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

doi:10.6023/cjoc201708051

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

Notes

含喹唑啉-4-酮片段的新型1,2,4-三唑酰腙类衍生物的合成及抗菌活性

杜欢, 范治江, 杨岚, 鲍小平

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 E-mail:baoxp_1980@aliyun.com
基金资助:
国家自然科学基金（No.21362003）和贵州省农业攻关（No.20093010）资助项目.

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

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 E-mail:baoxp_1980@aliyun.com
Supported by:
Project supported by the National Natural Science Foundation of China (No. 21362003) and the Agricultural Research Projects of Guizhou Province (No. 20093010).

1. Synthesis and Antimicrobial Activities of Novel 1,2,4-Triazole-acyl-hydrazone Derivatives Containing the Quinazolin-4-one Moiety.PDF(3859KB)

Abstract

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

Cite this article

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]. Chin. J. Org. Chem., 2018, 38(2): 531-538.

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[1] Sun, X.; Cao, Y.; Yang, Z.; Xu, C.; Li, X.; Wang, S.; Zhang, Q. Plant J. 2004, 37, 517.
[2] Graham, J. H.; Gottwald, T. R.; Cubero, J.; Achor, D. S. Mol. Plant Pathol. 2004, 5, 1.
[3] Salanoubat M.; Genin S.; Artiguenave F.; Gouzy J.; Mangenot S.; Arlat M.; Billaultk A.; Brottier P.; Camus J. C.; Cattolico L.; Chandler M.; Choisne N.; Claudel-Renard C.; Cunnac S.; Demange, N.; Gaspin C.; Lavie M.; Moisan A.; Robert C.; Saurin W.; Schiex T.; Siguier P.; Thébault P.; Whalen M.; Wincker P.; Levy M.; Weissenbach J.; Boucher C. A. Nature 2002, 415, 497.
[4] Ryan R. P.; Vorhölter F. J.; Potnis N.; Jones J. B.; Van Sluys M. A.; Bogdanove A. J.; Dow J. M. Nat. Rev. Microbiol. 2011, 9, 344.
[5] Li J.; Wang N. PLoS One 2011, 6, e21804.
[6] Chang, Y. H.; Zhang, L.; Liu Y. Z.; Chen, Z. Y. Jiangsu Agric. Sci. 2012, 40, 89(in Chinese). (常有宏, 张磊, 刘邮洲, 陈志谊, 江苏农业科学, 2012, 40, 89.)
[7] Sun, N.; Du, R. L.; Zheng, Y. Y.; Huang, B. H.; Guo, Q.; Zhang, R. F.; Wong, K. Y.; Lu, Y. J. Eur. J. Med. Chem. 2017, 135, 1.
[8] Shavit, M.; Pokrovskaya, V.; Belakhov, V.; Baasov, T. Bioorg. Med. Chem. 2017, 25, 2917.
[9] Zhang, F.; Wen, Q.; Wang, S. F.; Shahla, K. B.; Yang, Y. S.; Liu, J. J.; Zhang, W. M.; Zhu, H. L. Bioorg. Med. Chem. Lett. 2014, 24, 90.
[10] Somagond, S. M.; Kamble, R. R.; Kattimani, P. P.; Joshi, S. D.; Dixit, S. R. Heterocycl. Commun. 2017, 23, 317.
