Citation: Yang Rui, Ma Yanni, Huang Ting, Xie Wei, Zhang Xia, Huang Guoshuang, Liu Xiaodong. Synthesis and Antifungal Activities of 4-Thioquinoline Compounds[J]. Chinese Journal of Organic Chemistry, ;2018, 38(8): 2143-2150. doi: 10.6023/cjoc201801024 shu

Synthesis and Antifungal Activities of 4-Thioquinoline Compounds

Yang Rui ^a,, ,
Ma Yanni ^b ,
Huang Ting ^c ,
Xie Wei ^c ,
Zhang Xia ^c ,
Huang Guoshuang ^c ,
Liu Xiaodong ^c

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

Corresponding author: Yang Rui, yangrui15@cdut.edu.cn
Received Date: 16 January 2018
Revised Date: 21 April 2018
Available Online: 14 August 2018
Fund Project: 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)the Youth Science Foundation of Chengdu University of Technology 2017QJ02the National Natural Science Foundation of China 31601670the Foundation of Department of Education of Sichuan Province 18ZB0079

Figures(1)

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.
- quinoline,
- thioether,
- antifungal activity,
- synthesis
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