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Chinese Journal of Organic Chemistry >

2020 , Vol. 40 >Issue 4: 1055 - 1061

DOI: https://doi.org/10.6023/cjoc201910023

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

  • Zhang Junhui ,
  • Zhu Yabo ,
  • Weng Jianquan ,
  • Yu Qian ,
  • Yuan Jing ,
  • Chen Jie
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  • 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 date: 2019-10-18

  Revised date: 2019-11-13

  Online published: 2020-05-06

Supported by

Project supported by the Natural Science Foundation of Zhejiang Province (No. LY17C140003).

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Abstract

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

Cite this article

Zhang Junhui , Zhu Yabo , Weng Jianquan , Yu Qian , Yuan Jing , Chen Jie . Synthesis and Biological Activity of Natural Stilbene-Inspired Substituted Styrylthiazole Derivatives[J]. Chinese Journal of Organic Chemistry, 2020 , 40(4) : 1055 -1061 . DOI: 10.6023/cjoc201910023

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