Synthesis and Biological Activity of Novel 2-(Substituted-benzylthio)-5-(4,6-dimethylpyrimidin-2-thiomethyl)-1,3,4-oxadiazoles

doi:10.6023/cjoc201804044

Chin. J. Org. Chem. ›› 2018, Vol. 38 ›› Issue (11): 3112-3117.DOI: 10.6023/cjoc201804044 Previous Articles Next Articles

Notes

新型2-(取代苄硫基)-5-(4,6-二甲基嘧啶-2-硫甲基)-1,3,4-噁二唑化合物的合成及生物活性

汪洲洋^a, 徐涵靖^a, 赵建平^b, 刘幸海^a, 翁建全^a

a 浙江工业大学化学工程学院杭州 310032;
b National Center for Natural Products Research, University of Mississippi, Oxford, MS 38677

收稿日期:2018-04-25 修回日期:2018-06-24 发布日期:2018-07-05
通讯作者: 翁建全 E-mail:jqweng@zjut.edu.cn
基金资助:
国家自然科学基金（No.30900959）和浙江省自然科学基金（No.LY17C140003）资助项目.

Synthesis and Biological Activity of Novel 2-(Substituted-benzylthio)-5-(4,6-dimethylpyrimidin-2-thiomethyl)-1,3,4-oxadiazoles

Wang Zhouyang^a, Xu Hanjing^a, Zhao Jianping^b, Liu Xinghai^a, Weng Jianquan^a

a College of Chemical Engineering, Zhejiang University of Technology, Hangzhou 310032;
b National Center for Natural Products Research, University of Mississippi, Oxford, MS 38677

Received:2018-04-25 Revised:2018-06-24 Published:2018-07-05
Supported by:
Project supported by the National Natural Science Foundation of China (No. 30900959) and the Zhejiang Provincial Natural Science Foundation (No. LY17C140003).

1. Synthesis and Biological Activity of Novel 2-(Substituted-benzylthio)-5-(4,6-dimethylpyrimidin-2-thiomethyl)-1,3,4-oxadiazoles.PDF(1569KB)

Abstract

In order to find novel biologically active heterocyclic compounds, thirteen new 2-(substitutedbenzylthio)-5-(4,6-dimethylpyrimidin-2-thiomethyl)-1,3,4-oxadiazoles were prepared with thiocarbamide and 2,4-pentanedione as the staring materials via cyclization, etherification, hydrazination, cyclization and finally a benzylation reaction under microwave irradiation condition. The preliminary bioassay results indicated that some target compounds exhibited good inhibition activity against Colletrotichum acutatum, Colletrotichum gloeosporioides and Colletrotichum fragariae at 50 μg/mL, and the inhibition rate of the compound with 3-fluoro against Colletrotichum acutatum reached 80.22%. Several compounds also showed that good antileishmanial activities against Leishmania donovani, the IC₅₀ values of those compounds with 3-chloro, 4-bromo, 3-fluoro and 4-tert-butyl substituent respectively were all less than 25 μg/mL and were more active than the control drug paromomycin.

Key words: pyrimidine moiety, 1,3,4-oxadiazole, thioether, synthesis, antifungal activity, antileishanial activity

Cite this article

Wang Zhouyang, Xu Hanjing, Zhao Jianping, Liu Xinghai, Weng Jianquan. Synthesis and Biological Activity of Novel 2-(Substituted-benzylthio)-5-(4,6-dimethylpyrimidin-2-thiomethyl)-1,3,4-oxadiazoles[J]. Chin. J. Org. Chem., 2018, 38(11): 3112-3117.

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新型2-(取代苄硫基)-5-(4,6-二甲基嘧啶-2-硫甲基)-1,3,4-噁二唑化合物的合成及生物活性

Synthesis and Biological Activity of Novel 2-(Substituted-benzylthio)-5-(4,6-dimethylpyrimidin-2-thiomethyl)-1,3,4-oxadiazoles

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