Synthesis and Biological Activity of Novel 1,3,4-Thiadiazole Thioether Derivatives Containing Pyrimidine Moiety

doi:10.6023/cjoc201610026

Chin. J. Org. Chem. ›› 2017, Vol. 37 ›› Issue (4): 1009-1015.DOI: 10.6023/cjoc201610026 Previous Articles Next Articles

Notes

新型含嘧啶环结构的1,3,4-噻二唑硫醚类化合物的合成及生物活性

李倩梅^a, 庞凯胜^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 38677

收稿日期:2016-10-17 修回日期:2016-12-20 发布日期:2017-01-17
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）和浙江省公益性（No.2014C31127）资助项目.

Synthesis and Biological Activity of Novel 1,3,4-Thiadiazole Thioether Derivatives Containing Pyrimidine Moiety

Li Qianmei^a, Pang Kaisheng^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 38677

Received:2016-10-17 Revised:2016-12-20 Published:2017-01-17
Contact: 10.6023/cjoc201610026 E-mail:jqweng@zjut.edu.cn
Supported by:
Project supported by the National Natural Science Foundation of China (No. 30900959) and the Public Project of Zhejiang Province (No. 2014C31127).

1. Synthesis and Biological Activity of Novel 1,3,4-Thiadiazole Thioether Derivatives Containing Pyrimidine Moiety.PDF(2211KB)

Abstract

In order to find novel biologically active heterocyclic compounds, fifteen novel 1,3,4-thiadiazole thioether derivatives carrying pyrimidine moiety were prepared by using thiocarbamide and 2,4-pentanedione as the staring materials via cyclization, etherification, hydrazination, cyclization and the last benzylation reaction under microwave irradiation. The structures of the synthesized compounds were characterized by ¹H NMR, ¹³C NMR, IR, ESI-MS and elemental analysis. The preliminary bioassay results indicated that some target compounds exhibited moderate inhibition activity against Colletrotichum acutatum, Colletrotichum gloeosporioides and Colletrotichum fragariae at 50 μg/mL, and the inhibition rate of 2-(((4,6- dimethylpyrimidin-2-yl)thio)methyl)-5-((3-fluorobenzyl)thio)-1,3,4-thiadiazole (7i) against Colletrotichum acutatum and Colletrotichum fragariae were 79.84% and 73.46% respectively. Several compounds also showed good antileishmanial activities against Leishmania donovani, 2-(((4,6-dimethylpyrimidin-2-yl)thio)methyl)-5-((2-fluorobenzyl)thio)-1,3,4-thiadiazole (7h) and 2-(((4,6-dimethylpyrimidin-2-yl)thio)methyl)-5-((4-fluorobenzyl)thio)-1,3,4-thiadiazole (7j) were found highly active with IC₅₀ values of 21.3 and 23.6 μg/mL, respectively.

Key words: pyrimidine moiety, 1,3,4-thiadiazole, thioether, microwave assisted synthesis, antifungal activity, antileishanial activity

Cite this article

Li Qianmei, Pang Kaisheng, Zhao Jianping, Liu Xinghai, Weng Jianquan. Synthesis and Biological Activity of Novel 1,3,4-Thiadiazole Thioether Derivatives Containing Pyrimidine Moiety[J]. Chin. J. Org. Chem., 2017, 37(4): 1009-1015.

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新型含嘧啶环结构的1,3,4-噻二唑硫醚类化合物的合成及生物活性

Synthesis and Biological Activity of Novel 1,3,4-Thiadiazole Thioether Derivatives Containing Pyrimidine Moiety

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