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2013 , Vol. 33 >Issue 05: 995 - 999

DOI: https://doi.org/10.6023/cjoc201212009

研究论文

7-位含1,3,4-噁二唑硫醚单元的新型1,2,4-三唑并[1,5-a]嘧啶类衍生物的合成及其生物活性研究

  • 鲍小平 ,
  • 林选福 ,
  • 蹇军友 ,
  • 张峰 ,
  • 邹林波
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  • 贵州大学精细化工研究开发中心 教育部绿色农药与农业生物工程重点实验室 贵阳 550025

收稿日期: 2012-12-06

  修回日期: 2013-01-25

  网络出版日期: 2013-02-05

基金资助

贵州省优秀科技教育人才省长专项资金(No. 200817)和贵州省自然科学基金(No. 20082265)资助项目.

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Synthesis and Bioactivities of Novel 1,2,4-Triazolo[1,5-a]pyrimidine Derivatives Containing 7-(1,3,4-Oxadiazolyl)thioether Moiety

  • Bao Xiaoping ,
  • Lin Xuanfu ,
  • Jian Junyou ,
  • Zhang Feng ,
  • Zou Linbo
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  • Key Laboratory of Green Pesticide and Agricultural Bioengineering, Ministry of Education, Center for Research and Development of Fine Chemicals, Guizhou University, Guiyang 550025

Received date: 2012-12-06

  Revised date: 2013-01-25

  Online published: 2013-02-05

Supported by

Project supported by the Governor's Foundation for Excellent Talents of Science, Technology & Education of Guizhou Province (No. 200817) and the Natural Science Foundation of Guizhou Province (No. 20082265).

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摘要

以2-苄硫基-5-甲基-7-羟基-1,2,4-三唑并[1,5-a]嘧啶为起始原料, 经过醚化、肼解、环化和硫醚化反应合成了10个新型的2-苄硫基-5-甲基-7-(5-取代苄硫基-1,3,4-噁二唑-2)-亚甲氧基-1,2,4-三唑并[1,5-a]嘧啶类化合物5a～5j, 并通过1H NMR, IR, MS和元素分析对目标化合物的结构进行了表征. 初步生物活性测试结果表明, 部分化合物表现出了较好的抗烟草花叶病毒(TMV)或一定的体外抑菌活性. 在500 μg/mL浓度下, 化合物5b, 5f和5j对烟草花叶病毒的抑制率分别为45%, 45%和43%.

关键词： 1,2,4-三唑并[1,5-a]嘧啶; 1,3,4-噁二唑; 硫醚; 合成; 生物活性

本文引用格式

鲍小平 , 林选福 , 蹇军友 , 张峰 , 邹林波 . 7-位含1,3,4-噁二唑硫醚单元的新型1,2,4-三唑并[1,5-a]嘧啶类衍生物的合成及其生物活性研究[J]. 有机化学, 2013 , 33(05) : 995 -999 . DOI: 10.6023/cjoc201212009

Abstract

Using 2-benzylthio-5-methyl-7-hydroxyl-1,2,4-triazolo[1,5-a]pyrimidine as starting material, ten novel 2-benzyl- thio-5-methyl-7-(5-substituted benzylthio-1,3,4-oxadiazol-2-yl)-methyleneoxyl-1,2,4-triazolo[1,5-a]pyrimidine derivatives 5a～5j were synthesized via sequential reactions of etherification, hydrazinolysis, cyclization and thioetherification. The structures of target compounds were fully characterized by 1H NMR, IR, MS and elemental analysis. The preliminary bioassay showed that some compounds possessed good anti-TMV (tobacco mosaic virus) or certain fungicidal activities in vitro. At the concentration of 500 μg/mL, the inhibition rates of compounds 5b, 5f and 5j against TMV were 45%, 45% and 43%, respectively.

Key words： 1,2,4-triazolo[1,5-a]pyrimidine; 1,3,4-oxadiazole; thioether; synthesis; bioactivity

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