Carbonic anhydrase inhibitors: Synthesis and inhibition of the human carbonic anhydrase isoforms I, II, VII, IX and XII with benzene sulfonamides incorporating 4,5,6,7-tetrabromophthalimide moiety

Bioorganic and Medicinal Chemistry

Volumn 21, Issue 19, 2013, Pages 5973-5982

  Sethi, Kalyan K ^a   Vullo, Daniella ^b   Verma, Saurabh M ^a   Tanç, Muhammet ^b   Carta, Fabrizio ^b   Supuran, Claudiu T ^b  

^a BIRLA INSTITUTE OF TECHNOLOGY   (India)

^b UNIVERSITY OF FLORENCE   (Italy)

Author keywords

Benzenesulfonamide 4,5,6,7 Tetrabromo 1,3 dioxoisoindolin 2 yl benzenesulfonamide; Docking; Human carbonic anhydrase inhibitors; Structure activity relationship

Indexed keywords

2 (4,5,6,7 TETRABROMO 1,3 DIOXOISOINDOLIN 2 YL)BENZENESULFONAMIDE; 3 (4,5,6,7 TETRABROMO 1,3 DIOXOISOINDOLIN 2 YL)BENZENESULFONAMIDE; 3 BROMO 4 (4,5,6,7 TETRABROMO 1,3 DIOXOISOINDOLIN 2 YL)BENZENESULFONAMIDE; 3 CHLORO 4 (4,5,6,7 TETRABROMO 1,3 DIOXOISOINDOLIN 2 YL)BENZENESULFONAMIDE; 3 FLUORO 4 (4,5,6,7 TETRABROMO 1,3 DIOXOISOINDOLIN 2 YL)BENZENESULFONAMIDE; 4 (4,5,6,7 TETRABROMO 1,3 DIOXOISOINDOLIN 2 YL)BENZENESULFONAMIDE; 4 [(4,5,6,7 TETRABROMO 1,3 DIOXOISOINDOLIN 2 YL)ETHYL]BENZENESULFONAMIDE; 4 [(4,5,6,7 TETRABROMO 1,3 DIOXOISOINDOLIN 2 YL)METHYL]BENZENESULFONAMIDE; 4,5,6,7 TETRABROMOPHTHALIMIDE DERIVATIVE; ACETAZOLAMIDE; BRINZOLAMIDE; CARBONATE DEHYDRATASE; CARBONATE DEHYDRATASE I; CARBONATE DEHYDRATASE II; CARBONATE DEHYDRATASE INHIBITOR; CARBONATE DEHYDRATASE IX; CARBONATE DEHYDRATASE VII; CARBONATE DEHYDRATASE XII; CELECOXIB; DORZOLAMIDE; ETHOXZOLAMIDE; INDISULAM; METHAZOLAMIDE; SULFACETAMIDE; SULPIRIDE; TOPIRAMATE; UNCLASSIFIED DRUG; VALDECOXIB; ZONISAMIDE;

AMINO ACID SEQUENCE; ARTICLE; CHEMICAL ANALYSIS; CHEMICAL INTERACTION; CONTROLLED STUDY; DRUG PROTEIN BINDING; DRUG SELECTIVITY; DRUG STRUCTURE; DRUG SYNTHESIS; ENZYME INHIBITION; MOLECULAR DOCKING; STRUCTURE ACTIVITY RELATION;

4,5,6,7-TETRABROMO-1,3-DIOXOISOINDOLIN-2-YL BENZENESULFONAMIDE; ACETAZOLAMIDE; ASN; ASPARAGINE; AZM; BENZENESULFONAMIDE; BENZOLAMIDE; BRINZOLAMIDE; BRZ; BZA; CA; CAI; CARBONIC ANHYDRASE; CARBONIC ANHYDRASE INHIBITOR; CELECOXIB; CENTRAL NERVOUS SYSTEM; CLX; CNS; COX; CYCLO-OXYGENASE ENZYME; DCP; DIBROMOPHENAMIDE; DIMETHYL SULFOXIDE; DMSO; DOCKING; DORZOLAMIDE; DZA; ETHOXZOLAMIDE; EXTRA PRECISION; EZA; FOURIER TRANSFORM INFRARED; FT-IR; GLN; GLUTAMINE; HCA; HIF; HIS; HISTIDINE; HUMAN CARBONIC ANHYDRASE; HUMAN CARBONIC ANHYDRASE INHIBITORS; HYPOXIA INDUCIBLE FACTOR; IND; INDISULAM; METHAZOLAMIDE; MILIMOLAR; MM; MZA; NANOMOLAR; NM; NMR; NUCLEAR MAGNETIC RESONANCE; PDB; PROTEIN DATA BANK; RMSD; ROOT MEAN SQUARE DEVIATION; SAR; SLP; STRUCTURE-ACTIVITY RELATIONSHIP; SULPIRIDE; THIN LAYER CHROMATOGRAPHY; THR; THREONINE; TLC; TOPIRAMATE; TPM; TRP; TRYPTOPHAN; ULTRAVIOLET; UV; VALDECOXIB; VHL; VLX; VON HIPPEL-LINDAS PROTEIN; XP; ZINC; ZN; ZNS; ZONISAMIDE;

