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


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   

  1. 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;
  • 基金资助:

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

Shao Lihuia, Gan Yiyuana, Hou Mia, Tao Shilina, Zhang Liqionga, Wang Zhenchaoa,b,c, Ouyang Guipinga,b,c,d   

  1. 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).

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