Journal
BIOORGANIC & MEDICINAL CHEMISTRY
Volume 21, Issue 17, Pages 5168-5174Publisher
PERGAMON-ELSEVIER SCIENCE LTD
DOI: 10.1016/j.bmc.2013.06.035
Keywords
Human carbonic anhydrase inhibitors; Benzenesulfonamide; 4,5,6,7-Tetrachloro-1,3-dioxoisoindolin-2-yl benzenesulfonamide; Structure-activity relationship
Funding
- EU
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A series of 4,5,6,7-tetrachloro-1,3-dioxoisoindolin-2-yl benzenesulfonamide derivatives (compounds 1-8) was synthesized by reaction of benzene sulfonamides incorporating primary amino moieties with 4,5,6,7-tetrachlorophthalic anhydride. These sulfonamides were assayed as inhibitors of the metalloenzyme carbonic anhydrase (CA, EC 4.2.1.1). Some of these compounds showed very good in vitro human carbonic anhydrase (hCA) isoforms I, II and VII inhibitory properties, with affinities in the low nanomolar range. Inhibition activities against hCA I were in the range of 159-444 nM; against hCA II in the range of 2.4-4515 nM, and against hCA VII in the range of 1.3-469 nM. The structure-activity relationship (SAR) with this series of sulfonamides is straightforward, with the main features leading to good activity for each isoform being established. (C) 2013 Elsevier Ltd. All rights reserved.
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