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.

Carbonic anhydrase inhibitors: novel compounds containing S-NH moieties: sulfenamido-sulfonamides, sulfenimido-sulfonamides and their interaction with isozymes I, II and IV / A. Scozzafava;C. T. Supuran. - In: JOURNAL OF ENZYME INHIBITION. - ISSN 8755-5093. - STAMPA. - 13:(1998), pp. 419-442.

Carbonic anhydrase inhibitors: novel compounds containing S-NH moieties: sulfenamido-sulfonamides, sulfenimido-sulfonamides and their interaction with isozymes I, II and IV.

SCOZZAFAVA, ANDREA;SUPURAN, CLAUDIU TRANDAFIR
1998

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.
1998
13
419
442
A. Scozzafava;C. T. Supuran
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Utilizza questo identificatore per citare o creare un link a questa risorsa: https://hdl.handle.net/2158/774583
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