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2013 , Vol. 33 >Issue 02: 383 - 388

DOI: https://doi.org/10.6023/cjoc201209039

研究简报

1-对甲苯基-5-取代苯基亚胺基-1,2,3-三唑甲酸/甲酰胺的合成及生物活性研究

  • 彭春勇 ,
  • 辛春伟 ,
  • 李建发 ,
  • 戢丹 ,
  • 鲍秀荣 ,
  • 卢俊瑞
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  • 天津理工大学化学化工学院 天津 300384

收稿日期: 2012-09-28

  修回日期: 2012-10-14

  网络出版日期: 2012-10-26

基金资助

国家自然科学基金(Nos. 21176194, 20976135)资助项目.

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Synthesis and Biological Activities of 1-(4-Methyl)phenyl-5-sub- stituted phenylimino-1,2,3-triazole Carboxylic Acid/Caboxylic Acid Amide

  • Peng Chunyong ,
  • Xin Chunwei ,
  • Li Jianfa ,
  • Ji Dan ,
  • Bao Xiurong ,
  • Lu Junrui
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  • School of Chemistry and Chemical Engineering, Tianjin University of Technology, Tianjin 300384

Received date: 2012-09-28

  Revised date: 2012-10-14

  Online published: 2012-10-26

Supported by

Project supported by the National Natural Science Foundation of China (Nos. 20976135, 21176194).

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摘要

以对甲基苯胺为原料, 经过重氮化反应生成对甲基叠氮苯(1). 在强碱性条件下, 1分别与氰基乙酸乙酯、氰基乙酰胺反应, 制得中间体1-对甲苯基-5-氨基-1,2,3-三唑甲酸乙酯(2)和1-对甲苯基-5-氨基-1,2,3-三唑甲酰胺(5); 中间体2经水解生成1-对甲苯基-5-氨基-1,2,3-三唑甲酸(3), 进而在弱酸性条件下与取代苯甲醛反应得到6个未见文献报道的目标化合物1-对甲苯基-5-取代苯基亚胺基-1,2,3-三唑甲酸(4a～4f), 5与取代苯甲醛反应得到6个未见文献报道的目标化合物1-对甲苯基-5-取代苯基亚胺基-1,2,3-三唑甲酰胺(6a～6f), 化合物的结构均经IR, 1H NMR, 13C NMR确证. 初步生物测试表明, 12个化合物均表现出良好的抑菌活性, 其中化合物4d～4f和6d～6f对金黄色葡萄球菌、白色念球菌的最小抑菌浓度(MIC)值为2～8 μg/mL, 抗菌效果优于氟康唑和三氯生.

关键词： 1-对甲苯基-5-氨基-1,2,3-三唑甲酸; 1-对甲苯基-5-氨基-1,2,3-三唑甲酰胺; 1-对甲苯基-5-取代苯基亚胺基- 1,2,3-三唑甲酸; 1-对甲苯基-5-取代苯基亚胺基-1,2,3-三唑甲酰胺; 合成; 抗菌活性

本文引用格式

彭春勇 , 辛春伟 , 李建发 , 戢丹 , 鲍秀荣 , 卢俊瑞 . 1-对甲苯基-5-取代苯基亚胺基-1,2,3-三唑甲酸/甲酰胺的合成及生物活性研究[J]. 有机化学, 2013 , 33(02) : 383 -388 . DOI: 10.6023/cjoc201209039

Abstract

4-Methylphenylazide (1) was synthesized through diazotization reactions from 4-methylaniline, and then reacted with ethyl cyanoacetate or 2-cyano-acetamide to obtain 1-(4-methyl)phenyl-5-amino-1,2,3-triazole carboxylic ethyl ester (2) and 1-(4-methyl)phenyl-5-amino-1,2,3-triazole carboxylic acid amide (5) in strong alkaline condition. Compound 2 hydrolyzed into 1-(4-methyl)phenyl-5-amino-1,2,3-triazole carboxylic acid (3). Then, in weak acidic condition, 1-(4-methyl) phenyl-5-substituted phenylimino-1,2,3-triazole carboxylic acids (4a～4f) were obtained from compound 3 and substituted benzaldehyde. Meanwhile, other 6 novel 1-(4-methyl)phenyl-5-substituted phenylimino-1,2,3-triazole carboxylic acid amides (6a～6f) were synthesized from compound 5 and substituted benzaldehyde. The structures of all compounds have been confirmed by 1H NMR, 13C NMR and IR. The preliminary bioassay showed that, all target compounds possessed efficient antibacterial activities. Especially, the mic values of compounds 4d～4f and 6d～6f were 2～8 μg/mL, lower than fluconazole and triclosan.

Key words： 1-(4-methyl)phenyl-5-amino-1,2,3-triazole carboxylic acid; 1-(4-methyl)phenyl-5-Amino-1,2,3-triazole carboxylic acid amide; 1-(4-methyl)phenyl-5-substituted phenylimino-1,2,3-triazole carboxylic acid/carboxylic acid amide; synthesis; antibacterial activity

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