3-取代硫基-5-(1-羟基苯基)-4H-1,2,4-三唑类化合物的合成及抑菌活性  

Synthesis and Antibacterial Activities of 3-Substituted Sulfur-5-(1-hydroxyphenyl)-4H-1,2,4-triazole Compounds

作　　者：朱姗姗[1] 卢俊瑞[1] 辛春伟[1] 卢博为[2] 鲍秀荣[1] 邹敏[1] 刘倩[1] 

机构地区：[1]天津理工大学化学化工学院,天津300384 [2]南开大学化学学院,天津300071

出　　处：《高等学校化学学报》2010年第11期2228-2233,共6页Chemical Journal of Chinese Universities

基　　金：国家自然科学基金(批准号:20776114;20976135);天津市高校科技发展基金(批准号:2006ZD33)资助

摘　　要：依据邻羟基二苯醚及三唑类化合物的抗菌特性及生物活性叠加原理,将邻羟苯基和1,2,4-三唑分子片断有机结合,设计合成了12个新型3-取代硫基-5-(1-羟基苯基)-4H-1,2,4-三唑类化合物.首先,水杨酸甲酯与水合肼反应生成水杨酰肼,水杨酰肼再与硫氰酸铵和盐酸反应,生成5-(1-羟基苯基)-4H-1,2,4-三唑-3-硫酮(3),最后在碱性条件下化合物3与取代苯乙酮、氯苄和碘甲烷发生烷基化反应生成目标化合物,化合物结构经1H NMR及IR等表征确认.抑菌测试结果表明,当化合物质量分数为0.01%时,目标化合物对白色念珠菌和大肠杆菌的抑菌率高达90%,具有强抑菌活性;对金黄色葡萄球菌的抑菌率高达80%,具有一定的抑菌活性.According to antibacterial characteristics of o-hydroxydiphenyl ethers and 1,2,4-triazole and the superpostion principle of reinforcement of biological activities,twelve novel 3-substituted sulfur-5-（1-hydroxy-phenyl）-4H-1,2,4-triazole compounds were designd by means of combining segments o-hydroxy phenyl and 1,2,4-triazole.Firstly,salicylic hydrazide was synthesized by methylsalicylate with hydrazinehydrate in etha-nol;then,salicylic hydrazide reacted with ammonium thiocyanate and HCl to obtain 5-（1-hydroxyphenyl）-4H-1,2,4-triazole-3-thiones（3）;at last,under alkaline conditions,the target compounds were obtained by alkylation reaction of compound 3 with the halogenated acetophenone,chloride and iodomethane.The structures of final products were determined by 1H NMR and IR.The results of preliminary bioassay show that the title compounds have inhibitory rates about 99% against Monilia albican and Escherichia coli and a inhibitory rate about 85% against Staphylococcus aureus at 0.01% mass fraction.

关 键 词：3-取代硫基-5-(1-羟基苯基)-4H-1 2 4-三唑 抑菌活性 构效关系 

分 类 号：O626.26[理学—有机化学]