高等学校化学学报 ›› 2017, Vol. 38 ›› Issue (10): 1764.doi: 10.7503/cjcu20170239
张成路(), 孙晓娜, 李传银, 蔡继颖, 王静, 李益政, 王华玉
收稿日期:
2017-04-19
出版日期:
2017-10-10
发布日期:
2017-09-08
作者简介:
联系人简介: 张成路, 男, 博士, 教授, 主要从事有机合成合成方面的研究. E-mail:基金资助:
ZHANG Chenglu*(), SUN Xiaona, LI Chuanyin, CAI Jiying, WANG Jing, LI Yizheng, WANG Huayu
Received:
2017-04-19
Online:
2017-10-10
Published:
2017-09-08
Contact:
ZHANG Chenglu
E-mail:zhangchenglu@lnnu.edu.cn
Supported by:
摘要:
设计合成了18个以吡唑桥连1,3,4-噁二唑和1,3,5-三嗪的新型多杂环分子[7A(a~f), 7B(a~f)和7C(a~f)]; 通过红外光谱(IR)、 核磁共振波谱(NMR)和高分辨质谱(HRMS)等对目标分子进行了结构表征; 评价了目标分子对蛋白酪氨酸磷酸酯酶1B(PTP1B)和细胞分裂周期25磷酸酯酶B(Cdc25B)的抑制活性. 结果表明, 所有目标分子对PTP1B和Cdc25B均有较好的抑制活性, 其中, 9个目标分子表现出优异的PTP1B和Cdc25B抑制效果, IC50值低于齐墩果酸(PTP1B抑制活性测试参照物)和正钒酸钠(Cdc25B抑制活性测试阳性参照物), 有望成为潜在的PTP1B和Cdc25B抑制剂.
中图分类号:
TrendMD:
张成路, 孙晓娜, 李传银, 蔡继颖, 王静, 李益政, 王华玉. 新型1-(1,3,5-三嗪-6-基)-3-甲基-4-(5-苯基-1,3,4-噁二唑-2-基)吡唑的合成及活性评价. 高等学校化学学报, 2017, 38(10): 1764.
ZHANG Chenglu, SUN Xiaona, LI Chuanyin, CAI Jiying, WANG Jing, LI Yizheng, WANG Huayu. Synthesis and Bioactivities Evaluation of Novel 1-(1,3,5-Triazin-6-yl)-3-methyl-4-(5-phenyl-1,3,4-oxadiazol-2-yl) pyrazole†. Chem. J. Chinese Universities, 2017, 38(10): 1764.
Compd. | m. p.(Ref. )/℃ | Compd. | m. p.(Ref. )/℃ |
---|---|---|---|
1A | 173.1—173.9(173—174[ | 1C | 112.9—113.7(112—115[ |
1B | 114.6—115.5(114—117[ | 2A | 171.7—172.6(171—173[ |
Table 1 Melting points for compounds 1A—1C and 2A
Compd. | m. p.(Ref. )/℃ | Compd. | m. p.(Ref. )/℃ |
---|---|---|---|
1A | 173.1—173.9(173—174[ | 1C | 112.9—113.7(112—115[ |
1B | 114.6—115.5(114—117[ | 2A | 171.7—172.6(171—173[ |
Compd. | Appearance | Yield(%) | m. p./℃ | HRMS(positive-SIMS) m/z(calcd. ), [M+H]+ | IR(KBr), |
---|---|---|---|---|---|
2B | White solid | 75 | 192.3—193.2 | 278.2023(278.2015) | 3350, 3288, 2940, 1627, 1105 |
2C | White solid | 78 | 202.6—203.1 | 250.1711(250.1702) | 3352, 3285, 2933, 1625, 1110 |
3A | White solid | 88 | 78.6—79.5 | 394.2128(394.2125) | 3332, 2940, 2850, 1740, 1690, 1375, 1250 |
3B | White solid | 86 | 86.8—87.2 | 390.2546(390.2539) | 3312, 2935, 2850, 1728, 1680, 1370, 1250 |
3C | White solid | 71 | 125.0—126.0 | 362.2235(362.2226) | 3340, 2940, 2860, 1735, 1670, 1375, 1252 |
4A | Yellow solid | 55 | 230.2—230.9 | 404.1962(404.1968) | 3030, 2962, 1740, 1690, 1634, 1375, 1250, |
1110 | |||||
4B | Yellow solid | 61 | 137.1—138.0 | 400.2375(400.2383) | 3031, 2951, 1730, 1670, 1630, 1370, 1230, |
1110 | |||||
4C | Yellow solid | 60 | 176.6—177.1 | 372.2079(372.2070) | 3030, 2960, 1740, 1675, 1630, 1370, 1250, |
1105 | |||||
5A | Yellow solid | 70 | >300 | 376.1662(376.1655) | 3436, 3031, 2950, 1740, 1682, 1630, 1380, |
1250, 1105 | |||||
5B | Yellow solid | 79 | >300 | 372.2078(372.2070) | 3440, 3030, 2947, 1760, 1680, 1635, 1380, |
1105 | |||||
5C | Yellow solid | 70 | 278.9—279.7 | 344.1766(344.1757) | 3430, 3035, 2940, 1745, 1670, 1632, 1375, |
1110 | |||||
