Carbonic anhydrase inhibitors: Inhibition of cytosolic/tumor-associated carbonic anhydrase isozymes I, II, and IX with benzo[b]thiophene 1,1-dioxide sulfonamides

Bioorganic and Medicinal Chemistry Letters

Volumn 15, Issue 21, 2005, Pages 4872-4876

  Innocenti, Alessio ^a   Villar, Raquel ^b   Martinez Merino, Victor ^b   Gil, María J ^b   Scozzafava, Andrea ^a   Vullo, Daniela ^a   Supuran, Claudiu T ^a  

^a UNIVERSITY OF FLORENCE   (Italy)

^b PUBLIC UNIVERSITY OF NAVARRE   (Spain)

Author keywords

[No Author keywords available]

Indexed keywords

ACETAZOLAMIDE; BENZOTHIOPHENE; CARBONATE DEHYDRATASE INHIBITOR; DICLOFENAMIDE; ETHOXZOLAMIDE; INDISULAM; METHAZOLAMIDE; REACTIVE OXYGEN METABOLITE; SULFONAMIDE;

ANTINEOPLASTIC ACTIVITY; APOPTOSIS; ARTICLE; CANCER INHIBITION; CARCINOGENESIS; CONTROLLED STUDY; ENZYME INHIBITION; HUMAN; HUMAN CELL; UBIQUITINATION;

ANTIGENS, NEOPLASM; CARBONIC ANHYDRASE I; CARBONIC ANHYDRASE II; CARBONIC ANHYDRASE INHIBITORS; CARBONIC ANHYDRASES; CYTOSOL; HUMANS; NEOPLASM PROTEINS; STRUCTURE-ACTIVITY RELATIONSHIP;

EID: 25144469687     PISSN: 0960894X     EISSN: None     Source Type: Journal    
DOI: 10.1016/j.bmcl.2005.04.078     Document Type: Article

References (38)

