1,290
Views
22
CrossRef citations to date
0
Altmetric
Research Article

Design, synthesis and biological evaluation of N-(5-methyl-isoxazol-3-yl/1,3,4-thiadiazol-2-yl)-4-(3-substitutedphenylureido) benzenesulfonamides as human carbonic anhydrase isoenzymes I, II, VII and XII inhibitors

, , , , , , & show all
Pages 174-179 | Received 16 May 2016, Accepted 31 May 2016, Published online: 17 Jun 2016

References

  • Supuran CT. Carbonic anhydrases: novel therapeutic applications for inhibitors and activators. Nat Rev Drug Discov 2008;7:168–81
  • Del Pretea S, Vullo D, Fisher GM, et al. Discovery of a new family of carbonic anhydrases in the malaria pathogen Plasmodium falciparum-the η-carbonic anhydrases. Bioorg Med Chem Lett 2014;24:4389–96
  • Ceruso M, Antel S, Vullo D, et al. Inhibition studies of new ureido-substituted sulfonamides incorporating a GABA moiety against human carbonic anhydrase isoforms I-XIV. Bioorg Med Chem Lett 2014;22:6768–75
  • Supuran CT. Structure-based drug discovery of carbonic anhydrase inhibitors. J Enzyme Inhib Med Chem 2012;27:759–7
  • 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;8:4421–68
  • Supuran CT, Scozzafava A. Carbonic anhydrases as targets for medicinal chemistry. Bioorg Med Chem 2007;15:4336–50
  • Supuran CT. How many carbonic anhydrase inhibition mechanisms exist? J Enzyme Inhib Med Chem 2016;31:345–60
  • Neri D, Supuran CT. Interfering with pH regulation in tumours as a therapeutic strategy. Nat Rev Drug Discov 2011;10:767–77
  • Carta F, Supuran CT, Scozzafava A. Sulfonamides and their isosters as carbonic anhydrase inhibitors. Future Med Chem 2014;6:1149–65
  • Shah GN, Bonapace G, Hu PY, et al. Carbonic anhydrase II deficiency syndrome (osteopetrosis with renal tubular acidosis and brain calcification): novel mutations in CA2 identified by direct sequencing expand the opportunity for genotype-phenotype correlation. Hum Mutat 2004;3:1–9
  • Thiry A, Masereel B, Dogne JM, et al. Exploration of the binding mode of indanesulfonamides as selective inhibitors of human carbonic anhydrase type VII by targeting Lys 91. ChemMedChem 2007;2:1273–80
  • Supuran CT. Carbonic anhydrases: from biomedical applications of the inhibitors and activators to biotechnological use for CO(2) capture. J Enzyme Inhib Med Chem 2013;28:229–30
  • Supuran CT. Acetazolamide for the treatment of idiopathic intracranial hypertension. Expert Rev Neurother 2015;15:851–6
  • Supuran CT, Scozzafava A, Casini A. Carbonic anhydrase inhibitors. Med Res Rev 2003;2:146–89
  • Supuran CT, Winum JY. Designing carbonic anhydrase inhibitors for the treatment of breast cancer. Expert Opin Drug Discov 2015;10:591–7
  • 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
  • Bonneau A, Maresca A, Winum JY, et al. Metronidazole-coumarin conjugates and 3-cyano-7-hydroxy-coumarin act as isoform-selective carbonic anhydrase inhibitors. J Enzyme Inhib Med Chem 2013;28:397–401
  • 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
  • Innocenti A, Casini A, Alcaro MC, et al. Carbonic anhydrase inhibitors: the first on-resin screening of a 4-sulfamoylphenylthiourea library. J Med Chem 2004;47:5224–9
  • Casini A, Scozzafava A, Mincione F, et al. Carbonic anhydrase inhibitors: water-soluble 4-sulfamoylphenylthioureas as topical intraocular pressure-lowering agents with long-lasting effects. J Med Chem 2000;43:4884–92
  • Mincione F, Starnotti M, Masini E, et al. Carbonic anhydrase inhibitors: design of thioureido sulfonamides with potent isozyme II and XII inhibitory properties and intraocular pressure lowering activity in a rabbit model of glaucoma. Bioorg Med ChemLett 2005;15:3821–7
  • Supuran CT, Scozzafava A, Bogdan C, et al. Carbonic anhydrase inhibitors – Part 49: Synthesis of substituted ureido and thioureido derivatives of aromatic/heterocyclic sulfonamides with increased affinities for isozyme I. Eur J Med Chem 1998;33:83–93
  • Avvaru BS, Wagner JM, Maresca A, et al. Carbonic anhydrase inhibitors. The X-ray crystal structure of human isoform II in adduct with an adamantyl analogue of acetazolamide resides in a less utilized binding pocket than most hydrophobic inhibitors. Bioorg Med ChemLett 2010;20:4376–81
  • Wagner J, Avvaru BS, Robbins AH, et al. Coumarinyl-substituted sulfonamides strongly inhibit several human carbonic anhydrase isoforms: solution and crystallographic investigations. Bioorg Med Chem 2010;18:4873–8
  • Carta F, Garaj V, Maresca A, et al. Sulfonamides incorporating 1,3,5-triazine moieties selectively and potently inhibit carbonic anhydrase transmembrane isoforms IX, XII and XIV over cytosolic isoforms I and II: Solution and X-ray crystallographic studies. Bioorg Med Chem 2011;19:3105–19
  • Hen N, Bialer M, Yagen B, et al. Anticonvulsant 4-aminobenzenesulfonamide derivatives with branched-alkylamide moieties: X-ray crystallography and inhibition studies of human carbonic anhydrase isoforms I, II, VII, and XIV. J Med Chem 2011;54:3977–81
  • Biswas S, Carta F, Scozzafava A, et al. Structural effect of phenyl ring compared to thiadiazole based adamantyl-sulfonamides on carbonic anhydrase inhibition. Bioorg Med Chem 2013;21:2314–18
