Chin. J. Org. Chem. ›› 2018, Vol. 38 ›› Issue (2): 531-538.DOI: 10.6023/cjoc201708051 Previous Articles     Next Articles



杜欢, 范治江, 杨岚, 鲍小平   

  1. 贵州大学精细化工研究开发中心 绿色农药与农业生物工程国家重点实验室培育基地 教育部绿色农药与农业生物工程重点实验室 贵阳 550025
  • 收稿日期:2017-08-24 修回日期:2017-09-28 发布日期:2017-10-20
  • 通讯作者: 鲍小平
  • 基金资助:


Synthesis and Antimicrobial Activities of Novel 1,2,4-Triazole-acyl-hydrazone Derivatives Containing the Quinazolin-4-one Moiety

Du Huan, Fan Zhijiang, Yang Lan, Bao Xiaoping   

  1. State Key Laboratory Breeding Base of Green Pesticide and Agricultural Bioengineering, Key Laboratory of Green Pesticide and Agricultural Bioengineering, Ministry of Education, Center for Research and Development of Fine Chemicals, Guizhou University, Guiyang 550025
  • Received:2017-08-24 Revised:2017-09-28 Published:2017-10-20
  • Contact: 10.6023/cjoc201708051
  • 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.

Key words: 1,2,4-triazole-acylhydrazone, quinazolin-4-one, synthesis, antimicrobial activity