Articles

Synthesis and Biological Activity of N-Substituted Benzylidene-4-(4-methoxyphenyl)-5-(1H-1,2,4-triazol-1-yl)-1,3-thiazol-2-amine

  • Dai Hong ,
  • Zhou Xin ,
  • Shao Ling ,
  • Liu Jianbing ,
  • Qin Xue ,
  • Fang Jianxin
Expand
  • a State Key Laboratory of Elemento-organic Chemistry, Nankai University, Tianjin 300071;
    b College of Chemistry and Chemical Engineering, Nantong University, Nantong 226019

Received date: 2012-02-24

  Revised date: 2012-05-11

  Online published: 2012-03-30

Supported by

Project supported by the National Natural Science Foundation of China (No.20772068), the Science and Technology Projects Fund of Nantong City (Nos.AS2010005, AS2011011)

Abstract

Reaction of 2-amino-4-(4-methoxyphenyl)-5-(1H-1,2,4-triazol-1-yl)-1,3-thiazole with various substituted benzal-dehydes produced a series of novel thiazole Schiff bases containing 1H-1,2,4-triazole ring. Their structures were characterized by 1H NMR spectra and elemental analysis. The bioassay data indicated that some of the title compounds showed certain antitumor activities.

Cite this article

Dai Hong , Zhou Xin , Shao Ling , Liu Jianbing , Qin Xue , Fang Jianxin . Synthesis and Biological Activity of N-Substituted Benzylidene-4-(4-methoxyphenyl)-5-(1H-1,2,4-triazol-1-yl)-1,3-thiazol-2-amine[J]. Chinese Journal of Organic Chemistry, 2012 , 32(9) : 1715 -1718 . DOI: 10.6023/cjoc1202242

References

[1] Es-Sayed, M.; Jeschke, P.; Loesel, P.; Nauen, R.; Ebbinghaus- Kintscher, U.; Malsam, O.; Stecker, B.; De Meijere, A.; Brackmann, F. DE 102004013528, 2005 [Chem. Abstr. 2005, 143, 387035].

[2] Huang, W.; Yang, G. F. Bioorg. Med. Chem. 2006, 14, 8280.   

[3] Yan, M.; Shi, D. Q. Chin. J. Org. Chem. 2008, 28, 736 (in Chinese). (严曼, 石德清, 有机化学, 2008, 28, 736.)

[4] Li, N.; Wei, X.; Fan, H. T.; Bi, L.; Li, X. Y.; Yang, S.; Hu, D. Y.; Song, B. A. Chin. J. Org. Chem. 2011, 31, 1300 (in Chinese). (李娜, 魏学, 范会涛, 毕亮, 李向阳, 杨松, 胡德禹, 宋宝安, 有机化学, 2011, 31, 1300.)

[5] Aberle, N.; Catimel, J.; Nice, E. C.; Watson, K. G. Bioorg. Med. Chem. Lett. 2007, 17, 3741.   

[6] Rai, N. P.; Venu, T. D.; Manuprasad, B. K.; Shashikanth, S.; Arunachalam, P. N.; Firdouse, A. Chem. Biol. Drug Des. 2010, 75, 400.

[7] Sharma, R. N.; Xavier, F. P.; Vasu, K. K.; Chaturvedi, S. C.; Pancholi, S. S. J. Enzyme Inhib. Med. Chem. 2009, 24, 890.

[8] Calderone, V.; Fiamingo, F. L.; Giorgi, I.; Leonardi, M.; Livi, O.; Martelli, A.; Martinotti, E. Eur. J. Med. Chem. 2006, 41, 761.

[9] Weng, J. Q.; Liu, H. J.; Liu, X. H.; Tan, C. X.; Shen, D. L. Chin. J. Pestic. Sci. 2010, 12, 463 (in Chinese). (翁建全, 刘会君, 刘幸海, 谭成侠, 沈德隆, 农药学学报, 2010, 12, 463.)

[10] Franchetti, P.; Cappellacci, L.; Pasqualini, M.; Petrelli, R.; Jayaprakasan, V.; Jayaram, H. N.; Boyd, D. B.; Jain, M. D.; Grifantini, M. Bioorg. Med. Chem. 2005, 13, 2045.   

[11] Luo, J.; Zhao, G. L.; Wang, Y. L.; Shao, H.; Qu, B. H.; Tang, L. D. Chin. J. Synth. Chem. 2011, 19, 41 (in Chinese). (罗杰, 赵桂龙, 王玉丽, 邵华, 曲宝涵, 汤立达, 合成化学, 2011, 19, 41.)

[12] Li, Q. Z., Song, B. A.; Cai, X. J.; Zheng, Y. G.; Guo, Q. Q. Chin. J. Org. Chem. 2010, 30, 569 (in Chinese). (李黔柱, 宋宝安, 蔡学建, 郑玉国, 郭晴晴, 有机化学, 2010, 30, 569.)

[13] Xu, W. M.; Song, B. A.; Yang, S.; Hu, D. Y.; Zeng, S. Chin. J. Pestic. 2010, 49, 625 (in Chinese). (徐维明, 宋宝安, 杨松, 胡德禹, 曾松, 农药, 2010, 49, 625.)

[14] Bayrak, H.; Demirbas, A.; Karaoglu, S. A.; Demirbas, N. Eur. J. Med. Chem. 2009, 44, 1057.

[15] Isloor, A. M.; Kalluraya, B.; Shetty, P. Eur. J. Med. Chem. 2009, 44, 3784.

[16] Li, Y. C.; Cheng, J. A.; Zheng, J. Y. Chin. J. Pestic. 1993, 32(6), 11 (in Chinese). (李煜昶, 成俊然, 郑健禺, 农药, 1993, 32(6), 11.)   

[17] Li, Y. C. Chin. J. Pestic. 1993, 32(1), 20 (in Chinese). (李煜昶, 农药, 1993, 32(1), 20.)   

[18] Goa, K. L.; Barradell, L. B. Drugs 1996, 50, 658.

[19] Haria, M.; Bryson, H. M.; Goa, K. L. Drugs 1996, 51, 585.   

[20] Casali, A.; Sega, F. M.; Casali, M.; Giuntini, T.; Cappellini, G. C.; Terzoli, E. J. Exp. Clin. Cancer Res. 2000, 19, 17.

[21] Wang, J.; Bei, F. L.; Li, R. Y.; Yang, X. J.; Wang, X. Chin. J. Org. Chem. 2004, 24, 550 (in Chinese). (王军, 卑凤利, 李人宇, 杨绪杰, 汪信, 有机化学, 2004, 24, 550.)

[22] Yu, H. B.; Shao, L.; Fang, J. X. J. Organomet. Chem. 2007, 692, 991.

[23] Qin, X.; Yu, H. B.; Dai, H.; Qin, Z. F.; Zhang, X.; Bing, G. F.; Wang, T. T.; Fang, J. X. Chin. Chem. Lett. 2010, 21, 283.

[24] Qin, X.; Yu, H. B.; Liu, J. B.; Dai, H.; Bing, G. F.; Qin, Z. F.; Zhang, X.; Wang, T. T.; Fang, J. X. ARKIVOC 2009, (ii), 201.

[25] Liu, J. B.; Li, L. C.; Dai, H.; Liu, Z.; Fang, J. X. J. Organomet. Chem. 2006, 691, 2686.

[26] Shao, L.; Zhou, X.; Zhang, Q.; Liu, J. B.; Jin, Z.; Fang, J. X. Synth. Commun. 2007, 37, 199.  

Outlines

/