Multicomponent chemistry in the synthesis of carbonic anhydrase inhibitors

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
• 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
   PubMed Web of Science ®Google Scholar
• Thiry A, Dogné JM, Masereel B, Supuran CT. Targeting tumor-associated carbonic anhydrase IX in cancer therapy. Trends Pharmacol Sci 2006;27:566–73
   PubMed Web of Science ®Google Scholar
• Vullo D, Innocenti A, Nishimori I, et al. Carbonic anhydrase inhibitors. Inhibition of the transmembrane isozyme XII with sulfonamides – a new target for the design of antitumor and antiglaucoma drugs? Bioorg Med Chem Lett 2005;15:963–9
   PubMed 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
• Supuran CT, Scozzafava A, Casini A. Carbonic anhydrase inhibitors. Med Res Rev 2003;23:146–89
   PubMed Web of Science ®Google Scholar
• Boehm HJ, Flohr A, Stahl M. Scaffold hopping. Drug Discov Today Technol 2004;1:217–24
   PubMedGoogle Scholar
• Supuran CT. Structure-based drug discovery of carbonic anhydrase Inhibitors. J Enzyme Inhib Med Chem 2012;27:759–72
   PubMed Web of Science ®Google Scholar
• Maresca A, Scozzafava A, Supuran CT. 7,8-Di substituted- 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;20:7255–8
   PubMed Web of Science ®Google Scholar
• Nair SK, Ludwig PA, Christianson DW. Two-site binding of phenol in the active site of human carbonic anhydrase II: structural implications for substrate association. J Am Chem Soc 1994;116:3659–60
   Web of Science ®Google Scholar
• Carta F, Temperini C, Innocenti A, et al. Polyamines inhibit carbonic anhydrases by anchoring to the zinc-coordinated water molecule. J Med Chem 2010;53:5511–22
   PubMed Web of Science ®Google Scholar
• Doemling A. Recent developments in isocyanide based multicomponent reactions in applied chemistry. Chem Rev 2006;106:17–89
   PubMed Web of Science ®Google Scholar
• Biggs-Houck JE, Younai A, Shaw JT. Recent advances in multicomponent reactions for diversity-oriented synthesis. Curr Opin Chem Biol 2010;14:371–82
   PubMed Web of Science ®Google Scholar
• Gore RP, Rajput AP. A review on recent progress in multicomponent reactions of pyrimidine synthesis. Drug Invent Today 2013;5:148–52
   Google Scholar
• Allouche F, Chabchoub F, Carta F, Supuran CT. Synthesis of aminocyanopyrazoles via a multi-component reaction and anti-carbonic anhydrase inhibitory activity of their sulfamide derivatives against cytosolic and transmembrane isoforms. J Enzyme Inhib Med Chem 2013;28:343–9
   PubMed Web of Science ®Google Scholar
• Alp C, Maresca A, Alp NA, et al. Secondary/tertiary benzenesulfonamides with inhibitory action against the cytosolic human carbonic anhydrase isoforms I and II. J Enzyme Inhib Med Chem 2012;28:294–8
   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
• Demirci T, Arslan M, Bilen Ç, et al. Synthesis and carbonic anhydrase inhibitory properties of 1,3-dicarbonyl derivatives of methylaminobenzene-sulfonamide. J Enzyme Inhib Med Chem 2014;29:132–6
   PubMed Web of Science ®Google Scholar
• al-Rashida M, Ashraf M, Hussain M, et al. Discovery of new chromone containing sulfonamides as potent inhibitors of bovine cytosolic carbonic anhydrase. Eur J Med Chem 2015;19:3367–71
   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
• Celik F, Arslan M, Yavuz E, et al. Synthesis and carbonic anhydrase inhibitory properties of novel 1,4-dihydropyrimidinone substituted diarylureas. J Enzyme Inhib Med Chem 2014;29:18–22
   PubMed Web of Science ®Google Scholar
• Celik F, Arslan M, Kaya MO, et al. Synthesis and carbonic anhydrase inhibitory properties of tetrazole- and oxadiazole substituted 1,4-dihydropyrimidinone compounds. Artif Cells Nanomed Biotechnol 2014;42:58–62
   PubMed Web of Science ®Google Scholar
• Berber N, Arslan M, Yavuz E, et al. Synthesis and evaluation of new phthalazine urea and thiourea derivatives as carbonic anhydrase inhibitors. J Chem 2013;2013:742178
   Web of Science ®Google Scholar
• Berber N, Arslan M, Yavuz E, et al. Synthesis and evaluation of new phthalazine substituted β-lactam derivatives as carbonic anhydrase inhibitors. Russ J Bioorg Chem 2015;41:414–20
   Web of Science ®Google Scholar
• 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
   PubMed Web of Science ®Google Scholar
• Koike T, Takamura M, Kimura E. Role of Zn(II) in β-lactamase II: a model study with a Zn(II)-cyclen complex. J Am Chem Soc 1994;116:8443–9
   Web of Science ®Google Scholar
• Suthar SK, Bansal S, Lohan S, et al. Design and synthesis of novel 4-(4-oxo-2-arylthiazolidin-3-yl)benzenesulfonamides as selective inhibitors of carbonic anhydrase IX over I and II with potential anticancer activity. Eur J Med Chem 2013;66:372–9