Compd. | Appearance | Yield(%) | m. p./℃ | HRMS(positive-SIMS) m/z(calcd. ), [M+H]+ | IR(KBr), |
7Aa | Yellow solid | 67 | 170.1—170.9 | 476.2080(476.2085) | 3030, 2945, 1634, 1601,1555, 1429, 1380, |
1250,1097, 745 | |||||
7Ab | Yellow solid | 63 | 168.3—169.7 | 490.2237(490.2241) | 3031, 2930, 1640, 1610, 1541, 1438, 1375, |
1250, 1105, 838 | |||||
7Ac | Yellow solid | 60 | 280.1—280.9 | 492.2030(492.2024) | 3280, 3030, 2935, 1642, 1621, 1545, 1432, |
1380, 1230, 1105, 840 | |||||
7Ad | Brownish solid | 61 | 163.4—164.6 | 506.2186(506.2179) | 3030, 2935, 1630, 1601, 1550, 1450, 1380, |
1200, 1100, 841 | |||||
7Ae | Yellow solid | 58 | 195.6—196.4 | 510.1691(510.1699) | 3030, 2940, 1635, 1613, 1545, 1431, 1380, |
1210, 1100, 824 | |||||
7Af | Yellow solid | 51 | 202.9—204.1 | 491.2189(491.2198) | 3426, 3030, 2940, 1630, 1610, 1540, 1425, |
1380, 1210, 1092, 835 | |||||
7Ba | Brownish solid | 62 | 180.0—181.8 | 472.2495(472.2488) | 3030, 2935, 1630, 1610, 1545, 1441, 1375, |
1240, 1090, 709 | |||||
7Bb | Yellow solid | 62 | 198.7—199.3 | 486.2652(486.2649) | 3030, 2930, 1635, 1615, 1540, 1440, 1375, |
1245, 1100, 845 | |||||
7Bc | Brownish solid | 50 | 230.2—231.7 | 488.2444(488.2436) | 3260, 3030, 2940, 1635, 1625, 1540, 1445, |
1380, 1200, 1102, 825 | |||||
7Bd | Yellow solid | 68 | 240.7—242.0 | 502.2601(502.2606) | 3030, 2940, 1631, 1615, 1545, 1438, 1375, |
1225, 1095, 831 | |||||
7Be | Yellow solid | 50 | 165.3—166.1 | 506.2105(506.2114) | 3030, 2930, 1630, 1610, 1540, 1445, 1375, |
1225, 1100, 811 | |||||
7Bf | Yellow solid | 47 | 232.8—233.8 | 487.2604(487.2607) | 3425, 3030, 2940, 1635, 1612, 1543, 1445, |
1375, 1220, 1105, 836 | |||||
7Ca | Brownish solid | 67 | 138.3—139.9 | 444.2182(444.2174) | 3035, 2930, 1635, 1612, 1543, 1435, 1375, |
1235, 1105, 735 | |||||
7Cb | Yellow solid | 52 | 171.1—172.0 | 458.2339(458.2347) | 3030, 2930, 1651, 1610, 1540, 1430, 1375, |
1220, 1110, 839 | |||||
7Cc | Yellow solid | 40 | 212.2—213.1 | 460.2131(460.2139) | 3265, 3030, 2940, 1635, 1625, 1540, 1438, |
1380, 1229, 1105, 831 | |||||
7Cd | Brownish solid | 42 | 222.4—223.4 | 474.2288(474.2292) | 3030, 2940, 1645, 1612, 1540, 1440, 1375, |
1210, 1110, 845 | |||||
7Ce | Yellow solid | 39 | 175.9—176.5 | 478.1792(478.1788) | 3030, 2945, 1635, 1610, 1535, 1445, 1380, |
1205, 1105, 814 | |||||
7Cf | Yellow solid | 38 | 222.6—223.2 | 459.2291(459.2298) | 3424, 3030, 2945, 1650, 1615, 1530, 1445, |
1375, 1240, 1115, 845 |
Table 2 Appearance, yields, melting points, IR and HRMS data for compounds 2B, 2C, 3A—3C,4A—4C, 5A—5C, 7A(a—f), 7B(a—f) and 7C(a—f)
Compd. | Appearance | Yield(%) | m. p./℃ | HRMS(positive-SIMS) m/z(calcd. ), [M+H]+ | IR(KBr), |
---|---|---|---|---|---|
2B | White solid | 75 | 192.3—193.2 | 278.2023(278.2015) | 3350, 3288, 2940, 1627, 1105 |
2C | White solid | 78 | 202.6—203.1 | 250.1711(250.1702) | 3352, 3285, 2933, 1625, 1110 |
3A | White solid | 88 | 78.6—79.5 | 394.2128(394.2125) | 3332, 2940, 2850, 1740, 1690, 1375, 1250 |
