Sulfonamides incorporating boroxazolidone moieties are potent inhibitors of the transmembrane, tumor-associated carbonic anhydrase isoforms IX and XII

Bioorganic and Medicinal Chemistry Letters

Volumn 21, Issue 10, 2011, Pages 2975-2979

  Rami, Marouan ^a   Maresca, Alfonso ^b   Smaine, Fatma Zhora ^a,c   Montero, Jean Louis ^a   Scozzafava, Andrea ^b   Winum, Jean Yves ^a   Supuran, Claudiu T ^b  

^a INSTITUT CHARLES GERHARDT   (France)

^b UNIVERSITY OF FLORENCE   (Italy)

^c BADJI MOKHTAR UNIVERSITY   (Algeria)

Author keywords

Boroxazolidones; Carbonic anhydrase; Hypoxic tumor; Isoform I, II, IX, XII; Sulfonamides; Thioureas

Indexed keywords

BOROXAZOLIDONE; CARBONATE DEHYDRATASE II; CARBONATE DEHYDRATASE INHIBITOR; CARBONATE DEHYDRATASE IX; CARBONATE DEHYDRATASE XII; OXAZOLIDINONE DERIVATIVE; SULFONAMIDE; THIOUREA DERIVATIVE; UNCLASSIFIED DRUG;

ARTICLE; DRUG SYNTHESIS; ENZYME INHIBITION; NEUTRON CAPTURE THERAPY;

ANTIGENS, NEOPLASM; ANTINEOPLASTIC AGENTS; BORON COMPOUNDS; CARBONIC ANHYDRASE INHIBITORS; CARBONIC ANHYDRASES; ENZYME ACTIVATION; HUMANS; MOLECULAR STRUCTURE; NEOPLASM PROTEINS; OXAZOLIDINONES; PROTEIN ISOFORMS; STRUCTURE-ACTIVITY RELATIONSHIP; SULFONAMIDES;

EID: 79955566849     PISSN: 0960894X     EISSN: None     Source Type: Journal    
DOI: 10.1016/j.bmcl.2011.03.055     Document Type: Article

References (54)

