1,508
Views
39
CrossRef citations to date
0
Altmetric
Research Paper

Synthesis and biological evaluation of benzenesulphonamide-bearing 1,4,5-trisubstituted-1,2,3-triazoles possessing human carbonic anhydrase I, II, IV, and IX inhibitory activity

, , , &
Pages 1187-1194 | Received 19 Jul 2017, Accepted 11 Aug 2017, Published online: 11 Sep 2017

References

  • Supuran CT. Carbonic anhydrases: novel therapeutic applications for inhibitors and activators. Nat Rev Drug Discov 2008;7:168–81.
  • 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.
  • Prete SD, 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.
  • Supuran CT. How many carbonic anhydrase inhibition mechanisms exist? J Enzyme Inhib Med Chem 2016;31:345–60.
  • Supuran CT. Structure-based drug discovery of carbonic anhydrase inhibitors. J Enzyme Inhib Med Chem 2012; 27:759–72.
  • Kikutani S, Nakajima K, Nagasato C, et al. Thylakoid luminal θ-carbonic anhydrase critical for growth and photosynthesis in the marine diatom Phaeodactylum tricornutum. Proc Natl Acad Sci 2016; 113:9828–33.
  • 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.
  • Capasso C, Supuran CT. Sulfa and trimethoprim-like drugs–antimetabolites acting as carbonic anhydrase, dihydropteroate synthase and dihydrofolate reductase inhibitors. J Enzyme Inhib Med Chem 2014; 29:379–87.
  • Bozdag M, Carta F, Vullo D, et al. Synthesis of a new series of dithiocarbamates with effective human carbonic anhydrase inhibitory activity and antiglaucoma action. Bioorg Med Chem 2015;23:2368–76.
  • 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.
  • Arechederra RL, Waheed A, Sly WS, et al. Effect of sulfonamides as carbonic anhydrase VA and VB inhibitors on mitochondrial metabolic energy conversion. Bioorg Med Chem 2013;21:1544–8.
  • Svastova E, Hulikova A, Rafajova M, et al. Hypoxia activates the capacity of tumor‐associated carbonic anhydrase IX to acidify extracellular pH. FEBS Lett 2004;577:439–45.
  • Gawad NMA, Amin NH, Elsaadi MT, et al. Synthesis of 4-(thiazol-2-ylamino)-benzenesulfonamides with carbonic anhydrase I, II and IX inhibitory activity and cytotoxic effects against breast cancer cell lines. Bioorg Med Chem 2016;24:3043–51.
  • Wykoff CC, Beasley NJ, Watson PH, et al. Hypoxia-inducible expression of tumor-associated carbonic anhydrases. Cancer Res 2000;60:7075–83.
  • Guler OO, De Simone G, Supuran CT. Drug design studies of the novel antitumor targets carbonic anhydrase IX and XII. Curr Med Chem 2010;17:1516–26.
  • Masini E, Carta F, Scozzafava A, Supuran CT. Antiglaucoma carbonic anhydrase inhibitors: a patent review. Expert Opin Ther Patents 2013;23:705–16.
  • Scozzafava A, Supuran CT, Carta F. Antiobesity carbonic anhydrase inhibitors: a literature and patent review. Expert Opin Ther Patents 2013;23:725–35.
  • Yaseen R, Ekinci D, Senturk M, et al. Pyridazinone substituted benzenesulfonamides as potent carbonic anhydrase inhibitors. Bioorg Med Chem Lett 2016;26:1337–41.
  • Maresca A, Vullo D, Scozzafava A, et al. Inhibition of the β-class carbonic anhydrases from Mycobacterium tuberculosis with carboxylic acids. J Enzyme Inhib Med Chem 2013;28:392–406.
  • Monti SM, Supuran CT, Simone GD. Anticancer carbonic anhydrase inhibitors: a patent review (2008–2013). Expert Opin Ther Patents 2013;23:737–49.
  • Pastorekova S, Parkkila S, Pastorek J, Supuran CT. Carbonic anhydrases: current state of the art, therapeutic applications and future prospects. J Enzyme Inhib Med Chem 2004;19:199–229.
  • Ram S, Celik G, Khloya P, et al. Benzenesulfonamide bearing 1, 2, 4-triazole scaffolds as potent inhibitors of tumor associated carbonic anhydrase isoforms hCA IX and hCA XII. Bioorg Med Chem 2014;22:1873–82.
  • Ram S, Ceruso M, Khloya P, et al. 4-Functionalized 1, 3-diarylpyrazoles bearing 6-aminosulfonylbenzothiazole moiety as potent inhibitors of carbonic anhydrase isoforms hCA I, II, IX and XII. Bioorg Med Chem 2014;22:6945–52.
  • Kumar R, Bua S, Ram S, et al. Benzenesulfonamide bearing imidazothiadiazole and thiazolotriazole scaffolds as potent tumor associated human carbonic anhydrase IX and XII inhibitors. Bioorg Med Chem 2017; 25:1286–93.
  • Zhang SY, Fu DJ, Yue XX, et al. Design, Synthesis and structure-activity relationships of novel chalcone-1, 2, 3-triazole-azole derivates as antiproliferative agents. Molecules 2016;21:653.
