Chinese Journal of Organic Chemistry >
Synthesis and Antimicrobial Activities of Novel 1,2,4-Triazole-acyl-hydrazone Derivatives Containing the Quinazolin-4-one Moiety
Received date: 2017-08-24
Revised date: 2017-09-28
Online published: 2017-10-20
Supported by
Project supported by the National Natural Science Foundation of China (No. 21362003) and the Agricultural Research Projects of Guizhou Province (No. 20093010).
A total of twenty novel 1, 2, 4-triazole-acylhydrazone derivatives containing the quinazolin-4-one moiety were synthesized via the condensation reaction of triazole hydrazide with various aromatic aldehydes, and fully characterized by 1H NMR, 13C NMR and HRMS spectra. Antimicrobial assays in vitro indicated that most of the target compounds exhibited good antibacterial activities against the pathogenic phytobacteria Xanthomonas oryzae pv. oryzae(Xoo) and Xanthomonas axonopodis pv. citri(Xac). Notably, N'-(2-methoxybenzylidene)-1-(2-(4-oxoquinazolin-3(4H)-yl) ethyl)-1H-1, 2, 4-triazole-3-acylhy-drazone)(7q) displayed the inhibition rate of 100% against the above two bacteria at 100 μg/mL. Additionally, 1-(2-(4-oxo-quinazolin-3(4H)-yl) ethyl)-N'-(4-(trifluoromethyl) benzylidene)-1H-1, 2, 4-triazole-3-acylhydrazone (7i), N'-(2-bromobenzyli-dene)-1-(2-(4-oxoquinazolin-3(4H)-yl) ethyl)-1H-1, 2, 4-triazole-3-acylhydrazone (7j), N'-(4-bromobenzylidene)-1-(2-(4-oxo-quinazolin-3(4H)-yl) ethyl)-1H-1, 2, 4-triazole-3-acylhydrazone (7l), and N'-(4-methoxybenzylidene)-1-(2-(4-oxoquinazolin-3(4H)-yl) ethyl)-1H-1, 2, 4-triazole-3-acylhydrazone (7o) were found to possess the inhibition rate of >55% against the fungus Botrytis cinerea Pers. at 50 μg/mL.
Du Huan , Fan Zhijiang , Yang Lan , Bao Xiaoping . Synthesis and Antimicrobial Activities of Novel 1,2,4-Triazole-acyl-hydrazone Derivatives Containing the Quinazolin-4-one Moiety[J]. Chinese Journal of Organic Chemistry, 2018 , 38(2) : 531 -538 . DOI: 10.6023/cjoc201708051
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