Heterocyclic compounds as carbonic anhydrase inhibitor

Journal of Enzyme Inhibition and Medicinal Chemistry

Volumn 27, Issue 6, 2012, Pages 773-783

  Husain, Asif ^a   Madhesia, Diwakar ^a  

^a HAMDARD UNIVERSITY   (India)

Author keywords

Carbonic anhydrase; Evaluation; Sulfonamide; Synthesis

Indexed keywords

ACETAZOLAMIDE; BENZENESULFONAMIDE DERIVATIVE; CARBONATE DEHYDRATASE; CARBONATE DEHYDRATASE INHIBITOR; HETEROCYCLIC COMPOUND; INDOLE DERIVATIVE; OXADIAZOLE DERIVATIVE; PYRIDINE DERIVATIVE; PYRROLE DERIVATIVE; QUINOLINE DERIVATIVE; SULFONAMIDE; THIADIAZOLE DERIVATIVE; THIOPHENE DERIVATIVE; TRIAZINE DERIVATIVE; TRIAZOLE DERIVATIVE;

BLURRED VISION; DRUG MECHANISM; DRUG POTENCY; DRUG STRUCTURE; DRUG SYNTHESIS; ENZYME ACTIVITY; ENZYME INHIBITION; GLAUCOMA; HUMAN; NONHUMAN; PARESTHESIA; POLLAKISURIA; PRIORITY JOURNAL; REVIEW; SKIN TINGLING; TASTE DISORDER;

ACID-BASE EQUILIBRIUM; ANOXIA; ANTINEOPLASTIC AGENTS; AZOLES; CARBONIC ANHYDRASE INHIBITORS; CARBONIC ANHYDRASES; EPILEPSY; GLAUCOMA; HUMANS; INDOLES; ISOENZYMES; NEOPLASMS; STRUCTURE-ACTIVITY RELATIONSHIP; SULFONAMIDES; THIOPHENES;

EID: 84865850355     PISSN: 14756366     EISSN: 14756374     Source Type: Journal    
DOI: 10.3109/14756366.2011.617882     Document Type: Review

References (39)