  • Gill C, Jadhav G, Shaikh M, Kale R. Clubbed [1, 2, 3] triazoles by fluorine benzimidazole: a novel approach to H37Rv inhibitors as a potential treatment for tuberculosis. Bioorg Med Chem Lett 2008;18:6244–7.
  • Holla BS, Mahalinga M, Karthikeyen MS, et al. Synthesis, characterization and antimicrobial activity of some substituted 1,2,3-triazoles. Eur J Med Chem 2005;40:1173–8.
  • Ebner DC, Culhane JC, Winkelman TN, et al. Synthesis of novel oxazolidinone antimicrobial agents. Bioorg Med Chem 2008;16:2651–6.
  • Pagliai F, Pirali T, Grosso ED, et al. Rapid synthesis of triazole-modified resveratrol analogues via click chemistry. J Med Chem 2006;49:467–70.
  • Khazir J, Hyder I, Gayatri JL, et al. Design and synthesis of novel 1,2,3-triazole derivatives of coronopilin as anti-cancer compounds. Eur J Med Chem 2014;82:255–62.
  • Olomola TO, Klein R, Lobb KA, et al. Towards the synthesis of coumarin derivatives as potential dual-action HIV-1 protease and reverse transcriptase inhibitors. Tetrahedron Lett 2010;51:6325–8.
  • Sangshetti JN, Nagawade RR, Shinde DB. Synthesis of novel 3-(1-(1-substituted piperidin-4-yl)-1H-1, 2, 3-triazol-4-yl)-1, 2, 4-oxadiazol-5 (4H)-one as antifungal agents. Bioorg Med Chem Lett 2009;19:3564–7.
  • Wuest F, Tang X, Kniess T, et al. Synthesis and cyclooxygenase inhibition of various (aryl-1, 2, 3-triazole-1-yl)-methanesulfonylphenyl derivatives. Bioorg Med Chem 2009;17:1146–51.
  • Poulsen SA, Wilkinson BL, Innocenti A. Inhibition of human mitochondrial carbonic anhydrases VA and VB with para-(4-phenyltriazole-1-yl)-benzenesulfonamide derivatives. Bioorg Med Chem Lett 2008;18:4624–7.
  • Jordao AK, Afonso PP, Ferreira VF, et al. Antiviral evaluation of N-amino-1,2,3-triazoles against Cantagalo virus replication in cell culture. Eur J Med Chem 2009;44:3777–83.
  • Lin H, Walsh CT. A chemoenzymatic approach to glycopeptide antibiotics. J Am Chem Soc 2004;126:13998–4003.
  • Casas-Solvas JM, Vargas-Berenguel A, CapitànVallvey LF, Santovo-Gonzalez F. Convenient methods for the synthesis of ferrocene − carbohydrate conjugates. Org Lett 2004;6:3687–90.
  • Bennett I, Broom NJP, Bruton G, et al. 6-(Substituted methylene) penems, potent broad spectrum inhibitors of bacterial β-lactamase. J Antibiot 1991;44:331–7.
  • 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.
  • Nocentini A, Carta F, Ceruso M, et al. Click-tailed coumarins with potent and selective inhibitory action against the tumor-associated carbonic anhydrases IX and XII. Bioorg Med Chem 2015;23:6955–66.
  • Kumar P, Chandak N, Kaushik P, et al. Synthesis and biological evaluation of some pyrazole derivatives as anti-inflammatory–antibacterial agents. Med Chem Res 2012;21:3396–405.
  • Kumar S, Namkung W, Verkman AS, Sharma PK. Novel 5-substituted benzyloxy-2-arylbenzofuran-3-carboxylic acids as calcium activated chloride channel inhibitors. Bioorg Med Chem 2012;20:4237–44.
  • Khloya P, Celik G, Ram S, et al. 4-Functionalized 1, 3-diarylpyrazoles bearing benzenesulfonamide moiety as selective potent inhibitors of the tumor associated carbonic anhydrase isoforms IX and XII. Eur J Med Chem 2014;76:284–90.
  • Khloya P, Ceruso M, Ram S, et al. Sulfonamide bearing pyrazolylpyrazolines as potent inhibitors of carbonic anhydrase isoforms I, II, IX and XII. Bioorg Med Chem Lett 2015;25:3208–12.
  • Kumar S, Ceruso M, Tuccinardi T, et al. Pyrazolylbenzo[d]imidazoles as new potent and selective inhibitors of carbonic anhydrase isoforms hCA IX and XII. Bioorg Med Chem 2016;24:2907–13.
  • Chandak N, Ceruso M, Supuran CT, Sharma PK. Novel sulfonamide bearing coumarin scaffolds as selective inhibitors of tumor associated carbonic anhydrase isoforms IX and XII. Bioorg Med Chem 2016;24:2882–6.
  • Morimoto Y, Matsuda F, Shirahama H. Synthetic studies on virantmycin. 1. Total synthesis of (±)-virantmycin and determination of its relative stereochemistry. Tetrahedron 1996;52:10609–30.
  • Rogez-Florent T, Meignan S, Foulon C, et al. New selective carbonic anhydrase IX inhibitors: synthesis and pharmacological evaluation of diarylpyrazole-benzenesulfonamides. Bioorg Med Chem 2013;21:1451–64.
  • Khalifah RJ. The carbon dioxide hydration activity of carbonic anhydrase I. Stop-flow kinetic studies on the native human isoenzymes B and C. J Bio Chem 1971;246:2561–73.
  • Ferraroni M, Tilli S, Briganti F, et al. Crystal structure of a zinc-activated variant of human carbonic anhydrase I, CA I Michigan 1: evidence for a second zinc binding site involving arginine coordination. Biochemistry 2002;41:6237–44.