Carbonic Anhydrases inhibitory effects of new benzenesulfonamides synthesized by using superacid chemistry

References

• Supuran CT. Carbonic anhydrases: Novel therapeutic applications for inhibitors and activators. Nat Rev Drug Discov 2008;7:168–181.
   PubMed Web of Science ®Google Scholar
• Supuran CT. Carbonic Anhydrases as Drug Targets—General Presentation. In: Supuran CT, Winum JY, (eds). Drug Design of Zinc-Enzyme Inhibitors: Functional, Structural, and Disease Applications. Hoboken, NJ: Wiley; 2009. pp 15–38.
   Google Scholar
• Winum JY, Rami M, Scozzafava A, Montero JL, Supuran C. Carbonic anhydrase IX: A new druggable target for the design of antitumor agents. Med Res Rev 2008;28:445–463.
   PubMed Web of Science ®Google Scholar
• Supuran CT, Scozzafava A, Casini A. Carbonic anhydrase inhibitors. Med Res Rev 2003;23:146–189.
   PubMed Web of Science ®Google Scholar
• Thiry A, Dogné JM, Masereel B, Supuran CT. Targeting tumor-associated carbonic anhydrase IX in cancer therapy. Trends Pharmacol Sci 2006;27:566–573.
   PubMed Web of Science ®Google Scholar
• Supuran CT, Scozzafava A. Carbonic anhydrases as targets for medicinal chemistry. Bioorg Med Chem 2007;15:4336–4350.
   PubMed Web of Science ®Google Scholar
• 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.
   PubMed Web of Science ®Google Scholar
• Rami M, Maresca A, Smaine FZ, Montero JL, Scozzafava A, Winum JY et al. Sulfonamides incorporating boroxazolidone moieties are potent inhibitors of the transmembrane, tumor-associated carbonic anhydrase isoforms IX and XII. Bioorg Med Chem Lett 2011;21:2975–2979.
   PubMed Web of Science ®Google Scholar
• Capkauskaite E, Baranauskiene L, Golovenko D, Manakova E, Gražulis S, Tumkevicius S et al. Indapamide-like benzenesulfonamides as inhibitors of carbonic anhydrases I, II, VII, and XIII. Bioorg Med Chem 2010;18:7357–7364.
   PubMed Web of Science ®Google Scholar
• Mader P, Brynda J, Gitto R, Agnello S, Pachl P, Supuran CT et al. Structural basis for the interaction between carbonic anhydrase and 1,2,3,4-tetrahydroisoquinolin-2-ylsulfonamides. J Med Chem 2011;54:2522–2526.
   PubMed Web of Science ®Google Scholar
• Mincione F, Benedini F, Biondi S, Cecchi A, Temperini C, Formicola G et al. Synthesis and crystallographic analysis of new sulfonamides incorporating NO-donating moieties with potent antiglaucoma action. Bioorg Med Chem Lett 2011;21:3216–3221.
   PubMed Web of Science ®Google Scholar
• Bertucci A, Innocenti A, Scozzafava A, Tambutté S, Zoccola D, Supuran CT. Carbonic anhydrase inhibitors. Inhibition studies with anions and sulfonamides of a new cytosolic enzyme from the scleractinian coral Stylophora pistillata. Bioorg Med Chem Lett 2011;21:710–714.
   PubMed Web of Science ®Google Scholar
• Supuran CT. Carbonic anhydrase inhibitors. Bioorg Med Chem Lett 2010;20:3467–3474.
   PubMed Web of Science ®Google Scholar
• Olah GA, Prakash GKS, Molnar A, Sommer J. Superacids, 2nd Edition. New York: Wiley; 2009.
   Google Scholar
• Khalifah RG. The carbon dioxide hydration activity of carbonic anhydrase. I. Stop-flow kinetic studies on the native human isoenzymes B and C. J Biol Chem 1971;246:2561–2573.
   PubMed Web of Science ®Google Scholar
• Ilies MA, Vullo D, Pastorek J, Scozzafava A, Ilies M, Caproiu MT et al. Carbonic anhydrase inhibitors. Inhibition of tumor-associated isozyme IX by halogenosulfanilamide and halogenophenylaminobenzolamide derivatives. J Med Chem 2003;46:2187–2196.
   PubMed Web of Science ®Google Scholar
• Biswas S, Aggarwal M, Güzel Ö, Scozzafava A, McKenna R, Supuran CT. Conformational variability of different sulfonamide inhibitors with thienyl-acetamido moieties attributes to differential binding in the active site of cytosolic human carbonic anhydrase isoforms. Bioorg Med Chem 2011;19:3732–3738.
