Inhibition studies on a panel of human carbonic anhydrases with N1-substituted secondary sulfonamides incorporating thiazolinone or imidazolone-indole tails

References

• (a) Supuran CT. Carbon- versus sulphur-based zinc binding groups for carbonic anhydrase inhibitors? J Enzyme Inhib Med Chem 2018;33:485–95. (b) Carta F, Supuran CT, Scozzafava A. Sulfonamides and their isosters as carbonic anhydrase inhibitors. Future Med Chem 2014;6:1149–65.
   PubMed Web of Science ®Google Scholar
• (a) Supuran CT. Carbonic anhydrases: novel therapeutic applications for inhibitors and activators. Nat Rev Drug Discovery 2008;7:168–81. (b) Supuran CT. Structure and function of carbonic anhydrases. Biochem J 2016;473:2023–32.
   PubMed Web of Science ®Google Scholar
• (a) Alterio V, Di Fiore A, D’Ambrosio K, et al. Multiple binding modes of inhibitors to carbonic anhydrases: how to design specific drugs targeting 15 different isoforms? Chem Rev 2012;1:4421–68. (b) Supuran CT. Carbonic anhydrases: from biomedical applications of the inhibitors and activators to biotechnological use for CO2 capture. J Enzyme Inhib Med Chem 2013;28:229–30.
   Web of Science ®Google Scholar
• (a) Supuran CT, Winum JY. Drug design of zinc-enzyme inhibitors: functional, structural, and disease applications. Hoboken (NJ): John Wiley & Sons; 2009:3–12. Supuran CT, Vullo D, Manole G, et al. Designing of novel carbonic anhydrase inhibitors and activators. Curr Med Chem Cardiovasc Hematol Agents 2004;2:49–68.
   Google Scholar
• Bozdag M, Ferraroni M, Nuti E, et al. Combining the tail and the ring approaches for obtaining potent and isoform-selective carbonic anhydrase inhibitors: solution and X-ray crystallographic studies. Bioorg Med Chem 2014;22:334–40.
   PubMed Web of Science ®Google Scholar
• (a) Supuran CT. How many carbonic anhydrase inhibition mechanisms exist? J Enzyme Inhib Med Chem 2016;31:345–60. (b) Supuran CT. Advances in structure-based drug discovery of carbonic anhydrase inhibitors. Expert Opin Drug Discov 2017;12:61–88.
   PubMed Web of Science ®Google Scholar
• Scozzafava A, Menabuoni L, Mincione F, et al. Carbonic anhydrase inhibitors. Synthesis of water-soluble, topically effective, intraocular pressure-lowering aromatic/heterocyclic sulfonamides containing cationic or anionic moieties: is the tail more important than the ring? J Med Chem 1999;42:2641–50.
   PubMed Web of Science ®Google Scholar
• Maren TH. Carbonic anhydrase: chemistry, physiology, and inhibition. Physiol Rev 1967;47:595–781.
   PubMed Web of Science ®Google Scholar
• Wilkinson BL, Bornaghi LF, Houston TA, et al. A novel class of carbonic anhydrase inhibitors: glycoconjugate benzene sulfonamides prepared by “click-tailing”. J Med Chem 2006;49:6539–48.
   PubMed Web of Science ®Google Scholar
• Lopez M, Salmon AJ, Supuran CT, et al. Carbonic anhydrase inhibitors developed through “click tailing”. Curr Pharm Des 2010;16:3277–87.
   PubMed Web of Science ®Google Scholar
• Di Fiore A, Maresca A, Alterio V, et al. Carbonic anhydrase inhibitors: x-ray crystallographic studies for the binding of N-substituted benzenesulfonamides to human isoform II. Chem Comm 2011;47:11636–8.
   PubMed Web of Science ®Google Scholar
• (a) Köhler K, Hillebrecht A, Schulze Wischeler J, et al. Saccharin inhibits carbonic anhydrases: possible explanation for its unpleasant metallic aftertaste. Angew Chem Int Ed Engl 2007;4:7697–9. (b) Mahon BP, Hendon AM, Driscoll JM, et al. Saccharin: a lead compound for structure-based drug design of carbonic anhydrase IX inhibitors. Bioorg Med Chem 2015;23:849–54.
