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  • Title: Carbonic anhydrase inhibitors: novel compounds containing S-NH moieties: sulfenamido-sulfonamides, sulfenimido-sulfonamides and their interaction with isozymes I, II and IV.
    Author: Scozzafava A, Supuran CT.
    Journal: J Enzyme Inhib; 1998 Sep; 13(6):419-42. PubMed ID: 9825306.
    Abstract:
    Reaction of 2-nitrophenyl- and 4-nitrophenylsulfenyl chlorides with aromatic/heterocyclic sulfonamides/bis-sulfonamides containing a free amino, hydrazino or imino group afforded sulfenamido-sulfonamides, or sulfenimido-sulfonamides. Oxidation of these derivatives with potassium permanganate in acetone led to the corresponding bis-sulfonamides. The obtained compounds were assayed as inhibitors of the zinc enzyme carbonic anhydrase (CA), isozymes hCA I, hCA II (human cytosolic forms from red cells) and bCA IV (bovine membrane-associated form). Good inhibition of the three CA isozymes was observed with some of the new compounds, the bis-sulfonamides being more active than the sulfenamido-sulfonamides. Structure-active correlations for the new series of inhibitors are discussed. Some of the sulfenamido-sulfonamides (but not the corresponding bis-sulfonamides) showed topical intraocular pressure lowering effects when applied as a 2% solution directly into the rabbit eye.
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