1. C.T. Supuran Nat. Rev. Drug Disc. 7 2008 168
2. E. Švastová, A. Hulíková, M. Rafajová, M. Zatovičová, A. Gibadulinová, A. Casini, A. Cecchi, A. Scozzafava, C.T. Supuran, and J. Pastorek FEBS Lett. 577 2004 439
3. P. Ebbesen, E.O. Pettersen, T.A. Gorr, G. Jobst, K. Williams, J. Kienninger, R.H. Wenger, S. Pastorekova, L. Dubois, P. Lambin, B.G. Wouters, C.T. Supuran, L. Poellinger, P. Ratcliffe, A. Kanopka, A. Görlach, M. Gasmann, A.L. Harris, P. Maxwell, and A. Scozzafava J. Enzyme Inhib. Med. Chem. 24 2009 1
4. L. Dubois, N.G. Lieuwes, A. Maresca, A. Thiry, C.T. Supuran, A. Scozzafava, B.G. Wouters, and P. Lambin Radiother. Oncol. 92 2009 423
5. J.K.J. Ahlskog, C.E. Dumelin, S. Trüssel, J. Marlind, and D. Neri Bioorg. Med. Chem. Lett. 19 2009 4851
6. J.K. Ahlskog, C. Schliemann, J. Mrlind, U. Qureshi, A. Ammar, R.B. Pedleym, and D. Neri Br. J. Cancer 101 2009 645
7. P. Swietach, S. Wigfield, P. Cobden, C.T. Supuran, A.L. Harris, and R.D. Vaughan-Jones J. Biol. Chem. 283 2008 20473
8. P. Swietach, S. Wigfield, C.T. Supuran, A.L. Harris, and R.D. Vaughan-Jones BJU Int. 101 Suppl 4 2008 22
9. J.Y. Winum, M. Rami, A. Scozzafava, J.L. Montero, and C. Supuran Med. Res. Rev. 28 2008 445
10. C.T. Supuran, A. Scozzafava, and A. Casini Med. Res. Rev. 23 2003 146
11. C.T. Supuran Carbonic Anhydrases as Drug Targets - General Presentation C.T. Supuran, J.Y. Winum, Drug Design of Zinc-Enzyme Inhibitors: Functional, Structural, and Disease Applications 2009 Wiley Hoboken (NJ) 15 38
12. C.T. Supuran Bioorg. Med. Chem. Lett. 20 2010 3467
13. V. Alterio, M. Hilvo, A. Di Fiore, C.T. Supuran, P. Pan, S. Parkkila, A. Scaloni, J. Pastorek, S. Pastorekova, C. Pedone, A. Scozzafava, S.M. Monti, and G. De Simone Proc. Natl. Acad. Sci. U.S.A. 106 2009 16233
14. A. Thiry, J.M. Dogné, B. Masereel, and C.T. Supuran Trends Pharmacol. Sci. 27 2006 566
15. S. Pastorekova, S. Parkkila, J. Pastorek, and C.T. Supuran J. Enzyme Inhib. Med. Chem. 19 2004 199
16. D. Vullo, M. Franchi, E. Gallori, J. Pastorek, A. Scozzafava, S. Pastorekova, and C.T. Supuran J. Enzyme Inhib. Med. Chem. 18 2003 403
17. M. Franchi, D. Vullo, E. Gallori, J. Pastorek, A. Russo, A. Scozzafava, S. Pastorekova, and C.T. Supuran J. Enzyme Inhib. Med. Chem. 18 2003 333
18. C.C. Wykoff, N.J. Beasley, P.H. Watson, K.J. Turner, J. Pastorek, A. Sibtain, G.D. Wilson, H. Turley, K.L. Talks, P.H. Maxwell, C.W. Pugh, P.J. Ratcliffe, and A.L. Harris Cancer Res. 60 2000 7075
19. M. Bartosova, S. Parkkila, K. Pohlodek, T.J. Karttunen, S. Galbavy, V. Mucha, A.L. Harris, J. Pastorek, and S. Pastorekova J. Pathol. 197 2002 1
20. S. Pastoreková, and J. Pastorek Cancer-related Carbonic Anhydrase Isozymes and Their Inhibition C.T. Supuran, A. Scozzafava, J. Conway, Carbonic Anhydrase: Its Inhibitors and Activators 2004 CRC Press Boca Raton, FL 255 281
21. H.M. Said, C.T. Supuran, C. Hageman, A. Staab, B. Polat, A. Katzer, A. Scozzafava, J. Anacker, M. Flentje, and D. Vordermark Curr. Pharm. Des. 16 2010 3288
22. M. Zatovicova, L. Jelenska, A. Hulikova, L. Csaderova, Z. Ditte, P. Ditte, T. Goliasova, J. Pastorek, and S. Pastorekova Curr. Pharm. Des. 16 2010 3255
23. D. Vullo, A. Innocenti, I. Nishimori, J. Pastorek, A. Scozzafava, S. Pastorekova, and C.T. Supuran Bioorg. Med. Chem. Lett. 15 2005 963
24. Battke, C.; Kremmer, E.; Mysliwietz, J.; Gondi, G.; Dumitru, C.; Brandau, S.; Lang, S.; Vullo, D.; Supuran, C.; Zeidler, R. Cancer Immunol. Immunother., in press.