1. Supuran CT. Carbonic anhydrases: novel therapeutic applications for inhibitors and activators. Nat Rev Drug Discov 2008;7:168-181.
2. Supuran CT. Carbonic anhydrase inhibitors. Bioorg Med Chem Lett 2010;20:3467-3474.
3. Supuran CT. Carbonic anhydrase inhibition/activation: trip of a scientist around the world in the search of novel chemotypes and drug targets. Curr Pharm Des 2010;16:3233-3245.
4. Güzel O, Innocenti A, Scozzafava A, Salman A, Supuran CT. Carbonic anhydrase inhibitors. Aromatic/heterocyclic sulfonamides incorporating phenacetyl, pyridylacetyl and thienylacetyl tails act as potent inhibitors of human mitochondrial isoforms VA and VB. Bioorg Med Chem 2009;17:4894-4899.
5. Nishimori I, Vullo D, Innocenti A, Scozzafava A, Mastrolorenzo A, Supuran CT. Carbonic anhydrase inhibitors. The mitochondrial isozyme VB as a new target for sulfonamide and sulfamate inhibitors. J Med Chem 2005;48:7860-7866.
6. Hilvo M, Innocenti A, Monti SM, De Simone G, Supuran CT, Parkkila S. Recent advances in research on the most novel carbonic anhydrases, CA XIII and XV. Curr Pharm Des 2008;14:672-678.
7. Pastorekova S, Parkkila S, Pastorek J, Supuran CT. Review article. J Enz Inhib Med Chem 2004;19:199-229.
8. Supuran CT. Carbonic anhydrase inhibitors in the treatment and prophylaxis of obesity. Expert Opin Ther Pat 2003;13(10):1545-1550.
9. Svastová E, Hulíková A, Rafajová M, Zat'ovicová M, Gibadulinová A, Casini A et al. Hypoxia activates the capacity of tumor-associated carbonic anhydrase IX to acidify extracellular pH. FEBS Lett 2004;577:439-445.
10. Supuran CT. Indisulam: an anticancer sulfonamide in clinical development. Expert Opin Investig Drugs 2003;12:283-287.
11. Scozzafava A, Owa T, Mastrolorenzo A, Supuran CT. Anticancer and antiviral sulfonamides. Curr Med Chem 2003;10:925-953.
12. Vullo D, Franchi M, Gallori E, Pastorek J, Scozzafava A, Pastorekova S et al. Carbonic anhydrase inhibitors. inhibition of cytosolic isozymes I and II and transmembrane, cancer-associated isozyme IX with anions. J Enzyme Inhib Med Chem 2003;18:403-406.
13. Vullo D, Franchi M, Gallori E, Pastorek J, Scozzafava A, Pastorekova S et al. Carbonic anhydrase inhibitors: inhibition of the tumor-associated isozyme IX with aromatic and heterocyclic sulfonamides. Bioorg Med Chem Lett 2003;13:1005-1009.
14. Winum JY, Vullo D, Casini A, Montero JL, Scozzafava A, Supuran CT. Carbonic anhydrase inhibitors: inhibition of transmembrane, tumor-associated isozyme IX, and cytosolic isozymes I and II with aliphatic sulfamates. J Med Chem 2003;46:5471-5477.
15. Winum JY, Vullo D, Casini A, Montero JL, Scozzafava A, Supuran CT. Carbonic anhydrase inhibitors. Inhibition of cytosolic isozymes I and II and transmembrane, tumor-associated isozyme IX with sulfamates including EMATE also acting as steroid sulfatase inhibitors. J Med Chem 2003;46:2197-2204.
16. Abdel-Hamid MK, Abdel-Hafez AA, El-Koussi NA, Mahfouz NM, Innocenti A, Supuran CT. Design, synthesis, and docking studies of new 1,3,4-thiadiazole-2- thione derivatives with carbonic anhydrase inhibitory activity. Bioorg Med Chem 2007;15:6975-6984.
17. Santos MA, Marques S, Vullo D, Innocenti A, Scozzafava A, Supuran CT. Carbonic anhydrase inhibitors: inhibition of cytosolic/tumorassociated isoforms I, II, and IX with iminodiacetic carboxylates/ hydroxamates also incorporating benzenesulfonamide moieties. Bioorg Med Chem Lett 2007;17:1538-1543.
18. Wilkinson BL, Bornaghi LF, Houston TA, Innocenti A, Vullo D, Supuran CT et al. Carbonic anhydrase inhibitors: inhibition of isozymes I, II, and IX with triazole-linked O-glycosides of benzene sulfonamides. J Med Chem 2007;50:1651-1657.
19. Smaine FZ, Pacchiano F, Rami M, Barragan-Montero V, Vullo D, Scozzafava A et al. Carbonic anhydrase inhibitors: 2-substituted- 1,3,4-thiadiazole-5- sulfamides act as powerful and selective inhibitors of the mitochondrial isozymes VA and VB over the cytosolic and membrane-associated carbonic anhydrases I, II and IV. Bioorg Med Chem Lett 2008;18:6332-6335.
20. Temperini C, Cecchi A, Boyle NA, Scozzafava A, Cabeza JE, Wentworth P Jr et al. Carbonic anhydrase inhibitors. Interaction of 2-N,N-dimethylamino-1,3,4- thiadiazole-5-methanesulfonamide with 12 mammalian isoforms: kinetic and X-ray crystallographic studies. Bioorg Med Chem Lett 2008;18:999-1005.
21. Kasimogullari R, Bülbül M, Günhan H, Güleryüz H. Effects of new 5-amino-1,3,4-thiadiazole-2-sulfonamide derivatives on human carbonic anhydrase isozymes. Bioorg Med Chem 2009;17: 3295-3301.