  • Di Fiore A, De Simone G, Menchise V, et al. Carbonic anhydrase inhibitors: X-ray crystal structure of a benzenesulfonamide strong CA II and CA IX inhibitor bearing a pentafluorophenylaminothioureido tail in complex with isozyme II. Bioorg Med Chem Lett 2005;15:1937–42
  • Vitale RM, Alterio V, Innocenti A, et al. Carbonic anhydrase inhibitors. Comparison of aliphatic sulfamate/bis-sulfamate adducts with isozymes II and IX as a platform for designing tight-binding, more isoform-selective inhibitors. J Med Chem 2009;52:5990–8
  • Temperini C, Cecchi A, Boyle NA, 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
  • De Simone G, Di Fiore A, Menchise V, et al. Carbonic anhydrase inhibitors. Zonisamide is an effective inhibitor of the cytosolic isozyme II and mitochondrial isozyme V: solution and X-ray crystallographic studies. Bioorg Med Chem Lett 2005;15:2315–20
  • Truppo E, Supuran CT, Sandomenico A, et al. Carbonic anhydrase VII is S-glutathionylated without loss of catalytic activity and affinity for sulfonamide inhibitors. Bioorg Med Chem Lett. 2012;22:1560–4
  • Lou Y, McDonald PC, Oloumi A, et al. Targeting tumor hypoxia: suppression of breast tumor growth and metastasis by novel carbonic anhydrase IX inhibitors. Cancer Res 2011;71:3364–76
  • Pacchiano F, Carta F, McDonald PC, et al. Ureido-substituted benzenesulfonamides potently inhibit carbonic anhydrase IX and show antimetastatic activity in a model of breast cancer metastasis. J Med Chem 2011;54:1896–902
  • Scozzafava A, Carta F, Supuran CT. Secondary and tertiary sulfonamides: a patent review (2008 - 2012). Expert Opin Ther Pat 2013;23:203–13
  • Alp C, Ozsoy S, Alp NA, et al. Sulfapyridine-like benzenesulfonamide derivatives as inhibitors of carbonic anhydrase isoenzymes I, II and VI. J Enzyme Inhib Med Chem 2012;27:818–24
  • Ekinci D, Fidan I, Durdagi S, et al. Kinetic and in silico analysis of thiazolidin-based inhibitors of α-carbonic anhydrase isoenzymes. J Enzyme Inhib Med Chem 2013;28:370–4
  • Abdel-Aziz AA, 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
  • Arslan M, Şentürk M, Fidan I, et al. Synthesis of 3,4-dihydroxypyrrolidine-2,5-dione and 3,5-dihydroxybenzoic acid derivatives and evaluation of the carbonic anhydrase I and II inhibition. J Enzyme Inhib Med Chem 2015;30:896–900
  • Liu F, Martin-Mingot A, Lecornué F, et al. Carbonic Anhydrases inhibitory effects of new benzenesulfonamides synthesized by using superacid chemistry. J Enzyme Inhib Med Chem 2012;27:886–91
  • Compain G, Martin-Mingot A, Maresca A, et al. Superacid synthesis of halogen containing N-substituted-4-aminobenzene sulfonamides: new selective tumor-associated carbonic anhydrase inhibitors. Bioorg Med Chem 2013;21:1555–63
  • Métayer B, Mingot A, Vullo D, et al. New superacid synthesized (fluorinated) tertiary benzenesulfonamides acting as selective hCA IX inhibitors: toward a new mode of carbonic anhydrases inhibition by sulfonamides. Chem Commun 2013;49:6015–17
  • Le Darz A, Mingot A, Bouazza F, et al. Fluorinated pyrrolidines and piperidines containing tertiary benzenesulfonamides: selective carbonic anhydrase II inhibitors. J Enzyme Inhib Med Chem 2015;30:737–45
  • 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
  • De Monte C, Carradori S, Secci D, et al. Cyclic tertiary sulfamates: selective inhibition of the tumor-associated carbonic anhydrases IX and XII by N- and O-substituted acesulfame derivatives. Eur J Med Chem 2014;84:240–6
  • D'Ascenzio M, Carradori S, Secci D, et al. Selective inhibition of human carbonic anhydrases by novel amide derivatives of probenecid: synthesis, biological evaluation and molecular modelling studies. Bioorg Med Chem 2014;22:3982–8
  • Carradori S, Mollica A, Ceruso M, et al. New amide derivatives of Probenecid as selective inhibitors of carbonic anhydrase IX and XII: biological evaluation and molecular modelling studies. Bioorg Med Chem 2015;23:2975–81
  • Mollica A, Costante R, Akdemir A, et al. Exploring new Probenecid-based carbonic anhydrase inhibitors: synthesis, biological evaluation and docking studies. Bioorg Med Chem 2015;23:5311–18
  • Gavernet L, Gonzalez Funes JL, Palestro PH, et al. Inhibition pattern of sulfamide-related compounds in binding to carbonic anhydrase isoforms I, II, VII, XII and XIV. Bioorg Med Chem 2013;21:1410–18

Reprints and Corporate Permissions

Please note: Selecting permissions does not provide access to the full text of the article, please see our help page How do I view content?

To request a reprint or corporate permissions for this article, please click on the relevant link below:

Academic Permissions

Please note: Selecting permissions does not provide access to the full text of the article, please see our help page How do I view content?

Obtain permissions instantly via Rightslink by clicking on the button below:

If you are unable to obtain permissions via Rightslink, please complete and submit this Permissions form. For more information, please visit our Permissions help page.