Synthesis and biological evaluation of 4-(1,2,3-triazol-1-yl)coumarin derivatives as potential antitumor agents

Bioorganic and Medicinal Chemistry Letters

Volumn 24, Issue 3, 2014, Pages 799-807

  Zhang, Wenjuan ^a   Li, Zhi ^a   Zhou, Meng ^a   Wu, Feng ^a   Hou, Xueyan ^a   Luo, Hao ^a   Liu, Hao ^a   Han, Xuan ^a   Yan, Guoyi ^a   Ding, Zhenyu ^a   Li, Rui ^a  

^a SICHUAN UNIVERSITY   (China)

Author keywords

1,2,3 Triazole; Antiproliferative activity; Apoptosis; Coumarin; G2 M cell cycle arrest

Indexed keywords

4 (1,2,3 TRIAZOL 1 YL)COUMARIN DERIVATIVE; ANTINEOPLASTIC AGENT; COUMARIN DERIVATIVE; DOXORUBICIN; UNCLASSIFIED DRUG;

ANTINEOPLASTIC ACTIVITY; ANTIPROLIFERATIVE ACTIVITY; APOPTOSIS; ARTICLE; CANCER CELL CULTURE; CELL STRAIN MCF 7; COLON CARCINOMA; CONTROLLED STUDY; DRUG CONJUGATION; DRUG POTENCY; DRUG SCREENING; DRUG SYNTHESIS; G2 PHASE CELL CYCLE CHECKPOINT; HUMAN; HUMAN CELL; IC 50; IN VITRO STUDY; LUNG CARCINOMA; STRUCTURE ACTIVITY RELATION;

1,2,3-TRIAZOLE; ANTIPROLIFERATIVE ACTIVITY; APOPTOSIS; COUMARIN; G(2)/M CELL-CYCLE ARREST;

ANTINEOPLASTIC AGENTS; APOPTOSIS; CELL CYCLE; CELL LINE, TUMOR; CELL PROLIFERATION; COUMARINS; FLOW CYTOMETRY; HUMANS; INHIBITORY CONCENTRATION 50; MCF-7 CELLS; TRIAZOLES;

EID: 84893685355     PISSN: 0960894X     EISSN: 14643405     Source Type: Journal    
DOI: 10.1016/j.bmcl.2013.12.095     Document Type: Article

References (31)

