Citation: 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 shu

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

Zhang Junhui ^a ,
Zhu Yabo ^a ,
Weng Jianquan ^a,, ,
Yu Qian ^b,, ,
Yuan Jing ^c ,
Chen Jie ^c,,

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

Corresponding author: Weng Jianquan, jqweng@zjut.edu.cn Yu Qian, yuxi024@163.com Chen Jie, chenjie@zafu.edu.cn
Received Date: 18 October 2019
Revised Date: 13 November 2019
Available Online: 2 December 2019
Fund Project: Project supported by the Natural Science Foundation of Zhejiang Province (No. LY17C140003)the Natural Science Foundation of Zhejiang Province LY17C140003

Figures(3)

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.
- stilbene,
- styrylthiazole,
- synthesis,
- biological activity
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