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Research Article

Benzenesulfonamides with benzimidazole moieties as inhibitors of carbonic anhydrases I, II, VII, XII and XIII

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Pages 124-131 | Received 18 Oct 2012, Accepted 06 Dec 2012, Published online: 28 Jan 2013

References

  • Alterio V, Fiore AD, 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
  • Aggarwal M, Kondeti B, McKenna R. Insights towards sulfonamide drug specificity in α-carbonic anhydrases. Bioorg Med Chem 2012; doi: 10.1016/j.bmc.2012.08.019
  • Supuran CT. Carbonic anhydrases as drug targets – an overview. Curr Top Med Chem 2007;7:825–33
  • Supuran CT. Carbonic anhydrases – an overview. Curr Pharm Des 2008;14:603–14
  • Nordfors K, Haapasalo J, Korja M, et al. The tumour-associated carbonic anhydrases CA II, CA IX and CA XII in a group of medulloblastomas and supratentorial primitive neuroectodermal tumours: an association of CA IX with poor prognosis. BMC Cancer 2010;10:148–58
  • Chien MH, Ying TH, Hsieh YH, et al. Tumor-associated carbonic anhydrase XII is linked to the growth of primary oral squamous cell carcinoma and its poor prognosis. Oral Oncol 2012;48:417–23
  • Swietach P, Hulikova A, Vaughan-Jones RD, Harris AL. New insights into the physiological role of carbonic anhydrase IX in tumour pH regulation. Oncogene 2010;29:6509–21
  • Said HM, Supuran CT, Hageman C, et al. Modulation of carbonic anhydrase 9 (CA9) in human brain cancer. Curr Pharm Des 2010;16:3288–99
  • Pastorekova S, Parkkila S, Zavada J. Tumor-associated carbonic anhydrases and their clinical significance. Adv Clin Chem 2006;42:167–216
  • Winum JY, Carta F, Ward C, et al. Ureido-substituted sulfamates show potent carbonic anhydrase IX inhibitory and antiproliferative activities against breast cancer cell lines. Bioorg Med Chem Lett 2012;22:4681–85
  • Rodriguez OM, Maresca A, Tempera CA, et al. N-β-glycosyl sulfamides are selective inhibitors of the cancer associated carbonic anhydrase isoforms IX and XII. Bioorg Med Chem Lett 2011;21:4447–50
  • 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
  • Supuran CT. Carbonic anhydrase inhibition with natural products: novel chemotypes and inhibition mechanisms. Mol Divers 2011;15:305–16
  • Supuran CT, Scozzafava A, Conway J. Carbonic anhydrase – its inhibitors and activators. Boca Raton, FL: CRC Press; 2004:1–363
  • Supuran CT, Innocenti A, Mastrolorenzo A, Scozzafava A. Antiviral sulfonamide derivatives. Mini Rev Med Chem 2004;4:189–200
  • Carta F, Scozzafava A, Supuran CT. Sulfonamides: a patent review (2008–2012). Expert Opin Ther Pat 2012; 22:747–58
  • Carta F, Supuran CT, Scozzafava A. Novel therapies for glaucoma: a patent review 2007–2011. Expert Opin Ther Pat 2012; 22:79–88
  • Thiry A, Dogne JM, Supuran CT, Masereel B. Anticonvulsant sulfonamides/sulfamates/sulfamides with carbonic anhydrase inhibitory activity: drug design and mechanism of action. Curr Pharm Des 2008;14:661–71
  • Temperini C, Cecchi A, Scozzafava A, Supuran CT. Carbonic anhydrase inhibitors. interaction of indapamide and related diuretics with 12 mammalian isozymes and X-ray crystallographic studies for the indapamide-isozyme II adduct. Bioorg Med Chem Lett 2008;18:2567–73
  • Capkauskaite E, Zubriene A, Baranauskiene L, et al. Design of [(2-pyrimidinylthio)acetyl]benzenesulfonamides as inhibitors of human carbonic anhydrases. Eur J Med Chem 2012;51:259–70
  • Sudzius J, Golovenko D, Matuliene J, et al. 4-[n-(substituted 4-pyrimidinyl)amino]benzenesulfonamides as inhibitors of carbonic anhydrase isozymes I, II, VII and XIII. Bioorg Med Chem 2010;18:7413–21
  • Dudutiene V, Baranauskiene L, Matulis D. Benzimidazo[1,2-c][1,2,3]thiadiazole-7-sulfonamides as inhibitors of carbonic anhydrase. Bioorg Med Chem Lett 2007;17:3335–8
  • Capkauskaite E, Baranauskiene L, Golovenko D, et al. Indapamide-like benzenesulfonamides as inhibitors of carbonic anhydrases I, II, VII, and XIII. Bioorg Med Chem 2010;18:7357–64
  • Fujikura T, Miigata K, Hashimoto S, et al. Studies on benzenesulfonamide derivatives with alpha- and beta-adrenergic antagonistic and antihypertensive activities. Chem Pharm Bull (Tokyo) 1982;30:4092–101
  • Zanka A, Kubota A. Practical and efficient chlorination of deactivated anilines and anilides with ncs in 2-propanol. Synlett 1999;12:1984–6
  • Nickson TE, Roche-Dolson CA. A convenient procedure for the chlorination of deactivated anilines. Synthesis 1985;6/7:669–70
  • Phillips MA. The formation of 2-substituted benzimidazoles. J Chem Soc 1928;CCCXVII:2393–9
  • Baranauskiene L, Hilvo M, Matuliene J, et al. Inhibition and binding studies of carbonic anhydrase isozymes I, II and IX with benzimidazo[1,2-c][1,2,3]thiadiazole-7-sulphonamides. J Enzyme Inhib Med Chem 2010;25:863–70
  • Cimmperman P, Baranauskiene L, Jachimoviciute S, et al. A quantitative model of thermal stabilization and destabilization of proteins by ligands. Biophys J 2008;95:3222–31
  • Jogaite V, Zubriene A, Michailoviene V, et al. Characterization of human carbonic anhydrase XII stability and inhibitor binding. Bioorg Med Chem 2012; doi: 10.1016/j.bmc.2012.10.016
  • Kazlauskas E, Petrikaite V, Michailoviene V, et al. Thermodynamics of aryl-dihydroxyphenyl-thiadiazole binding to human Hsp90. PLoS ONE 2012;7:e36899
  • Supuran CT. Diuretics: from classical carbonic anhydrase inhibitors to novel applications of the sulfonamides. Curr Pharm Des 2008;14:641–8
  • Zubriene A, Kazlauskas E, Baranauskiene L, et al. Isothermal titration calorimetry and thermal shift assay in drug design. European pharmaceutical review 2011;16:56–9

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