3B | White solid | 86 | 86.8—87.2 | 390.2546(390.2539) | 3312, 2935, 2850, 1728, 1680, 1370, 1250 |
3C | White solid | 71 | 125.0—126.0 | 362.2235(362.2226) | 3340, 2940, 2860, 1735, 1670, 1375, 1252 |
4A | Yellow solid | 55 | 230.2—230.9 | 404.1962(404.1968) | 3030, 2962, 1740, 1690, 1634, 1375, 1250, |
1110 | |||||
4B | Yellow solid | 61 | 137.1—138.0 | 400.2375(400.2383) | 3031, 2951, 1730, 1670, 1630, 1370, 1230, |
1110 | |||||
4C | Yellow solid | 60 | 176.6—177.1 | 372.2079(372.2070) | 3030, 2960, 1740, 1675, 1630, 1370, 1250, |
1105 | |||||
5A | Yellow solid | 70 | >300 | 376.1662(376.1655) | 3436, 3031, 2950, 1740, 1682, 1630, 1380, |
1250, 1105 | |||||
5B | Yellow solid | 79 | >300 | 372.2078(372.2070) | 3440, 3030, 2947, 1760, 1680, 1635, 1380, |
1105 | |||||
5C | Yellow solid | 70 | 278.9—279.7 | 344.1766(344.1757) | 3430, 3035, 2940, 1745, 1670, 1632, 1375, |
1110 | |||||
Compd. | Appearance | Yield(%) | m. p./℃ | HRMS(positive-SIMS) m/z(calcd. ), [M+H]+ | IR(KBr), |
7Aa | Yellow solid | 67 | 170.1—170.9 | 476.2080(476.2085) | 3030, 2945, 1634, 1601,1555, 1429, 1380, |
1250,1097, 745 | |||||
7Ab | Yellow solid | 63 | 168.3—169.7 | 490.2237(490.2241) | 3031, 2930, 1640, 1610, 1541, 1438, 1375, |
1250, 1105, 838 | |||||
7Ac | Yellow solid | 60 | 280.1—280.9 | 492.2030(492.2024) | 3280, 3030, 2935, 1642, 1621, 1545, 1432, |
1380, 1230, 1105, 840 | |||||
7Ad | Brownish solid | 61 | 163.4—164.6 | 506.2186(506.2179) | 3030, 2935, 1630, 1601, 1550, 1450, 1380, |
1200, 1100, 841 | |||||
7Ae | Yellow solid | 58 | 195.6—196.4 | 510.1691(510.1699) | 3030, 2940, 1635, 1613, 1545, 1431, 1380, |
1210, 1100, 824 | |||||
7Af | Yellow solid | 51 | 202.9—204.1 | 491.2189(491.2198) | 3426, 3030, 2940, 1630, 1610, 1540, 1425, |
1380, 1210, 1092, 835 | |||||
7Ba | Brownish solid | 62 | 180.0—181.8 | 472.2495(472.2488) | 3030, 2935, 1630, 1610, 1545, 1441, 1375, |
1240, 1090, 709 | |||||
7Bb | Yellow solid | 62 | 198.7—199.3 | 486.2652(486.2649) | 3030, 2930, 1635, 1615, 1540, 1440, 1375, |
1245, 1100, 845 | |||||
7Bc | Brownish solid | 50 | 230.2—231.7 | 488.2444(488.2436) | 3260, 3030, 2940, 1635, 1625, 1540, 1445, |
1380, 1200, 1102, 825 | |||||
7Bd | Yellow solid | 68 | 240.7—242.0 | 502.2601(502.2606) | 3030, 2940, 1631, 1615, 1545, 1438, 1375, |
1225, 1095, 831 | |||||
7Be | Yellow solid | 50 | 165.3—166.1 | 506.2105(506.2114) | 3030, 2930, 1630, 1610, 1540, 1445, 1375, |
1225, 1100, 811 | |||||
7Bf | Yellow solid | 47 | 232.8—233.8 | 487.2604(487.2607) | 3425, 3030, 2940, 1635, 1612, 1543, 1445, |
1375, 1220, 1105, 836 | |||||
7Ca | Brownish solid | 67 | 138.3—139.9 | 444.2182(444.2174) | 3035, 2930, 1635, 1612, 1543, 1435, 1375, |
1235, 1105, 735 | |||||
7Cb | Yellow solid | 52 | 171.1—172.0 | 458.2339(458.2347) | 3030, 2930, 1651, 1610, 1540, 1430, 1375, |
1220, 1110, 839 | |||||
