摘要/Abstract

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¹H 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.
关键词: 喹唑啉酮衍生物, 腙, 抑菌活性, 构效关系
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 ¹H 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)benzenesulfonohydrazi-de (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.
Key words: quinazolinone derivative, hydrazone, antibacterial activity, structure-activity relationship


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