25. F. Pacchiano, F. Carta, P.C. McDonald, Y. Lou, D. Vullo, A. Scozzafava, S. Dedhar, and C.T. Supuran J. Med. Chem. 54 2011 1896
26. V. Alterio, A. Di Fiore, K. D'Ambrosio, C.T. Supuran, and G. De Simone X-ray Crystallography of CA Inhibitors and Its Importance in Drug Design C.T. Supuran, J.Y. Winum, Drug Design of Zinc-Enzyme Inhibitors: Functional, Structural, and Disease Applications 2009 Wiley Hoboken 73 138
27. C.T. Supuran Curr. Pharm. Des. 14 2008 641
28. C.T. Supuran, A. Di Fiore, and G. De Simone Expert Opin. Emerg. Drugs 13 2008 383
29. G. De Simone, A. Di Fiore, and C.T. Supuran Curr. Pharm. Des. 14 2008 655
30. F. Mincione, A. Scozzafava, and C.T. Supuran Antiglaucoma Carbonic Anhydrase Inhibitors as Ophthalomologic Drugs C.T. Supuran, J.Y. Winum, Drug Design of Zinc-Enzyme Inhibitors: Functional, Structural, and Disease Applications 2009 Wiley Hoboken (NJ) 139 154
31. J. Krungkrai, and C.T. Supuran Curr. Pharm. Des. 14 2008 631
32. J. Borras, A. Scozzafava, L. Menabuoni, F. Mincione, F. Briganti, G. Mincione, and C.T. Supuran Bioorg. Med. Chem. 7 1999 2397
33. C.T. Supuran, and A. Scozzafava Bioorg. Med. Chem. 15 2007 4336
34. C. Temperini, A. Cecchi, A. Scozzafava, and C.T. Supuran Bioorg. Med. Chem. Lett. 18 2008 2567
35. C.T. Supuran Curr. Pharm. Des. 14 2008 603
36. C. Temperini, A. Cecchi, A. Scozzafava, and C.T. Supuran Org. Biomol. Chem. 6 2008 2499
37. C. Temperini, A. Cecchi, A. Scozzafava, and C.T. Supuran J. Med. Chem. 52 2009 322
38. C. Temperini, A. Cecchi, A. Scozzafava, and C.T. Supuran Bioorg. Med. Chem. 17 2009 1214
39. J.R. Casey, P.E. Morgan, D. Vullo, A. Scozzafava, A. Mastrolorenzo, and C.T. Supuran J. Med. Chem. 47 2004 2337
40. J.Y. Winum, C. Temperini, K. El Cheikh, A. Innocenti, D. Vullo, S. Ciattini, J.L. Montero, A. Scozzafava, and C.T. Supuran J. Med. Chem. 49 2006 7024
41. D. Vullo, J. Voipio, A. Innocenti, C. Rivera, H. Ranki, A. Scozzafava, K. Kaila, and C.T. Supuran Bioorg. Med. Chem. Lett. 15 2005 971
42. -.
43. G.H.L. Nefkens, and B. Zwanenburg Tetrahedron 39 1983 2995
44. A. Casini, A. Scozzafava, F. Mincione, L. Menabuoni, M.A. Ilies, and C.T. Supuran J. Med. Chem. 43 2000 4884
45. A. Cecchi, J.-Y. Winum, A. Innocenti, D. Vullo, J.-L. Montero, A. Scozzafava, and C.T. Supuran Bioorg. Med. Chem. Lett. 14 2004 5775
46. L. Puccetti, G. Fasolis, A. Cecchi, J.-Y. Winum, A. Gamberi, J.-L. Montero, A. Scozzafava, and C.T. Supuran Bioorg. Med. Chem. Lett. 15 2005 2359
47. F. Mincione, M. Starnotti, E. Masini, L. Bacciottini, C. Scrivanti, A. Casini, D. Vullo, A. Scozzafava, and C.T. Supuran Bioorg. Med. Chem. Lett. 15 2005 3281
48. J.Y. Winum, A. Thiry, K. El Cheikh, J.M. Dogné, J.L. Montero, D. Vullo, A. Scozzafava, B. Masereel, and C.T. Supuran Bioorg. Med. Chem. Lett. 17 2007 2685
49. F.Z. Smaine, J.Y. Winum, J.L. Montero, D. Vullo, A. Scozzafava, and C.T. Supuran Bioorg. Med. Chem. Lett. 17 2007 5096
50. A. Di Fiore, G. De Simone, V. Menchise, C. Pedone, A. Casini, A. Scozzafava, and C.T. Supuran Bioorg. Med. Chem. Lett. 15 2005 1937
51. J.-Y. Winum, A. Cecchi, J.-L. Montero, A. Innocenti, A. Scozzafava, and C.T. Supuran Bioorg. Med. Chem. Lett. 15 2005 3302
52. 18,20
53. O. Özensoy, G. De Simone, and C.T. Supuran Curr. Med. Chem. 17 2010 1516
54. G. De Simone, and C.T. Supuran Biochim. Biophys. Acta 1804 2010 404