Novel 2-substituted-benzimidazole-6-sulfonamides as carbonic anhydrase inhibitors: synthesis, biological evaluation against isoforms I, II, IX and XII and molecular docking studies

References

• Supuran CT. Structure and function of carbonic anhydrases. Biochem J 2016;473:2023–32.
   PubMed Web of Science ®Google Scholar
• Supuran CT. Carbonic anhydrases: novel therapeutic applications for inhibitors and activators. Nat Rev Drug Discov 2008;7:168–81.
   PubMed Web of Science ®Google Scholar
• Supuran CT, Scozzafava A. Carbonic anhydrases as targets for medicinal chemistry. Bioorg Med Chem 2007;15:4336–50.
   PubMed Web of Science ®Google Scholar
• Supuran CT. Carbonic anhydrases as drug targets-an overview. Curr Top Med Chem 2007;7:825–33.
   PubMed Web of Science ®Google Scholar
• Supuran CT. Carbonic anhydrase inhibitors as emerging agents for the treatment and imaging of hypoxic tumors. Expert Opin Investig Drugs 2018;27:963–70.
   PubMed Web of Science ®Google Scholar
• 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
• Supuran CT. How many carbonic anhydrase inhibition mechanisms exist? J Enzyme Inhib Med Chem 2016;31:345–60.
   PubMed Web of Science ®Google Scholar
• Durgun M, Turkmen H, Ceruso M, Supuran CT. Synthesis of 4-sulfamoylphenyl-benzylamine derivatives with inhibitory activity against human carbonic anhydrase isoforms i, ii, ix and xii. Bioorganic Med Chem 2016;24:982–8.
   PubMed Web of Science ®Google Scholar
• Ceruso M, Carta F, Osman SM, et al. Inhibition studies of bacterial, fungal and protozoan β-class carbonic anhydrases with schiff bases incorporating sulfonamide moieties. Bioorganic Med Chem 2015;23:4181–7.
   PubMed Web of Science ®Google Scholar
• Nasr G, Cristian A, Barboiu M, et al. Carbonic anhydrase inhibitors. Inhibition of human cytosolic isoforms i and ii with (reduced) Schiff’s bases incorporating sulfonamide, carboxylate and carboxymethyl moieties. Bioorganic Med Chem 2014;22:2867–74.
   PubMed Web of Science ®Google Scholar
• Supuran CT, Clare BW. Carbonic anhydrase inhibitors – part 47: quantum chemical quantitative structure-activity relationships for a group of sulfanilamide Schiff base inhibitors of carbonic anhydrase. Europ J Med Chem 1998;33:489–500.
   Web of Science ®Google Scholar
• Castellano S, Kuck D, Viviano M, et al. Synthesis and biochemical evaluation of δ2-isoxazoline derivatives as DNA methyltransferase 1 inhibitors. J Med Chem 2011;54:7663–77.
   PubMed Web of Science ®Google Scholar
• Castellano S, Kuck D, Sala M, et al. Constrained analogues of procaine as novel small molecule inhibitors of DNA methyltransferase-1. J Med Chem 2008;51:2321–5.
   PubMed Web of Science ®Google Scholar
• Crocetti L, Maresca A, Temperini C, et al. A thiabendazole sulfonamide shows potent inhibitory activity against mammalian and nematode α-carbonic anhydrases. Bioorg Med Chem Lett 2009;19:1371–5.
   PubMed Web of Science ®Google Scholar
• Karioti A, Carta F, Supuran CT. Phenols and polyphenols as carbonic anhydrase inhibitors. Molecules 2016;21:1649.
   PubMed Web of Science ®Google Scholar
• Durdagi S, Şentürk M, Ekinci D, et al. Kinetic and docking studies of phenol-based inhibitors of carbonic anhydrase isoforms i, ii, ix and xii evidence a new binding mode within the enzyme active site. Bioorg Med Chem 2011;19:1381–9.
   PubMed Web of Science ®Google Scholar
• Davis RA, Hofmann A, Osman A, et al. Natural product-based phenols as novel probes for mycobacterial and fungal carbonic anhydrases. J Med Chem 2011;54:1682–92.
   PubMed 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
• Supuran CT. Carbon- versus sulphur-based zinc binding groups for carbonic anhydrase inhibitors? J Enzyme Inhib Med Chem 2018;33:485–95.
   PubMed Web of Science ®Google Scholar
• Alterio V, Esposito D, Monti SM, et al. Crystal structure of the human carbonic anhydrase ii adduct with 1-(4-sulfamoylphenyl-ethyl)-2,4,6-triphenylpyridinium perchlorate, a membrane-impermeant, isoform selective inhibitor. J Enzyme Inhib Med Chem 2018;33:151–7.
   PubMed Web of Science ®Google Scholar
• Abdoli M, Angeli A, Bozdag M, et al. Synthesis and carbonic anhydrase i, ii, vii, and ix inhibition studies with a series of benzo[d]thiazole-5- and 6-sulfonamides. J Enzyme Inhib Med Chem 2017;32:1071–8.
