Carbonic anhydrase inhibitors. Novel sulfanilamide/acetazolamide derivatives obtained by the tail approach and their interaction with the cytosolic isozymes I and II, and the tumor-associated isozyme IX

Bioorganic and Medicinal Chemistry Letters

Volumn 15, Issue 2, 2005, Pages 367-372

  Turkmen, Hasan ^a   Durgun, Mustafa ^a   Yilmaztekin, Serpil ^a   Emul, Mahmut ^a   Innocenti, Alessio ^b   Vullo, Daniela ^b   Scozzafava, Andrea ^b   Supuran, Claudiu T ^b  

^a HARRAN UNIVERSITY   (Turkey)

^b UNIVERSITY OF FLORENCE   (Italy)

Author keywords

[No Author keywords available]

Indexed keywords

4 (3 CHLOROPROPIONYLAMINO)BENZENESULFONAMIDE; 4 (3 METHYLPIPERAZINOPROPIONYLAMINO)BENZENESULFONAMIDE; 5 AMINO 1,3,4 THIADIAZOLE 2 SULFONAMIDE; ACETAZOLAMIDE; BENZENE DERIVATIVE; CARBON; CARBONATE DEHYDRATASE INHIBITOR; CHLORINE DERIVATIVE; ISOENZYME; MORPHOLINE DERIVATIVE; PIPERAZINE DERIVATIVE; PIPERIDINE DERIVATIVE; SULFANILAMIDE DERIVATIVE; SULFONAMIDE; TUMOR ASSOCIATED ISOENZYME IX; UNCLASSIFIED DRUG;

ARTICLE; ATOM; CATALYSIS; CONTROLLED STUDY; CYTOSOL; DRUG SYNTHESIS; ENZYME INHIBITION; HUMAN; NONHUMAN;

ACETAZOLAMIDE; AMINES; CARBONIC ANHYDRASE INHIBITORS; CATALYSIS; CYTOSOL; HETEROCYCLIC COMPOUNDS; HUMANS; ISOENZYMES; MORPHOLINES; PIPERAZINES; PIPERIDINES; STRUCTURE-ACTIVITY RELATIONSHIP; SULFANILAMIDES; TUMOR MARKERS, BIOLOGICAL;

EID: 10644254283     PISSN: 0960894X     EISSN: None     Source Type: Journal    
DOI: 10.1016/j.bmcl.2004.10.070     Document Type: Article

References (40)

