Chinese Journal of Organic Chemistry >
Design, Synthesis and Biological Activities of Novel Quinazolinone Derivatives Bearing 4-Phenyl-5-thioxo-1,2,4-triazole Mannich Bases
Received date: 2015-06-24
Revised date: 2015-08-18
Online published: 2015-09-15
Supported by
Project supported by the National Natural Science Foundation of China (No. 21362003).
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.
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]. Chinese Journal of Organic Chemistry, 2016 , 36(1) : 207 -212 . DOI: 10.6023/cjoc201506026
[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.)
/
| 〈 |
|
〉 |
