3H-1,2-benzoxathiepine 2,2-dioxides: a new class of isoform-selective carbonic anhydrase inhibitors

References

• a) Grandane A, Belyakov S, Trapencieris P, et al. Facile synthesis of coumarin bioisosteres – 1,2-benzoxathiine 2,2-dioxides. Tetrahedron 2012;68:5541–6. b) 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.
   Web of Science ®Google Scholar
• Tanc M, Carta F, Bozdag M, et al. 7-Substituted-sulfocoumarins are isoform-selective, potent carbonic anhydrase II inhibitors. Bioorg Med Chem 2013;21:4502–10.
   PubMed Web of Science ®Google Scholar
• a) Grandane A, Tanc M, Zalubovskis R, et al. Synthesis of 6-tetrazolyl-substituted sulfocoumarins acting as highly potent and selective inhibitors of the tumor-associated carbonic anhydrase isoforms IX and XII. Bioorg Med Chem 2014;22:1522–8. b) Grandane A, Tanc M, Zalubovskis R, et al. 6-Triazolyl-substituted sulfocoumarins are potent, selective inhibitors of the tumor-associated carbonic anhydrases IX and XII. Bioorg Med Chem Lett 2014;24:1256–60.
   PubMed Web of Science ®Google Scholar
• Grandane A, Tanc M, Di Cesare Mannelli L, et al. 6-Substituted sulfocoumarins are selective carbonic anhdydrase IX and XII Inhibitors with significant cytotoxicity against colorectal cancer cells. J Med Chem 2015;58:3975–83.
   PubMed Web of Science ®Google Scholar
• Grandane A, Tanc M, Žalubovskis R, et al. Synthesis of 6-aryl-substituted sulfocoumarins and investigation of their carbonic anhydrase inhibitory action. Bioorg Med Chem 2015;23:1430–6.
   PubMed Web of Science ®Google Scholar
• Nocentini A, Ceruso M, Carta F, et al. 7-Aryl-triazolyl-substituted sulfocoumarins are potent, selective inhibitors of the tumor-associated carbonic anhydrase IX and XII. J Enzyme Inhib Med Chem 2016;31:1226–33.
   PubMed Web of Science ®Google Scholar
• (a) Maresca A, Temperini C, Vu H, et al. Non-zinc mediated inhibition of carbonic anhydrases: coumarins are a new class of suicide inhibitors. J Am Chem Soc 2009;131:3057–62. b) Maresca A, Temperini C, Pochet L, et al. Deciphering the mechanism of carbonic anhydrase inhibition with coumarins and thiocoumarins. J Med Chem 2010;53:335–44. c) Maresca A, Supuran CT. Coumarins incorporating hydroxy- and chloro-moieties selectively inhibit the transmembrane, tumor-associated carbonic anhydrase isoforms IX and XII over the cytosolic ones I and II. Bioorg Med Chem Lett 2010;20:4511–14.
   PubMed Web of Science ®Google Scholar
• a) Maresca A, Scozzafava A, Supuran CT. 7,8-Disubstituted- but not 6,7-disubstituted coumarins selectively inhibit the transmembrane, tumor-associated carbonic anhydrase isoforms IX and XII over the cytosolic ones I and II in the low nanomolar/subnanomolar range. Bioorg Med Chem Lett 2010;20:7255–58. b) Touisni N, Maresca A, McDonald PC, et al. Glycosyl coumarin carbonic anhydrase IX and XII inhibitors strongly attenuate the growth of primary breast tumors. J Med Chem 2011;54:8271–7. c) Carta F, Maresca A, Scozzafava A, et al. Novel coumarins and 2-thioxo-coumarins as inhibitors of the tumor-associated carbonic anhydrases IX and XII. Bioorg Med Chem 2012;20:2266–73. d) Davis RA, Vullo D, Maresca A, et al. Natural product coumarins that inhibit human carbonic anhydrases. Bioorg Med Chem 2013;21:1539–43. e) Sharma A, Tiwari M, Supuran CT. Novel coumarins and benzocoumarins acting as isoform-selective inhibitors against the tumor-associated carbonic anhydrase IX. J Enzyme Inhib Med Chem 2014;29:292–6. f) Ferraroni M, Carta F, Scozzafava A, Supuran CT. Thioxocoumarins show an alternative carbonic anhydrase inhibition mechanism compared to coumarins. J Med Chem 2016;59:462–73.
