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

doi:10.6023/cjoc202003013

Chinese Journal of Organic Chemistry ›› 2020, Vol. 40 ›› Issue (7): 1975-1982.DOI: 10.6023/cjoc202003013 Previous Articles Next Articles

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

邵利辉^a, 甘宜远^a, 侯迷^a, 陶世林^a, 张丽琼^a, 王贞超^a,b,c, 欧阳贵平^a,b,c,d

a 贵州大学药学院贵阳 550025;
b 贵州医科大学药用植物功效与利用国家重点实验室贵阳 550014;
c 贵州大学精细化工研究开发中心贵阳 550025;
d 贵州省合成药物工程实验室贵阳 550025

收稿日期:2020-03-05 修回日期:2020-04-10 发布日期:2020-05-08
通讯作者: 王贞超, 欧阳贵平 E-mail:wzc.4884@163.com;oygp710@163.com
基金资助:
国家自然科学基金（No.20161055）、药用植物功效与利用国家重点实验室（No.FAMP201707K）和贵州省科技计划（No.20185781）资助项目.

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

Shao Lihui^a, Gan Yiyuan^a, Hou Mi^a, Tao Shilin^a, Zhang Liqiong^a, Wang Zhenchao^a,b,c, Ouyang Guiping^a,b,c,d

a College of Pharmacy, Guizhou University, Guiyang 550025;
b State Key Laboratory of Functions and Application of Medicinal Plants, Guizhou Medicinal University, Guiyang 550014;
c Center for Research of Fine Chemicals, Guizhou University, Guiyang 550025;
d Guizhou Engineering Laboratory for Synthetic Drugs, Guizhou University, Guiyang 550025

Received:2020-03-05 Revised:2020-04-10 Published:2020-05-08
Supported by:
Project supported by the National Natural Science Foundation of China (No. 21867004), the State Key Laboratory of Functions and Applications of Medicinal Plants (No. FAMP201707K) and the Guizhou Provincial Science Technology Program for Platform and Talents (No. 20185781).

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Abstract

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

Cite this article

Shao Lihui, Gan Yiyuan, Hou Mi, Tao Shilin, Zhang Liqiong, Wang Zhenchao, Ouyang Guiping. Design, Synthesis and Biological Activity of Quinazolinone Derivatives Containing Hydrazone Structural Units[J]. Chinese Journal of Organic Chemistry, 2020, 40(7): 1975-1982.

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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

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