7Cc | Yellow solid | 40 | 212.2—213.1 | 460.2131(460.2139) | 3265, 3030, 2940, 1635, 1625, 1540, 1438, |
1380, 1229, 1105, 831 | |||||
7Cd | Brownish solid | 42 | 222.4—223.4 | 474.2288(474.2292) | 3030, 2940, 1645, 1612, 1540, 1440, 1375, |
1210, 1110, 845 | |||||
7Ce | Yellow solid | 39 | 175.9—176.5 | 478.1792(478.1788) | 3030, 2945, 1635, 1610, 1535, 1445, 1380, |
1205, 1105, 814 | |||||
7Cf | Yellow solid | 38 | 222.6—223.2 | 459.2291(459.2298) | 3424, 3030, 2945, 1650, 1615, 1530, 1445, |
1375, 1240, 1115, 845 |
Compd. | 1H NMR(500 MHz), δ |
---|---|
2B | 6.10(s, 1H), 4.01(s, 2H), 3.75(t, J=4.9 Hz, 8H), 1.66—1.62(m, 12H) |
2C | 6.15(s, 1H), 3.99(s, 2H), 3.55—3.50(m, 8H), 2.05—1.89(m, 8H) |
3A | 7.68(s, 1H), 4.21(q, J=7.2 Hz, 2H), 3.79—3.71(m, 16H), 3.36(s, 2H), 2.27(s, 3H), 1.30(t, J=7.2 Hz, 3H) |
3B | 7.61(s, 1H), 4.17(q, J=7.1 Hz, 2H), 3.74(t, J=4.9 Hz, 8H), 3.34(s, 2H), 2.15(s, 3H), 1.63—1.50(m, 12H), 1.29 |
(t, J=7.1 Hz, 3H) | |
3C | 7.65(s, 1H), 4.17(q, J=7.1 Hz, 2H), 3.57—3.50(m, 8H), 3.43(s, 2H), 2.15(s, 3H), 2.0—1.86(m, 8H), 1.28(t, |
J=7.1 Hz, 3H) | |
4A | 8.86(s, 1H), 4.26(q, J=7.1 Hz, 2H), 3.81—3.65(m, 16H), 2.43(s, 3H), 1.31(t, J=7.1 Hz, 3H) |
4B | 9.04(s, 1H), 4.34(q, J=7.0 Hz, 2H), 3.71(t, J=4.9 Hz, 8H), 2.58(s, 3H), 1.67—1.53(m, 12H), 1.37(t, J=7.0 Hz, |
3H) | |
4C | 8.95(s, 1H), 4.31(q, J=7.1 Hz, 2H), 3.71—3.59(m, 8H), 2.56(s, 3H), 2.10—1.87(m, 8H), 1.37(t, J=7.1 Hz, 3H) |
5A | 12.63(s,1H), 8.92(s, 1H), 3.80—3.63(m, 16H), 2.41(s, 3H) |
5B | 12.38(s, 1H), 9.02(s, 1H), 3.74(t, J=5.0 Hz, 8H), 2.58(s, 3H), 1.63—1.52(m, 12H) |
5C | 12.11(s, 1H),9.06(s, 1H), 3.80—3.59(m, 8H), 2.58(s, 3H), 1.95—1.86(m, 8H) |
7Aa | 8.96(s, 1H), 7.87(d, J=7.5 Hz, 2H), 7.75—7.60(m, 3H), 3.79—3.62(m, 16H), 2.34(s, 3H) |
Compd. | 1H NMR(500 MHz), δ |
7Ab | 8.91(s, 1H), 8.01(d, J=8.5 Hz, 2H), 7.43(d, J=8.5 Hz, 2H), 3.74—3.60(m, 16H), 2.42(s, 3H), 2.33(s, 3H) |
7Ac | 10.17(s, 1H), 8.90(s, 1H), 8.12(d, J=8.5 Hz, 2H), 7.40(d, J=8.5 Hz, 2H), 3.79—3.62(m, 16H), 2.34(s, 3H) |
7Ad | 8.90(s, 1H), 8.06(d, J=8.6 Hz, 2H), 7.16(d, J=8.6 Hz, 2H), 3.85(s, 3H), 3.81—3.62(m, 16H), 2.39(s, 3H) |
7Ae | 8.90(s, 1H), 8.13(d, J=8.25 Hz, 2H), 7.62(d, J=8.3 Hz, 2H), 3.75—3.55(m, 16H), 2.41(s, 3H) |
7Af | 8.89(s, 1H), 7.90(d, J=8.2 Hz, 2H), 6.71(d, J=8.2 Hz, 2H), 5.60(s, 2H), 3.76—3.61(m, 16H), 2.40(s, 3H) |
7Ba | 8.82(s, 1H), 7.90(d, J=7.7 Hz, 2H), 7.64—7.51(m, 3H), 3.49(t, J=4.9 Hz, 8H), 2.36(s, 3H), 1.88—1.61(m, 12H) |
7Bb | 8.83(s, 1H), 8.01(d, J=8.5 Hz, 2H), 7.43(d, J=8.5 Hz, 2H), 3.74(t, J=4.9 Hz, 8H), 2.49(s, 3H), 2.36(s, 3H), |
1.61—1.51(m, 12H) | |
7Bc | 10.13(s, 1H), 8.83(s, 1H), 8.09(d, J=8.5 Hz, 2H), 7.23(d, J=8.5 Hz, 2H), 3.75(t, J=4.9 Hz, 8H), 2.41(s, 3H), |
1.61—1.51(m, 12H) | |
7Bd | 8.83(s, 1H), 8.04(d, J=8.6 Hz, 2H), 7.10(d, J=8.6 Hz, 2H), 3.80(s, 3H), 3.69(t, J=4.9 Hz, 8H), 2.41(s, 3H), |
1.60—1.50(m, 12H) | |
7Be | 8.83(s, 1H), 8.09(d, J=8.3 Hz, 2H), 7.57(d, J=8.3 Hz, 2H), 3.72(t, J=4.9 Hz, 8H), 2.40(s, 3H), 1.61—1.51 |