[11] Kulabas, N.; Tatar, E.; Özakpinar, Ö. B.; Özsavci, D.; Pannecouque, C.; Clercq, E. D.; Küçükgüzel, I. Eur. J. Med. Chem. 2016, 121, 58.
[12] Basaran, E.; Karakucuk-Iyidogan, A.; Schols, D.; Oruc-Emre, E. E. Chirality 2016, 28, 495.
[13] Xiong, Q.; Liu, J.; Lin, X.; Bao, X. Chin. J. Org. Chem. 2012, 32, 1951(in Chinese). (熊启中, 刘军虎, 林选福, 鲍小平, 有机化学, 2012, 32, 1951.)
[14] Che, Z.; Zhang, S.; Shao, Y.; Fan, L.; Xu, H.; Yu, X.; Zhi, X. Y.; Yao, X. J.; Zhang, R. J. Agric. Food Chem. 2013, 61, 5696.
[15] Wang, X.; Yin, J.; Shi, L.; Zhang, G. P.; Song, B. A. Eur. J. Med. Chem. 2014, 77, 65.
[16] Zhang, J.; Liu, J.; Ma, Y.; Ren, D.; Cheng, P.; Zhao, J. W.; Zhang, F.; Yao, Y. Bioorg. Med. Chem. Lett. 2016, 26, 2273.
[17] Ding, P. P.; Gao, M.; Mao, B. B.; Cao, S. L.; Liu, C. H.; Yang, C. R.; Li, Z. F.; Liao, J.; Zhao, H.; Li, Z.; Li, J.; Wang, H.; Xu, X. Eur. J. Med. Chem. 2016, 108, 364.
[18] Chen, M.; Li, P.; Hu, D.; Zeng, S.; Li, T.; Jin, L.; Xue, W.; Song, B. Bioorg. Med. Chem. Lett. 2016, 26, 168.
[19] Zhu, S. S.; Lu, J. R.; Xin, C. W.; Lu, B. W.; Bao, X. R.; Zou, M.; Liu, Q. Chem. J. Chin. Univ. 2010, 31, 2228(in Chinese). (朱姗姗, 卢俊瑞, 辛春伟, 卢博为, 鲍秀荣, 邹敏, 刘倩, 高等学校化学学报, 2010, 31, 2228.)
[20] Zhang, M.; Lu, J.; Xin, C.; Liu, F.; Wang, J.; Li, H.; Wei, R.; Bao, X. Chin. J. Org. Chem. 2009, 29, 1645(in Chinese). (张明, 卢俊瑞, 辛春伟, 刘芳, 王菁菁, 李红姬, 魏荣宝, 鲍秀荣, 有机化学, 2009, 29, 1645.)
[21] Liu, J.; Liu, Y.; Jian, J.; Bao, X. Chin. J. Org. Chem. 2013, 33, 370(in Chinese). (刘军虎, 刘勇, 蹇军友, 鲍小平, 有机化学, 2013, 33, 370.)
[22] Yan, B.; Lv, X.; Du, H.; Bao, X. Chin. J. Org. Chem. 2016, 36, 207(in Chinese). (闫柏任, 吕新阳, 杜欢, 鲍小平, 有机化学, 2016, 36, 207.)
[23] Yan, B. R.; Lv, X. Y.; Du, H.; Gao, M. N.; Huang, J.; Bao, X. P. Chem. Pap. 2016, 70, 983.
[24] Zhang, G.; Fu, X.; Peng, X.; Li, X.; Chen, J. J. Chem. Res. 2013, 37, 730.
[25] Yao, Y. P.; Dai, F. Y.; Dong, K. K.; Mao, Q.; Wang, Y. L.; Chen, T. J. Chem. Res. 2011, 35, 4.
[26] Okuda, K.; Ohtomo, H.; Tagata, T.; Hirota, T.; Sasaki, K. Synth. Commun. 2011, 41, 812.
[27] Yang, L.; Bao, X. RSC Adv. 2017, 7, 34005.
[28] Fan, Z.; Shi, Z.; Zhang, H.; Liu, X.; Bao, L.; Ma, L.; Zuo, X.; Zheng, Q.; Mi, N. J. Agric. Food Chem. 2009, 57, 4279.
[29] Chen, C. J.; Song, B. A.; Yang, S.; Xu, G. F.; Bhadury, P. S.; Jin, L. H.; Hu, D. Y.; Li, Q. Z.; Liu, F.; Xue, W.; Lu, P.; Chen, Z. Bioorg. Med. Chem. 2007, 15, 3981.

含喹唑啉-4-酮片段的新型1,2,4-三唑酰腙类衍生物的合成及抗菌活性

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

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