Synthesis and biological evaluation of a new family of anti-benzylanilinosulfonamides as CA IX inhibitors.
(2008) European Journal of Medicinal Chemistry — Vol. 44, n° 2, p. 511-518 (2009)
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- Abstract
- We report the synthesis and the pharmacological evaluation of a new class of human carbonic anhydrase (hCA) inhibitors prepared regio- and stereoselectively by reacting sulfanilamide with ethyl trans-phenylglycidate in the presence of cobalt(II) chloride. Various derivatizations of the ester moiety in the parent compound led to a small library of derivatives (2R,3R and 2S,3S) which displayed interesting inhibitory activities towards the human tumor-associated isoform CA IX. One of the new compounds shows high selectivity in inhibiting hCA IX compared to the two physiologically relevant, cytosolic isozymes hCA I and hCA II. A molecular modeling study was conducted in order to simulate the binding mode of this new family of enzyme inhibitors within the active sites of hCA IX and hCA II.
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Thiry, A., Delayen, A., Goossens, L., Houssin, R., Ledecq, M., Frankart, A., Dogné, J.-M., Wouters, J., Supuran, C. T., Hénichart, J.-P., & Masereel, B. (2008). Synthesis and biological evaluation of a new family of anti-benzylanilinosulfonamides as CA IX inhibitors. European Journal of Medicinal Chemistry, 44(2), 511-518. https://doi.org/10.1016/j.ejmech.2008.03.034 (Original work published 2009)