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

doi:10.6023/cjoc201212009

Chin. J. Org. Chem. ›› 2013, Vol. 33 ›› Issue (05): 995-999.DOI: 10.6023/cjoc201212009 Previous Articles Next Articles

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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

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 发布日期:2013-02-05
通讯作者: 鲍小平,baoxp_1980@yahoo.com.cn E-mail:baoxp_1980@yahoo.com.cn
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.

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

Key Laboratory of Green Pesticide and Agricultural Bioengineering, Ministry of Education, Center for Research and Development of Fine Chemicals, Guizhou University, Guiyang 550025

Received:2012-12-06 Revised:2013-01-25 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).

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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Bao Xiaoping, Lin Xuanfu, Jian Junyou, Zhang Feng, Zou Linbo. Synthesis and Bioactivities of Novel 1,2,4-Triazolo[1,5-a]pyrimidine Derivatives Containing 7-(1,3,4-Oxadiazolyl)thioether Moiety[J]. Chin. J. Org. Chem., 2013, 33(05): 995-999.

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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

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

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