CARBONIC ANHYDRASE INHIBITORS; CARBONIC ANHYDRASES; ENZYME ACTIVATION; HUMANS; MODELS, BIOLOGICAL; MOLECULAR STRUCTURE; PHTHALIMIDES; PROTEIN ISOFORMS; STRUCTURE-ACTIVITY RELATIONSHIP;

EID: 84883452849     PISSN: 09680896     EISSN: 14643391     Source Type: Journal    
DOI: 10.1016/j.bmc.2013.07.044     Document Type: Article

References (46)

1. V. Alterio, A. Di Fiore, K. D'Ambrosio, C.T. Supuran, and G. De Simone Chem. Rev. 112 2012 4421
2. C.T. Supuran Nat. Rev. Drug Disc. 7 2008 168
3. C.T. Supuran Future Med. Chem. 3 2011 1165
4. J.L. Rummer, D.J. McKenzie, A. Innocenti, C.T. Supuran, and C.J. Brauner Science 340 2013 1327
5. E.T. Mack, P.W. Snyder, R. Perez-Castillejos, B. Bilgicer, D.T. Moustakas, M.J. Butte, and G.M. Whitesides J. Am. Chem. Soc. 134 2012 333
6. S. Breton J. Pancreas 2 2001 159
7. J.Y. Winum, D. Vullo, A. Casini, J.L. Montero, A. Scozzafava, and C.T. Supuran J. Med. Chem. 46 2003 2197
8. F. Abbate, J.Y. Winum, B.V. Potter, A. Casini, J.L. Montero, A. Scozzafava, and C.T. Supuran Bioorg. Med. Chem. Lett. 14 2004 231
9. J.Y. Winum, A. Scozzafava, J.L. Montero, and C.T. Supuran Curr. Pharm. Des. 14 2008 615
10. J.Y. Winum, A. Scozzafava, J.L. Montero, and C.T. Supuran Med. Res. Rev. 26 2006 767
11. C.T. Supuran Curr. Pharm. Des. 14 2008 641
12. I.P. Kaur, R. Smitha, D. Aggarwal, and M. Kapil Int. J. Pharm. 248 2002 1
13. F. Mincione, A. Scozzafava, and C.T. Supuran C.T. Supuran, J.Y. Winum, Drug Design of Zinc-Enzyme Inhibitors: Functional, Structural, and Disease Applications 2009 Wiley Hoboken 139
14. A. Thiry, J.M. Dognè, B. Masereel, and C.T. Supuran Curr. Top. Med. Chem. 7 2007 855
15. G. De Simone, A. Di Fiore, and C.T. Supuran Curr. Pharm. Des. 14 2008 655
16. 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
17. J.K. Ahlskog, C.E. Dumelin, S. Trüssel, J. Marlind, and D. Neri Bioorg. Med. Chem. Lett. 19 2009 4851
18. F. Buller, M. Steiner, K. Frey, D. Mircsof, J. Scheuermann, M. Kalisch, P. Bühlmann, C.T. Supuran, and D. Neri ACS Chem. Biol. 6 2011 336
19. C.T. Supuran J. Enzyme Inhib. Med. Chem. 27 2012 759
20. D. Neri, and C.T. Supuran Nat. Rev. Drug Discovery 10 2011 767
21. O.O. Guler, G. De Simone, and C.T. Supuran Curr. Med. Chem. 17 2010 1516
22. G. De Simone, and C.T. Supuran Biochim. Biophys. Acta 1804 2010 404
23. C. Battke, E. Kremmer, J. Mysliwietz, G. Gondi, C. Dumitru, S. Brandau, S. Lang, D. Vullo, C.T. Supuran, and R. Zeidler Cancer Immunol. Immunother. 60 2011 649
24. B. Basnyat, J.H. Gertsch, E.W. Johnson, F. Castro-Marin, Y. Inoue, and C. Yeh High Alt. Med. Biol. 4 2003 45
