Carbonic anhydrase inhibitors. Regioselective synthesis of novel series 1-substituted 1,4-dihydro-4-oxo-3-pyridinesulfonamides and their inhibition of the human cytosolic isozymes i and II and transmembrane cancer-associated isozymes IX and XII

European Journal of Medicinal Chemistry

Volumn 56, Issue , 2012, Pages 282-291

  Brzozowski, Zdzisław ^a   Sławiński, Jarosław ^a   Vullo, Daniela ^b   Supuran, Claudiu T ^b  

^a MEDICAL UNIVERSITY OF GDANSK   (Poland)

^b UNIVERSITY OF FLORENCE   (Italy)

Author keywords

1,4 Dihydro 4 oxo 3 pyridinesulfonamides; Carbonic anhydrase isozymes I, II, IX and XII inhibitors; Synthesis

Indexed keywords

1 (2 AMINO 4 DIMETHYLAMINO 1,3,5 TRIAZIN 6 YL)METHYL 1,4 DIHYDRO 4 OXO 3 PYRIDINESULFONAMIDE; 1 (2 AMINO 4 MORPHOLINO 1,3,5 TRIAZIN 6 YL)METHYL 1,4 DIHYDRO 4 OXO 3 PYRIDINESULFONAMIDE; 1 (3,5 DIMETHYLISOXAZOL 4 YL)METHYL 1,4 DIHYDRO 4 OXO 3 PYRIDINESULFONAMIDE; 1 [(2 CHLOROBENZENESULFONAMIDOCARBONYL)METHYL] 1,4 DIHYDRO 4 OXO 3 PYRIDINESULFONAMIDE; 1 [(4 CHLORO 3 NITROPHENYLCARBAMOYL)METHYL] 1,4 DIHYDRO 4 OXO 3 PYRIDINESULFONAMIDE; 1 [(4 CHLOROBENZENESULFONAMIDOCARBONYL)METHYL] 1,4 DIHYDRO 4 OXO 3 PYRIDINESULFONAMIDE; 1 [2 AMINO 4 (3 METHYL 2 PYRAZOLINO) 1,3,5 TRIAZIN 6 YL] METHYL 1,4 DIHYDRO 4 OXO 3 PYRIDINESULFONAMIDE; 1 [2 AMINO 4 (3,5,5 TRIMETHYL 2 PYRAZOLINO) 1,3,5 TRIAZIN 6 YL] METHYL 1,4 DIHYDRO 4 OXO 3 PYRIDINESULFONAMIDE; 1 METHYL 1,1 DIHYDRO 4 OXO 3 PYRIDINESULFONAMIDE; 1,4 DIHYDRO 1 [(2 FUORYLHYDRAZINOCARBONYL)METHYL] 4 OXO 3 PYRIDINESULFONAMIDE; 1,4 DIHYDRO 1 [(2,6 DIMETHYLPHENYLCARBAMOYL)METHYL] 4 OXO 3 PYRIDINESULFONAMIDE; 1,4 DIHYDRO 1 [(3 NITROPHENYLCARBAMOYL)METHYL] 4 OXO 3 PYRIDINESULFONAMIDE; 1,4 DIHYDRO 1 [(4 NITROBENZENESULFONAMIDOCARBONYL)METHYL] 4 OXO 3 PYRIDINESULFONAMIDE; 1,4 DIHYDRO 1 [(4 SULFAMOYLPHENYLCARBAMOYL)METHYL] 4 OXO 3 PYRIDINESULFONAMIDE; ACETAZOLAMIDE; CARBONATE DEHYDRATASE; CARBONIC ANHYDRASE ISOZYME I; CARBONIC ANHYDRASE ISOZYME II; CARBONIC ANHYDRASE ISOZYME IX; CARBONIC ANHYDRASE ISOZYME XII; DICLOFENAMIDE; ENZYME INHIBITOR; ETHOXZOLAMIDE; INDISULAM; METHAZOLAMIDE; SULFONAMIDE; UNCLASSIFIED DRUG;

ARTICLE; CONCENTRATION RESPONSE; CONTROLLED STUDY; DRUG ACTIVITY; DRUG STRUCTURE; DRUG SYNTHESIS; HUMAN; STRUCTURE ACTIVITY RELATION; SUBSTITUTION REACTION;

CARBONIC ANHYDRASE INHIBITORS; CARBONIC ANHYDRASES; DOSE-RESPONSE RELATIONSHIP, DRUG; HUMANS; ISOENZYMES; MOLECULAR STRUCTURE; PYRIDINES; STEREOISOMERISM; STRUCTURE-ACTIVITY RELATIONSHIP; SULFONAMIDES;

EID: 84867980077     PISSN: 02235234     EISSN: 17683254     Source Type: Journal    
DOI: 10.1016/j.ejmech.2012.08.006     Document Type: Article

References (40)

