Design, Synthesis and Structure-Activity Relationships of Plant-Based 2-Aryl-3,4-dihydroisoquinolin-2-iums as Potential Antifungal Agents

doi:10.6023/cjoc201905020

Chin. J. Org. Chem. ›› 2019, Vol. 39 ›› Issue (8): 2317-2322.DOI: 10.6023/cjoc201905020 Previous Articles Next Articles

Special Issue: 陈茹玉先生诞辰100周年

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2-芳基-3,4-二氢异喹啉类植物源抑菌剂的设计合成及构效关系研究

陈伟^a, 左怀龙^a, 李玉新^b, 刘江^a, 周先礼^a

a 西南交通大学生命科学与工程学院成都 610031;
b 南开大学元素有机化学国家重点实验室天津 300071

收稿日期:2019-05-10 修回日期:2019-06-02 发布日期:2019-06-24
通讯作者: 陈伟 E-mail:chenweicstq@163.com
基金资助:
国家自然科学基金（No.21702173）、中央高校基本科研业务费（No.2682016CX104）和四川省科技创新苗子工程（No.2682017QY04）资助项目.

Design, Synthesis and Structure-Activity Relationships of Plant-Based 2-Aryl-3,4-dihydroisoquinolin-2-iums as Potential Antifungal Agents

Chen Wei^a, Zuo Huailong^a, Li Yuxin^b, Liu Jiang^a, Zhou Xianli^a

a School of Life Science and Engineering, Southwest Jiaotong University, Chengdu 610031;
b State Key Laboratory of Elemento-organic Chemistry, Nankai University, Tianjin 300071

Received:2019-05-10 Revised:2019-06-02 Published:2019-06-24
Contact: 10.6023/cjoc201905020 E-mail:chenweicstq@163.com
Supported by:
Project supported by the National Natural Science Foundation of China (No. 21702173), the Fundamental Research Funds for the Central Universities (No. 2682016CX104) and the Miaozi Project of Scientific and Technological Innovation of Sichuan Province (No. 2018090).

1. Design, Synthesis and Structure-Activity Relationships of Plant-Based 2-Aryl-3,4-dihydroisoquinolin-2-iums as Potential Antifungal Agents.PDF(6930KB)

Abstract

In order to discover more potent antifungal, a series of 2-aryl-3,4-dihydroisoquinolin-2-iums were reasonable designed and productive synthesized by introducing benzoic acid and phenol pharmacophores into the 2-position of isoquinoline. Their structures were identified by NMR and HRMS. The preliminary in vitro antifungal results showed that most of the title compounds exhibited moderate to significant inhibitory activities against various phytopathogenic fungi at 50 mg·mL^-1, and were equal to controls (chlorothalonil, carbendazim). The concentration of 50% inhibition rate (EC₅₀) of 2-(3-ethoxycarbonyl-phenyl)-3,4-dihydroisoquinolin-2-ium (4j) against R. solani was 3.8495 mg·mL^-1, which was significantly superior to chlorothalonil (4.6328 mg·mL^-1). All the EC₅₀ values of 5 compounds (7.4583~15.4495 mg·mL^-1) against R. cerealis were better than chlorothalonil (16.0137 mg·mL^-1), and 2-(4-methoxycarbonylphenyl)-3,4-dihydroisoquinolin-2-ium (4f) is the best one. The present results provide valuable information for development of plant-based antifungal agents.

Key words: 2-aryl-3,4-dihydroisoquinolin-2-ium, botanical, antifungal activity, structure-activity relationship

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Chen Wei, Zuo Huailong, Li Yuxin, Liu Jiang, Zhou Xianli. Design, Synthesis and Structure-Activity Relationships of Plant-Based 2-Aryl-3,4-dihydroisoquinolin-2-iums as Potential Antifungal Agents[J]. Chin. J. Org. Chem., 2019, 39(8): 2317-2322.

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2-芳基-3,4-二氢异喹啉类植物源抑菌剂的设计合成及构效关系研究

Design, Synthesis and Structure-Activity Relationships of Plant-Based 2-Aryl-3,4-dihydroisoquinolin-2-iums as Potential Antifungal Agents

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