Structural modifications on the phenazine N,N′-dioxide-scaffold looking for new selective hypoxic cytotoxins

European Journal of Medicinal Chemistry

Volumn 45, Issue 11, 2010, Pages 5362-5369

  Lavaggi, María Laura ^a   Nieves, Marcos ^a   Cabrera, Mauricio ^a   Olea Azar, Claudio ^b   López De Ceráin, Adela ^c   Monge, Antonio ^c   Cerecetto, Hugo ^a   González, Mercedes ^a  

^a UNIVERSIDAD DE LA REPÚBLICA   (Uruguay)

^b UNIVERSITY OF CHILE   (Chile)

^c UNIVERSITY OF NAVARRA   (Spain)

Author keywords

Bioreductive agents; Cancer; Phenazine N,N dioxides

Indexed keywords

2 AMINO 7(8) FLUORO 8(7) METHYLPHENAZINE 5,10 DIOXIDE; 2 AMINO 7,8 DICHLOROPHENAZINE 5,10 DIOXIDE; 2 BENZYLOXY 7(8) BROMOPHENAZINE 5,10 DIOXIDE; 5 HYDROXY 9(10) METHYLPYRIDO[3,2 A]PHENAZINE 7,12 DIOXIDE; 5,10 DIOXIDE 7(8) BROMOPHENAZIN 2 YL 2 CHLOROETANOATE; 7(8) FLUORO 2 HYDROXY 8(7) METHYLPHENAZINE 5,10 DIOXIDE; 7,8 DICHLORO 2 HYDROXYPHENAZINE 5,10 DIOXIDE; ANTINEOPLASTIC AGENT; CYTOTOXIN; MOLECULAR SCAFFOLD; PHENAZINE DERIVATIVE; PRODRUG; UNCLASSIFIED DRUG;

ARTICLE; CARBON NUCLEAR MAGNETIC RESONANCE; CELL HYPOXIA; CELL STRAIN V 79; CYTOTOXICITY; DRUG DNA INTERACTION; DRUG STRUCTURE; DRUG SYNTHESIS; ELECTROCHEMISTRY; FLUORESCENCE SPECTROSCOPY; HETERONUCLEAR MULTIPLE BOND CORRELATION; HETERONUCLEAR MULTIPLE QUANTUM COHERENCE; PROTON NUCLEAR MAGNETIC RESONANCE; REDUCTION; ULTRAVIOLET SPECTROSCOPY;

ANIMALS; ANOXIA; CELL LINE; CRICETINAE; CYTOTOXINS; ELECTROCHEMISTRY; MAGNETIC RESONANCE SPECTROSCOPY; MOLECULAR STRUCTURE; PHENAZINES; SPECTROMETRY, MASS, ELECTROSPRAY IONIZATION;

EID: 77957828614     PISSN: 02235234     EISSN: 17683254     Source Type: Journal    
DOI: 10.1016/j.ejmech.2010.08.061     Document Type: Article

References (32)

