Synthesis of 5-amino-1,3,4-thiadiazole-2-sulphonamide derivatives and their inhibition effects on human carbonic anhydrase isozymes

References

• Supuran CT, Casini A, Mastrolorenzo A, Scozzafava A. COX–2 selective inhibitors, carbonic anhydrase inhibition and anticancer properties of sulfonamides belonging to this class of pharmacological agents. Mini Rev Med Chem 2004;4:625–632.
   PubMed Web of Science ®Google Scholar
• Kasımoğulları R, Bülbül M, Günhan H, Güleryüz H. Effects of new 5-amino-1,3,4-thiadiazole-2-sulfonamide derivatives on human carbonic anhydrase isozymes. Bioorg Med Chem 2009;17:3295–3301.
   PubMed Web of Science ®Google Scholar
• Bülbül M, Kasımoğulları R, Küfrevioğlu Öİ. Amide derivatives with pyrazole carboxylic acids of 5-amino-1,3,4-thiadiazole 2-sulfonamide as new carbonic anhydrase inhibitors: Synthesis and investigation of inhibitory effects. J Enzyme Inhib Med Chem 2008;23:895–900.
   PubMed Web of Science ®Google Scholar
• Owa T, Nagasu T. Novel sulphonamide derivatives for the treatment of cancer. Expert Opin Ther Pat 2000;10:1725–1740.
   Web of Science ®Google Scholar
• Robinson C, Hartman RF, Rose SD. Emollient, humectant, and fluorescent alpha, beta-unsaturated thiol esters for long-acting skin applications. Bioorg Chem 2008;36:265–270.
   PubMedGoogle Scholar
• Sova M, Kovac A, Turk S, Hrast M, Blanot D, Gobec S. Phosphorylated hydroxyethylamines as novel inhibitors of the bacterial cell wall biosynthesis enzymes MurC to MurF. Bioorg Chem 2009;37:217–222.
   PubMed Web of Science ®Google Scholar
• Rega MF, Leone M, Jung D, Cotton NJH, Stebbins JL, Pellecchia M. Structure-based discovery of a new class of Bcl-x (L) antagonists. Bioorg Chem 2007;35:344–353.
   PubMedGoogle Scholar
• Scozzafava A, Owa T, Mastrolorenzo A, Supuran CT. Anticancer and antiviral sulfonamides. Curr Med Chem 2003;10:925–953.
   PubMed Web of Science ®Google Scholar
• Chohan ZH, Hassan M, Khan MK, Supuran CT. In-vitro antibacterial, antifungal and cytotoxic properties of sulfonamide-derived Schiff’s bases and their metal complexes. J Enzyme Inhib Med Chem 2005;20:183–188.
   PubMed Web of Science ®Google Scholar
• Weber A, Casini A, Heine A, Kuhn D, Supuran CT, Scozzafava A, Klebe G. Unexpected nanomolar inhibition of carbonic anhydrase by COX-2-selective celecoxib: New pharmacological opportunities due to related binding site recognition. J Med Chem 2004;47:550–557.
   PubMed Web of Science ®Google Scholar
• Pastorekova S, Casini A, Scozzafava A, Vullo D, Pastorek J, Supuran CT. Carbonic anhydrase inhibitors: The first selective, membrane-impermeant inhibitors targeting the tumor-associated isozyme IX. Bioorg Med Chem Lett 2004;14:869–873.
   PubMed Web of Science ®Google Scholar
• Casey JR, Morgan PE, Vullo D, Scozzafava A, Mastrolorenzo A, Supuran CT. Carbonic anhydrase inhibitors. Design of selective, membrane-impermeant inhibitors targeting the human tumor-associated isozyme IX. J Med Chem 2004;47:2337–2347.
   PubMed Web of Science ®Google Scholar
• Brown JM, William WR. Exploiting tumour hypoxia in cancer treatment. Nat Rev Cancer 2004;4:437–447.
   PubMed Web of Science ®Google Scholar
• Scozzafava A, Banciu MD, Popescu A, Supuran CT. Carbonic anhydrase inhibitors: Inhibition of isozymes I, II and IV by sulfamide and sulfamic acid derivatives. J Enzyme Inhib Med Chem 2000;15:443–453.
