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New Anacardic Acid‐Inspired Benzamides: Histone Lysine Acetyltransferase Activators
Author(s) -
Souto José A.,
Benedetti Rosaria,
Otto Katharina,
Miceli Marco,
Álvarez Rosana,
Altucci Lucia,
de Lera Angel R.
Publication year - 2010
Publication title -
chemmedchem
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 0.817
H-Index - 100
eISSN - 1860-7187
pISSN - 1860-7179
DOI - 10.1002/cmdc.201000158
Subject(s) - acetylation , pcaf , lysine , histone acetyltransferase , histone acetyltransferases , chemistry , histone , histone h3 , acetyltransferase , stereochemistry , biochemistry , enzyme , alkyl , amino acid , organic chemistry , gene
A series of N ‐(4‐cyano‐3‐trifluoromethyl‐phenyl)‐2‐ethoxy‐6‐alkyl (and alkenyl) benzamides related to the anacardic acid derivative CTPB have been prepared from 2,6‐dihydroxybenzoic acid with a Suzuki coupling and addition of the anion of 4‐cyano‐3‐trifluoromethylphenylamine to a benzodioxinone as the key steps. In U937 cells, these analogues, in particular 7 c , 7 d , 7 f and 7 j , induced cell‐cycle arrest in the G1 phase, caused apoptosis in about 20 % of the cells, and increased the acetylation levels of H3. These activities correlate with the enzymatic activation of histone lysine acetyltransferases (KATs): CBP and PCAF.
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