1. S. Rockwell, and J.E. Moulder Int. J. Radiat. Oncol. Biol. Phys. 19 1990 197 202
2. W.A. Denny Eur. J. Med. Chem. 36 2001 577 595
3. K. Ruan, G. Song, and G. Ouyang J. Cell. Biochem. 107 2009 1053 1062
4. J.M. Brown, and W.R. Wilson Nat. Rev. Cancer 4 2004 437 447
5. A.J. Lin, L.A. Cosby, C.W. Shansky, and A.C. Sartorelli J. Med. Chem. 15 1972 1247 1252
6. P. Wardman Curr. Med. Chem. 8 2001 739 761
7. H. Cerecetto, and M. González Minirev. Med. Chem. 1 2001 219 231
8. H. Cerecetto, M. González, and M.L. Lavaggi Med. Chem. 2 2006 315 327
9. H. Cerecetto, M. González, M.L. Lavaggi, and W. Porcal J. Braz. Chem. Soc. 6 2005 1290 1296
10. H. Cerecetto, M. González, M.L. Lavaggi, M.A. Aravena, C. Rigol, C. Olea-Azar, A. Azqueta, A. López de Ceráin, A. Monge, and A.M. Bruno Med. Chem. 2 2006 511 521
11. H. Cerecetto, M. González, M.L. Lavaggi, A. Azqueta, O. Ezpeleta, A. López de Ceraín, and A. Monge-Vega J. Med. Chem. 48 2005 21 23
12. M.L. Lavaggi, M. Cabrera, M.A. Aravena, C. Olea-Azar, A. López de Ceráin, A. Monge, G. Pachón, M. Cascante, A.M. Bruno, L.I. Pietrasanta, M. González, and H. Cerecetto Bioorg. Med. Chem. 18 2010 4433 4440
13. M.L. Lavaggi, M. Cabrera, M. González, and H. Cerecetto Chem. Res. Toxicol. 21 2008 1900 1906
14. O.G. Pachón, A. Azqueta, M.L. Lavaggi, A. López de Ceraín, E. Creppy, A. Collins, H. Cerecetto, M. González, J.J. Centelles, and M. Cascante Chem. Res. Toxicol. 21 2008 1578 1585
15. G.-W. Ludwig, and H. Baumgartel Chem. Ber. 115 1982 2380 2383
16. E. Vicente, R. Villar, A. Burguete, B. Solano, S. Ancizu, S. Pérez-Silanes, I. Aldana, and A. Monge Molecules 13 2008 86 95
17. M.J. Abu El-Haj, B.W. Dominy, and J.D. Johnston J. Org. Chem. 37 1972 589 593
18. A.J. Boulton, A.R. Katritzky, M.J. Sewell, and B. Wallis J. Chem. Soc. B 9 1967 914 917
19. A.J. Boulton, P.J. Halls, and A.R. Katritzky J. Chem. Soc. B 1970 636 640
20. A. Monge, J.A. Palop, A. López de Ceráin, V. Senador, F.J. Martínez-Crespo, Y. Sáinz, S. Narro, E. García, C. de Miguel, M. González, A.J. Barker, E. Hamilton, E.D. Clarke, and D.T. Greenhow J. Med. Chem. 38 1995 1786 1792
21. C. Urquiola, M. Vieites, M.H. Torre, M. Cabrera, M.L. Lavaggi, H. Cerecetto, M. González, A. López de Cerain, A. Monge, P. Smircich, B. Garat, and D. Gambino Bioorg. Med. Chem. 17 2009 1623 1629
22. J.D. Aguirre, A.M. Angeles-Boza, A. Chouai, J.P. Pellois, C. Turro, and K.R. Dunbar J. Am. Chem. Soc. 131 2009 11353 11360
23. J. Wang, and X. Yang Spectrochim. Acta A Mol. Biomol. Spectrosc. 74 2009 421 426
24. P.U. Maheswari, V. Rajendiran, M. Palaniandavar, R. Parthasarathi, and V. Subramanian J. Inorg. Biochem. 100 2006 3 17
25. X. Jiang, L. Shang, Z. Wang, and S. Dong Biophys. Chem. 118 2005 42 50
26. Y.N. Ni, and X.Z. Zhong Chin. Chem. Lett. 18 2007 569 572
27. H. Heli, S.Z. Bathaie, and M.F. Mousavi Electrochem. Commun. 6 2004 1114 1118
28. Y. Li, X.J. Yao, J. Jin, X.G. Chen, and Z.D. Hu Biochim. Biophys. Acta 1774 2007 51 58
29. H. Cerecetto, R. Di Maio, M. González, M. Risso, P. Saenz, G. Seoane, A. Denicola, G. Peluffo, C. Quijano, and C. Olea-Azar J. Med. Chem. 42 1999 1941 1950
30. L.A. Fernández, M.R. Santo, M. Reta, L. Giacomelli, R. Cattana, J.J. Silber, M. Risso, H. Cerecetto, M. González, and C. Olea-Azar Molecules 10 2005 1197 1208
31. J. Rodríguez, A. Gerpe, G. Aguirre, U. Kemmerling, O.E. Piro, V.J. Arán, J.D. Maya, C. Olea-Azar, M. González, and H. Cerecetto Eur. J. Med. Chem. 44 2009 1545 1553
32. Y. Cao, and X.W. He Spectrochim. Acta, Part A 54 1998 883 892