(m, 12H) | |
7Bf | 8.83(s, 1H), 7.81(d, J=8.2 Hz, 2H), 6.70(d, J=8.2 Hz, 2H), 5.61(s, 2H), 3.73(t, J=4.9 Hz, 8H), 2.41(s, 3H), |
1.60—1.52(m, 12H) | |
7Ca | 8.82(s, 1H), 7.91(d, J=7.5 Hz, 2H), 7.64—7.48(m, 3H), 3.56—3.46(m, 8H), 2.40(s, 3H), 1.92—1.82(m, 8H) |
7Cb | 8.82(s, 1H), 7.98(d, J=8.5 Hz, 2H), 7.39(d, J=8.5 Hz, 2H), 3.57—3.45(m, 8H), 2.42(s, 3H), 2.36(s, 3H), |
1.92—1.84(m, 8H) | |
7Cc | 10.12(s, 1H), 8.86(s, 1H), 7.99(d, J=8.5 Hz, 2H), 7.32(d, J=8.5 Hz, 2H), 3.56—3.45(m, 8H), 2.42(s, 3H), |
1.93—1.84(m, 8H) | |
7Cd | 8.82(s, 1H), 8.02(d, J=8.6 Hz, 2H), 7.16(d, J=8.6 Hz, 2H), 3.85(s, 3H), 3.53—3.48(m, 8H), 2.39(s, 3H), |
1.88—1.79(m, 8H) | |
7Ce | 8.82(s, 1H), 8.17(d, J=8.3 Hz, 2H), 7.60(d, J=8.3 Hz, 2H), 3.57—3.48(m, 8H), 2.42(s, 3H), 1.92—1.85(m, 8H) |
7Cf | 8.83(s, 1H), 7.89(d, J=8.2 Hz, 2H), 6.80(d, J=8.2 Hz, 2H), 5.60(s, 2H), 3.50—3.41(m, 8H), 2.42(s, 3H), |
1.87—1.80(m, 8H) |
Table 3 1H NMR for compounds 2B, 2C, 3A—3C, 4A—4C, 5A—5C, 7A(a—f), 7B(a—f) and 7C(a—f)*
Compd. | 1H NMR(500 MHz), δ |
---|---|
2B | 6.10(s, 1H), 4.01(s, 2H), 3.75(t, J=4.9 Hz, 8H), 1.66—1.62(m, 12H) |
2C | 6.15(s, 1H), 3.99(s, 2H), 3.55—3.50(m, 8H), 2.05—1.89(m, 8H) |
3A | 7.68(s, 1H), 4.21(q, J=7.2 Hz, 2H), 3.79—3.71(m, 16H), 3.36(s, 2H), 2.27(s, 3H), 1.30(t, J=7.2 Hz, 3H) |
3B | 7.61(s, 1H), 4.17(q, J=7.1 Hz, 2H), 3.74(t, J=4.9 Hz, 8H), 3.34(s, 2H), 2.15(s, 3H), 1.63—1.50(m, 12H), 1.29 |
(t, J=7.1 Hz, 3H) | |
3C | 7.65(s, 1H), 4.17(q, J=7.1 Hz, 2H), 3.57—3.50(m, 8H), 3.43(s, 2H), 2.15(s, 3H), 2.0—1.86(m, 8H), 1.28(t, |
J=7.1 Hz, 3H) | |
4A | 8.86(s, 1H), 4.26(q, J=7.1 Hz, 2H), 3.81—3.65(m, 16H), 2.43(s, 3H), 1.31(t, J=7.1 Hz, 3H) |
4B | 9.04(s, 1H), 4.34(q, J=7.0 Hz, 2H), 3.71(t, J=4.9 Hz, 8H), 2.58(s, 3H), 1.67—1.53(m, 12H), 1.37(t, J=7.0 Hz, |
3H) | |
4C | 8.95(s, 1H), 4.31(q, J=7.1 Hz, 2H), 3.71—3.59(m, 8H), 2.56(s, 3H), 2.10—1.87(m, 8H), 1.37(t, J=7.1 Hz, 3H) |
5A | 12.63(s,1H), 8.92(s, 1H), 3.80—3.63(m, 16H), 2.41(s, 3H) |
5B | 12.38(s, 1H), 9.02(s, 1H), 3.74(t, J=5.0 Hz, 8H), 2.58(s, 3H), 1.63—1.52(m, 12H) |
5C | 12.11(s, 1H),9.06(s, 1H), 3.80—3.59(m, 8H), 2.58(s, 3H), 1.95—1.86(m, 8H) |
7Aa | 8.96(s, 1H), 7.87(d, J=7.5 Hz, 2H), 7.75—7.60(m, 3H), 3.79—3.62(m, 16H), 2.34(s, 3H) |
Compd. | 1H NMR(500 MHz), δ |
7Ab | 8.91(s, 1H), 8.01(d, J=8.5 Hz, 2H), 7.43(d, J=8.5 Hz, 2H), 3.74—3.60(m, 16H), 2.42(s, 3H), 2.33(s, 3H) |
7Ac | 10.17(s, 1H), 8.90(s, 1H), 8.12(d, J=8.5 Hz, 2H), 7.40(d, J=8.5 Hz, 2H), 3.79—3.62(m, 16H), 2.34(s, 3H) |
7Ad | 8.90(s, 1H), 8.06(d, J=8.6 Hz, 2H), 7.16(d, J=8.6 Hz, 2H), 3.85(s, 3H), 3.81—3.62(m, 16H), 2.39(s, 3H) |
7Ae | 8.90(s, 1H), 8.13(d, J=8.25 Hz, 2H), 7.62(d, J=8.3 Hz, 2H), 3.75—3.55(m, 16H), 2.41(s, 3H) |
7Af | 8.89(s, 1H), 7.90(d, J=8.2 Hz, 2H), 6.71(d, J=8.2 Hz, 2H), 5.60(s, 2H), 3.76—3.61(m, 16H), 2.40(s, 3H) |
7Ba | 8.82(s, 1H), 7.90(d, J=7.7 Hz, 2H), 7.64—7.51(m, 3H), 3.49(t, J=4.9 Hz, 8H), 2.36(s, 3H), 1.88—1.61(m, 12H) |