   Web of Science ®Google Scholar
• a) Supuran CT. Carbonic anhydrases: novel therapeutic applications for inhibitors and activators. Nat Rev Drug Discov 2008;7:168–81. b) Neri D, Supuran CT. Interfering with pH regulation in tumours as a therapeutic strategy. Nat Rev Drug Discov 2011;10:767–77. c) Durdagi S, Vullo D, Pan P, et al. Protein-protein interactions: Inhibition of mammalian carbonic anhydrases I-XV by the murine inhibitor of carbonic anhydrase and other members of the transferrin family. J Med Chem 2012;55:5529–35. d) Di Cesare Mannelli L, Micheli L, Carta F, et al. Carbonic anhydrase inhibition for the management of cerebral ischemia: in vivo evaluation of sulfonamide and coumarin inhibitors. J Enzyme Inhib Med Chem 2016;31:894–9.
   PubMed Web of Science ®Google Scholar
• a) Supuran CT. Structure and function of carbonic anhydrases. Biochem J 2016;473:2023–32. b) Supuran CT. How many carbonic anhydrase inhibition mechanisms exist? J Enzyme Inhib Med Chem 2016;31:345–60. c) Supuran CT. Carbonic anhydrases. Bioorg Med Chem 2013;21:1377–8. d) Supuran CT. Advances in structure-based drug discovery of carbonic anhydrase inhibitors. Expert Opin Drug Discov 2017;12:61–88. e) 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;112:4421–68. f) Supuran CT. Legionella pneumophila carbonic anhydrases: underexplored antibacterial drug targets. Pathogens 2016;5:E44.
   PubMed Web of Science ®Google Scholar
• (a) De Simone G, Alterio V, Supuran CT. Exploiting the hydrophobic and hydrophilic binding sites for designing carbonic anhydrase inhibitors. Expert Opin Drug Discov 2013;8:793–810. (b) Masini E, Carta F, Scozzafava A, et al. Antiglaucoma carbonic anhydrase inhibitors: a patent review. Expert Opin Ther Pat 2013;23:705–16. (c) Supuran CT, Carbonic anhydrase inhibitors. Bioorg Med Chem Lett 2010;2:3467–74. (d) 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. e) D’Ambrosio K, Carradori S, Monti SM, et al. Out of the active site binding pocket for carbonic anhydrase inhibitors. Chem Commun 2015;51:302–5.
   PubMed Web of Science ®Google Scholar
• a) Supuran CT. Structure-based drug discovery of carbonic anhydrase inhibitors. J Enzyme Inhib Med Chem 2012;27:759–72. b) Supuran CT. Carbonic anhydrase inhibitors: an editorial. Expert Opin Ther Pat 2013;23:677–9. c) Winum JY, Supuran CT. Recent advances in the discovery of zinc-binding motifs for the development of carbonic anhydrase inhibitors. J Enzyme Inhib Med Chem 2015;30:321–4. d) De Luca V, Del Prete S, Supuran CT, et al. Protonography, a new technique for the analysis of carbonic anhydrase activity. J Enzyme Inhib Med Chem 2015;30:277–82. e) Lomelino CL, Supuran CT, McKenna R, Non-classical inhibition of carbonic anhydrase. Int J Mol Sci 2016;1:E1150.
   PubMed Web of Science ®Google Scholar
• a) Supuran CT. Acetazolamide for the treatment of idiopathic intracranial hypertension. Expert Rev Neurother 2015;15:851–6. b) Di Fiore A, De Simone G, Alterio V, et al. The anticonvulsant sulfamide JNJ-26990990 and its: S,S-dioxide analog strongly inhibit carbonic anhydrases: solution and X-ray crystallographic studies. Org Biomol Chem 2016;14:4853–8. c) Supuran CT. Drug interaction considerations in the therapeutic use of carbonic anhydrase inhibitors. Expert Opin Drug Metab Toxicol 2016;12:423–31.
   PubMed Web of Science ®Google Scholar
• Albert S, Horbach R, Deising HB, et al. Synthesis and antimicrobial activity of (E) stilbene derivatives. Bioorg Med Chem 2011;19:5155–66.