   Web of Science ®Google Scholar
• Nocentini A, Vullo D, Bartolucci G, et al. N-Nitrosulfonamides: a new chemotype for carbonic anhydrase inhibition. Bioorg Med Chem 2016;24:3612–7.
   PubMed Web of Science ®Google Scholar
• Carradori S, Secci D, De Monte C, et al. A novel library of saccharin and acesulfame derivatives as potent and selective inhibitors of carbonic anhydrase IX and XII isoforms. Bioorg Med Chem 2016;24:1095–105.
   PubMed Web of Science ®Google Scholar
• D’Ascenzio M, Carradori S, De Monte C, et al. Design, synthesis and evaluation of N-substituted saccharin derivatives as selective inhibitors of tumor-associated carbonic anhydrase XII. Bioorg Med Chem 2014;22:1821–31.
   PubMed Web of Science ®Google Scholar
• Eldehna WM, Abo-Ashour MF, Nocentini A, et al. Novel 4/3-((4-oxo-5-(2-oxoindolin-3-ylidene)thiazolidin-2-ylidene)amino)benzenesulfonamides: synthesis, carbonic anhydrase inhibitory activity, anticancer activity and molecular modelling studies. Eur J Med Chem 2017;139:250–62.
   PubMed Web of Science ®Google Scholar
• Eldehna WM, Al-Ansary GH, Bua S, et al. Novel indolin-2-one-based sulfonamides as carbonic anhydrase inhibitors: Synthesis, in vitro biological evaluation against carbonic anhydrases isoforms I, II, IV and VII and molecular docking studies. Eur J Med Chem 2017;127:521–30.
   PubMed Web of Science ®Google Scholar
• (a) Ibrahim HS, Abou-Seri SM, Tanc M, et al. Isatin-pyrazole benzenesulfonamide hybrids potently inhibit tumor-associated carbonic anhydrase isoforms IX and XII. Eur J Med Chem 2015;103:583–93. (b) Carta F, Supuran CT. Diuretics with carbonic anhydrase inhibitory action: a patent and literature review (2005–2013). Expert Opin Ther Pat 2013;23:681–91. (c) Masini E, Carta F, Scozzafava A, Supuran CT. Antiglaucoma carbonic anhydrase inhibitors: a patent review. Expert Opin Ther Pat 2013;23:705–16. (d) Scozzafava A, Supuran CT, Carta F. Antiobesity carbonic anhydrase inhibitors: a literature and patent review. Expert Opin Ther Pat 2013;23:725–35.
   PubMed Web of Science ®Google Scholar
• Monti SM, Supuran CT, De Simone G. Anticancer carbonic anhydrase inhibitors: a patent review (2008–2013). Expert Opin Ther Pat 2013;23:737–49.
   PubMed Web of Science ®Google Scholar
• Ekinci D, Cavdar H, Durdagi S, et al. Structure-activity relationships for the interaction of 5,10-dihydroindeno[1,2-b]indole derivatives with human and bovine carbonic anhydrase isoforms I, II, III, IV and VI. Eur J Med Chem 2012;49:68–73.
   PubMed Web of Science ®Google Scholar
• Awadallah FM, El-Waei TA, Hanna MM, et al. Synthesis, carbonic anhydrase inhibition and cytotoxic activity of novel chromone-based sulfonamide derivatives. Eur J Med Chem 2015;96:425–35.
   PubMed Web of Science ®Google Scholar
• James PN, Snyder HR. Indole-3-aldehyde. Org Synth 1969;4:539.
   Google Scholar
• Ragab AF, Heiba HI, El-Hazek MR. Anticancer and radio-sensitizing evaluation of some new thiazolopyrane and thiazolopyranopyrimidine derivatives bearing a sulfonamide moiety. Eur J Med Chem 2011;46:5120–6.
   PubMed Web of Science ®Google Scholar
• Ghorab MM, Ragab AF, Heiba HI, et al. Synthesis of some novel sulfonamides containing biologically active alkanoic acid, acetamide, thiazole and pyrrole moieties of expected antitumor and radiosensitizing activities. J Basic Appl Chem 2011;1:8–14.