7Bb | 8.83(s, 1H), 8.01(d, J=8.5 Hz, 2H), 7.43(d, J=8.5 Hz, 2H), 3.74(t, J=4.9 Hz, 8H), 2.49(s, 3H), 2.36(s, 3H), |
1.61—1.51(m, 12H) | |
7Bc | 10.13(s, 1H), 8.83(s, 1H), 8.09(d, J=8.5 Hz, 2H), 7.23(d, J=8.5 Hz, 2H), 3.75(t, J=4.9 Hz, 8H), 2.41(s, 3H), |
1.61—1.51(m, 12H) | |
7Bd | 8.83(s, 1H), 8.04(d, J=8.6 Hz, 2H), 7.10(d, J=8.6 Hz, 2H), 3.80(s, 3H), 3.69(t, J=4.9 Hz, 8H), 2.41(s, 3H), |
1.60—1.50(m, 12H) | |
7Be | 8.83(s, 1H), 8.09(d, J=8.3 Hz, 2H), 7.57(d, J=8.3 Hz, 2H), 3.72(t, J=4.9 Hz, 8H), 2.40(s, 3H), 1.61—1.51 |
(m, 12H) | |
7Bf | 8.83(s, 1H), 7.81(d, J=8.2 Hz, 2H), 6.70(d, J=8.2 Hz, 2H), 5.61(s, 2H), 3.73(t, J=4.9 Hz, 8H), 2.41(s, 3H), |
1.60—1.52(m, 12H) | |
7Ca | 8.82(s, 1H), 7.91(d, J=7.5 Hz, 2H), 7.64—7.48(m, 3H), 3.56—3.46(m, 8H), 2.40(s, 3H), 1.92—1.82(m, 8H) |
7Cb | 8.82(s, 1H), 7.98(d, J=8.5 Hz, 2H), 7.39(d, J=8.5 Hz, 2H), 3.57—3.45(m, 8H), 2.42(s, 3H), 2.36(s, 3H), |
1.92—1.84(m, 8H) | |
7Cc | 10.12(s, 1H), 8.86(s, 1H), 7.99(d, J=8.5 Hz, 2H), 7.32(d, J=8.5 Hz, 2H), 3.56—3.45(m, 8H), 2.42(s, 3H), |
1.93—1.84(m, 8H) | |
7Cd | 8.82(s, 1H), 8.02(d, J=8.6 Hz, 2H), 7.16(d, J=8.6 Hz, 2H), 3.85(s, 3H), 3.53—3.48(m, 8H), 2.39(s, 3H), |
1.88—1.79(m, 8H) | |
7Ce | 8.82(s, 1H), 8.17(d, J=8.3 Hz, 2H), 7.60(d, J=8.3 Hz, 2H), 3.57—3.48(m, 8H), 2.42(s, 3H), 1.92—1.85(m, 8H) |
7Cf | 8.83(s, 1H), 7.89(d, J=8.2 Hz, 2H), 6.80(d, J=8.2 Hz, 2H), 5.60(s, 2H), 3.50—3.41(m, 8H), 2.42(s, 3H), |
1.87—1.80(m, 8H) |
Compd. | 13C NMR(500 MHz), δ |
---|---|
5A | 172.05, 170.86, 166.52, 140.33, 136.66, 104.32, 64.88, 43.97, 13.56 |
5B | 172.21, 170.63, 166.25, 140.82, 136.73, 104.25, 47.72, 25.65, 22.18, 13.75 |
5C | 172.18, 170.77, 166.33, 141.15, 136.23, 104.37, 54.68, 25.32, 13.68 |
7Aa | 170.57, 166.58, 162.52, 141.16, 140.30, 137.58, 133.83, 131.27, 129.39, 127.27, 104.28, 64.96, 44.78, 13.82 |
7Ab | 170.56, 166.57, 162.54, 141.05, 140.35, 137.57, 135.24, 129.35, 127.20, 125.27, 104.27, 64.86, 44.57, 20.37, 13.97 |
7Ac | 170.56, 166.59, 162.57, 146.29, 141.17, 137.54, 136.68, 131.26, 124.27, 122.13, 104.25, 64.57, 44.28, 13.90 |
7Ad | 170.23, 166.44, 162.54, 148.29, 141.34, 138.66, 137.52, 131.68, 123.25, 120.14, 104.25, 64.28, 55.18, 44.39, 13.92 |
7Ae | 170.48, 166.25, 162.33, 141.06, 140.12, 137.28, 132.29, 125.23, 122.82, 120.35, 104.27, 64.57, 44.35, 13.92 |
7Af | 170.48, 166.62, 162.19, 141.26, 139.55, 137.33, 132.12, 125.76, 122.93, 120.34, 104.58, 64.29, 44.47, 13.83 |
7Ba | 170.27, 166.47, 162.47, 141.12, 140.44, 137.54, 133.82, 131.27, 129.25, 127.26, 104.10, 47.64, 25.06, 22.37, 13.83 |
7Bb | 170.45, 166.52, 162.54, 141.17, 139.86, 137.58, 135.25, 129.34, 127.20, 125.16, 104.27, 47.58, 25.62, 22.27, |
20.32, 13.67 | |
7Bc | 170.87, 166.48, 162.57, 146.27, 141.28, 137.39, 136.52, 131.79, 124.64, 122.36, 104.20, 47.56, 25.36, 22.13, 13.97 |
7Bd | 170.29, 166.48, 162.39, 148.29, 141.37, 137.23, 136.58, 131.54, 123.25, 120.38, 104.25, 55.29, 47.64, 25.36, |
