Citation: 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 shu

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,,

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

Corresponding author: Wang Zhenchao, wzc.4884@163.com Ouyang Guiping, oygp710@163.com
Received Date: 5 March 2020
Revised Date: 10 April 2020

Fund Project: the State Key Laboratory of Functions and Applications of Medicinal Plants FAMP201707KNational Natural Science Foundation of China 21867004National 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)and the Guizhou Provincial Science Technology Program for Platform and Talents 20185781

Figures(2)

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.
- quinazolinone derivative,
- hydrazone,
- antibacterial activity,
- structure-activity relationship
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