Sulfenamido-sulfonamides as inhibitors of carbonic anhydrase isozymes I, II and IV.
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.
Supuran
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CT
Università degli Studi, Laboratorio di Chimica Inorganica e Bioinorganica, Firenze, Italia.
Briganti
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F
Scozzafava
A
A
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
D002257:Carbonic Anhydrase Inhibitors; D007527:Isoenzymes; D013449:Sulfonamides; D002256:Carbonic Anhydrases