Chin. J. Org. Chem. ›› 2018, Vol. 38 ›› Issue (8): 2143-2150.DOI: 10.6023/cjoc201801024 Previous Articles     Next Articles



杨锐a, 马艳妮b, 黄婷c, 解伟c, 张霞c, 黄国双c, 刘小东c   

  1. a 成都理工大学材料与化学化工学院 成都 610059;
    b 河南省科学院天然产物重点实验室 郑州 450002;
    c 成都理工大学环境学院 成都 610059
  • 收稿日期:2018-01-16 修回日期:2018-04-21 发布日期:2018-05-14
  • 通讯作者: 杨锐
  • 基金资助:


Synthesis and Antifungal Activities of 4-Thioquinoline Compounds

Yang Ruia, Ma Yannib, Huang Tingc, Xie Weic, Zhang Xiac, Huang Guoshuangc, Liu Xiaodongc   

  1. a College of Materials, Chemistry & Chemical Engineering, Chengdu University of Technology, Chengdu 610059;
    b Key Laboratory of Natural Products, Henan Academy of Sciences, Zhengzhou 450002;
    c College of Environment, Chengdu University of Technology, Chengdu 610059
  • Received:2018-01-16 Revised:2018-04-21 Published:2018-05-14
  • Contact: 10.6023/cjoc201801024
  • Supported by:

    Project supported by the National Natural Science Foundation of China (No. 31601670), the Foundation of Department of Education of Sichuan Province (No. 18ZB0079) and the Youth Science Foundation of Chengdu University of Technology (No. 2017QJ02).

Based on the scaffold of 4-substituted quinoline, twenty-four 4-thioquinoline compounds were designed and synthesized by molecular hybridization. Their structures were identified by 1H NMR, 13C NMR and HRMS. Meanwhile, all target compounds were evaluated for antifungal activities. The results indicated that the majority of target compounds displayed some activity against each of the fungi. Among them, 4-(ethylthio)-2-phenylquinoline (4a), 4-(isopropylthio)-2-phenylquinoline (4c) and 4-(allylthio)-2-phenylquinoline (4h) were more potent than others, whose inhibition rates against some fungi were comparable to the positive drug azoxystrobin. The structure-activity relationship (SAR) showed that different substituents on 4-position could significantly affect activities. Generally, the presence of aliphatic group could be more beneficial to antifungal activity than aromatic group, and the activity weakened with an increase of steric hindrance. Moreover, the kinds and positions of substituents on the aromatic ring had little or negative effects on the activity.

Key words: quinoline, thioether, antifungal activity, synthesis