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

doi:10.6023/cjoc201910023

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

天然stilbene导向的取代苯乙烯基噻唑化合物的合成和生物活性

章俊辉^a, 朱亚波^a, 翁建全^a, 余茜^b, 袁静^c, 陈杰^c

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 E-mail:jqweng@zjut.edu.cn;yuxi024@163.com;chenjie@zafu.edu.cn
基金资助:
浙江省自然科学基金（No.LY17C140003）资助项目.

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

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).

1. 201055S.pdf(1332KB)

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

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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.

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天然stilbene导向的取代苯乙烯基噻唑化合物的合成和生物活性

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

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