Chinese Journal of Organic Chemistry ›› 2020, Vol. 40 ›› Issue (4): 1055-1061.DOI: 10.6023/cjoc201910023 Previous Articles     Next Articles


章俊辉a, 朱亚波a, 翁建全a, 余茜b, 袁静c, 陈杰c   

  1. a 浙江工业大学化学工程学院 杭州 310032;
    b 广东药科大学临床药学院(整合药学院、整合药学研究院) 广州 510006;
    c 浙江农林大学绿色农药协同创新中心 杭州 311300
  • 收稿日期:2019-10-18 修回日期:2019-11-13 发布日期:2020-05-06
  • 通讯作者: 翁建全, 余茜, 陈杰;;
  • 基金资助:

Synthesis and Biological Activity of Natural Stilbene-Inspired Substituted Styrylthiazole Derivatives

Zhang Junhuia, Zhu Yaboa, Weng Jianquana, Yu Qianb, Yuan Jingc, Chen Jiec   

  1. a College of Chemical Engineering, Zhejiang University of Technology, Hangzhou 310032;
    b Clinical Pharmacy(School of Integrative Pharmacy, Institute of Integrative Pharmaceutical Research), Guangdong Pharmaceutical University, Guangzhou 510006;
    c Collaborative Innovation Center of Green Pesticide, Zhejiang A&F University, Hangzhou 311300
  • Received:2019-10-18 Revised:2019-11-13 Published:2020-05-06
  • Supported by:
    Project supported by the Natural Science Foundation of Zhejiang Province (No. LY17C140003).

In order to find novel drug leads, a series of natural stilbene-inspired substituted styrylthiazole derivatives were designed and synthesized by hybridization of the structures of both bioactive 2,6-difluorophenylthiazole moiety and stilbene. The structures of the title compounds were confirmed by 1H NMR, 13C NMR and ESI-HRMS. The in vitro antifungal bioassay results indicated that some compounds showed moderate inhibition activity against FusaHum graminearum, Helminthosporium maydis and Mycosphaerella melonis at 100 μg/mL, and the inhibition rate of (E)-5-bromo-4-(2,6-difluorophenyl)-2-(4-tri-fluoromethylstyryl)thiazole (6p) against FusaHum graminearum reached 86.7%. These compounds were also screened for their topoisomerase I inhibitory activity using Top1-mediated relaxation assay. The results showed that all of them exhibited certain Top1 inhibitory activity at 50 μmol·L-1, and amongst them (E)-5-bromo-4-(2,6-difluorophenyl)-2-(2-chlorosty-ryl)thiazole (6k) displayed promising Top1 inhibitory activity, which still remained certain activity at 0.2 μmol·L-1.

Key words: stilbene, styrylthiazole, synthesis, biological activity