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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

J Enzyme Inhib. 1998 Sep;13(6):419-42.

PMID: 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.

Chemicals Related in the Paper:

Catalog Number Product Name Structure CAS Number Price
AP9001030-A Carbonic Anhydrase Isozyme II human Carbonic Anhydrase Isozyme II human 9001-03-0 Price
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