含腙结构单元的喹唑啉酮衍生物的设计、合成与生物活性研究

Design,Synthesis and Biological Activity of Quinazolinone Derivatives Containing Hydrazone Structural Units

以靛红酸酐为起始原料,设计并合成了一系列新颖的含腙结构单元的喹唑啉酮类衍生物.所有目标化合物经1 H NMR、13C NMR和高分辨质谱(HRMS)表征确证其结构.初步抗菌活性结果显示,该类化合物对水稻白叶枯病菌(Xanthomonas oryzae pv.Oryzae,Xoo)、猕猴桃溃疡病菌(Pseudomonassyringae pv.actinidae,Psa)和柑橘溃疡病菌(Xanthomonas axonopodis pv.Citri,Xac)均表现出一定的抑制活性.其中3-甲基-2-(((4-((2-(4-甲基苯磺酰基)肼基)甲基)苯氧基)甲基)喹唑啉-4(3H)-酮(G18)、3-甲基-2-(((4-((2-(2,6-二氯苯基)肼基)甲基)苯氧基)甲基)喹唑啉-4(3H)-酮(G12)和3-甲基-2-(((4-((2-(苯磺酰基)肼基)甲基)苯氧基)甲基)喹唑啉-4(3H)-酮(G16)对Xoo、Psa和Xac三种细菌的抑制活性分别优于对照药叶枯唑和噻菌铜.另外,3-甲基-2-(((4-((2-(3,5-二氯苯基)肼基)甲基)苯氧基)甲基)喹唑啉-4(3H)-酮(G5)对Xoo、Psa和Xac三种细菌均表现出良好的广谱抗菌活性.

A series of novel quinazolinone derivatives containing hydrazone structural units were designed and synthesized with isatoic anhydride as the starting material.All target compounds were characterized by 1 H NMR,13C NMR and HRMS.The preliminary antibacterial activity results showed that the compounds exhibited a certain inhibitory activity against Xanthomonas oryzae pv.oryzae(Xoo),Pseudomonas syringae pv.actinidiae(Psa)and Xanthomonas axonopodis pv.citri(Xac).Among them,(E)-4-methyl-N'-(4-((3-methyl-4-oxo-3,4-dihydroquinazolin-2-yl)methoxy)benzylidene)benzenesulfonohydrazide(G18),(E)-2-((4-((2-(2,6-dichlorophenyl)hydrazono)methyl)phenoxy)methyl)-3-methylquinazolin-4(3H)-one(G12)and(E)-N'-(4-((3-methyl-4-oxo-3,4-dihydroquinazolin-2-yl)methoxy)benzylidene)benzenesulfonohydrazide(G16)displayed better antibacterial activity against Xoo,Xac and Psa than the control drugs of bismerthiazol and thiediazole-copper,respectively.Notably,(E)-2-((4-((2-(3,5-dichlorophenyl)hydrazono)methyl)phenoxy)methyl)-3-methylquinazolin-4(3H)-one(G5)displayed fine broad-spectrum antimicrobial activity against Xoo,Xac and Psa.