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

doi:10.6023/cjoc1110112

Chin. J. Org. Chem. ›› 2012, Vol. 32 ›› Issue (06): 1101-1107.DOI: 10.6023/cjoc1110112 Previous Articles Next Articles

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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^a, 卢博为^b, 卢俊瑞^a, 辛春伟^a, 戢丹^a, 李建发^a, 鲍秀荣^a

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 发布日期:2012-02-06
通讯作者: 卢俊瑞 E-mail:lujunrui@tjut.edu.cn
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.

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^a, Lu bowei^b, Lu Junrui^a, Xin Chunwei^a, Ji Dan^a, Li Jianfa^a, Bao Xiurong^a

a School of Chemistry and Chemical Engineering, Tianjin University of Technology, Tianjin 300384;
b College of Chemistry, Nankai University, Tianjin 300071

Received:2011-10-11 Revised:2011-12-26 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).

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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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]. Chin. J. Org. Chem., 2012, 32(06): 1101-1107.

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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

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

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