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   

  1. 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 出版日期:2017-04-25 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 Qianmeia, Pang Kaishenga, Zhao Jianpingb, Liu Xinghaia, Weng Jianquana   

  1. 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 Online:2017-04-25 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).

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