, 1165, 1064, 942, 832 |
2e | 8.06(s, 4H), 3.15(t, J=7.5 Hz, 4H), 1.97—1.91(m, 4H), 1.53—1.44(m, 4H), 1.37—1.26(m, 44H), 0.87(t, J=6.6 Hz, 6H) | 161.14, 155.16, 144.97, 132.52, 127.42, 31.78, 29.16, 23.21, 22.68, 22.46, 14.11 | 3437, 3304, 3117, 2920, 2842, 1653, 1589, 1456, 1375, 1154, 1015, 937, 825 |
2f | 8.06(s, 4H), 3.15(t, J=7.5 Hz, 4H), 1.97—1.91(m, 4H), 1.52—1.44(m, 4H), 1.38—1.35(m, 4H), 1.29—1.25(m, 48H), 0.88(t, J=6.7 Hz, 6H) | 160.47, 155.37, 145.92, 132.32, 127.20, 31.81, 29.14, 23.22, 22.76, 22.53, 14.04 | 3441, 3323, 3145, 2927, 2847, 1652, 1458, 1387, 1168, 1057, 948, 857, 714 |
2g | 8.30(m, 4H), 7.85(d, J=7.4 Hz, 4H), 7.50—7.45(m, 6H) | 160.59, 155.13, 143.31, 133.47, 130.62, 129.16, 128.03, 127.45 | 3410, 3218, 2845, 2820, 1630, 1550, 1500, 1438, 1215, 944, 885, 765, 655 |
3a | 7.68(d, J=8.3 Hz, 1H), 7.56(s, 1H), 7.21(d, J=8.2 Hz, 1H), 7.09(s, 2H), 3.10(t, J=7.4 Hz, 2H), 3.05(t, J=7.5 Hz, 2H), 1.84—1.79(m, 4H), 1.38—1.25(m, 16H), 0.87—0.83(m, 6H) | 171.13, 160.32, 155.36, 145.73, 145.13, 134.32, 128.81, 123.09, 118.02, 114.56, 31.69, 29.22, 23.27, 22.68, 22.37, 14.04 | 3424, 3335, 3178, 2935, 2841, 1608, 1456, 1378, 1156, 1057, 935, 846 |
3b | 7.66(d, J=8.3 Hz, 1H), 7.55(s, 1H), 7.19(d, J=8.2 Hz, 1H), 7.08(s, 2H), 3.10(t, J=7.4 Hz, 2H), 3.05(t, J=7.5 Hz, 2H), 1.83—1.79(m, 4H),1.39—1.26(m, 24H), 0.87—0.82(m, 6H) | 171.04, 160.26, 155.36, 145.81, 145.13, 134.34, 128.82, 123.23, 118.01, 114.58, 31.71, 29.20, 23.38, 22.71, 22.41, 14.04 | 3413, 3320, 3154, 2933, 2865, 1617, 1456, 1390, 1160, 1063, 905, 850 |
3c | 7.72(d, J=8.3 Hz, 1H), 7.58(s, 1H), 7.23(d, J=10.0 Hz, 1H), 7.08(s, 1H), 3.09(t, J=7.5 Hz, 2H), 3.04(t, J=7.4 Hz, 2H), 1.83—1.78(m, 4H), 1.35—1.21(m, 32H), 0.85—0.83(m, 6H) | 171.36, 160.33, 155.41, 145.71, 144.95, 134.28, 128.76, 123.12, 118.41, 114.59, 31.72, 29.17, 23.28, 22.71, 22.30, 14.16 | 3434, 3307, 3125, 2935, 2805, 1614, 1456, 1414, 1161, 1026, 934, 851 |
3d | 7.68(d, J=8.3 Hz, 1H), 7.50(s, 1H), 7.20(d, J=8.2 Hz, 1H), 7.08(s, 2H), 3.10(t, J=7.4 Hz, 2H), 3.05(t, J=7.5 Hz, 2H), 1.85—1.79(m, 4H), 1.38—1.26(m, 40H), 0.87—0.82(m, 6H) | 171.18, 160.31, 155.27, 145.68, 145.12, 134.19, 128.81, 123.13, 118.00, 114.62, 31.67, 29.14, 23.31, 22.69, 22.51, 14.03 | 3438, 3325, 2917, 2837, 1645, 1608, 1458, 1378, 1198, 1057, 915, 847 |
