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



汪洲洋a, 徐涵靖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, 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
  • 基金资助:


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

Wang Zhouyanga, Xu Hanjinga, 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, 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).

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