1-(2-羟基苯甲酰基)-3-甲基-4-取代苯腙基-吡唑啉酮及其中间体的合成、表征及抑菌活性  

Synthesis,Characterization and Antibacterial Activities of 1-(2-Hydroxybenzoyl)-3-methyl-4-substituted phenylhydrazono-pyrazolones and Their Intermediates

作　　者：邹敏[1] 卢俊瑞[1] 辛春伟[1] 鲍秀荣[1] 杨波 朱姗姗[1] 刘倩[1] 李迎辉[1] 陶继强[1] 

机构地区：[1]天津理工大学化学化工学院,天津300384 [2]河南省医药科学研究院河南省肝病药理重点实验室,郑州450052

出　　处：《有机化学》2010年第8期1201-1206,共6页Chinese Journal of Organic Chemistry

基　　金：国家自然科学基金(Nos.20776114;20976135);天津市高校科技发展基金(No.2006ZD33)资助项目

摘　　要：依据生物活性叠加原理,将邻羟苯基、吡唑啉酮、苯腙基团进行合理组合,构建并合成了2-取代苯腙基-3-(2-羟基苯甲酰腙基)-丁酸乙酯(3a～3f)和1-(2-羟基苯甲酰基)-3-甲基-4-取代苯腙基-吡唑啉酮(4a～4f)两类、共计12种化合物,其中8种化合物未见报道,12种化合物的抑菌活性均未见报道.以芳胺为原料,经重氮化、与乙酰乙酸乙酯反应,与水杨酰肼缩合制得3a～3f,3a～3f经分子内关环制得4a～4f,化合物的结构经IR,1HNMR,元素分析等证实.生物活性测试表明,质量浓度为0.01%时,化合物3b,3c对大肠杆菌的抑菌率高达100%,具有很强的抑菌活性;化合物3a～3f对白色念珠菌、金黄色葡萄球菌的抑菌率均达70%以上,具有较强的抑菌活性;化合物4a～4f对白色念珠菌、大肠杆菌的抑菌率均接近或达到100%,具有很强的抑菌活性,对金黄色葡萄球菌的抑菌率均达78%以上,具有较强抑菌活性;与3a～3f相比,形成吡唑啉酮环后的化合物4a～4f的抗菌活性更高.A series of 1-（2-hydroxybenzoyl）-3-methyl-4-substituted phenylhydrazono-pyrazolones （4a～4f） and their intermediates 3a～3f were designed and synthesized by combining o-hydroxyl pheny,pyrazoleone and phenylhydrazone groups,according to the superposition principle of biological activities.Eight compounds and antibacterial-activity of all compounds have not been reported so far.Substituted anilines were diazotized and subsequently reacted with ethylacetoacetate,then condensed with salicylic hydrazide to obtain 3a～3f.The title compounds were acquired by intramolecular cyclization reaction of 3a～3f.The structures of all compounds were confirmed by IR,^1H NMR spectra and elemental analysis.The results of preliminary bioassay showed that the inhibitory rates against Escherichia coli of compounds 3b,3c were high to 100% at 0.01% mass concentration,which displayed excellent antibacterial activities;and the inhibitory rates against Monilia albican and Staphlococcus aureus were over 70%,which exhibited a certain extent antibacterial activities.The inhibitory rates against Moniliaalbican and Escherichia coli of the compounds 4a～4f reached to 100% at 0.01% mass concentration,which displayed excellent antibacterial activities.The inhibitory rates against Staphlococcus aureus were over 78%,which exhibited a certain extent antibacterial activities.Comparing with those of 3a～3f,the inhibitory rates of the compounds 4a～4f were enhanced.

关 键 词：2-取代苯腙基-3-邻羟基苯甲酰腙基-丁酸乙酯 1-邻羟基苯甲酰基-4-取代苯腙基-吡唑啉酮 合成 表征 抑菌活性 

分 类 号：O626[理学—有机化学]