New hydroxypyrimidinone-containing sulfonamides as carbonic anhydrase inhibitors also acting as MMP inhibitors

Bioorganic and Medicinal Chemistry Letters

Volumn 20, Issue 12, 2010, Pages 3623-3627

  Esteves, M Alexandra ^a   Ortet, Osvaldo ^a   Capelo, Anabela ^a   Supuran, Claudiu T ^b   Marques, Sérgio M ^c   Santos, M Amélia ^c  

^a LABORATÓRIO NACIONAL DE ENERGIA E GEOLOGIA   (Portugal)

^b UNIVERSITY OF FLORENCE   (Italy)

^c INSTITUTO SUPERIOR TÉCNICO   (Portugal)

Author keywords

Carbonic anhydrase inhibitors; Hydroxypyrimidinones; MMP inhibitors; Sulfonamides

Indexed keywords

1 (BENZYLOXY) 4 (1',2',4 TRIAZOL 1' YL) 2 (1H) PYRIMIDINONE; 3 (4 SULFAMOYL PHENYLCARBAMOYL) PROPYLCARBAMIC ACID BENZYL ESTER; 4 [3 [(4 SULFAMOYL PHENYL)CARBAMOYL]PROPYLAMINO] 1 (BENZYLOXY) 2 (1H) PYRIMIDINONE; 4 [3 [(4 SULFAMOYL PHENYL)CARBAMOYL]PROPYLAMINO] 1 HYDROXY 2 (1H) PYRIMIDINONE; 4 [5 (METHYLOXYCARBONYL)PENTYLAMINO] 1 (BENZYLOXY) 2 (1H) PYRIMIDINONE; ANTINEOPLASTIC AGENT; BENZENESULFONAMIDE DERIVATIVE; CARBONATE DEHYDRATASE; CARBONATE DEHYDRATASE INHIBITOR; ISOENZYME; MATRIX METALLOPROTEINASE; MATRIX METALLOPROTEINASE INHIBITOR; N (4 SULFAMOYL PHENYL) 4 AMINOBUTANAMIDE; PYRIMIDINONE DERIVATIVE; SULFONAMIDE; UNCLASSIFIED DRUG;

ANTINEOPLASTIC ACTIVITY; ARTICLE; COMPETITIVE INHIBITION; CYTOSOL; DRUG ACTIVITY; DRUG STRUCTURE; DRUG SYNTHESIS;

ANTIGENS, NEOPLASM; ANTINEOPLASTIC AGENTS; CARBONIC ANHYDRASE I; CARBONIC ANHYDRASE II; CARBONIC ANHYDRASE INHIBITORS; CARBONIC ANHYDRASES; ENZYME INHIBITORS; HUMANS; ISOENZYMES; MATRIX METALLOPROTEINASES; PYRIMIDINONES; SULFONAMIDES;

EID: 77954244965     PISSN: 0960894X     EISSN: None     Source Type: Journal    
DOI: 10.1016/j.bmcl.2010.04.109     Document Type: Article

References (28)

1. C.T. Supuran, J.-Y. Winum, Drug Design of Zinc-Enzyme Inhibitors 2009 John Wiley & Sons, Inc. New Jersey pp 13-486, and references cited therein
2. C.T. Supuran, J.-Y. Winum, Drug Design of Zinc-Enzyme Inhibitors 2009 John Wiley & Sons, Inc. New Jersey pp 489-671, and references cited therein
3. C.T. Supuran Nat. Rev. Drug Disc. 7 2008 168
4. C.T. Supuran, A. Scozzafava, and A. Casini Med. Res. Rev. 23 2003 146
5. C.T. Supuran Curr. Pharm. Des. 14 2008 603
6. B.I. Wilkinson, L.F. Bornaghi, T.A. Houston, A. Innocenti, D. Vullo, C.T. Supuran, and S.A. Poulsen J. Med. Chem. 50 2007 1651
7. M.P. Leese, B. Leblond, A. Smith, S.P. Newman, A. Di Fiore, G. De Simone, C.T. Supuran, A. Purohit, M.J. Reed, and B. Potter J. Med. Chem. 49 2006 7683
8. S.M. Marques, E. Nuti, A. Rossello, C.T. Supuran, T. Tuccinardi, A. Martinelli, and M.A. Santos J. Med. Chem. 51 2008 7968
9. D.T. Puerta, J. Mongan, B.L. Tran, J.A. Mc Cammon, and S.M. Cohen J. Am. Chem. Soc. 127 2005 14148
10. Y.L. Yan, M.T. Miller, Y. Cao, and S.M. Cohen Bioorg. Med. Chem. Lett. 19 2009 1970
11. J.A. Blagg, M.C. Noe, L.A. Wolf-Gouveia, L.A. Reiter, E.R. Laird, and S.P. Chang Bioorg. Med. Chem. Lett. 15 2005 1807
12. M.A. Esteves, A. Cachudo, C. Ribeiro, S. Chaves, and M.A. Santos Metal Ions in Biol. & Med Vol. 9 2006 John Libbey Eurotext Paris pp 35-39
13. D.T. Puerta, J.A. Lewis, and S.M. Cohen J. Am. Chem. Soc. 126 2004 8388
14. 2), 127.1, 128.0, 129.7, 142.2
15. J. Ohkanda, and A. Katoh Tetrahedron 51 1995 12995
16. W.L. Sung J. Chem. Soc., Chem. Commun. 1981 1089
17. C.M. Jakobsen, S.R. Denmeade, J.T. Isaacs, A. Gady, C.E. Olsen, and S.B. Christensen J. Med. Chem. 44 2001 4696
18. A. Cecchi, A. Hulikova, J. Pastorek, S. Pastorekova, A. Scozzafava, J.-Y. Winum, J.-L. Montero, and C.T. Supuran J. Med. Chem. 48 2005 4834
19. J.R. Casey, P.E. Morgan, D. Vullo, A. Scozzafava, A. Mastrolorenzo, and C.T. Supuran J. Med. Chem. 47 2004 2337
20. L.R. Sconik, A.M. Clements, J. Liao, M. Hellberg, J. May, D.R. Dean, and D.W. Christiason J. Am. Chem. Soc. 119 1997 850
21. A. Innocenti, D. Vullo, A. Scozzafava, and C.T. Supuran Bioorg. Med. Chem. 2008 1583
22. M.A. Esteves, A. Cachudo, S. Chaves, and M.A. Santos Eur. J. Inorg. Chem. 2005 597
23. R.M. Smith, and A.E. Martell Critical Stability Constants Vol. 3 1977 Plenum Press New York p 181
24. M.W. Duffel, I.S. Ing, T.M. Segarra, J.A. Dixson, C.F. Barfknecht, and R.D. Schoenwald J. Med. Chem. 29 1986 1488
25. H.M. Berman, J. Westbrook, Z. Feng, G. Gilliland, T.N. Bhat, H. Weissig, I.N. Shindyalov, and P.E. Bourne Nucleic Acids Res. 28 2000 235
26. G. Jones, P. Willett, R.C. Glen, A.R. Leach, and R. Taylor J. Mol. Biol. 267 1997 727
27. T. Tuccinardi, E. Nuti, G. Ortore, C.T. Supuran, A. Rossello, and A. Martinelli J. Chem. Inf. Model. 47 2007 515
28. The UniProt Consortium. The Universal Protein Resource (UniProt) in 2010, Nucleic Acids.