水杨醛类不饱和季铵盐的合成及抑菌活性测定

Synthesis and Antitumor Activity of Salicylaldehyde Unsaturated Quaternary Ammonium

摘要:

以5-氯甲基水杨醛为原料分别与甲基丙烯酸二甲氨基乙酯、N,N-二甲基烯丙基胺和N-甲基二烯丙基胺三种不饱和叔胺反应，合成了含有碳碳双键的季铵盐，并对反应条件进行了优化。确定较佳的合成条件为：二氯甲烷溶液中，反应摩尔配比为1:1，反应温度为0℃，反应时间为８～10 h。在最优条件下，合成的目标化合物产率均在90%以上。通过IR、1HNMR、13CNMR、MS(ESI)等分析手段对含有碳碳双键的季铵盐结构进行了表征。采用牛津杯法对目标化合物抑菌活性测试，结果显示，三种不饱和季铵盐对金黄色葡萄球菌均具有较好的抑菌活性，而对大肠杆菌没有明显抑菌活性。

Abstract:

Three kinds of novel unsaturated quaternary ammonium were synthesized with the starting material of 5-chloromethylsalicylaldehyde and unsaturated tertiary amines including dimethylaminoethyl methacrylate(DMAEA), N,N-dimethyl allyl amine(DMAA) and N-methyl-diallylamine(DAMA), and optimized conditions of the model reaction. Through optimizing the reaction conditions, we concluded the ideal conditions：dichloromethane as a solvent, the reaction molar ratio of 5-chloromethylsalicylaldehyde and unsaturated tertiary amines is n(1):n(2a)= 1:1, the reaction temperature is 0℃, and the reaction time is 10 h. Under optimal conditions, the yield of the compounds is all above 90%. The obtained products have been characterized by melting point, IR, 1HNMR, 13CNMR and ESI-MS spectra. Antibacterial activity of the compounds using Oxford Cup were tested. The results showed that three kinds of quaternary ammonium (3a, 3b, 3c) all have good antibacterial activity against Staphylococcus aureus, while there is no significant antibacterial activity against E. coli.