   Google Scholar
• Song M, Mei W, Weijuan G, et al. 5-(1H-indolyl-3-methylene)-1,3-thiazolidinyl-4-one derivatives, and synthesis method and application thereof. CN 104059060 A. 2014;1–27.
   Google Scholar
• Crawford M, Little WT. The Erlenmeyer reaction with aliphatic aldehydes, 2-phenyloxazol-5-one being used instead of hippuric acid. J Chem Soc 1959;729–31.
   Web of Science ®Google Scholar
• Achesond RM, Booth DA, Brettle R, et al. The synthesis of some acylglycines and related oxazolone. J Chem Soc 1960;3457–60.
   Web of Science ®Google Scholar
• Daniele AG, Aaron N, Benedetto M, et al. Conformationally constrained tryptophan analogs. Synthesis of (±)-(Z)- and (±)-(E)-2-amino-2,3-methano-3-(indol-3-yl)-propanoic acids. Tetrahedron 1996;52:9901–8.
   Web of Science ®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;246:2561–73.
   PubMed Web of Science ®Google Scholar
• Akocak S, Lolak N, Nocentini A, et al. Synthesis and biological evaluation of novel aromatic and heterocyclic bis-sulfonamide Schiff bases as carbonic anhydrase I, II, VII and IX inhibitors. Bioorg Med Chem 2017;25:3093–7.
   PubMed Web of Science ®Google Scholar
• Entezari Heravi Y, Bua S, Nocentini A, et al. Inhibition of Malassezia globosa carbonic anhydrase with phenols. Bioorg Med Chem 2017;25:2577–82.
   PubMed Web of Science ®Google Scholar
• Altug C, Güneş H, Nocentini A, et al. Synthesis of isoxazole-containing sulfonamides with potent carbonic anhydrase II and VII inhibitory properties. Bioorg Med Chem 2017;25:1456–64.
   PubMed Web of Science ®Google Scholar
• Zhang Z, Lau J, Zhang C, et al. Design, synthesis and evaluation of 18F labeled cationic carbonic anhydrase IX inhibitors for PET imaging. J Enzyme Inhib Med Chem 2017;32:722–30.
   PubMed Web of Science ®Google Scholar
• Nocentini A, Cadoni R, Del Prete S, et al. Benzoxaboroles as efficient inhibitors of the β-carbonic anhydrases from pathogenic fungi: activity and modeling study. ACS Med Chem Lett 2017;8:1194–8.
   PubMed Web of Science ®Google Scholar
• Nocentini A, Bua S, Lomelino CL, et al. Discovery of new sulfonamide carbonic anhydrase IX inhibitors incorporating nitrogenous bases. ACS Med Chem Lett 2017;8:1314–19.
   PubMed Web of Science ®Google Scholar
• (a) Nocentini A, Vullo D, Del Prete S, et al. Inhibition of the β-carbonic anhydrase from the dandruff-producing fungus Malassezia globosa with monothiocarbamates. J Enzyme Inhib Med Chem 2017;32:1064–70. (b) Supuran CT, Capasso C. An overview of the bacterial carbonic anhydrases. Metabolites 2017;7:E56.
   PubMed Web of Science ®Google Scholar
• Ebrahimi H, Hadi JS, Al-Ansari HS. A new series of Schiff bases derived from sulfa drugs and indole-3-carboxaldehyde: synthesis, characterization, spectral and DFT computational studies. J Molec Struc 2013;1039:37–45.
   Web of Science ®Google Scholar
• Naqvi A, Shahnawaaz M, Rao AV, et al. Synthesis of Schiff bases via environmentally benign and energy-efficient greener methodologies. El J Chem 2009;6:75–8.
   Web of Science ®Google Scholar
• Neri D, Supuran CT. Interfering with pH regulation in tumours as a therapeutic strategy. Nat Rev Drug Discov 2011;10:767–77.
   PubMed Web of Science ®Google Scholar
• (a) Supuran CT. Carbonic anhydrase inhibition and the management of hypoxic tumors. Metabolites 2017;7:E48. (b) Iessi E, Logozzi M, Mizzoni D, et al. Rethinking the combination of proton exchanger inhibitors in cancer therapy. Metabolites 2018;8:E2.
   PubMed Web of Science ®Google Scholar