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J Med Chem. 2013 Jul 25;56(14):5773-81. doi: 10.1021/jm400418p. Epub 2013 Jul 10.

A class of sulfonamides with strong inhibitory action against the α-carbonic anhydrase from Trypanosoma cruzi.

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Department of Pharmaceutical Chemistry, Faculty of Pharmacy, Istanbul University , 34116, Beyazit, Istanbul, Turkey.


Trypanosoma cruzi, the causative agent of Chagas disease, encodes for an α-carbonic anhydrase (CA, EC possessing high catalytic activity (TcCA) which was recently characterized (Pan et al. J. Med. Chem. 2013, 56, 1761-1771). A new class of sulfonamides possessing low nanomolar/subnanomolar TcCA inhibitory activity is described here. Aromatic/heterocyclic sulfonamides incorporating halogeno/methoxyphenacetamido tails inhibited TcCA with KIs in the range of 0.5-12.5 nM, being less effective against the human off-target isoforms hCA I and II. A homology model of TcCA helped us to rationalize the excellent inhibition profile of these compounds against the protozoan enzyme, a putative new antitrypanosoma drug target. These compounds were ineffective antitrypanosomal agents in vivo due to penetrability problems of these highly polar molecules that possess sulfonamide moieties.

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