   PubMed Web of Science ®Google Scholar
• Dauban P, Dodd RH. Synthesis of cyclic sulfonamides via intramolecular copper-catalyzed reaction of unsaturated iminoiodinanes. Org Lett 2000;2:2327–9.
   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
• Leitans J, Sprudza A, Tanc M, et al. 5-Substituted-(1,2,3-triazol-4-yl)thiophene-2-sulfonamides strongly inhibit human carbonic anhydrases I, II, IX and XII: solution and X-ray crystallographic studies. Bioorg Med Chem 2013;21:5130–8.
   PubMed Web of Science ®Google Scholar
• a) Korkmaz N, Obaidi OA, Senturk M, et al. Synthesis and biological activity of novel thiourea derivatives as carbonic anhydrase inhibitors. J Enzyme Inhib Med Chem 2015;30:75–80. b) Abdel-Aziz AAM, El-Azab AS, Ekinci D, et al. Investigation of arenesulfonyl-2-imidazolidinones as potent carbonic anhydrase inhibitors. J Enzyme Inhib Med Chem 2015;30:81–4. c) Akdemir A, De Monte C, Carradori S, et al. Computational investigation of the selectivity of salen and tetrahydrosalen compounds towards the tumor-associated hCA XII isozyme. J Enzyme Inhib Med Chem 2015;3:114–18. d) 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. e) Göçer H, Akincioğlu AS, Gülçin GI, et al. Carbonic anhydrase and acetylcholinesterase inhibitory effects of carbamates and sulfamoylcarbamates. J Enzyme Inhib Med Chem 2015;30:316–20. f) Ceruso M, Bragagni M, AlOthman Z, et al. New series of sulfonamides containing amino acid moiety act as effective and selective inhibitors of tumor-associated carbonic anhydrase XII. J Enzyme Inhib Med Chem 2015;3:430–4. g) Zolfaghari Emameh R, Syrjänen L, Barker H, et al. Drosophila melanogaster: a model organism for controlling dipteran vectors and pests. J Enzyme Inhib Med Chem 2015;30:505–13.
   PubMed Web of Science ®Google Scholar
• Otwinowski Z, Minor W. Processing of X-ray diffraction data collected in oscillation mode. Methods Enzymol 1997;276:307–26.
   PubMed Web of Science ®Google Scholar
• Burla MC, Caliandro R, Camalli M, et al. SIR2004: an improved tool for crystal structure determination and refinement. J Appl Crystallogr 2005;38:381–8.
   Web of Science ®Google Scholar
• Sheldrick GM. A short history of SHELX. Acta Crystallogr 2008;64:112–22.
   PubMed Web of Science ®Google Scholar
• Farrugia LJ. WinGX and ORTEP for windows: an update. J Appl Crystallogr 2012;45:849–54.
   Web of Science ®Google Scholar
• a) Gieling RG, Babur M, Mamnani L, et al. Antimetastatic effect of sulfamate carbonic anhydrase IX inhibitors in breast carcinoma xenografts. J Med Chem 2012;55:5591–600. b) Winum JY, Maresca A, Carta F, et al. Polypharmacology of sulfonamides: pazopanib, a multitargeted receptor tyrosine kinase inhibitor in clinical use, potently inhibits several mammalian carbonic anhydrases. Chem Commun 2012;48:8177–9. c) Lock EF, McDonald PC, Lou Y, et al. Targeting carbonic anhydrase IX depletes breast cancer stem cells within the hypoxic niche. Oncogene 2013;32:5210–19. d) Ward C, Langdon SP, Mullen P, et al. New strategies for targeting the hypoxic tumour microenvironment in breast cancer. Cancer Treat Rev 2013;39:171–9.
   PubMed Web of Science ®Google Scholar
• a) Pan J, Lau J, Mesak F, et al. Synthesis and evaluation of 18F-labeled carbonic anhydrase IX inhibitors for imaging with positron emission tomography. J Enzyme Inhib Med Chem 2014;29:249–55. b) Pettersen EO, Ebbesen P, Gieling RG, et al. Targeting tumour hypoxia to prevent cancer metastasis. From biology, biosensing and technology to drug development: The METOXIA consortium. J Enzyme Inhib Med Chem 2015;30:689–721.
   PubMed Web of Science ®Google Scholar