   PubMed Web of Science ®Google Scholar
• Jacquesy J-C. Organic Synthesis in Superacid. In: Olah GA, (ed). Carbocation Chemistry. New York: Wiley; 2009. pp 359–376.
   Google Scholar
• Thibaudeau S, Martin-Mingot A, Jouannetaud M-P, Karam O, Zunino F. A novel, facile route to β-fluoroamines by hydrofluorination reaction in superacid HF-SbF5. Chem Commun 2007;3198–3200.
   PubMed Web of Science ®Google Scholar
• Vardelle E, Gamba-Sanchez D, Martin-Mingot A, Jouannetaud M-P, Thibaudeau S, Marrot J. Cyclisation/fluoriantion of nitrogen containing dienes in superacid HF-SbF5: A new route to 3- and 4-fluoropiperidines. Chem Commun 2008;1473–1475.
   PubMed Web of Science ®Google Scholar
• Fahy J, Duflos A, Ribert J-P, Jacquesy J-C, Berrier C, Jouannetaud M-P, Zunino F. Vinca alkaloids in superacidic media: A method for creating a new family of antitumor derivatives. J Am Chem Soc 1997;119:8576–8577.
   Web of Science ®Google Scholar
• Debarge S, Thibaudeau S, Violeau B, Martin-Minfot A, Jouannetaud M-P, Jacquesy J-C, Cousson A. Rearrangement or gem-difluorination of quinine and 9-epiquinine and their acetates in superacid. Tetrahedron 2005;61:2065–2073.
   Web of Science ®Google Scholar
• Liu F, Martin-Mingot A, Jouannetaud MP, Zunino F, Thibaudeau S. Superelectrophilic activation in superacid HF/SbF(5) and synthesis of benzofused sultams. Org Lett 2010;12:868–871.
   PubMed Web of Science ®Google Scholar
• Olah GA, Klumpp D. Superelectrophiles and their chemistry. New York: Wiley; 2008.
   Google Scholar
• Liu F, Musadji NY, Lecornué F, Jouannetaud M-P, Thibaudeau S. Superacid mediated reactions applied to 4-aminobenzofused sultams and fluorinated 4-aminobenzene sulfonamides synthesis. Tetrahedron 2010;66:7112–7118.
   Web of Science ®Google Scholar
• Thiry A, Supuran CT, Masereel B, Dogné JM. Recent developments of carbonic anhydrase inhibitors as potential anticancer drugs. J Med Chem 2008;51:3051–3056.
   PubMed Web of Science ®Google Scholar
• Alterio V, Hilvo M, Di Fiore A, Supuran CT, Pan P, Parkkila S et al. Crystal structure of the catalytic domain of the tumor-associated human carbonic anhydrase IX. Proc Natl Acad Sci USA 2009;106:16233–16238.
   PubMed Web of Science ®Google Scholar
• Vullo D, Scozzafava A, Pastorekova S, Pastorek J, Supuran CT. Carbonic anhydrase inhibitors: Inhibition of the tumor-associated isozyme IX with fluorine-containing sulfonamides. The first subnanomolar CA IX inhibitor discovered. Bioorg Med Chem Lett 2004;14:2351–2356.
   PubMed Web of Science ®Google Scholar
• O’Hagan D. Understanding organofluorine chemistry. An introduction to the C-F bond. Chem Soc Rev 2008;37:308–319.
   PubMed Web of Science ®Google Scholar
• Blackburn GM, Türkmen H. Synthesis of alpha-fluoro- and alpha, alpha-difluoro-benzenemethanesulfonamides: New inhibitors of carbonic anhydrase. Org Biomol Chem 2005;3:225–226.
   PubMed Web of Science ®Google Scholar
• Alterio V, Di Fiore A, D’Ambrosio K, Supuran CT, De Simone G. X-ray crystallography of ca inhibitors and its importance in drug design. In: Supuran CT, Winum JY ed,. Drug Design of Zinc-Enzyme Inhibitors: Functional, Structural, and Disease Applications. Hoboken, NJ: Wiley; 2009. pp 73–138.
   Google Scholar
• Neri D, Supuran CT. Interfering with pH regulation in tumours as a therapeutic strategy. Nat Rev Drug Discov 2011;10:767–777.
   PubMed Web of Science ®Google Scholar