22.77, 13.97 | |
7Be | 170.43, 166.06, 162.32, 141.12, 140.01, 137.35, 132.59, 125.22, 122.37, 120.45, 104.43, 47.28, 25.62, 22.39, 13.66 |
7Bf | 170.48, 166.25, 162.15, 141.23, 140.21, 137.22, 132.34, 125.35, 122.87, 120.28, 104.37, 47.25, 25.42, 22.77, 13.98 |
7Ca | 170.55, 166.58, 162.32, 141.23, 139.88, 137.63, 133.25, 131.27, 129.42, 127.16, 104.15, 54.76, 25.03, 13.82 |
7Cb | 170.27, 166.42, 162.38, 141.22, 140.22, 137.61, 135.24, 129.35, 127.10, 125.28, 104.07, 54.97, 25.38, 22.02, 13.79 |
7Cc | 170.31, 166.28, 162.38, 146.27, 141.17, 137.58, 136.25, 131.25, 124.30, 122.23, 104.05, 54.28, 25.66, 13.62 |
7Cd | 170.28, 166.34, 162.25, 148.17, 141.32, 137.55, 136.82, 131.43, 123.57, 120.26, 104.25, 56.27, 54.28, 25.66, 13.82 |
7Ce | 170.29, 166.42, 162.27, 141.02, 139.95, 137.25, 132.28, 125.23, 122.45, 120.46, 104.25, 54.28, 25.46, 13.93 |
7Cf | 170.48, 166.27, 162.38, 141.27, 140.78, 137.33, 132.14, 125.78, 122.28, 120.34, 104.25, 54.28, 25.34, 13.92 |
Table 4 13C NMR for compounds 5A—5C, 7A(a—f), 7B(a—f) and 7C(a—f)*
Compd. | 13C NMR(500 MHz), δ |
---|---|
5A | 172.05, 170.86, 166.52, 140.33, 136.66, 104.32, 64.88, 43.97, 13.56 |
5B | 172.21, 170.63, 166.25, 140.82, 136.73, 104.25, 47.72, 25.65, 22.18, 13.75 |
5C | 172.18, 170.77, 166.33, 141.15, 136.23, 104.37, 54.68, 25.32, 13.68 |
7Aa | 170.57, 166.58, 162.52, 141.16, 140.30, 137.58, 133.83, 131.27, 129.39, 127.27, 104.28, 64.96, 44.78, 13.82 |
7Ab | 170.56, 166.57, 162.54, 141.05, 140.35, 137.57, 135.24, 129.35, 127.20, 125.27, 104.27, 64.86, 44.57, 20.37, 13.97 |
7Ac | 170.56, 166.59, 162.57, 146.29, 141.17, 137.54, 136.68, 131.26, 124.27, 122.13, 104.25, 64.57, 44.28, 13.90 |
7Ad | 170.23, 166.44, 162.54, 148.29, 141.34, 138.66, 137.52, 131.68, 123.25, 120.14, 104.25, 64.28, 55.18, 44.39, 13.92 |
7Ae | 170.48, 166.25, 162.33, 141.06, 140.12, 137.28, 132.29, 125.23, 122.82, 120.35, 104.27, 64.57, 44.35, 13.92 |
7Af | 170.48, 166.62, 162.19, 141.26, 139.55, 137.33, 132.12, 125.76, 122.93, 120.34, 104.58, 64.29, 44.47, 13.83 |
7Ba | 170.27, 166.47, 162.47, 141.12, 140.44, 137.54, 133.82, 131.27, 129.25, 127.26, 104.10, 47.64, 25.06, 22.37, 13.83 |
7Bb | 170.45, 166.52, 162.54, 141.17, 139.86, 137.58, 135.25, 129.34, 127.20, 125.16, 104.27, 47.58, 25.62, 22.27, |
20.32, 13.67 | |
7Bc | 170.87, 166.48, 162.57, 146.27, 141.28, 137.39, 136.52, 131.79, 124.64, 122.36, 104.20, 47.56, 25.36, 22.13, 13.97 |
7Bd | 170.29, 166.48, 162.39, 148.29, 141.37, 137.23, 136.58, 131.54, 123.25, 120.38, 104.25, 55.29, 47.64, 25.36, |
22.77, 13.97 | |
7Be | 170.43, 166.06, 162.32, 141.12, 140.01, 137.35, 132.59, 125.22, 122.37, 120.45, 104.43, 47.28, 25.62, 22.39, 13.66 |
7Bf | 170.48, 166.25, 162.15, 141.23, 140.21, 137.22, 132.34, 125.35, 122.87, 120.28, 104.37, 47.25, 25.42, 22.77, 13.98 |
7Ca | 170.55, 166.58, 162.32, 141.23, 139.88, 137.63, 133.25, 131.27, 129.42, 127.16, 104.15, 54.76, 25.03, 13.82 |