   Google Scholar
• Schuman JS. Antiglaucoma medications: A review of safety and tolerability issues related to their use. Clin Ther 2000;22:167–208.
   PubMed Web of Science ®Google Scholar
• Wilkinson BL, Bornaghi LF, Houston TA, Innocenti A, Vullo D, Supuran CT, Poulsen SA. Inhibition of membrane-associated carbonic anhydrase isozymes IX, XII and XIV with a library of glycoconjugate benzenesulfonamides. Bioorg Med Chem Lett 2007;17:987–982.
   PubMed Web of Science ®Google Scholar
• Santos MA, Marques S, Vullo D, Innocenti A, Scozzafava A, Supuran CT. Carbonic anhydrase inhibitors: Inhibition of cytosolic/tumor-associated isoforms I, II, and IX with iminodiacetic carboxylates/hydroxamates also incorporating benzenesulfonamide moieties. Bioorg Med Chem Lett 2007;17:1538–1543.
   PubMed Web of Science ®Google Scholar
• Güzel Ö, Maresca A, Scozzafava A, Salman A, Balaban AT, Supuran CT. Carbonic anhydrase inhibitors. Synthesis of 2,4,6-trimethylpyridinium derivatives of 2-(hydrazinocarbonyl)-3-aryl-1H-indole-5-sulfonamides acting as potent inhibitors of the tumor-associated isoform IX and XII. Bioorg Med Chem Lett 2009;19:2931–2934.
   PubMed Web of Science ®Google Scholar
• Carta F, Maresca A, Scozzafava A, Vullo D, Supuran CT. Carbonic anhydrase inhibitors. Diazenylbenzenesulfonamides are potent and selective inhibitors of the tumor-associated isozymes IX and XII over the cytosolic isoforms I and II. Bioorg Med Chem 2009;17:7093–7099.
   PubMedGoogle Scholar
• Güzel, Ö,Maresca, A, Scozzafava, A, Salman, A, Balaban, AT, Supuran, CT. Discovery of low nanomolar and subnanomolar inhibitors of the Mycobacterial beta-carbonic anhydrases Rv1284 and Rv3273. J Med Chem 2009;52:4063–4067.
   PubMed Web of Science ®Google Scholar
• Akbas E, Berber I. Antibacterial and antifungal activities of new pyrazolo[3,4-d] pyridazin derivatives. Eur J Med Chem 2006;41:904.
   Web of Science ®Google Scholar
• Supuran CT. Carbonic anhydrases: Novel therapeutic applications for inhibitors and activators. Nat Rev Drug Discovery 2008;7:168–181.
   PubMed Web of Science ®Google Scholar
• Aggarwal D, Pal D, Mitra AK, Kaur IP. Study of the extent of ocular absorption of acetazolamide from a developed niosomal formulation, by microdialysis sampling of aqueous humor. Int J Pharm 2007;338:21–26.
   PubMed Web of Science ®Google Scholar
• Sugrue MF. Pharmacological and ocular hypotensive properties of topical carbonic anhydrase inhibitors. Prog Ret Eye Res 2000;19:87–112.
   PubMed Web of Science ®Google Scholar
• Ingram CJ, Brubaker RF. Effect of brinzolamide and dorzolamide on aqueous humor flow in human eyes. Am J Ophthalmol 1999;128:292–296.
   PubMed Web of Science ®Google Scholar
• Konowal A, Morrison JC, Brown SVL, Cooke DL, Maguire LJ, Verdier DV, Fraunfelder FT, Dennis RF, Epstein RJ. Irreversible corneal decompensation in patients treated with topical dorzolamide. Am J Ophthalmol 1999;127:403–406.
   PubMed Web of Science ®Google Scholar
• Arslan O, Nalbantoğlu B, Demir N, Özdemir H, Küfrevioğlu Öİ. A new method for the purification of carbonic anhydrase isozymes by affinity chromatography. Turk J Med Sci 1996;26:163–166.
   Google Scholar
• Rickli EE, Ghazanfar SA, Gibbson BH, Edsall JT. Carbonic anhydrases from human erythrocytes. Preparation and properties of two enzymes. J Biol Chem 1964;239:1065–1078.