3e | 7.72(d, J=8.3 Hz, 1H), 7.57(s, 1H), 7.24(d, J=10.0 Hz, 1H), 7.08(s, 1H), 3.09(t, J=7.5 Hz, 2H), 3.05(t, J=7.4 Hz, 2H), 1.84—1.78(m, 4H), 1.37—1.25(m, 48H), 0.83—0.81(m, 6H) | 171.21, 160.28, 155.41, 145.67, 145.30, 134.31, 128.73, 123.13, 117.98, 114.63, 31.71, 29.16, 23.31, 22.80, 22.45, 14.15 | 3437, 3298, 3078, 2914, 2784, 1654, 1605, 1434, 1154, 1034, 951, 838 |
3f | 7.68(d, J=8.3 Hz, 1H), 7.55(s, 1H), 7.17(d, J=8.3 Hz, 1H), 7.08(s, 2H), 3.09(t, J=7.4 Hz, 2H), 3.04(t, J=7.4 Hz, 2H), 1.81—1.79(m, 4H), 1.35—1.26(m, 56H), 0.86—0.82(m, 6H) | 171.26, 160.31, 155.24, 145.63, 145.14, 134.29, 128.78, 123.30, 118.12, 114.58, 31.71, 29.12, 23.26, 22.72, 22.46, 14.03 | 3324, 3152, 2921, 2845, 1672, 1598, 1452, 1168, 1058, 949, 848, 718 |
3g | 8.25—8.15(m, 4H), 7.75(d, J=7.1 Hz, 1H), 7.63(d, J=7.5 Hz, 1H), 7.51—7.45(m, 7H), 6.27(s, 2H) | 171.13, 161.61, 155.08, 145.73, 143.31, 134.28, 131.08, 130.62, 129.23, 128.80, 127.47, 123.12, 118.07, 114.65 | 3320, 3120, 2923, 2856, 1658, 1599, 1480, 1410, 1205, 955, 845, 766, 680 |
Table 3 1H NMR, 13C NMR and IR data for compounds 2 and 3
Compd. | 1 H NMR(500 MHz, DMSO-d6), δ | 13 C NMR(125 MHz, DMSO-d6 ), δ | IR(KBr), |
---|---|---|---|
2a | 8.06(s, 4H), 3.18(t, J=7.6 Hz, 4H), 1.98—1.92(m, 4H), 1.51—1.44(m, 4H), 1.38—1.35(m, 4H), 1.29—1.25(m, 8H), 0.88(t, J=7.1 Hz, 6H) | 161.32, 155.39, 145.31, 132.50, 127.02, 31.78, 29.20, 23.21, 22.66, 22.46, 14.05 | 3426, 3322, 3158, 2936, 2846, 1673, 1599, 1465, 1391, 1153, 1063, 959, 841 |
2b | 8.06(s, 4H), 3.15(t, J=7.6 Hz, 4H), 1.96—1.91(m, 4H), 1.50—1.44(m, 4H), 1.42—1.34(m, 4H), 1.27—1.22(m, 16H), 0.87(t, J=7.1 Hz, 6H) | 161.17, 155.38, 145.20, 132.28, 127.14, 31.77, 29.23, 23.19, 22.73, 22.28, 14.01 | 3420, 3322, 3138, 2924, 2835, 1646, 1578, 1452, 1401, 1156, 959, 852 |
2c | 8.06(s, 4H), 3.15(t, J=7.5 Hz, 4H), 1.96—1.91(m, 4H), 1.51—1.41(m, 4H), 1.32—1.26(m, 28H), 0.87(t, J=6.6 Hz, 6H) | 161.21, 155.36, 145.31, 132.03, 126.96, 31.78, 29.12, 23.23, 22.76, 22.51, 14.10 | 3423, 3330, 3117, 2920, 2856, 1647, 1569, 1456, 1415, 1148, 1067, 944, 827 |
2d | 8.06(s, 4H), 3.15(t, J=7.1 Hz, 4H), 1.94—1.90(m, 4H), 1.48—1.45(m, 4H), 1.36—1.35(m, 4H), 1.27—1.25(m, 32H), 0.87(t, J=6.5 Hz, 6H) | 161.28, 155.37, 145.29, 132.72, 127.79, 31.71, 29.23, 23.38, 22.68, 22.45, 14.17 | 3438, 3222, 3131, 2921, 2842, 1648, 1607, 1459, 1386, 1165, 1064, 942, 832 |