1. J. Pastorek, S. Pastorekova, I. Callebuant, I.P. Mornan, V. Zelnik, R. Opavsky, M. Zatovicova, S. Liao, D. Portetelle, E.J. Stanbridge, J. Zavada, A. Burny, and R. Katlmann Oncogene 9 1994 2788 2888
2. R. Opavsky, S. Pastorekova, V. Zelnik, A. Gibadulinova, E.J. Stanbridge, J. Zavada, R. Kettmann, and J. Pastorek Genomics 33 1996 480 487
3. O. Türeci, 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. USA 95 1998 7608 7613
4. C.T. Supuran Nat. Rev. Drug Discov. 7 2008 168 181
5. A. Scozzafava, A. Mastrolorenzo, and C.T. Supuran Expert Opin. Ther. Pat. 14 2004 667 702
6. C.T. Supuran, A. Scozzafava, and A. Casini Med. Res. Rev. 23 2003 146 189
7. E. Svastova, N. Zilka, M. Zatovicova, M. Gibadulinova, F. Ciampor, J. Pastorek, and S. Pastorekova Exp. Cell. Res. 290 2003 332 345
8. S. Pastorekova, S. Parkkila, and J. Zavada Adv. Clin. Chem. 42 2006 167 216
9. P. Swietach, R.D. Vaughen-Jones, and A.L. Harris Cancer Metastasis Rev. 26 2007 299 310
10. H.M. Said, C.T. Supuran, C. Hageman, A. Staab, B. Polat, A. Katzer, A. Scozzafava, J. Anecker, M. Flentje, and D. Vordemark Curr. Pharm. Des. 16 2010 3288 3299
11. M.A. Esteves, O. Orted, A. Capelo, C.T. Supuran, S.M. Marques, and M.A. Santos Bioorg. Med. Chem. Lett. 20 2010 2623 2627
12. F. Pocchiono, F. Carta, P.C. McDonald, Y. Lou, D. Vullo, A. Scozzafava, S. Dedhar, and C.T. Supuran J. Med. Chem. 54 2011 1896 1902
13. M.S. Al-Said, M.M. Ghorab, M.S. Al-Dosari, and M.M. Hamed Eur. J. Med. Chem. 46 2011 201 207
14. M. Rami, A. Maresca, F.Z. Smaine, J.L. Montero, A. Scozzafava, J.Y. Winum, and C.T. Supuran Bioorg. Med. Chem. Lett. 21 2011 2975 2979
15. A.L. Haris Nat. Rev. Cancer 21 2011 2975 2979
16. C.P.S. Potter, and A.L. Harris Br. J. Cancer 89 2003 2 7
17. A. Thiry, J.M. Donge, B. Masereel, and C.T. Supuran Trends Pharmacol. Sci. 27 2006 566 573
18. J.Y. Winum, M. Rami, A. Scozzafava, J.Li. Montero, and C.T. Supuran Med. Res. Rev. 28 2008 445 463
19. Y. Lou, P.C. McDonald, A. Olumi, S.K. Chia, C. Ostland, and A. Ahmadi Cancer Res. 71 2011 3364 3376
20. C.T. Supuran, and A. Scozzafava Expert Opin. Ther. Pat. 10 2000 575 600
21. G. Kim, J. Selengut, and R. Levine Arch. Biochem. Biophys. 377 2000 334 340
22. F. Abbate, C.T. Supuran, A. Scozzafava, P. Orioli, M.T. Stubbs, and G. Klebe J. Med. Chem. 45 2002 3583 3587
23. T. Stams, S.K. Nair, T. Okuyma, A. Wahead, W.S. Sly, and D.W. Christianson Proc. Natl. Acad. Sci. USA 93 1996 13589 13594
24. G. de Simone, and C.T. Supuran Biochim. Biophys. Acta 1804 2010 404 409
25. F. Saczewski, J. Sławiński, A. Kornicka, Z. Brzozowski, E. Pomarnacka, A. Innocenti, A. Scozzafava, and C.T. Supuran Bioorg. Med. Chem. Lett. 16 2006 4846 4851
26. F. Saczewski, A. Innocenti, Z. Brzozowski, J. Sławiński, E. Pomarnacka, A. Kornicka, A. Scozzafava, and C.T. Supuran J. Enzym. Inhibit. Med. Chem. 21 2006 536 568
27. F. Saczewski, A. Innocenti, Z. Brzozowski, J. Sławiński, E. Pomarnacka, A. Kornicka, A. Scozzafava, and C.T. Supuran Bioorg. Med. Chem. 16 2008 3933 3940
28. Z. Brzozowski, J. Sławiński, F. Saczewski, A. Innocenti, and C.T. Supuran Eur. J. Med. Chem. 45 2010 2396 2404
29. Z. Brzozowski, J. Sławiński, M. Gdaniec, A. Innocenti, and C.T. Supuran Eur. J. Med. Chem. 46 2011 4403 4410
30. Z. Brzozowski, J. Sławiński, A. Innocenti, and C.T. Supuran Eur. J. Med. Chem. 45 2010 3656 3661
31. A.A. Munshi, N.M. Shah, and J.P. Trivedi J. Indian Chem. Soc. 40 1963 963 965
32. Z. Brzozowski, and F. Saczewski Eur. J. Med. Chem. 37 2002 709 720
33. P.A. Petyunin, and Yu. V. Kozhevnikov Khim. Geterotsikl. Soedin Sb. 1: Azotsoderzhoshchie Geterotsikly Riga 1967 pp. 415-418. Language: Russian, Database: CAPLUS
34. E.R. Buchman J. Am. Chem. Soc. 14 1953 1990
35. J.R. Durig, and W.H. Green J. Chem. Phys. 47 1967 673
36. A.C. Dupont Synth. Commun. 20 1990 1011 1021
37. R.G. Khalifah J. Biol. Med. 246 1971 2561 2573
38. J.R. Casey, P.E. Morgan, D. Vullo, A. Scozzafava, A. Mastrolorenzo, and C.T. Supuran J. Med. Chem. 47 2004 2337 2347
39. 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 4841
40. D. Vullo, A. Innocenti, I. Nishimori, J. Pastorek, A. Scozzafava, and C.T. Supuran Bioorg. Med. Chem. Lett. 15 2005 963 969