1. S. Pastorekova, S. Parkkila, J. Pastorek, and C.T. Supuran J. Enzym. Inhib. Med. Chem. 19 2004 199 229
2. C.T. Supuran, D. Vullo, G. Manole, A. Casini, and A. Scozzafava Curr. Med. Chem. Cardiovasc. Hematol. Agents 2 2004 49 68
3. C.T. Supuran A. Scozzafava J. Conway Carbonic Anhydrase-its Inhibitors and Activators 2004 CRC (Taylor and Francis Group) Boca Raton, FL 1 363 and references cited therein
4. T. Mann, and D. Keilin Nature 164 1940 146 148
5. C.T. Supuran, and A. Scozzafava Expert Opin. Ther. Pat. 10 2000 575 600
6. C.T. Supuran, and A. Scozzafava Expert Opin. Ther. Pat. 12 2002 217 242
7. C.T. Supuran, A. Scozzafava, and A. Casini Med. Res. Rev. 23 2003 146 189
8. A. Scozzafava, A. Mastrolorenzo, and C.T. Supuran Expert Opin. Ther. Pat. 14 2004 667 702
9. C.T. Supuran, A. Casini, and A. Scozzafava Development of Sulfonamide Carbonic Anhydrase Inhibitors (CAIs) C.T. Supuran A. Scozzafava J. Conway Carbonic Anhydrase - its Inhibitors and Activators 2004 CRC Boca Raton, FL, USA 67 148
10. A. Scozzafava, T. Owa, A. Mastrolorenzo, and C.T. Supuran Curr. Med. Chem. 10 2003 925 953
11. A. Casini, A. Scozzafava, A. Mastrolorenzo, and C.T. Supuran Curr. Cancer Drug Targets 2 2002 55 75
12. F. Abbate, A. Casini, T. Owa, A. Scozzafava, and C.T. Supuran Bioorg. Med. Chem. Lett. 14 2004 217 223
13. A. Weber, A. Casini, A. Heine, D. Kuhn, C.T. Supuran, A. Scozzafava, and G. Klebe J. Med. Chem. 47 2004 550 557
14. S. Pastorekova, A. Casini, A. Scozzafava, D. Vullo, J. Pastorek, and C.T. Supuran Bioorg. Med. Chem. Lett. 14 2004 869 873
15. J.R. Casey, P.E. Morgan, D. Vullo, A. Scozzafava, A. Mastrolorenzo, and C.T. Supuran J. Med. Chem. 47 2004 2337 2347
16. C.T. Supuran Expert Opin. Invest. Drugs 12 2003 283 287
17. J.M. Brown, and W.R. Wilson Nat. Rev. Cancer 4 2004 437 447
18. Švastová, E.; Hulíková, A.; Rafajová, M.; Zat'ovičová, M.; Gibadulinová, A.; Casini, A.; Cecchi, A.; Scozzafava, A.; Supuran, C. T.; Pastorek, J.; Pastoreková, S. FEBS Lett., in press
19. S. Pastorekova, 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 Boca Raton, FL, USA 255 281
20. N. Robertson, C. Potter, and A.L. Harris Cancer Res. 64 2004 6160 6165
21. J.-Y. Winum, D. Vullo, A. Casini, J.-L. Montero, A. Scozzafava, and C.T. Supuran J. Med. Chem. 46 2003 2197 2204
22. J.-Y. Winum, D. Vullo, A. Casini, J.-L. Montero, A. Scozzafava, and C.T. Supuran J. Med. Chem. 46 2003 5471 5477
23. J.-Y. Winum, A. Scozzafava, J.-L. Montero, and C.T. Supuran Expert Opin. Ther. Pat. 14 2004 1273 1308
24. Zhang, X.-R.; Blackburn, G. M. Ph.D. Thesis, The University of Sheffield, UK, 1995
25. Turkmen, H.; Blackburn, G. M. Ph.D. Thesis, The University of Sheffield, UK, 1998
26. A. Scozzafava, L. Menabuoni, F. Mincione, F. Briganti, G. Mincione, and C.T. Supuran J. Med. Chem. 42 1999 2641 2650
27. A. Scozzafava, F. Briganti, G. Mincione, L. Menabuoni, F. Mincione, and C.T. Supuran J. Med. Chem. 42 1999 3690 3700
28. C.T. Supuran, F. Briganti, S. Tilli, W.R. Chegwidden, and A. Scozzafava Bioorg. Med. Chem. 9 2001 703 714
29. C.T. Supuran, and A. Scozzafava J. Enzym. Inhib. 15 2000 597 610
30. C.T. Supuran, and A. Scozzafava Eur. J. Med. Chem. 35 2000 867 874
31. +
32. 9
33. S. Lindskog, G. Behravan, C. Engstrand, C. Forsman, B.H. Jonsson, Z. Liang, X. Ren, and Y. Xue Structure-Function Relations in Human Carbonic Anhydrase II as Studied by Site-Directed Mutagenesis F. Botrè G. Gros B.T. Storey Carbonic Anhydrase-From Biochemistry and Genetics to Physiology and Clinical Medicine 1991 VCH Weinheim 1 13
34. G. Behravan, B.H. Jonsson, and S. Lindskog Eur. J. Biochem. 190 1990 351 357
35. R.G. Khalifah, D.J. Strader, S.H. Bryant, and S.M. Gibson Biochemistry 16 1977 2241 2247
36. S. Lindskog, and J.E. Coleman Proc. Natl. Acad. Sci. U.S.A. 70 1964 2505 2508
37. H. Steiner, B.H. Jonsson, and S. Lindskog Eur. J. Biochem. 59 1975 253 259
38. J. Pastorek, S. Pastorekova, I. Callebaut, J.P. Mornon, V. Zelnik, R. Opavsky, M. Zatovicova, S. Liao, D. Portetelle, E.J. Stanbridge, J. Zavada, A. Burny, and R. Kettmann Oncogene 9 1994 2877 2888
39. R.G. Khalifah J. Biol. Chem. 246 1971 2561 2573
40. D. Vullo, M. Franchi, E. Gallori, J. Pastorek, A. Scozzafava, S. Pastorekova, and C.T. Supuran Bioorg. Med. Chem. Lett. 13 2003 1005 1009