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Bioorg Med Chem Lett. 2004 Dec 6;14(23):5781-6.

Carbonic anhydrase inhibitors. Design of anticonvulsant sulfonamides incorporating indane moieties.

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Université Joseph Fourier de Grenoble, Laboratoire d'Etudes Dynamiques et Structurales de la Sélectivité, Bât. C Chimie, 301 rue de la chimie, Domaine Universitaire, 38400 Saint-Martin d'Hères (Grenoble), France.


A series of aromatic sulfonamides incorporating indane moieties were prepared starting from commercially available 1- and 2-indanamine, and their activity as inhibitors of two carbonic anhydrase (CA, EC isozymes, hCA I and II was studied. The new sulfonamides incorporating acetamido, 4-chloro-benzoyl, valproyl, tetra-, and pentafluorobenzoyl moieties acted as very potent inhibitors of the slow red blood cell isozyme hCA I (K(i)s in the range of 1.6-8.5 nM), which usually has a lower affinity for such inhibitors, as compared to isozyme II. Some derivatives also showed excellent hCA II inhibitory properties (K(i)s in the range of 2.3-12 nM), but the anticonvulsant activity of these sulfonamides was rather low as compared to that of other sulfonamide/sulfamate CA inhibitors, such as methazolamide. Furthermore, the 2-amino/acetamido-indane-5-sulfonic acids prepared during this work also showed interesting CA inhibitory properties, with inhibition constants in the range of 43-89 nM against the two isozymes, being among the most potent sulfonic acid CA inhibitors reported so far.

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