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Synthesis of rigid trichostatin A analogs as HDAC inhibitors.

Abstract：

:New inhibitors of histone deacetylase (HDAC) have been synthesized and evaluated for their activity toward non small lung cancer cell line H661. Their design is based on indanone (or tetralone) systems leading to trichostatin A (TSA) analogs with limited conformational mobility. Molecular modelization at the AM1 level revealed that the conformations of indane-based analogs and TSA bound to HDAC like protein are similar. The synthesis of these new analogs was achieved by alkylation of an appropriate indanone (or tetralone) to introduce the side chain bearing a terminal ester group, the latter being a precursor of hydroxamic acid and aminobenzamide derivatives. Hydroxamic acids with the TSA side chain were found to be the most active compounds and the presence of the dimethylamino group on the phenyl ring turned out to be essential to achieve low micromolar activities against H661 cancer cells.

journal_name

Bioorg Med Chem Lett

journal_title

Bioorganic & medicinal chemistry letters

authors

Charrier C,Bertrand P,Gesson JP,Roche J

doi

10.1016/j.bmcl.2006.07.080

subject

Has Abstract

pub_date

2006-10-15 00:00:00

pages

5339-44

issue

20

eissn

0960-894X

issn

1464-3405

pii

S0960-894X(06)00866-3

journal_volume

16

pub_type

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