几种苯甲醛类Schiff base的研究

【作者】 王加彦；

【导师】 王麟生；

【作者基本信息】 华东师范大学 ， 无机化学， 2004， 硕士

【摘要】 Schiff base是一类非常重要的配体，其核心结构C=N基团具有重要的化学和生物意义，Schiff base配体可以与大多数的金属配位形成配合物，配体及其配合物广泛应用于医药、催化、材料等方面，Schiff base及其配合物特殊的结构和功能，一直是引人注目的研究对象。醇胺类、氨基硫脲类、含氟类物质用途较广，它们分子中含有的活泼胺基、羟基和高电负性的氟原子会对分子的化学和生物活性产生很大的影响，广泛用作医药、农药及有机合成中间体等精细化学品，近年来它们的研究领域显得非常活跃。 本文从改变席夫碱结构着手选择含有不同吸电子、给电子效应取代基的芳香醛、醇胺、氨基硫脲为原料，用直接法合成了八种Schiff base，其中2—羟基—1，3，5—苯三醛缩醇胺类Schiff base, 3，4，5-三甲氧基苯甲醛单缩氨基硫脲的产率较高，有五种未见文献报道。对2—羟基—1，3，5—苯三醛单缩乙醇胺、2—羟基—1，3，5—苯三醛三缩乙醇胺、2—羟基—1，3，5—苯三醛单缩丙醇胺、3，4，5-三甲氧基苯甲醛单缩氨基硫脲和对氟苯甲醛单缩氨基硫脲进行了熔点测定，红外光谱、质谱、元素分析等测试，综合分析各项表征结果，它们的组成与结构基本与理论设计相吻合。 测试了这几种苯甲醛类Schiff base对革兰氏阳性菌(金葡萄球菌、枯草菌)和革兰氏阴性菌(大肠杆菌)的抑制情况。采用国际药典通用的管碟法(又称杯碟法)进行抑菌测试，测得的抑菌圈直径数据做出抑菌曲线图，可以看出所合成的Schiff base对不同细菌均具有不同程度抑制作用，在一定的范围内具有一个最佳浓度，此时的抑菌圈直径最大；同时比较了其抑菌性能的高低差异，含氟Schiff base对细菌显示较强的抑制作用；比较氨基全部发生取代和含有未取代氨基的Schiff base发现，后者的抑菌活性更高一些；本文合成的Schiff base对大肠杆菌的杀菌效果均不如对枯草杆菌、金黄色葡萄球菌的杀菌效果，在此基础上对其抑菌机理做出了推测。更多还原

【Abstract】 Schiff bases and their metal complexes are very important compounds because their core group C=N has chemical and biological significance. Hitherto, research work about this field is being done by researchers in the world, who have synthesized and estimated a plenty of Schiff bases and their metal complexes, studied and exploited many uses, such as catalyst, antibacterial medicines, material, etc.The alcohol amine compounds, fluoride and thiosemicarbazide containing labile amine group, hydroxyl group, fluorine atom and sulphur atom which can influence the chemical property and biological activity of compounds tremendously were applied to drug, pesticide and organic intermediate extensively. The last few years, they have become the most challenging building blocks for chemistry.In this paper, we chose benzaldehyde with electron withdrawing group or donor group, alcohol amine and thiosemicarbazide. Eight Schiff bases have been synthesized directly and five of them have not been reported by literatures. The rate of alcohol amine Schiff bases and 3,4,5-trimethoxybenzylideno monothiosemicarbazide is high. Melting Point, IR, Mass spectrum and elemental analyses have been performed about 2-hydroxy-1,3,5-benzenetricarbaldehyde monoethanolamine, 2-hydroxy-1,3,5-benzenetricarbaldehyde triethanolamine, 2-hydroxy-1,3,5-benzenetricarbaldehyde monopropanolamine, 3,4,5-trimethoxybenzylideno monothiosemicarbazide, p-fluorobenzylidene monothiosemicarbazide, 2-4[(fluorobenzylidene)-amino]-propanol. Their structures and compositions are in agreement with targets.The antibacterial activities of the Schiff bases have been tested against gram-positive (Staphylococcus aureus, Bacillus subtilis) and gram-negativebacterium (Escherichia coli). The international codex current method (pipe-plate method or cup-plate method) was used. The inhibition curves were drew by datum of zone of inhibition. We found that these Schiff bases had antibacterial activity. Among these compounds, Schiff bases containing fluorine atom markedly inhibited bacteria from breeding. Schiff bases with unsubstitutional amine group had higher activity than those without unsubstitutional amine group. Schiff bases had lower antibacterial activities in inhibiting Escherichia coli than in inhibiting Staphylococcus aureus and Bacillus subtilis. Antibacterial activity mechanism was predicted.更多还原