2e | 8.06(s, 4H), 3.15(t, J=7.5 Hz, 4H), 1.97—1.91(m, 4H), 1.53—1.44(m, 4H), 1.37—1.26(m, 44H), 0.87(t, J=6.6 Hz, 6H) | 161.14, 155.16, 144.97, 132.52, 127.42, 31.78, 29.16, 23.21, 22.68, 22.46, 14.11 | 3437, 3304, 3117, 2920, 2842, 1653, 1589, 1456, 1375, 1154, 1015, 937, 825 |
2f | 8.06(s, 4H), 3.15(t, J=7.5 Hz, 4H), 1.97—1.91(m, 4H), 1.52—1.44(m, 4H), 1.38—1.35(m, 4H), 1.29—1.25(m, 48H), 0.88(t, J=6.7 Hz, 6H) | 160.47, 155.37, 145.92, 132.32, 127.20, 31.81, 29.14, 23.22, 22.76, 22.53, 14.04 | 3441, 3323, 3145, 2927, 2847, 1652, 1458, 1387, 1168, 1057, 948, 857, 714 |
2g | 8.30(m, 4H), 7.85(d, J=7.4 Hz, 4H), 7.50—7.45(m, 6H) | 160.59, 155.13, 143.31, 133.47, 130.62, 129.16, 128.03, 127.45 | 3410, 3218, 2845, 2820, 1630, 1550, 1500, 1438, 1215, 944, 885, 765, 655 |
3a | 7.68(d, J=8.3 Hz, 1H), 7.56(s, 1H), 7.21(d, J=8.2 Hz, 1H), 7.09(s, 2H), 3.10(t, J=7.4 Hz, 2H), 3.05(t, J=7.5 Hz, 2H), 1.84—1.79(m, 4H), 1.38—1.25(m, 16H), 0.87—0.83(m, 6H) | 171.13, 160.32, 155.36, 145.73, 145.13, 134.32, 128.81, 123.09, 118.02, 114.56, 31.69, 29.22, 23.27, 22.68, 22.37, 14.04 | 3424, 3335, 3178, 2935, 2841, 1608, 1456, 1378, 1156, 1057, 935, 846 |
3b | 7.66(d, J=8.3 Hz, 1H), 7.55(s, 1H), 7.19(d, J=8.2 Hz, 1H), 7.08(s, 2H), 3.10(t, J=7.4 Hz, 2H), 3.05(t, J=7.5 Hz, 2H), 1.83—1.79(m, 4H),1.39—1.26(m, 24H), 0.87—0.82(m, 6H) | 171.04, 160.26, 155.36, 145.81, 145.13, 134.34, 128.82, 123.23, 118.01, 114.58, 31.71, 29.20, 23.38, 22.71, 22.41, 14.04 | 3413, 3320, 3154, 2933, 2865, 1617, 1456, 1390, 1160, 1063, 905, 850 |
3c | 7.72(d, J=8.3 Hz, 1H), 7.58(s, 1H), 7.23(d, J=10.0 Hz, 1H), 7.08(s, 1H), 3.09(t, J=7.5 Hz, 2H), 3.04(t, J=7.4 Hz, 2H), 1.83—1.78(m, 4H), 1.35—1.21(m, 32H), 0.85—0.83(m, 6H) | 171.36, 160.33, 155.41, 145.71, 144.95, 134.28, 128.76, 123.12, 118.41, 114.59, 31.72, 29.17, 23.28, 22.71, 22.30, 14.16 | 3434, 3307, 3125, 2935, 2805, 1614, 1456, 1414, 1161, 1026, 934, 851 |
3d | 7.68(d, J=8.3 Hz, 1H), 7.50(s, 1H), 7.20(d, J=8.2 Hz, 1H), 7.08(s, 2H), 3.10(t, J=7.4 Hz, 2H), 3.05(t, J=7.5 Hz, 2H), 1.85—1.79(m, 4H), 1.38—1.26(m, 40H), 0.87—0.82(m, 6H) | 171.18, 160.31, 155.27, 145.68, 145.12, 134.19, 128.81, 123.13, 118.00, 114.62, 31.67, 29.14, 23.31, 22.69, 22.51, 14.03 | 3438, 3325, 2917, 2837, 1645, 1608, 1458, 1378, 1198, 1057, 915, 847 |
3e | 7.72(d, J=8.3 Hz, 1H), 7.57(s, 1H), 7.24(d, J=10.0 Hz, 1H), 7.08(s, 1H), 3.09(t, J=7.5 Hz, 2H), 3.05(t, J=7.4 Hz, 2H), 1.84—1.78(m, 4H), 1.37—1.25(m, 48H), 0.83—0.81(m, 6H) | 171.21, 160.28, 155.41, 145.67, 145.30, 134.31, 128.73, 123.13, 117.98, 114.63, 31.71, 29.16, 23.31, 22.80, 22.45, 14.15 | 3437, 3298, 3078, 2914, 2784, 1654, 1605, 1434, 1154, 1034, 951, 838 |