   PubMed Web of Science ®Google Scholar
• Kohler 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;46:7697–9.
   PubMed Web of Science ®Google Scholar
• Winum JY, Temperini C, El Cheikh K, et al. Carbonic anhydrase inhibitors: clash with ala65 as a means for designing inhibitors with low affinity for the ubiquitous isozyme ii, exemplified by the crystal structure of the topiramate sulfamide analogue. J Med Chem 2006;49:7024–31.
   PubMed Web of Science ®Google Scholar
• Pastorekova S, Casini A, Scozzafava A, et al. Carbonic anhydrase inhibitors: the first selective, membrane-impermeant inhibitors targeting the tumor-associated isozyme ix. Bioorg Med Chem Lett 2004;14:869–73.
   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
• Borras J, Scozzafava A, Menabuoni L, et al. Carbonic anhydrase inhibitors: synthesis of water-soluble, topically effective intraocular pressure lowering aromatic/heterocyclic sulfonamides containing 8-quinoline-sulfonyl moieties: is the tail more important than the ring? Bioorg Med Chem 1999;7:2397–406.
   PubMed Web of Science ®Google Scholar
• Pustenko A, Stepanovs D, Zalubovskis R, et al. 3h-1,2-benzoxathiepine 2,2-dioxides: a new class of isoform-selective carbonic anhydrase inhibitors. J Enzyme Inhib Med Chem 2017;32:767–75.
   PubMed Web of Science ®Google Scholar
• Tars K, Vullo D, Kazaks A, et al. Sulfocoumarins (1,2-benzoxathiine-2,2-dioxides): a class of potent and isoform-selective inhibitors of tumor-associated carbonic anhydrases. J Med Chem 2013;56:293–300.
   PubMed Web of Science ®Google Scholar
• Briganti F, Pierattelli R, Scozzafava A, Supuran CT. Carbonic anhydrase inhibitors. Part 37. Novel classes of isozyme i and ii inhibitors and their mechanism of action. Kinetic and spectroscopic investigations on native and cobalt-substituted enzymes. European J Med Chem 1996;31:1001–10.
   Web of Science ®Google Scholar
• Morris GM, Huey R, Lindstrom W, et al. Autodock4 and autodocktools4: automated docking with selective receptor flexibility. J Comput Chem 2009;30:2785–91.
   PubMed Web of Science ®Google Scholar
• Santos-Martins D, Forli S, Ramos MJ, Olson AJ. AutoDock4(Zn): an improved AutoDock force field for small-molecule docking to zinc metalloproteins. J Chem Inf Model 2014;54:2371–9.
   PubMed Web of Science ®Google Scholar
• Leitans J, Kazaks A, Balode A, et al. Efficient expression and crystallization system of cancer-associated carbonic anhydrase isoform ix. J Med Chem 2015;58:9004–9.
   PubMed Web of Science ®Google Scholar
• Schrödinger, Release 2018-3: Maestro, Schrödinger, (2018).
   Google Scholar
• Bozdag M, Carta F, Ceruso M, et al. Discovery of 4-hydroxy-3-(3-(phenylureido)benzenesulfonamides as slc-0111 analogues for the treatment of hypoxic tumors overexpressing carbonic anhydrase ix. J Med Chem 2018;61:6328–38.
   PubMed Web of Science ®Google Scholar
• Behnke CA, Le Trong I, Godden JW, et al. Atomic resolution studies of carbonic anhydrase ii. Acta Crystallographica Section D 2010;66:616–27.
   PubMedGoogle Scholar
• Smirnov A, Manakova E, Grazulis S, et al. 5MSA Crystal structure of human carbonic anhydrase isozyme XII with 2,3,5,6-Tetrafluoro-4-(propylthio)benzenesulfonamide, Protein Data Bank. RCSB 2018; DOI:10.2210/pdb5MSA/pdb
   Google Scholar
• Cosconati S, Forli S, Perryman AL, et al. Virtual screening with autodock: theory and practice. Exp Opin Drug Disc 2010;5:597–607.
   PubMed Web of Science ®Google Scholar
• Arienti KL, Brunmark A, Axe FU, et al. Checkpoint kinase inhibitors: SAR and radioprotective properties of a series of 2-arylbenzimidazoles. J Med Chem 2005;48:1873–85.
   PubMed Web of Science ®Google Scholar
• Salerno S, Barresi E, Amendola G, et al. 4-substituted benzenesulfonamides incorporating bi/tricyclic moieties act as potent and isoform-selective carbonic anhydrase ii/ix inhibitors. J Med Chem 2018;61:5765–70.
   PubMed Web of Science ®Google Scholar
• Alterio V, Hilvo M, Di Fiore A, et al. Crystal structure of the catalytic domain of the tumor-associated human carbonic anhydrase ix. Proc Natl Acad Sci USA 2009;106:16233–8.
   PubMed Web of Science ®Google Scholar