Design, Synthesis and Biological Activities of Novel Quinazolinone Derivatives Bearing 4-Phenyl-5-thioxo-1,2,4-triazole Mannich Bases

doi:10.6023/cjoc201506026

Chin. J. Org. Chem. ›› 2016, Vol. 36 ›› Issue (1): 207-212.DOI: 10.6023/cjoc201506026 Previous Articles Next Articles

Notes

新型含4-苯基-5-硫亚基-1,2,4-三唑曼尼希碱的喹唑啉酮类衍生物的设计合成及其生物活性研究 2017-2018 Awarded

闫柏任, 吕新阳, 杜欢, 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:2015-06-24 修回日期:2015-08-18 发布日期:2015-09-15
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)资助项目.

Design, Synthesis and Biological Activities of Novel Quinazolinone Derivatives Bearing 4-Phenyl-5-thioxo-1,2,4-triazole Mannich Bases

Yan Boren, Lü Xinyang, Du Huan, Bao Xiaoping

State Key Laboratory Breeding Base of Green Pesticide andAgricultural 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:2015-06-24 Revised:2015-08-18 Published:2015-09-15
Supported by:
Project supported by the National Natural Science Foundation of China (No. 21362003).

1. Design, Synthesis and Biological Activities of Novel Quinazolinone Derivatives Bearing 4-Phenyl-5-thioxo-1,2,4-triazole Mannich Bases.PDF(600KB)

Abstract

Using quinazolin-4-one as the starting compound, nine novel quinazolinone derivatives 6a～6i bearing the 4-phenyl-5- thioxo-1,2,4-triazole Mannich base unit were prepared through a five-step synthetic procedure. The structures of target compounds were characterized by ¹H NMR, ¹³C NMR, IR and elemental analysis. 3-((1-Morpholinomethyl-4-phenyl- 5-thioxo-4,5-dihydro-1H-1,2,4-triazol-3-yl)methyl)quinazolin-4(3H)-one was further confirmed by X-ray single crystal diffraction method. The preliminary biological test indicated that almost all of the title compounds had excellent antibacterial activities against Xanthomonas oryzae pv. oryzae and Xanthomonas axonopodis pv. citri at the concentration of 200 μg/mL. Moreover, compounds 6a～6i displayed a certain inhibitory effect against six kinds of tested fungi at the concentration of 50 μg/mL.

Key words: quinazolinone, 1,2,4-triazole, Mannich base, antibacterial/antifungal activity

Cite this article

Yan Boren, Lü Xinyang, Du Huan, Bao Xiaoping. Design, Synthesis and Biological Activities of Novel Quinazolinone Derivatives Bearing 4-Phenyl-5-thioxo-1,2,4-triazole Mannich Bases[J]. Chin. J. Org. Chem., 2016, 36(1): 207-212.

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References

[1] Cao, S.-L.; Feng, Y.-P.; Jiang, Y.-Y.; Liu, S.-Y.; Ding, G.-Y.; Li, R.-T. Bioorg. Med. Chem. Lett. 2005, 15, 1915.
[2] Wang, X.; Yin, J.; Shi, L.; Zhang, G.-P.; Song, B.-A. Eur. J. Med. Chem. 2014, 77, 65.
[3] Bartroli, J.; Turmo, E.; Algueró, M.; Boncompte, E.; Vericat, M. L.; Conte, L.; Ramis, J.; Merlos, M.; García-Rafanell, J.; Forn, J. J. Med. Chem. 1998, 41, 1869.
[4] Zhu, S.; Wang, J.; Chandrashekar, G.; Smith, E.; Liu, X.; Zhang, Y. Eur. J. Med. Chem. 2010, 45, 3864.
[5] Kumar, K. S.; Ganguly, S.; Veerasamy, R.; Clercq, E. D. Eur. J. Med. Chem. 2010, 45, 5474.
[6] Wang, X.; Li, P.; Li, Z.-N.; Yin, J.; He, M.; Xue, W.; Chen, Z.-W.; Song, B.-A. J. Agric. Food Chem. 2013, 61, 9575.
[7] Yang, X-H.; Wang, X.; Wu, M.-H. Chin. J. Org. Chem. 2014, 34, 1015 (in Chinese).(杨绪红, 王翔, 吴鸣虎, 有机化学, 2014, 34, 1015.)
[8] Al-Omar, M. A.; Al-Abdullah, E. S.; Shehata, I. A.; Habib, E. E.; Ibrahim, T. M.; El-Emam, A. A. Molecules 2010, 15, 2526.
[9] Plech, T.; Wujec, M.; Majewska, M.; Kosikowska, U.; Malm, A. Med. Chem. Res. 2013, 22, 2531.
[10] Wang, B.-L.; Liu, X.-H.; Zhang, X.-L.; Zhang, J.-F.; Song, H.-B.; Li, Z.-M. Chem. Biol.Drug Des. 2011, 78, 42.
[11] Koparir, M.; Orek, C.; Parlak, A. E.; Söylemez, A.; Koparir, P.; Karatepe, M.; Dastan, S. D. Eur. J. Med. Chem. 2013, 63, 340.
[12] Wang, B.-L.; Shi, Y.-X.; Ma, Y.; Liu, X.-H.; Li, Y.-H.; Song, H.-B.; Li, B.-J.; Li, Z.-M. J. Agric. Food Chem. 2010, 58, 5515.
[13] Alam, M. M.; Nazreen, S.; Haider. S.; Shafi, S.; Yar, M. S.; Hamid, H.; Alam, M. S. Arch. Pharm. Chem. Life Sci. 2012, 345, 203.
[14] Dai, H.; Liu, J.-B.; Zhang, X.; Yu, H.-B.; Qing, X.; Qin, Z.-F.; Wang, T.-T; Fang, J.-X. Chin. J. Org. Chem. 2009, 29, 123 (in Chinese). (戴红, 刘建兵, 张欣, 于海波, 秦雪, 秦振芳, 王婷婷, 方建新, 有机化学, 2009, 29, 123.)
[15] Zhang, M.; Lu, J.-R; Xin, C.-W.; Liu, F.; Wang, J.-J.; Li, H.-J.; Wei, R.-B.; Bao, X.-R. 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.)
[16] Sun, J.; Li, D.-D.; Li, J.-R.; Fang, F.; Du, Q.-R.; Qian, Y.; Zhu, H.-L. Org. Biomol. Chem. 2013, 11, 7676.
[17] Mali, J. R.; Pratap, U. R.; Netankar, P. D.; Mane, R. A. Tetrahedron Lett. 2009, 50, 5025.
[18] Kong, F.-B.; Gao, Y.-F.; Chen, X.-L.; Li, G.-L.; Chen, J. Guangxi Agric. Sci. 2006, 37, 148 (in Chinese).(孔凡彬, 高扬帆, 陈锡岭, 李广领, 陈军, 广西农业科学, 2006, 37, 148.)

新型含4-苯基-5-硫亚基-1,2,4-三唑曼尼希碱的喹唑啉酮类衍生物的设计合成及其生物活性研究 2017-2018 Awarded

Design, Synthesis and Biological Activities of Novel Quinazolinone Derivatives Bearing 4-Phenyl-5-thioxo-1,2,4-triazole Mannich Bases

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