含吡啶盐喹唑啉酮衍生物的合成及抑菌活性  

Synthesis and antimicrobial activities of pyridinium-containing quinazolin-4(3H)-one derivatives

作　　者：王晓斌 严莉莉 高希茗 王媛媛 张娟 顾一飞 WANG Xiao-bin;YAN Li-li;GAO Xi-ming;WANG Yuan-yuan;ZHANG Juan;GU Yi-fei(Jiangsu Key Laboratory of Marine Pharmaceutical Compound Screening,College of Pharmacy,Jiangsu Ocean University,Lianyungang 222005,China;Jiangsu Institute of Marine Resources Development,Lianyungang 222005,China;Research Center of Ocean Engineering Technology,Jiangsu Ocean University,Lianyungang 222005,China)

机构地区：[1]江苏海洋大学药学院,江苏省海洋药物活性分子筛选重点实验室,江苏连云港222005 [2]江苏省海洋资源开发研究院,江苏连云港222005 [3]江苏海洋大学海洋工程技术研究中心,江苏连云港222005

出　　处：《化学研究与应用》2024年第1期56-63,共8页Chemical Research and Application

基　　金：国家自然科学基金项目(32202334)资助;江苏省高等学校自然科学研究项目(22KJB210009)资助;江苏海洋大学人才引进项目(KQ21031)资助;江苏海洋大学研究生科研与实践创新计划项目(KYCX2023-40)资助。

摘　　要：为开发出新型绿色杀菌剂候选分子,本文将杀菌剂结构中频繁出现的吡啶单元有机融入喹唑啉-4(3H)-酮骨架的3位,设计并合成了8个含吡啶盐的喹唑啉酮分子。通过^(1)H NMR、^(13)C NMR和HRMS确证结构后,采用菌丝生长速率法和浊度法分别测定了上述目标分子对植物病原真菌和细菌的抑制活性,生测结果发现部分目标分子能显著抑制水稻白叶枯病菌和柑橘溃疡病菌。其中,1-((4-氧代喹唑啉-3(4H)-基)甲基)-1-氯化吡啶盐类分子7a对柑橘溃疡病菌的EC_(50)值达到了13.03μg·mL^(-1),抑菌效果约为商品化杀菌剂噻菌铜的3倍(40.88μg·mL^(-1))。上述研究表明含吡啶盐的喹唑啉酮分子对植物病原细菌具有较显著抑制作用,在其结构基础上进行深度的优化和改造有望得到可有效防控植物病原细菌的杀菌剂候选分子。Aiming to search for novel microbicide candidates,the pyridine fragment emerging frequently in microbicide structures was rationally introduced into the N-3 position of quinazolin-4(3H)-one skeletons to construct the eight pyridinium-containing quinazolin-4(3H)-one derivatives that were structurally confirmed by^(1)H NMR,^(13)C NMR and HRMS.The antimicrobial activities of target molecules against phytopathogenic fungi and bacteria were respectively estimated by a turbidimeter test method and a mycelium growth rate method.The above antimicrobial bioassays indicated that most of target molecules exhibited significant antibacterial effects against Xanthomonas oryzae py.oryzae and Xanthomonas axonopodis py.citri(Xac).Delightedly,the EC_(50)value of 1-((4-oxoquinazolin-3(4H)-yl)methyl)pyridin-l-ium chlorides 7a against Xac reached 13.03μg·mL^(-1),which was approximately 3-folds more effective than that of thiadiazole-copper(40.88μg·mL^(-1)).The above researches indicated that the pyridinium-containing quinazolin-4(3H)-one derivatives exhibiting inhibitory effects against phytopathogenic bacteria could be further studied as a template structure for developing novel agricultural bactericides.

关 键 词：抑菌先导发现 喹唑啉酮 吡啶盐 柑橘溃疡病菌 

分 类 号：O626[理学—有机化学]