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Chinese Journal of Organic Chemistry >

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

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

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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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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

Cite this article

Mu Manman , Lu bowei , Lu Junrui , Xin Chunwei , Ji Dan , Li Jianfa , Bao Xiurong . Synthesis and Biological Activities of 3-(N-Substituted-phenyl-2- acetamido)-sulfur-4-(N-substituted-2-hydroxyphenyl)imino- 5-methyl-1,2,4-triazoles[J]. Chinese Journal of Organic Chemistry, 2012 , 32(06) : 1101 -1107 . DOI: 10.6023/cjoc1110112

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