7Cb | 170.27, 166.42, 162.38, 141.22, 140.22, 137.61, 135.24, 129.35, 127.10, 125.28, 104.07, 54.97, 25.38, 22.02, 13.79 |
7Cc | 170.31, 166.28, 162.38, 146.27, 141.17, 137.58, 136.25, 131.25, 124.30, 122.23, 104.05, 54.28, 25.66, 13.62 |
7Cd | 170.28, 166.34, 162.25, 148.17, 141.32, 137.55, 136.82, 131.43, 123.57, 120.26, 104.25, 56.27, 54.28, 25.66, 13.82 |
7Ce | 170.29, 166.42, 162.27, 141.02, 139.95, 137.25, 132.28, 125.23, 122.45, 120.46, 104.25, 54.28, 25.46, 13.93 |
7Cf | 170.48, 166.27, 162.38, 141.27, 140.78, 137.33, 132.14, 125.78, 122.28, 120.34, 104.25, 54.28, 25.34, 13.92 |
Compd. | PTP1Ba | Cdc25Bb | ||
---|---|---|---|---|
Inhibitionc(%) | I | Inhibitionc(%) | I | |
7Aa | 65.03±3.09 | 9.04±1.37 | 88.00±1.36 | 6.75±0.42 |
7Ab | 73.95±1.99 | 8.69±1.61 | 91.30±1.81 | 5.19±0.35 |
7Ac | 91.02±1.82 | 1.08±0.07 | 92.50±0.06 | 1.59±0.01 |
7Ad | 81.44±3.93 | 8.01±0.58 | 81.12±0.16 | 3.90±0.05 |
7Ae | 90.63±0.51 | 1.19±0.05 | 93.74±0.31 | 1.81±0.04 |
7Af | 93.74±0.87 | 1.02±0.08 | 90.02±0.22 | 1.50±0.21 |
7Ba | 96.77±0.26 | 2.64±0.01 | 98.82±0.33 | 3.11±0.00 |
7Bb | 95.53±0.06 | 2.53±0.10 | 95.80±1.49 | 2.58±0.07 |
7Bc | 98.31±0.54 | 0.79±0.00 | 95.45±0.08 | 0.39±0.02 |
7Bd | 96.81±0.68 | 1.71±0.34 | 91.19±1.34 | 2.47±0.30 |
7Be | 97.08±0.44 | 1.05±0.01 | 90.00±6.67 | 1.34±0.05 |
7Bf | 96.93±0.01 | 0.74±0.06 | 96.65±0.16 | 0.32±0.52 |
7Ca | 76.60±6.47 | 8.58±1.66 | 87.34±0.05 | 6.62±0.36 |
7Cb | 84.00±0.04 | 8.33±0.08 | 93.33±0.51 | 3.16±0.72 |
7Cc | 91.60±0.10 | 0.84±0.06 | 97.91±0.34 | 0.69±0.10 |
7Cd | 86.11±1.29 | 7.91±1.49 | 90.98±4.50 | 3.02±0.21 |
7Ce | 91.09±0.32 | 1.10±0.07 | 97.84±0.98 | 1.43±0.07 |
7Cf | 95.14±0.15 | 0.89±0.04 | 93.17±1.30 | 0.59±0.13 |
Table 5 Inhibiting activity of target compounds against PTP1B and Cdc25B
Compd. | PTP1Ba | Cdc25Bb | ||
---|---|---|---|---|
Inhibitionc(%) | I | Inhibitionc(%) | I | |
7Aa | 65.03±3.09 | 9.04±1.37 | 88.00±1.36 | 6.75±0.42 |
7Ab | 73.95±1.99 | 8.69±1.61 | 91.30±1.81 | 5.19±0.35 |
7Ac | 91.02±1.82 | 1.08±0.07 | 92.50±0.06 | 1.59±0.01 |
7Ad | 81.44±3.93 | 8.01±0.58 | 81.12±0.16 | 3.90±0.05 |
7Ae | 90.63±0.51 | 1.19±0.05 | 93.74±0.31 | 1.81±0.04 |
7Af | 93.74±0.87 | 1.02±0.08 | 90.02±0.22 | 1.50±0.21 |
7Ba | 96.77±0.26 | 2.64±0.01 | 98.82±0.33 | 3.11±0.00 |
7Bb | 95.53±0.06 | 2.53±0.10 | 95.80±1.49 | 2.58±0.07 |
7Bc | 98.31±0.54 | 0.79±0.00 | 95.45±0.08 | 0.39±0.02 |
7Bd | 96.81±0.68 | 1.71±0.34 | 91.19±1.34 | 2.47±0.30 |
7Be | 97.08±0.44 | 1.05±0.01 | 90.00±6.67 | 1.34±0.05 |
7Bf | 96.93±0.01 | 0.74±0.06 | 96.65±0.16 | 0.32±0.52 |
7Ca | 76.60±6.47 | 8.58±1.66 | 87.34±0.05 | 6.62±0.36 |
7Cb | 84.00±0.04 | 8.33±0.08 | 93.33±0.51 | 3.16±0.72 |
7Cc | 91.60±0.10 | 0.84±0.06 | 97.91±0.34 | 0.69±0.10 |
7Cd | 86.11±1.29 | 7.91±1.49 | 90.98±4.50 | 3.02±0.21 |
7Ce | 91.09±0.32 | 1.10±0.07 | 97.84±0.98 | 1.43±0.07 |
7Cf | 95.14±0.15 | 0.89±0.04 | 93.17±1.30 | 0.59±0.13 |
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