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Carbonic Anhydrase Inhibitors: Inhibition of Cytosolic Carbonic Anhydrase Isozymes II and VII with Simple Aromatic Sulfonamides and Some Azo Dyes
Author(s) -
Carta Fabrizio,
Pothen Blessy,
Maresca Alfonso,
Tiwari Meena,
Singh Vineet,
Supuran Claudiu T.
Publication year - 2009
Publication title -
chemical biology and drug design
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 0.59
H-Index - 77
eISSN - 1747-0285
pISSN - 1747-0277
DOI - 10.1111/j.1747-0285.2009.00842.x
Subject(s) - carbonic anhydrase , sulfanilamide , chemistry , enzyme , carbonic anhydrase i , sulfonamide , cytosol , stereochemistry , isozyme , iodide , medicinal chemistry , biochemistry , organic chemistry
Several substituted benzenesulfonamides were synthesized by various pathways starting from sulfanilamide. The sulfanilamide diazonium salt was reacted with copper (I) halides, potassium iodide and/or aromatic derivatives, leading to 4‐halogeno‐, and 4‐hydroxy‐benzenesulfonamides as well as diazo dyes incorporating sulfamoyl moieties. These sulfonamides were assayed as inhibitors of two physiologically relevant isoforms of the zinc enzyme carbonic anhydrase (CA, EC 4.2.1.1), i.e., the cytosolic CA II (ubiquitous), and CA VII (brain‐specific enzyme). Good CA inhibitory activity was detected for some of these derivatives, with inhibition constants (Ki) in the range of 17.5–863 n m against CA II; and 30–4200 n m against CA VII.