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Archives of Physiology and Biochemistry
The Journal of Metabolic Diseases
Volume 123, 2017 - Issue 5
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Original Article

Synthesis and carbonic anhydrase inhibitory properties of new spiroindoline-substituted sulphonamide compounds

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Pages 306-312 | Received 14 Apr 2017, Accepted 16 May 2017, Published online: 31 May 2017

References

  • Allam, Y.A. and Nawwar, G.A., 2002. Facile synthesis of 3-spiroindolines. Heteroatom Chemistry, 13 (3), 207–210.
  • Arslan, O., et al., 1996. A new method for the purification of carbonic anhydrase isozymes by affinity chromatography. Turkish Journal of Medical Sciences, 26, 163–166.
  • Balci, A., et al., 2015. Synthesis and evaluation of N-heteroarylsubstituted triazolosulfonamides as carbonic anhydrase inhibitors. Journal of Enzyme Inhibition and Medicinal Chemistry, 30 (3), 377–382.
  • Berber, N., et al., 2013. Synthesis and evaluation of new phthalazine urea and thiourea derivatives as carbonic anhydrase inhibitors. Journal of Chemistry, 41 (4), 414–420.
  • Berber, N., et al., 2015. Synthesis and evaluation of new phthalazine substituted β-lactam derivatives as carbonic anhydrase inhibitors. Russian Journal of Bioorganic Chemistry, 41 (4), 414–420.
  • Carta, F., et al., 2010. Polyamines inhibit carbonic anhydrases by anchoring to the zinc-coordinated water molecule. Journal of Medicinal Chemistry, 53 (15), 5511–5522.
  • Celik, F., et al., 2014. Synthesis and carbonic anhydrase inhibitory properties of novel 1,4-dihydropyrimidinone substituted diarylureas. Journal of Enzyme Inhibition and Medicinal Chemistry, 29 (1), 18–22.
  • Congiu, C., et al., 2015. Synthesis of sulfonamides incorporating piperazinyl-ureido moieties and their carbonic anhydrase I, II, IX and XII inhibitory activity. Bioorganic and Medicinal Chemistry Letters, 25 (18), 3850–3853.
  • Demirci, T., et al., 2014. Synthesis and carbonic anhydrase inhibitory properties of 1,3-dicarbonyl derivatives of methylaminobenzene-sulfonamide. Journal of Enzyme Inhibition and Medicinal Chemistry, 29 (1), 132–136.
  • Demirhan, H., et al., 2014. In vitro inhibition of purified human carbonic anhydrase I and II by novel fluorene derivatives. Macedonian Journal of Chemistry and. Chemical Engineering, 33 (2), 199–207.
  • Feng, L.S., et al., 2010. Synthesis and in vitro antimycobacterial activity of balofloxacin ethylene isatin derivatives. European Journal of Medicinal Chemistry, 45 (8), 3407–3412.
  • Gupta, L., et al., 2010. Synthesis and biological evaluation of new [1,2,4]triazino[5,6-b]indol-3-ylthio-1,3,5-triazines and [1,2,4]triazino [5,6-b]indol-3-ylthio-pyrimidines against Leshmania donovani. European Journal of Medicinal Chemistry, 45 (6), 2359–2365.
  • Jahng, K.C., et al., 2008. One-pot synthesis of simple alkaloids: 2,3-polymethylene-4(3H)-quinazolinones, luotonin A, tryptanthrin, and rutaecarpine. Chemical and Pharmaceutical Bulletin, 56 (4), 607–609.
  • Jain, P., Saravanan, C., and Singh, S.K., 2013. Sulphonamides: deserving class as MMP inhibitors?. European Journal of Medicinal Chemistry, 60, 89–100.
  • Jorge, S.D., et al., 2009. Design, synthesis, antimicrobial activity and molecular modeling studies of novel benzofuroxan derivatives against Staphylococcus aureus. Bioorganic and Medicinal Chemistry, 17 (8), 3028–3036.
