Citation: 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]. Chinese Journal of Organic Chemistry, ;2018, 38(11): 3112-3117. doi: 10.6023/cjoc201804044 shu

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

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

Corresponding author: Weng Jianquan, jqweng@zjut.edu.cn
Received Date: 25 April 2018
Revised Date: 24 June 2018
Available Online: 5 November 2018
Fund Project: the Zhejiang Provincial Natural Science Foundation LY17C140003Project supported by the National Natural Science Foundation of China (No. 30900959) and the Zhejiang Provincial Natural Science Foundation (No. LY17C140003)the National Natural Science Foundation of China 30900959

Figures(1)

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.
- pyrimidine moiety,
- 1, 3, 4-oxadiazole,
- thioether,
- synthesis,
- antifungal activity,
- antileishanial activity
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