Synthesis and Antifungal Activities of 4-Thioquinoline Compounds

doi:10.6023/cjoc201801024

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

Notes

4-硫醚喹啉类化合物的合成与抗菌活性研究

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

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 E-mail:yangrui15@cdut.edu.cn
基金资助:
国家自然科学基金（No.31601670）、四川省教育厅基金（No.18ZB0079）和成都理工大学青年科学基金（No.2017QJ02）资助项目.

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

Received:2018-01-16 Revised:2018-04-21 Published:2018-05-14
Contact: 10.6023/cjoc201801024 E-mail:yangrui15@cdut.edu.cn
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).

1. Synthesis and Antifungal Activities of 4-Thioquinoline Compounds.PDF(2404KB)

Abstract

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

Cite this article

Yang Rui, Ma Yanni, Huang Ting, Xie Wei, Zhang Xia, Huang Guoshuang, Liu Xiaodong. Synthesis and Antifungal Activities of 4-Thioquinoline Compounds[J]. Chin. J. Org. Chem., 2018, 38(8): 2143-2150.

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4-硫醚喹啉类化合物的合成与抗菌活性研究

Synthesis and Antifungal Activities of 4-Thioquinoline Compounds

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