新型6-氟-4(3H)-喹唑啉酮类Schiff碱的合成及其抑菌活性  

Synthesis and Antibacterial Activities of Novel 6-Fluoride-4(3H)-Quinazolinone Schiff Bases

作　　者：刘杰[1] 沈昊 朱泽文 余梅霞 陈志 赵丰贝 唐俊[2] 苗慧[1] 刘昭第[1] 凡素华[1] 陈水生[1] LIU Jie;SHEN Hao;ZHU Ze-wen;YU Mei-xia;CHEN Zhi;ZHAO Feng-bei;TANG Jun;MIAO Hui;LIU Zhao-di;FAN Su-hua;CHEN Shui-sheng(School of Chemistry and Material Engineering,Fuyang Normal University,Fuyang 236037,China;School of Biology and Food Engineering,Fuyang Normal University,Fuyang 236037,China)

机构地区：[1]阜阳师范学院化学与材料工程学院,安徽阜阳236037 [2]阜阳师范学院生物与食品工程学院,安徽阜阳236037

出　　处：《合成化学》2019年第1期25-30,共6页Chinese Journal of Synthetic Chemistry

基　　金：安徽省自然科学基金资助项目(KJ2018ZD035;KJ2017ZD29;1708085MB43;1608085MB34);安徽省教育厅自然科学研究项目(KJ2018A0332;KJ2018A0333);安徽省大学生创新创业项目(201710371091;201710371095);阜阳市政府横向合作科研项目(XDHX2016030;XDHX2016013);校级青年人才基金重点项目(2017rcxm15);校级自然科学研究项目(2018FSKJ18)

摘　　要：以2-氨基-5-氟苯甲酸为起始原料,与醋酐酰化关环制得6-氟-2-甲基噁嗪-4-酮(1); 1在80%水合肼中回流反应制得6-氟-2-甲基-3-氨基-4(3H)-喹唑啉酮(2); 2分别与羟基芳醛和杂环芳醛反应合成了6个6-氟-4(3H)-喹唑啉酮类Schiff碱(3a～3f),其中3b～3f为新化合物,其结构经~1H NMR,^(13)C NMR,IR和元素分析表征。采用琼脂扩散法研究了3a～3f对大肠杆菌、金黄色葡萄球菌和枯草杆菌的抑制活性。结果表明:用药浓度为400μg·mL^(-1)时,3a～3f对受试菌种均有一定的抑制活性,其中6-氟-2-甲基-3-(4-吡咯苯亚甲氨基)-4(3H)-喹唑啉酮(3c)抑菌活性最强,对大肠杆菌和枯草杆菌的抑菌圈直径分别为9. 38 mm和9. 00 mm。3-Amino-6-fluoride-2-methyl-4( 3H)-quinazolinone( 2) was prepared by 80% N2H4·H2O and 6-fluoride-2-methyl-3,1-benzoxazin-4-one,which was obtained using 5-fluoride-anthranilic acid as the raw material by cyclization with acetic anhydride. Six 6-fluoride-4( 3H)-quinazolinone Schiff bases( 3a ~ 3f) were synthesized by the reaction of 2 with hydroxyl/heterocyclicaromaticaldehyde. Among them,3b ~ 3f were new compounds. The structures were characterized by1 H NMR,13 C NMR IR,and elementary analysis. The preliminary antibacterial activities of 3a ~ 3f against Escherichia coli,Staphylococcus aureus and Bacillus subtilis were investigated by agar diffusion method. The results showed that3 a ~ 3f exhibited certain antibacterial activities with concentration of 400 μg·m L-1 and 6-fluoride-2-methyl-(( 4-pyrryl) methylene amimo)-4( 3H)-quinazolinone( 3c) produced 9. 38 mm and 9. 00 mminbibition zone diameters against Escherichia coli and Bacillus subtilis,respectively.

关 键 词：6-氟邻氨基苯甲酸 4(3H)-喹唑啉酮 SCHIFF碱 合成 抑菌活性 

分 类 号：O625.63[理学—有机化学]