title: Sulfenamido-sulfonamides as inhibitors of carbonic anhydrase isozymes I, II and IV.
abstract: Reaction of 2-nitrophenyl- and 4-nitrophenylsulfenyl-chlorides with aromatic/heterocyclic sulfonamides containing a free amino group afforded sulfenamido-sulfonamides, which were inhibitors of the zinc enzyme carbonic anhydrase (CA). Oxidation of these derivatives with potassium permanganate in acetone led to the corresponding bis-sulfonamides. Good inhibition of three CA isozymes (CA I, II and IV, respectively) was observed with some of the new compounds, the bis-sulfonamides being more active than the sulfenamido-sulfonamides. A possible in vivo transformation of the last type of compounds, leading to an omeprazole-like gastric acid secretion inhibitor is also discussed.
authors.affiliation: Università degli Studi, Laboratorio di Chimica Inorganica e Bioinorganica, Firenze, Italia.
authors.forename: C T
authors.initials: CT
authors.lastname: Supuran
authors.forename: F
authors.initials: F
authors.lastname: Briganti
authors.forename: A
authors.initials: A
authors.lastname: Scozzafava
mesh_terms: D002257:Carbonic Anhydrase Inhibitors / Q000737:chemistry* / Q000378:metabolism; D002256:Carbonic Anhydrases / Q000145:classification / Q000378:metabolism*; D018360:Crystallography, X-Ray; D006801:Humans; D007527:Isoenzymes / Q000037:antagonists & inhibitors* / Q000145:classification / Q000378:metabolism; D013329:Structure-Activity Relationship; D013449:Sulfonamides / Q000737:chemistry* / Q000494:pharmacology
chemical_list: D002257:Carbonic Anhydrase Inhibitors; D007527:Isoenzymes; D013449:Sulfonamides; D002256:Carbonic Anhydrases