1-(4-取代苯基)-4-苯基-5-(2-羟基苄基)氨基-1,2,3-三唑类衍生物的合成及抑菌活性

将邻羟苯基引入1,2,3-三唑结构中, 设计合成了10个1-(4-取代苯基)-4-苯基-5-取代-1,2,3-三唑类衍生物. 首先, 以对位取代的芳胺为原料, 经重氮化、叠氮化、闭环和缩合反应制得1-(4-取代苯基)-4-苯基-5-水杨醛亚胺-1,2,3-三唑类衍生物(3a~3e), 再用硼氢化钠还原制得1-(4-取代苯基)-4-苯基-5-(2-羟基苄基)氨基-1,2,3-三唑类衍生物(4a~4e). 目标化合物的结构经核磁、IR及元素分析确认. 抑菌活性测试表明, 当质量浓度为0.1 mg/L时, 除化合物3e和4e外, 所有化合物对白色念球菌的抑菌率均达95%以上, 对大肠杆菌的抑菌率达85%以上, 具有强抑菌活性, 表明该类化合物在抗菌药物开发方面有重要应用价值.

Synthesis and Antibacterial Activities of 1-(4-Substituted phenyl)-4-phenyl-5- ( 2-hydroxy benzyl ) amino-1, 2,3-triazole Derivatives

In order to search  for novel and high active fungicides with triazole moiety, a series of novel 1-(4-substituted phenyl)-4-phenyl-5-substituted-1,2,3-triazole derivatives was designed and synthesized by means of combining segments o-hydroxy phenyl and 1,2,3-triazole. Firstly, 1-(4-substitutedphenyl)-4-phenyl-5-(2-iminomethyl phenol)-1,2,3-triazole derivatives(3a—3e) were designed and synthesized through diazotization, azidozation, ring-closure reaction and condensation, and then were reduced by sodium borohydride to synthesize 1-(4-substituted phenyl)-4-phenyl-5-(2-hydroxy benzyl)amino-1,2,3-triazole(4a—4e). The structures of final products were determined by 1H NMR, elemental analysis and IR. The results of antibacterial activity showed that the title compounds except 3e and  4e had over 95% inhibitory rate against Monilia albican, and over 85% inhibitory rate against Escherichia coliis at  a mass concentration of  0.1 mg/L. The results suggest that the title compounds might be potential candidates for antibacterial drugs.