Sulfonylmethanesulfonamide inhibitors of carbonic anhydrase.

Article Details

Citation

Copy to clipboard

Scholz TH, Sondey JM, Randall WC, Schwam H, Thompson WJ, Mallorga PJ, Sugrue MF, Graham SL

Sulfonylmethanesulfonamide inhibitors of carbonic anhydrase.

J Med Chem. 1993 Jul 23;36(15):2134-41.

PubMed ID

8340917 [ View in PubMed

]

Abstract

A series of sulfonylmethanesulfonamide derivatives is described, which are inhibitors of carbonic anhydrase (CA). The most potent of these is the racemic fluoro sulfone 9, which inhibits carbon dioxide hydration catalyzed by human CA II (CA-II) with an IC50 of 3 nM. Binding competition studies versus dansylamide indicate that the enantiomers of 9 have different affinities for CA-II, with equilibrium dissociation constants of 3.6 and 0.6 nM. QSAR analysis suggests that the key factors involved in achieving high affinity in this series are sulfonamide acidity, hydrophobicity, and minimization of steric demands at the carbon atom adjacent to the sulfonamide group.

DrugBank Data that Cites this Article

Binding Properties

Drug	Target	Property	Measurement	pH	Temperature (°C)
Acetazolamide	Carbonic anhydrase 2	IC 50 (nM)	10	N/A	N/A	Details