Citation: 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]. Chinese Journal of Organic Chemistry, ;2019, 39(8): 2317-2322. doi: 10.6023/cjoc201905020 shu

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

Corresponding author: Chen Wei, chenweicstq@163.com
Received Date: 10 May 2019
Revised Date: 2 June 2019
Available Online: 24 August 2019
Fund Project: 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)the Miaozi Project of Scientific and Technological Innovation of Sichuan Province 2018090the Fundamental Research Funds for the Central Universities 2682016CX104the National Natural Science Foundation of China 21702173

Figures(3)

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.
- 2-aryl-3, 4-dihydroisoquinolin-2-ium,
- botanical,
- antifungal activity,
- structure-activity relationship
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