Citation: 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]. Chinese Journal of Organic Chemistry, ;2017, 37(4): 1009-1015. doi: 10.6023/cjoc201610026 shu

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

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

Corresponding author: Weng Jianquan, jqweng@zjut.edu.cn
Received Date: 17 October 2016
Revised Date: 20 December 2016

Fund Project: the Public Project of Zhejiang Province 2014C31127the National Natural Science Foundation of China 30900959

Figures(1)

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.
- pyrimidine moiety,
- 1, 3, 4-thiadiazole,
- thioether,
- microwave assisted synthesis,
- antifungal activity,
- antileishanial activity
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