Chin. J. Org. Chem. ›› 2015, Vol. 35 ›› Issue (8): 1665-1672.DOI: 10.6023/cjoc201412014 Previous Articles     Next Articles

ARTICLE

新型三脚架型多苯并咪唑季铵盐类化合物的合成及性能

张成路, 国阳, 陈莹, 孙丽杰, 程安琪, 赵娜, 赵宝成, 唐杰, 袭焕   

  1. 辽宁师范大学化学化工学院 辽宁省生物与制药重点实验室 大连 116029
  • 收稿日期:2014-12-08 修回日期:2015-03-25 出版日期:2015-08-25 发布日期:2015-04-30
  • 通讯作者: 张成路 E-mail:zhangchenglu@lnnu.edu.cn
  • 基金资助:

    辽宁省教育厅科学技术研究(No. 2009A426)资助项目.

Synthesis and Properties of Novel Tripod Type Multi-benzimidazole Quaternary Ammonium Compounds

Zhang Chenglu, Guo Yang, Chen Ying, Sun Lijie, Cheng Anqi, Zhao Na, Zhao Baocheng, Tang Jie, Xi Huan   

  1. Liaoning Provincial Key Laboratory of Biotechnology and Drug Discovery, College of Chemistry and Chemical Engineering, Liaoning Normal University, Dalian 116029
  • Received:2014-12-08 Revised:2015-03-25 Online:2015-08-25 Published:2015-04-30
  • Supported by:

    Project supported by the Science and Technology Research Program of Liaoning Provincial Department of Education (No. 2009A426).

Fourteen novel tripod type multi-benzimidazole quaternary ammoniums (3a~3n) with complex functions were synthesized for the first time and the structures of the target molecules were well characterized. The inhibitory activities of Cdc25B and PTP1B of 3 were explored. The results showed that 3d, 3e, 3i, 3j and 3l exhibit excellent inhibitory activity against Cdc25B, wherein the IC50 values of 3d, 3e, 3j and 3l were lower than the reference Na3VO4, which were expected to be potential Cdc25B inhibitors for the treatment of cancer. Compounds 3d, 3e, 3i and 3l showed good inhibitory activity against PTP1B, wherein the IC50 value of 3l was lower than the reference oleanolic acid, which may be used as a potential PTP1B inhibitor for the treatment of diabetes. Meanwhile, the fluorescence quenching of six kinds of anions on four target compounds was also studied. It was found that I-exhibited excellent quenching effect, 3c and 3e behaved the best quenching effect and may be a potential recognition fluorescent I-sensor probe.

Key words: benzimidazole, drug activity, fluorescent sensor probe, CDc25B, PTP1B