   PubMed Web of Science ®Google Scholar
• Kaya M, Basar E, Çakir E, et al. Synthesis and characterization of novel dioxoacridine sulfonamide derivatives as new carbonic anhydrase inhibitors. J Enzyme Inhib Med Chem 2012;27:509–14
   PubMed Web of Science ®Google Scholar
• Yeşildağ I, Ulus R, Başar E, et al. Facile, highly efficient, and clean one-pot synthesis of acridine sulfonamide derivatives at room temperature and their inhibition of human carbonic anhydrase isoenzymes. Monatsh Für Chemie 2014;145:1027–34
   Web of Science ®Google Scholar
• Esirden I, Ulus R, Aday B, et al. Synthesis of novel acridine bis-sulfonamides with effective inhibitory activity against the carbonic anhydrase isoforms I, II, IX and XII. Bioorg Med Chem 2015;23:6573–80
   PubMed Web of Science ®Google Scholar
• Ulus R, Yeşildağ I, Tanc M, et al. Synthesis of novel acridine and bis acridine sulfonamides with effective inhibitory activity against the cytosolic carbonic anhydrase isoforms II and VII. Bioorg Med Chem 2013;21:5799–05
   PubMed Web of Science ®Google Scholar
• Scozzafava A, Menabuoni L, Mincione F, Supuran CT. Carbonic anhydrase inhibitors. A general approach for the preparation of water-soluble sulfonamides incorporating polyaminopolycarboxylate tails and of their metal complexes possessing long-lasting, topical intraocular pressure-lowering properties. J Med Chem 2002;45:1466–76
   PubMed Web of Science ®Google Scholar
• Subudhi BB, Panda PK, Swain SP, Sarangi P. Synthesis, characterization and anticonvulsant activity evaluation of some 1,4-dihydropyridines and 3,5-(substituted)oxycarbonyl-1,4-dihydro-2,6-dimethyl-N-[2-(4-sulfamoylphenylamino)-acetyl]-4-(substituted)pyridines. Acta Pol Pharm Drug Res 2009;66:147–53
   PubMed Web of Science ®Google Scholar
• Ghorab MM, Ragab FA, Hamed MM. Design, synthesis and anticancer evaluation of novel tetrahydroquinoline derivatives containing sulfonamide moiety. Eur J Med Chem 2009;4;4211–17
   Google Scholar
• Ghorab MM, Ragab FA, Heiba HI, et al. In vitro anticancer screening and radiosensitizing evaluation of some newquinolines and pyrimido[4,5-b]quinolines bearing a sulfonamide moiety. Eur J Med Chem 2010;45:3677–84
   PubMed Web of Science ®Google Scholar
• Hoelder S, Clarke PA, Workman P. Discovery of small molecule cancer drugs: successes, challenges and opportunities. Mol Oncol 2012;6:155–76
   PubMed Web of Science ®Google Scholar
• Al-Said MS, Ghorab MM, Al-Dosari MS, Hamed MM. Synthesis and in vitro anticancer evaluation of some novel hexahydroquinoline derivatives having a benzenesulfonamide moiety. Eur J Med Chem 2011;46:201–7
   PubMed Web of Science ®Google Scholar
• Hartman GD, Halczenko W, Smith RL, et al. 4-Substituted thiophene- and furan-2-sulfonamides as topical carbonic anhydrase inhibitors. J Med Chem 1992;35:3822–31
   PubMed Web of Science ®Google Scholar
• Ozgun DO, Yamali C, Gul HI, et al. Inhibitory effects of isatin Mannich bases on carbonic anhydrases, acetylcholinesterase, and butyrylcholinesterase. J Enzyme Inhib Med Chem 2016. [Epub ahead of print]. doi: 10.3109/14756366.2016.1149479
   PubMed Web of Science ®Google Scholar
• Büyükkidan N, Büyükkıdan B, Bülbül M, et al. Synthesis and characterization of phenolic Mannich bases and effects of these compounds on human carbonic anhydrase isozymes I and II. J Enzyme Inhib Med Chem 2013;28:337–42
   PubMed Web of Science ®Google Scholar
• Chow K, Lai R, Holmes JM, et al. 5-Substituted 3-thiophenesulfonamides as carbonic anhydrase inhibitors. Eur J Med Chem 1996;31:175–86
   Web of Science ®Google Scholar
• Yamali C, Tugrak M, Gul HI, et al. The inhibitory effects of phenolic Mannich bases on carbonic anhydrase I and II isoenzymes. J Enzyme Inhib Med Chem 2016. [Epub ahead of print]. doi: 10.3109/14756366.2015.1126715
   Web of Science ®Google Scholar
• Gul HI, Yamali C, Asiye TY, et al. Carbonic anhydrase inhibition and cytotoxicity studies of Mannich base derivatives of thymol. J Enzyme Inhib Med Chem 2016. [Epub ahead of print]. doi: 10.3109/14756366.2016.1140755
   Web of Science ®Google Scholar
• Ivachtchenko AV, Ivanenkov YA, Kysil VM, et al. Multicomponent reactions of isocyanides in the synthesis of heterocycles. Russ Chem Rev 2010;79:787–817
   Web of Science ®Google Scholar
• Krasavin M, Dar'in D. Current diversity of cyclic anhydrides for the Castagnoli-Cushman-type formal cycloaddition reactions: prospects and challenges. Tetrahedron Lett 2016;57:1635–40
   Web of Science ®Google Scholar