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

Abstract：

: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 4.2.1.1) 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.

journal_name

Bioorg Med Chem Lett

journal_title

Bioorganic & medicinal chemistry letters

authors

Chazalette C,Masereel B,Rolin S,Thiry A,Scozzafava A,Innocenti A,Supuran CT

doi

10.1016/j.bmcl.2004.09.061

subject

Has Abstract

pub_date

2004-12-06 00:00:00

pages

5781-6

issue

23

eissn

0960-894X

issn

1464-3405

pii

S0960-894X(04)01184-9

journal_volume

14

pub_type

杂志文章

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