25. P.H. Hackett, and R.C. Roach N. Engl. J. Med. 345 2001 107
26. B.B. Gao, A. Clermont, S. Rook, S.J. Fonda, V.J. Srinivasan, M. Wojtkowski, J.G. Fujimoto, R.L. Avery, P.G. Arrigg, S.E. Bursell, L.P. Aiello, and E.P. Feener Nat. Med. 13 2007 181
27. S. Chakravarty, and K.K. Kannan J. Mol. Biol. 243 1994 298
28. Honndorf, V.S.; Heine, A.; Klebe, G.; Supuran, C.T. http://dx.doi.org/10. 2210/pdb1zfq/pdb.
29. Ugochukwu, E.; Shafqat, N.; Pilka, E.; Chaikuad, A.; Krojer, T.; Muniz, J.; Kim, J.; Bray, J.; Bountra, C.; Arrowsmith, C. H.; Weigelt, J.; Edwards, A.; von Delft, F.; Carpenter, E.P.; Yue, W. W.; Oppermann, U. http://dx.doi.org/10. 2210/pdb3mdz/pdb.
30. N. Ban, C. Escobar, R. Garcia, K. Hasel, J. Day, A. Greenwood, and A. McPherson Proc. Natl. Acad. Sci. U.S.A. 91 1994 1604
31. D.A. Whittington, A. Waheed, B. Ulmasov, G.N. Shah, J.H. Grubb, W.S. Sly, and D.W. Christianson Proc. Natl. Acad. Sci. U.S.A. 98 2001 9545
32. A. Scozzafava, L. Menabuoni, F. Mincione, F. Briganti, G. Mincione, and C.T. Supuran J. Med. Chem. 42 1999 2641
33. A. Scozzafava, F. Mincione, L. Menabuoni, and C.T. Supuran Drug Des. Discov. 17 2001 337
34. K.K. Sethi, S.M. Verma, M. Tanç, F. Carta, and C.T. Supuran Bioorg. Med. Chem. 21 2013 5168
35. A. Maresca, D. Vullo, A. Scozzafava, G. Manole, and C.T. Supuran J. Enzyme Inhib. Med. Chem. 28 2013 392
36. A. Maresca, A. Scozzafava, D. Vullo, and C.T. Supuran J. Enzyme Inhib. Med. Chem. Med. Chem. 28 2013 384
37. F. Liu, A. Martin-Mingot, F. Lecornué, A. Maresca, S. Thibaudeau, and C.T. Supuran J. Enzyme Inhib. Med. Chem. 27 2012 886
38. D. Ekinci, N.I. Kurbanoglu, E. Salamci, M. Senturk, and C.T. Supuran J. Enzyme Inhib. Med. Chem. 27 2012 845
39. D. Vullo, W. Leewattanapasuk, F.A. Mühlschlegel, A. Mastrolorenzo, C. Capasso, and C.T. Supuran Bioorg. Med. Chem. Lett. 23 2013 2647
40. D. Vullo, S. Isik, S. Del Prete, V. De Luca, V. Carginale, A. Scozzafava, C.T. Supuran, and C. Capasso Bioorg. Med. Chem. Lett. 23 2013 1636
41. S.M. Monti, G. De Simone, N.A. Dathan, M. Ludwig, D. Vullo, A. Scozzafava, C. Capasso, and C.T. Supuran Bioorg. Med. Chem. Lett. 23 2013 1626
42. C.T. Supuran Front. Pharmacol. 2 2011 34
43. C.T. Supuran Carbonic Anhydrases: Off-Targets, Add-On Activities, or Emerging Novel Targets? J.U. Peters, Polypharmacology in Drug Discovery 2012 Wiley Hoboken 457
44. R.G. Khalifah J. Biol. Chem. 246 1971 2561
45. Y. Pocker, and J.T. Stone Biochemistry 6 1967 668
46. A. Innocenti, and C.T. Supuran Bioorg. Med. Chem. Lett. 20 2010 6208