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2012 , Vol. 32 >Issue 06: 1101 - 1107

DOI: https://doi.org/10.6023/cjoc1110112

研究论文

3-(N-取代苯基-2-乙酰胺基)硫基-4-N-取代邻羟苯基亚胺基-5-甲基-1,2,4-三唑类化合物的合成及生物活性研究

  • 穆曼曼 ,
  • 卢博为 ,
  • 卢俊瑞 ,
  • 辛春伟 ,
  • 戢丹 ,
  • 李建发 ,
  • 鲍秀荣
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  • a 天津理工大学化学化工学院 天津 300384;
    b 南开大学化学学院 天津 300071

收稿日期: 2011-10-11

  修回日期: 2011-12-26

  网络出版日期: 2012-02-06

基金资助

国家自然科学基金(Nos. 21176194, 20976135)和天津市高校科技发展基金(No. 2006ZD33)资助项目.

收起

Synthesis and Biological Activities of 3-(N-Substituted-phenyl-2- acetamido)-sulfur-4-(N-substituted-2-hydroxyphenyl)imino- 5-methyl-1,2,4-triazoles

  • Mu Manman ,
  • Lu bowei ,
  • Lu Junrui ,
  • Xin Chunwei ,
  • Ji Dan ,
  • Li Jianfa ,
  • Bao Xiurong
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  • a School of Chemistry and Chemical Engineering, Tianjin University of Technology, Tianjin 300384;
    b College of Chemistry, Nankai University, Tianjin 300071

Received date: 2011-10-11

  Revised date: 2011-12-26

  Online published: 2012-02-06

Supported by

Project supported by the National National Science Foundation of China (Nos. 21176194, 20976135) and the University Technology Development Foundation of Tianjin City (No. 2006ZD33).

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摘要

以对称二氨基硫脲为原料, 与冰醋酸反应生成5-甲基-4-氨基-1,2,4-三唑-3-硫酮(1); 在弱酸性条件下, 1 与取代水杨醛反应生成席夫碱中间体5-甲基-4-(N-取代邻羟苯基)亚胺基-1,2,4-三唑-3-硫酮(2a～2c); 最后在碱性条件下分别与N-取代苯基-2-氯乙酰胺发生烷基化反应生成15 种未见报道的目标化合物3-(N-取代苯基-2-乙酰胺基)硫基-4-(N-取代邻羟苯基)亚胺基-5-甲基-1,2,4-三唑(3a～3o), 其结构经IR, 1H NMR, 13C NMR 确证. 初步生物测试表明, 质量分数为0.01%时, 3a～3o 对白色念珠菌的抑菌率均达90%以上, 具有很强的抑菌活性; 对金黄色葡萄球菌、大肠杆菌的抑菌率达80%以上, 具有较强的抑菌活性.

关键词： 5-甲基-4-N-(取代邻羟苯基)亚胺基-1,2,4-三唑-3-硫酮; 3-取代硫基-4-N-(取代邻羟苯基)亚胺基-5-甲基-1,2,4-三唑; 合成; 抑菌活性

本文引用格式

穆曼曼 , 卢博为 , 卢俊瑞 , 辛春伟 , 戢丹 , 李建发 , 鲍秀荣 . 3-(N-取代苯基-2-乙酰胺基)硫基-4-N-取代邻羟苯基亚胺基-5-甲基-1,2,4-三唑类化合物的合成及生物活性研究[J]. 有机化学, 2012 , 32(06) : 1101 -1107 . DOI: 10.6023/cjoc1110112

Abstract

Firstly, 5-methyl-4-amino-1,2,4-triazole (1) was obtained by a cyclization reaction of glacial acetic acid with thiocarbohydrazide. In weak acidic conditions, the Schiff base 5-methyl-4-(N-substituted-2-hydroxyphenyl)imino-1,2,4-triazole- 3-thione (2a～2c) was obtained by the reaction of compound 1 with substituted salicyladehyde. Finally, the title compounds 3-(N-substitutedphenyl-2-acetamido)sulfur-4-(N-substituted-2-hydroxyphenyl)imino-5-methyl-1,2,4-triazoles (3a～3o) which have never been reported were synthesized by nucleophilic substitution reaction of compound 2 with N-substituted phenyl-2-acetamide under alkaline conditions. The structures of all compounds have been confirmed by IR, 1H NMR and 13C NMR spectra. The results of preliminary bioassay showed that, at the mass concentration of 0.01%, compounds 3a～3o have more than 90% inhibitory rate against Monilia albican, which displayed excellent bacterial activities. Meanwhile, the title compounds also have more than 80% inhibitory ratio against Staphylococcus aureus and Escherichia coli.

Key words： 5-methyl-4-(N-substituted-2-hydroxyphenyl)imino-1,2,4-triazole-3-thione; 3-substituted sulfur-4-N-(2-hydroxyphenyl) imino-5-methyl-1,2,4-triazole; systhesis; antibacterial activity

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