  • Kamal, A., et al., 2008. Synthesis, structural characterization and biological evaluation of novel [1,2,4]triazolo [1,5-b][1,2,4]benzothiadiazine-benzothiazole conjugates as potential anticancer agents. Chemical Biology and Drug Design, 71 (1), 78–86.
  • Karalı, N., et al., 2007. Synthesis and structure – antituberculosis activity relationship of 1H-indole-2, 3-dione derivatives. Bioorganic and Medicinal Chemistry, 15 (7), 5888–5904.
  • Lee, E.S., Park, J.G., and Jahng, Y., 2003. A facile synthesis of simple alkaloids - Synthesis of 2,3-polymethylene-4(3H)-quinazolinones and related alkaloids. Tetrahedron Letters, 44 (9), 1883–1886.
  • Lineweaver, H. and Burk, D., 1934. The determination of enzyme dissociation constants. Journal of the American Chemical Society, 56, 658–666.
  • Ma, J., et al., 2003. Pharmacodynamic-mediated effects of the angiogenesis inhibitor SU5416 on the tumor disposition of temozolomide in subcutaneous and intracerebral glioma xenograft models. The Journal of Pharmacology and Experimental Therapeutics, 305 (3), 833–839.
  • Majik, M.S., et al., 2014. Design and synthesis of marine natural product-based 1H-indole-2,3-dione scaffold as a new antifouling/antibacterial agent against fouling bacteria. Bioorganic Chemistry, 54, 89–95.
  • Maresca, A., et al., 2009. Non-zinc mediated inhibition of carbonic anhydrases: coumarins are a new class of suicide inhibitors. Journal of the American Chemical Society, 131 (8), 3057–3062.
  • Maresca, A., et al., 2010. Deciphering the mechanism of carbonic anhydrase inhibition with coumarins and thiocoumarins. Journal of Medicinal Chemistry, 53 (1), 335–344.
  • Marson, C.M., 2011. New and unusual scaffolds in medicinal chemistry. Chemical Society Reviews, 40 (11), 5514–5533.
  • McKiernan, J.M., et al., 1997. Expression of the tumor-associated gene MN: a potential biomarker for human renal cell carcinoma. Cancer Research, 57 (12), 2362–2365.
  • Nishimori, I., et al., 2005. Carbonic anhydrase inhibitors. The mitochondrial isozyme VB as a new target for sulfonamide and sulfamate inhibitors. Journal of Medicinal Chemistry, 48 (24), 7860–7866.
  • Nishimori, I., et al., 2007. Carbonic anhydrase inhibitors: cloning, characterization, and inhibition studies of the cytosolic isozyme III with sulfonamides. Bioorganic and Medicinal Chemistry, 15 (23), 7229–7236.
  • Nocentini, A., et al., 2016. Benzenesulfonamides incorporating flexible triazole moieties are highly effective carbonic anhydrase inhibitors: synthesis and kinetic, crystallographic, computational, and intraocular pressure lowering investigations. Journal of Medicinal Chemistry, 59 (23), 10692–10704.
  • Ozgeris, B., et al., 2016. Acetylcholinesterase and carbonic anhydrase inhibitory properties of novel urea and sulfamide derivatives incorporating dopaminergic 2-aminotetralin scaffolds. Bioorganic and Medicinal Chemistry, 24 (10), 2318–2329.
  • Pastorekova, S., et al., 2004. Carbonic anhydrases: Current state of the art, therapeutic applications and future prospects. Journal of Enzyme Inhibition and Medicinal Chemistry, 19 (3), 199–229.
  • Ranga, R., Sharma, V., and Kumar, V., 2013. New thiazolidinly analogs containing pyridine ring: synthesis, biological evaluation and QSAR studies. Medicinal Chemistry Research, 22 (4), 1538–1548.
