新型3-芳氧甲基喹喔啉-2-羧酸的简便有效合成及其抗菌活性研究  

Convenient and Effective Syntheses of Novel 3-Aroxymethylquinoxaline-2-carboxylic acids and Their Antibacterial Activities

作　　者：张红[1] 赫云鹤 李阳[1] 陈羽[2] Zhang Hong;He Yunhe;Li Yang;Chen Yu(College of Chemistry and Chemical Engineering,Bohai University,Jinzhou 121000;School of Life Science and Biopharmaceutics,Shenyang Pharmaceutical University,Shenyang 110016)

机构地区：[1]渤海大学化学化工学院,锦州121000 [2]沈阳药科大学生命科学与生物制药学院,沈阳110016

出　　处：《化学通报》2020年第9期828-836,769,共10页Chemistry

基　　金：国家自然科学基金项目(21878023,U1608222);辽宁省特聘教授支持计划资助项目;辽宁省教育厅“青年育苗”项目(LQ2019006);辽宁省科技厅博士启动项目(2019-BS-004)资助。

摘　　要：本文使用自制的3-溴甲基喹喔啉-2-甲酸乙酯(6)为反应物,经一锅连续的Williamson反应/酯基水解反应过程简便有效地合成一系列新型3-芳氧甲基喹喔啉-2-羧酸类化合物(4a^4l)。然后选用五种菌株为研究对象,进行了初步的体外抗菌活性实验,结果表明,含有叔丁基和卤素取代的化合物4j、4k和4l对革兰氏阳性菌金黄色葡萄球菌和枯草芽孢杆菌表现出很好的抑制活性,其中化合物4j的MIC值分别为15.625和7.8125μg/mL,活性高于参考药物环丙沙星。In the present work,a series of novel 3-aroxymethylquinoxaline-2-carboxylic acids(4a^4l)were synthesized by a simple and facile method using the newly-synthesized ethyl 3-bromomethylquinoxaline-2-carboxylate(6)as substrate through one-pot sequential Williamson reaction with various phenols(8a^8l)followed by ester hydrolysis reaction.A preliminary screening for their in vitro antibacterial activities against five bacterial strains revealed that compounds 4j,4k and 4l with tert-butyl and halo(F,Cl and Br)substituents exhibited significant activity against Gram(+)bacterials B.subtilis and S.aureus,among them 4j possessed the best activity with the MIC values of 15.625 and 7.8125μg/mL,respectively,better than the reference drug Ciprofoxacin.

关 键 词：喹喔啉 羧酸 Williamson反应 一锅法 抗菌活性 

分 类 号：O626[理学—有机化学] TQ460.1[理学—化学]