高等学校化学学报 ›› 2017, Vol. 38 ›› Issue (10): 1764-1771.doi: 10.7503/cjcu20170239

• 有机化学 • 上一篇    下一篇

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

张成路(), 孙晓娜, 李传银, 蔡继颖, 王静, 李益政, 王华玉   

  1. 辽宁师范大学化学化工学院, 大连 116029
  • 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:zhangchenglu@lnnu.edu.cn
  • 基金资助:
    辽宁省教育厅科学技术项目(批准号: 2009A426)资助

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

ZHANG Chenglu*(), SUN Xiaona, LI Chuanyin, CAI Jiying, WANG Jing, LI Yizheng, WANG Huayu   

  1. College of Chemistry and Chemical Engineering, Liaoning Normal University, Dalian 116029, China
  • Received:2017-04-19 Online:2017-10-10 Published:2017-09-08
  • Contact: ZHANG Chenglu E-mail:zhangchenglu@lnnu.edu.cn
  • Supported by:
    † Supported by the Science and Technology Research Program of Liaoning Provincial Department of Education, China(No.2009A426).

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.

关键词: 吡唑, 1,3,4-噁二唑, 1,3,5-三嗪, PTP1B抑制剂, Cdc25B抑制剂

Abstract:

Eighteen novel multi-heterocyclic molecules[7A(a—f), 7B(a—f), 7C(a—f)] were designed and synthesized by hybrid-linking 1,3,4-oxadiazole and 1,3,5-triazine onto pyrazole. The structures of all the compounds were confirmed by IR, NMR and HRMS. The inhibitory activities of target molecules against protein tyrosine phosphatase 1B(PTP1B) and cell division cycle 25 phosphatase B(Cdc25B) were evaluated. As a result, all of the target molecules behave good inhibitory activities against PTP1B and Cdc25B, in which nine compounds show excellent inhibitory activities, respectively. The inhibitory activities of nine compounds are better than the reference oleanolic acid and Na3VO4, respectively. The nine compounds are expected to become potential inhibitors of PTP1B and Cdc25B.

Key words: Pyrazole, 1,3,4-Oxadiazole, 1,3,5-Triazine, PTP1B inhibitor, Cdc25B inhibitor

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