  • Romagnoli, R., et al., 2009. Hybrid α-bromoacryloylamido chalcones. Design, synthesis and biological evaluation. Bioorganic and Medicinal Chemistry Letters, 19 (7), 2022–2028.
  • Sarikaya, S.B.O., et al., 2011. In vitro inhibition of alpha-carbonic anhydrase isozymes by some phenolic compounds. Bioorganic & Medicinal Chemistry Letters, 21 (14), 4259–4262.
  • Scozzafava, A.M., Mastrolorenzo, A., and Supuran, C.T., 2006. Carbonic anhydrase inhibitors and activators and their use in therapy. Expert Opinion on Therapeutic Patents, 16, 1627–1664.
  • Sen, E., et al., 2013. Inhibitory effect of novel pyrazole carboxamide derivatives on human carbonic anhydrase enzyme. Journal of Enzyme Inhibition and Medicinal Chemistry, 28 (2), 328–336.
  • Smith, K.S. and Ferry, J.G., 2000. Prokaryotic carbonic anhydrases. FEMS Microbiology Reviews, 24 (4), 335–366.
  • Solomon, V.R., Hu, C., and Lee, H., 2009. Hybrid pharmacophore desing and synthesis of isatin-benzothiazole analogs for their anti-breast cancer activity. Bioorganic and Medicinal Chemistry, 17 (21), 7585–7592.
  • Sridhar, S.K. and Ramesh, A., 2001. Synthesis and pharmacological activities of hydrazones, Schiff and Mannich bases of isatin derivatives. Biological and Pharmaceutical Bulletin, 24 (10), 1149–1152.
  • Sridhar, S.K., et al., 2002. Anticonvulsant activity of hydrazones, Schiff and Mannich bases of isatin derivatives. European Journal of Pharmaceutical Sciences, 16 (3), 129–132.
  • Supuran, C.T., 2008. Carbonic anhydrases: novel therapeutic applications for inhibitors and activators. Nature Reviews. Drug Discovery, 7 (2), 168–181.
  • Supuran, C.T., 2010. Carbonic anhydrase inhibitors. Bioorganic and Medicinal Chemistry Letters, 20 (12), 3467–3474.
  • Supuran, C.T., Scozzafava, A., and Casini, A., 2003. Carbonic anhydrase inhibitors. Medicinal Research Reviews, 23 (2), 146–189.
  • Thiry, A., et al., 2006. Indanesulfonamides as carbonic anhydrase inhibitors. Toward structure-based design of selective inhibitors of the tumor-associated isozyme CA IX. Journal of Medicinal Chemistry, 49, 2743–2749.
  • Verpoorte, J.A., Mehta, S., and Edsall, J.T., 1967. Esterase activities of human carbonic anhydrases B and C. The Journal of Biological Chemistry, 242, 4221–4229.
  • Vine, K.L., et al., 2007. An investigation into the cytotoxicity and mode of action of some novel N-alkyl-substituted isatins. Journal of Medicinal Chemistry, 50 (21), 5109–5117.
  • Vine, K.L., et al., 2009. Cytotoxic and anticancer activities of isatin and its derivatives: a comprehensive review from 2000-2008. Anti-Cancer Agents in Medicinal Chemistry, 9 (4), 397–414.
  • Vullo, D., et al., 2005. Carbonic anhydrase inhibitors. Inhibition of the human cytosolic isozyme VII with aromatic and heterocyclic sulfonamides. Bioorganic and Medicinal Chemistry Letters, 15 (4), 971–976.
  • Vullo, D., et al., 2005. Carbonic anhydrase inhibitors. Inhibition of the transmembrane isozyme XII with sulfonamides - A new target for the design of antitumor and antiglaucoma drugs?. Bioorganic and Medicinal Chemistry Letters, 15 (4), 963–969.
  • Wang, J., et al., 2011. Chemical synthesis, in vitro acetohydroxyacid synthase (AHAS) inhibition, herbicidal activity, and computational studies of isatin derivatives. Journal of Agricultural and Food Chemistry, 59 (18), 9892–9900.

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