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

Notes

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   

  1. 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 出版日期:2019-08-25 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 Weia, Zuo Huailonga, Li Yuxinb, Liu Jianga, Zhou Xianlia   

  1. 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 Online:2019-08-25 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).

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