1. R.D.H. Murray, J. Mendez, and S.A. Brown Chemistry and Biochemistry 1982 John Wiley & Sons Ltd New York 21
2. M.M. Garazd, Y.L. Garadz, and V.P. Khilya Chem. Nat. Comp. 39 2003 54
3. J.R. Hwu, R. Singha, S.C. Hong, Y.H. Chang, A.R. Das, I. Vliegen, E.D. Clercq, and J. Neyts Antiviral Res. 77 2008 157
4. J. Neyts, E.D. Clercq, R. Singha, Y.H. Chang, A.R. Das, S.K. Chakraborty, S.C. Hong, S.C. Tsay, M.H. Hsu, and J.R. Hwu J. Med. Chem. 52 2009 1486
5. J.R. Hwu, S.Y. Lin, S.C. Tsay, E.D. Clercq, P. Leyssen, and J. Neyts J. Med. Chem. 54 2011 2114
6. Z.P. Li, J.F. Hu, M.N. Sun, H.J. Ji, S.F. Chu, G. Liu, and N.H. Chen Int. Immunopharmacol. 14 2012 145
7. Z.P. Li, J.F. Hu, M.N. Sun, H.J. Ji, M. Zhao, D.H. Wu, G.Y. Li, G. Liu, and N.H. Chen Eur. J. Pharmacol. 661 2011 118
8. Y. Shi, and C.H. Zhou Bioorg. Med. Chem. Lett. 21 2011 956
9. F. Meggio, M.A. Pagano, S. Moro, G. Zagotto, M. Ruzzene, S. Sarno, G. Cozza, J. Bain, M. Elliott, A.D. Deana, A.M. Brunati, and L.A. Pinna Biochemistry 43 2004 12931
10. A. Chilin, R. Battistutta, A. Bortolato, G. Cozza, S. Zanatta, G. Poletto, M. Mazzorana, G. Zagotto, E. Uriarte, A. Guiotto, L.A. Pinna, F. Meggio, and S. Moro J. Med. Chem. 51 2008 752
11. G.L. Bras, C. Radanyi, J.F. Peyrat, J.D. Brion, M. Alami, V. Marsaud, B. Stella, and J.M. Renoir J. Med. Chem. 50 2007 6189
12. H.P. Zhao, A.C. Donnelly, B.R. Kusuma, G.E.L. Brandt, D. Brown, R.A. Rajewski, G. Vielhauer, J. Holzbeierlein, M.S. Cohen, and B.S.J. Blagg J. Med. Chem. 54 2011 3839
13. H.P. Zhao, B. Yan, L.B. Peterson, and B.S.J. Blagg ACS Med. Chem. Lett. 3 2012 327
14. A.C. Donnelly, J.R. Mays, J.A. Burlison, J.T. Nelson, G. Vielhauer, J. Holzbeierlein, and B.S.J. Blagg J. Org. Chem. 73 2008 8901
15. A. Purohit, L.W.L. Woo, B.V.L. Potter, and M.J. Reed Cancer Res. 60 2000 3394
16. L.W.L. Woo, A. Purohit, B. Malini, M.J. Reed, and B.V.L. Potter Chem. Biol. 7 2000 773
17. B. Malini, A. Purohit, D. Ganeshapillai, L.W.L. Woo, B.V.L. Potter, M.J. Reed, and J. Steroid Biochem Mol. Biol. 75 2000 253
18. H.C. Kolb, and K.B. Sharpless Drug Discovery Today 8 2003 1128
19. A.D. Moorhouse, and J.E. Moses Chem. Med. Chem. 3 2008 715
20. M. Whiting, J. Muldoon, Y.C. Lin, S.M. Silverman, W. Lindstrom, A.J. Olson, H.C. Kolb, M.G. Finn, K.B. Sharp less, J.H. Elder, and V.V. Fokin Chem. Int. Ed. 45 2006 1435
21. N. Boechat, V.F. Ferreira, S.B. Ferreira, M.L.G. Ferreira, F.C. Silva, M.M. Bastos, M.S. Costa, M.C.S. Lourenco, A.C. Pinto, A.U. Krettli, A.C. Aguiar, B.M. Teixeira, N.V. Silva, P.R.C. Martins, F.A.F.M. Bezerra, A.L.S. Camilo, G.P. Silva, and C.C.P. Costa J. Med. Chem. 54 2011 5988 5999
22. J. Hou, Z. Li, Q. Fang, C. Feng, H. Zhang, W. Guo, H. Wang, G. Gu, Y. Tian, P. Liu, R. Liu, J. Lin, Y. Shi, Z. Yin, J. Shen, and P.G. Wang J. Med. Chem. 55 2012 3066 3075
23. M. Glaser, J. Goggi, G. Smith, M. Morrison, S.K. Luthra, E. Robins, and E.O. Aboagye Bioorg. Med. Chem. Lett. 21 2011 6945 6949
24. G. Smith, M. Glaser, M. Perumal, Q.D. Nguyen, B. Shan, E. Arstad, and E.O. Aboagye J. Med. Chem. 24 2008 8057
25. Y.C. Duan, Y.C. Ma, E. Zhang, X.J. Shi, M.M. Wang, X.W. Ye, and H.M. Liu Eur. J. Med. Chem. 62 2013 11
26. L.B. Peterson, and B.S.J. Blagg Bioorg. Med. Chem. Lett. 20 2010 3957
27. H.A. Stefani, K. Gueogjan, F. Manarin, S.H.P. Farsky, J. Zukerman-Schpector, I. Caracelli, S.R.P. Rodrigues, M.N. Muscará, S.A. Teixeira, J.R. Santin, I.D. Machado, S.M. Bolonheis, R. Curi, and M.A. Vinolo Eur. J. Med. Chem. 58 2012 117
28. S.G. Ouellet, D. Gauvreau, M. Cameron, S. Dolman, L.C. Campeau, G. Hughes, P.D. O'Shea, and I.W. Davies Org. Process Res. Dev. 16 2012 214
29. D.D. Soto-Ortega, B.P. Murphy, F.J. Gonzalez-Velasquez, K.A. Wilson, F. Xie, Q. Wang, and M.A. Moss Bioorg. Med. Chem 19 2011 2596
30. K. Sivakumar, F. Xie, B.M. Cash, S. Long, H.N. Barnhill, and Q. Wang Org. Lett. 6 2004 4603
31. C.W. Tornøe, C. Christensen, and M. Meldal J. Org. Chem. 67 2002 3057