1. S. Pastorekova, S. Parkkila, J. Pastorek, and C.T. Supuran J. Enzyme Inhib. Med. Chem. 19 2004 199
2. J.Y. Winum, A. Scozzafava, J.L. Montero, and C.T. Supuran Med. Res. Rev. 25 2005 186
3. C.T. Supuran, A. Scozzafava, and A. Casini Med. Res. Rev. 23 2003 146
4. C.T. Supuran, and A. Scozzafava Eur. J. Med. Chem. 35 2000 867
5. C.T. Supuran, and A. Scozzafava J. Enzyme Inhib. 15 2000 597
6. A. Mastrolorenzo, A. Scozzafava, and C.T. Supuran Eur. J. Pharm. Sci. 11 2000 325
7. J. Pastorek, S. Pastorekova, I. Callebaut, J.P. Mornon, V. Zelnik, R. Opavsky, M. Zat'ovicova, S. Liao, D. Portetelle, and E.J. Stanbridge Oncogene 9 1994 2877
8. R. Opavsky, S. Pastorekova, V. Zelnik, A. Gibadulinova, E.J. Stanbridge, J. Zavada, R. Kettmann, and J. Pastorek Genomics 33 1996 480
9. O. Tureci, U. Sahin, E. Vollmar, S. Siemer, E. Gottert, G. Seitz, A.K. Parkkila, G.N. Shah, J.H. Grubb, M. Pfreundschuh, and W.S. Sly Proc. Natl. Acad. Sci. U.S.A. 95 1998 7608
10. A. Scozzafava, T. Owa, A. Mastrolorenzo, and C.T. Supuran Curr. Med. Chem. 10 2003 925
11. A. Casini, A. Scozzafava, A. Mastrolorenzo, and L.T. Supuran Curr. Cancer Drug Targets 2 2002 55
12. A. Giatromanolaki, M.I. Koukourakis, E. Sivridis, J. Pastorek, C.C. Wykoff, K.C. Gatter, and A.L. Harris Cancer Res. 61 2001 7992
13. J.A. Loncaster, A.L. Harris, S.E. Davidson, J.P. Logue, R.D. Hunter, C.C. Wycoff, J. Pastorek, P.J. Ratcliffe, I.J. Stratford, and C.M. West Cancer Res. 61 2001 6394
14. S.K. Chia, C.C. Wykoff, P.H. Watson, C. Han, R.D. Leek, J. Pastorek, K.C. Gatter, P. Ratcliffe, and A.L. Harris J. Clin. Oncol. 19 2001 3660
15. N.J. Beasley, C.C. Wykoff, P.H. Watson, R. Leek, H. Turley, K. Gatter, J. Pastorek, G.J. Cox, P. Ratcliffe, and A.L. Harris Cancer Res. 61 2001 5262
16. S. Ivanov, S.Y. Liao, A. Ivanova, A. Danilkovitch-Miagkova, N. Tarasova, G. Weirich, M.J. Merrill, M.A. Proescholdt, E.H. Oldfield, J. Lee, J. Zavada, A. Waheed, W. Sly, M.I. Lerman, and E.J. Stanbridge Am. J. Pathol. 158 2001 905
17. E. Svastova, A. Hulikova, M. Rafajova, M. Zat'ovicova, A. Gibadulinova, A. Casini, A. Cecchi, A. Scozzafava, C.T. Supuran, J. Pastorek, and S. Pastorekova FEBS Lett. 577 2004 439
18. R. Villar, I. Encio, M. Migliaccio, M.J. Gil, and V. Martinez-Merino Bioorg. Med. Chem. 12 2004 963
19. C.T. Supuran Expert Opin. Investig. Drugs 12 2003 283
20. F. Abbate, A. Casini, T. Owa, A. Scozzafava, and C.T. Supuran Bioorg. Med. Chem. Lett. 14 2004 217
21. Martínez-Merino V, Gil MJC, Encío I, Migliaccio M, Arteaga C. 2000. PCT Patent WO 00/63202.
22. 3 δ): 7.10 (d, J = 8 Hz,1H), 6.92 (d, J = 2.2 Hz, 1H), 6.83 (dd, J = 8 Hz, J′ = 2.2 Hz, 1H), 3.92 (s, 2H), 3.44 (t, J = 7 Hz, 2H), 3.22 (t, J = 7 Hz, 2H).
23. 3 δ): 8.29 (s, 1H, H-7), 8.19 (d, J = 8.06 Hz, 1H), 7.80 (d, 1H), 5.27 (t, J = 6.23 Hz, 1H); 4.97 (s, 2H), 3.99-3.89 (dd, J = 13.18 Hz, 1H), 3.66 (t, J = 6.23 Hz, 2H), 3.56-3.44 (dd, 1H), 1.73-1.37 (m, 4H), 0.95 (t, J = 7.33 Hz, 3H).
24. F. Abbate, C.T. Supuran, A. Scozzafava, P. Orioli, M. Stubbs, and G. Klebe J. Med. Chem. 45 2002 3583
25. A. Casini, J. Antel, F. Abbate, A. Scozzafava, S. David, H. Waldeck, S. Schäfer, and C.T. Supuran Bioorg. Med. Chem. Lett. 13 2003 841
26. A. Weber, A. Casini, A. Heine, D. Kuhn, C.T. Supuran, A. Scozzafava, and G. Klebe J. Med. Chem. 7 2004 550
27. F. Abbate, A. Casini, A. Scozzafava, and C.T. Supuran J. Enzyme Inhib. Med. Chem. 18 2003 303
28. F. Abbate, A. Coetzee, A. Casini, S. Ciattini, A. Scozzafava, and C.T. Supuran Bioorg. Med. Chem. Lett. 14 2004 337
29. F. Abbate, A. Casini, A. Scozzafava, and C.T. Supuran Bioorg. Med. Chem. Lett. 14 2004 2357
30. C.T. Supuran A. Scozzafava J. Conway Carbonic Anhydrase-Its Inhibitors and Activators 2004 CRC Press Boca Raton, London, New York
31. Supuran, C. T. In Carbonic Anhydrase - Its Inhibitors and Activators; Supuran, C. T., Scozzafava, A., Conway, J., Eds.; CRC Press: Boca Raton, 2004; pp 1-23.
32. M.M. Alonso, I. EncIÍo, V. Martínez-Merino, M. Gil, and M. Migliaccio Brit. J. Cancer 85 2001 1400
33. I. Encío, D.J. Morre, R. Villar, M.J. Gil, and V. Martínez-Merino Br. J. Cancer 92 2005 690
34. M.M. Alonso, A. Asumendi, J. Villar, M.J. Gil, V. Martínez-Merino, I. Encío, and M. Migliaccio Oncogene 22 2003 3759
35. 17,30
36. S. Pastorekova, A. Casini, A. Scozzafava, D. Vullo, J. Pastorek, and C.T. Supuran Bioorg. Med. Chem. Lett. 14 2004 869
37. J.R. Casey, P.E. Morgan, D. Vullo, A. Scozzafava, A. Mastrolorenzo, and C.T. Supuran J. Med. Chem. 47 2004 2337
38. D. Vullo, A. Scozzafava, S. Pastorekova, J. Pastorek, and C.T. Supuran Bioorg. Med. Chem. Lett. 14 2004 2351