3f | 7.68(d, J=8.3 Hz, 1H), 7.55(s, 1H), 7.17(d, J=8.3 Hz, 1H), 7.08(s, 2H), 3.09(t, J=7.4 Hz, 2H), 3.04(t, J=7.4 Hz, 2H), 1.81—1.79(m, 4H), 1.35—1.26(m, 56H), 0.86—0.82(m, 6H) | 171.26, 160.31, 155.24, 145.63, 145.14, 134.29, 128.78, 123.30, 118.12, 114.58, 31.71, 29.12, 23.26, 22.72, 22.46, 14.03 | 3324, 3152, 2921, 2845, 1672, 1598, 1452, 1168, 1058, 949, 848, 718 |
3g | 8.25—8.15(m, 4H), 7.75(d, J=7.1 Hz, 1H), 7.63(d, J=7.5 Hz, 1H), 7.51—7.45(m, 7H), 6.27(s, 2H) | 171.13, 161.61, 155.08, 145.73, 143.31, 134.28, 131.08, 130.62, 129.23, 128.80, 127.47, 123.12, 118.07, 114.65 | 3320, 3120, 2923, 2856, 1658, 1599, 1480, 1410, 1205, 955, 845, 766, 680 |
Compd. | Cdc25Ba | PTP1Bb | ||
---|---|---|---|---|
Inhibition(%)c | IC50/(μg·mL-1)d | Inhibition(%)c | IC50/(μg·mL-1)d | |
2a | 98.68±0.15 | NA | 84.39±4.91 | NA |
2b | 95.43±0.67 | NA | 62.49±3.71 | NA |
2c | 24.77±1.33 | NA | 34.16±1.87 | NA |
2d | 95.93±0.04 | NA | 40.98±0.48 | NA |
2e | 77.86±0.10 | NA | 9.68±7.30 | NA |
2f | 73.64±6.99 | 3.45±0.60 | 3.93±3.78 | NA |
2g | 7.29±9.63 | NA | 60.44±8.95 | NA |
3a | 99.90±0.03 | 0.69±0.10 | 88.85±4.41 | 0.98±0.13 |
3b | 1.98±0.28 | NA | 76.73±1.75 | 2.00±0.16 |
3c | 2.51±1.28 | NA | 82.89±2.30 | NA |
3d | 8.02±1.34 | NA | 74.48±0.10 | NA |
3e | 9.18±2.45 | NA | 61.77±4.98 | NA |
3f | 6.70±2.47 | NA | 62.89±0.64 | NA |
3g | 99.88±0.03 | 1.52±0.19 | 84.57±3.66 | NA |
Table 4 Inhibition of target compounds against Cdc25B and PTP1B
Compd. | Cdc25Ba | PTP1Bb | ||
---|---|---|---|---|
Inhibition(%)c | IC50/(μg·mL-1)d | Inhibition(%)c | IC50/(μg·mL-1)d | |
2a | 98.68±0.15 | NA | 84.39±4.91 | NA |
2b | 95.43±0.67 | NA | 62.49±3.71 | NA |
2c | 24.77±1.33 | NA | 34.16±1.87 | NA |
2d | 95.93±0.04 | NA | 40.98±0.48 | NA |
2e | 77.86±0.10 | NA | 9.68±7.30 | NA |
2f | 73.64±6.99 | 3.45±0.60 | 3.93±3.78 | NA |
2g | 7.29±9.63 | NA | 60.44±8.95 | NA |
3a | 99.90±0.03 | 0.69±0.10 | 88.85±4.41 | 0.98±0.13 |
3b | 1.98±0.28 | NA | 76.73±1.75 | 2.00±0.16 |
3c | 2.51±1.28 | NA | 82.89±2.30 | NA |
3d | 8.02±1.34 | NA | 74.48±0.10 | NA |
3e | 9.18±2.45 | NA | 61.77±4.98 | NA |
3f | 6.70±2.47 | NA | 62.89±0.64 | NA |
3g | 99.88±0.03 | 1.52±0.19 | 84.57±3.66 | NA |
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