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Chinese Journal of Organic Chemistry >

2020 , Vol. 40 >Issue 7: 1975 - 1982

DOI: https://doi.org/10.6023/cjoc202003013

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

  • Shao Lihui ,
  • Gan Yiyuan ,
  • Hou Mi ,
  • Tao Shilin ,
  • Zhang Liqiong ,
  • Wang Zhenchao ,
  • Ouyang Guiping
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  • 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 date: 2020-03-05

  Revised date: 2020-04-10

  Online 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 . DOI: 10.6023/cjoc202003013

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