   PubMed Web of Science ®Google Scholar
• Bradford MM. A rapid and sensitive method for quantitation of microgram quantities of protein utilizing the principle of protein-dye-binding. Anal Biochem 1976;72:248–254.
   PubMed Web of Science ®Google Scholar
• Laemmli DK. Clevage of structural proteins during in assembly of the head of bacteriophage T4. Nature 1970;227:680–685.
   PubMed Web of Science ®Google Scholar
• Wilbur KM, Anderson NG. Electrometric and colorimetric determination of carbonic anhydrase. J Biol Chem 1948;176:147–154.
   PubMed Web of Science ®Google Scholar
• Verpoorte JA, Mehta S, Edsall JT. Esterase activities of human carbonic anhydrases B and C. J Biol Chem 1967;242:4221–4229.
   PubMed Web of Science ®Google Scholar
• Innocenti A, Scozzafava A, Parkkila S, Pucceti L, De Simone G, Supuran CT. Investigations of the esterase, phosphatase, and sulfatase activities of the cytosolic mammalian carbonic anhydrase isoforms I, II, and XIII with 4-nitrophenyl esters as substrates. Bioorg Med Chem Lett 2008;18:2267–2271.
   PubMed Web of Science ®Google Scholar
• Landolfi C, Marchetti M, Ciocci G, Milanese C. Development and pharmacological characterization of a modified procedure for the measurement of carbonic anhydrase activity. J Pharmacol Toxicol Methods 1998;38:169–172.
   Web of Science ®Google Scholar
• Bülbül M, Hisar O, Beydemir Ş, Ciftci M, Kürevioğlu Öİ. The in vitro and in vivo inhibitory effects of some sulfonamide derivatives on rainbow trout (Oncorhynchus mykiss) erythrocyte carbonic anhydrase activity. J Enzyme Inhib Med Chem 2003;18:371–375.
   PubMed Web of Science ®Google Scholar
• Ciftci M, Bülbül M, Gül M, Gümüştekin K, Dane Ş, Süleyman H. Effects of nicotine and vitamin E on carbonic anhydrase activity in some rat tissues in vivo and in vitro. J Enzyme Inhib Med Chem 2005;20:103–108.
   PubMed Web of Science ®Google Scholar
• Hisar O, Beydemir Ş, Bülbül M, Yanık T. Kinetic properties of carbonic anhydrase purified from gills of rainbow trout (Oncorhynchus mykiss). J Appl Anim Res 2006;30:185–187.
   Web of Science ®Google Scholar
• Winum JY, Cecchi A, Montero JL, Innocenti A, Scozzafava A, Supuran CT. Carbonic anhydrase inhibitors. Synthesis and inhibition of cytosolic/tumor-associated carbonic anhydrase isozymes I, II, and IX with boron-containing sulfonamides, sulfamides, and sulfamates: Toward agents for boron neutron capture therapy of hypoxic tumors. Bioorg Med Chem Lett 2005;15:3302–3306.
   PubMed Web of Science ®Google Scholar
• Şener A, Kasımoğulları R, Sener MK, Bildirici İ, Akçamur Y. Studies on the reactions of cyclic oxalyl compounds with hydrazines or hydrazones: Synthesis and reactions of 4-benzoyl-1-(3-nitrophenyl)-5-phenyl-1H-pyrazole-3-carboxylic acid. J Heterocycl Chem 2002;39:869–875.
   Web of Science ®Google Scholar
• Şener A, Kasımoğulları R, Sener MK, Genç H, Studies on reactions of cyclic oxalyl compounds with hydrazines or hydrazones. Synthesis and reactions of 4-benzoyl-1-(4-nitrophenyl)-5-phenyl-1H-pyrazole-3-carboxylic acid. Chem Heterocycl Comp 2004;8:1201–1208.
   Google Scholar
• Kaymakçıoğlu BK, Rollas S. Synthesis, characterization and evaluation of antituberculosis activity of some hydrazones. Farmaco 2002;57:595–599.
   PubMedGoogle Scholar
• Secrist JA, Liu PS. Studies directed toward a total synthesis of nucleoside Q. Annulation of 2,6–diaminopyrimidin–4–one with alpha–halo carbonyls to form pyrrolo[2,3–d] pyrimidines. J Org Chem 1978;43:3937–3941.
   Web of Science ®Google Scholar