22. Kasimogullari R, Bülbül M, Arslan BS, Gökçe B. Synthesis, characterization and antiglaucoma activity of some novel pyrazole derivatives of 5-amino-1,3,4-thiadiazole-2-sulfonamide. Eur J Med Chem 2010;45:4769-4773.
23. Baranauskiene L, Hilvo M, Matuliene J, Golovenko D, Manakova E, Dudutiene V et al. Inhibition and binding studies of carbonic anhydrase isozymes I, II and IX with benzimidazo[1,2-c][1,2,3] thiadiazole-7-sulphonamides. J Enzyme Inhib Med Chem 2010;25:863-870.
24. Gitto R, Ferro S, Agnello S, De Luca L, De Sarro G, Russo E et al. Synthesis and evaluation of pharmacological profile of 1-aryl-6,7- dimethoxy-3,4-dihydroisoquinoline-2(1H)-sulfonamides. Bioorg Med Chem 2009;17:3659-3664.
25. Al-Said MS, Ghorab MM, Al-Qasoumi SI, El-Hossary EM, Noaman E. Synthesis and in vitro anticancer screening of some novel 4-[2- amino-3-cyano-4- substituted-5,6,7,8-tetrahydroquinolin-1- (4H)-yl]benzenesulfonamides. Eur J Med Chem 2010;45:3011-3018.
26. Garaj V, Puccetti L, Fasolis G, Winum JY, Montero JL, Scozzafava A et al. Carbonic anhydrase inhibitors: synthesis and inhibition of cytosolic/tumor- associated carbonic anhydrase isozymes I, II, and IX with sulfonamides incorporating 1,2,4-triazine moieties. Bioorg Med Chem Lett 2004;14:5427-5433.
27. Garaj V, Puccetti L, Fasolis G, Winum JY, Montero JL, Scozzafava A et al. Carbonic anhydrase inhibitors: novel sulfonamides incorporating 1,3,5-triazine moieties as inhibitors of the cytosolic and tumour-associated carbonic anhydrase isozymes I, II and IX. Bioorg Med Chem Lett 2005;15:3102-3108.
28. Katritzky AR, Caster KC, Maren TH, Conroy CW, Bar-Ilan A. Synthesis and physicochemical properties of thiadiazolo [3,2-a] pyrimidinesulfonamides and thiadiazolo [3,2-a]triazinesulfonamides as candidates for topically effective carbonic anhydrase inhibitors. J Med Chem 1987;30:2058-2062.
29. Brzozowski Z, Slawinski J, Saczewski F, Innocenti A, Supuran CT. Carbonic anhydrase inhibitors: synthesis and inhibition of the human cytosolic isozymes I and II and transmembrane isozymes IX, XII (cancer-associated) and XIV with 4-substituted 3-pyridinesulfonamides. Eur J Med Chem 2010;45:2396-2404.
30. Brzozowski Z, Slawinski J, Innocenti A, Supuran CT. Carbonic anhydrase inhibitors. Regioselective synthesis of novel 1-substituted 1,4-dihydro-4-oxo-3- pyridinesulfonamides and their inhibition of the human cytosolic isozymes I and II and transmembrane cancerassociated isozymes IX and XII. Eur J Med Chem 2010;45:3656-3661.
31. Graham SL, Hoffman JM, Gautheron P, Michelson SR, Scholz TH, Schwam H et al. Topically active carbonic anhydrase inhibitors. 3. Benzofuran- and indole-2-sulfonamides. J Med Chem 1990;33: 749-754.
32. Güzel O, Maresca A, Scozzafava A, Salman A, Balaban AT, Supuran CT. Carbonic anhydrase inhibitors. Synthesis of 2,4,6-trimethylpyridinium derivatives of 2-(hydrazinocarbonyl)- 3-aryl-1H-indole-5-sulfonamides acting as potent inhibitors of the tumor-associated isoform IX and XII. Bioorg Med Chem Lett 2009;19:2931-2934.
33. Innocenti A, Villar R, Martinez-Merino V, Gil MJ, Scozzafava A, Vullo D et al. Carbonic anhydrase inhibitors: inhibition of cytosolic/tumor-associated carbonic anhydrase isozymes I, II, and IX with benzo[b]thiophene 1,1-dioxide sulfonamides. Bioorg Med Chem Lett 2005;15:4872-4876.
34. Hartman GD, Halczenko W, Smith RL, Sugrue MF, Mallorga PJ, Michelson SR et al. 4-substituted thiophene- and furan-2- sulfonamides as topical carbonic anhydrase inhibitors. J Med Chem 1992;35:3822-3831.
35. Almajan GL, Barbuceanu SF, Innocenti A, Scozzafava A, Supuran CT. Carbonic anhydrase inhibitors. Inhibition of the cytosolic and tumor-associated carbonic anhydrase isozymes I, II and IX with some 1,3,4-oxadiazole- and 1,2,4-triazole-thiols. J Enzyme Inhib Med Chem 2008;23:101-107.
36. Gluszok S, Frédérick R, Foulon C, Klupsch F, Supuran CT, Vullo D et al. Design, solid-phase synthesis, and biological evaluation of novel 1,5-diarylpyrrole-3-carboxamides as carbonic anhydrase IX inhibitors. Bioorg Med Chem 2010;18:7392-7401.
37. Supuran CT, Scozzafava A, Casini A. Carbonic anhydrase inhibitors. Med Res Rev 2003;23:146-189.
38. Wilbur KM, Anderson NG. Electrometric and colorimetric determination of carbonic anhydrase. J Biol Chem 1948;176: 147-154.
39. Ozensoy O, Kockar F, Arslan O, Isik S, Supuran CT, Lyon M. An evaluation of cytosolic erythrocyte carbonic anhydrase and catalase in carcinoma patients: an elevation of carbonic anhydrase activity. Clin Biochem 2006;39:804-809.