In:
ChemMedChem, Wiley, Vol. 6, No. 11 ( 2011-11-04), p. 2055-2062
Abstract:
1‐Alkyl‐2,3,5‐triaryl‐1 H ‐pyrroles (for which alkyl=methyl, ethyl, n ‐propyl, or 2‐methylpropyl) were tested for stability, estrogen receptor (ER) binding, and inhibition of tumor cell growth. These pyrroles (type B) showed higher stability in aqueous solution than their 1,2,4‐triaryl‐1 H ‐pyrrole congeners (type A pyrroles), exclusive ERα binding (no ERβ interaction), and a hormonal profile of partial agonists at ERα. The most potent compound, 1‐(2‐methylpropyl)‐2,3,5‐tris(4‐hydroxyphenyl)‐1 H ‐pyrrole ( 5 d ), was less active than the lead structure 1,3,5‐tris(4‐hydroxyphenyl)‐4‐propyl‐1 H ‐pyrazole (PPT) in MCF‐7 cells stably transfected with the plasmid ERE wtc luc (MCF‐7/2a), but more potent in U2‐OS/α cells. Furthermore, 5 d showed weak anti‐estrogenic properties (IC 50 =310 n M ). An additional propyl chain at C4 decreased the stability and pharmacological effects.
Type of Medium:
Online Resource
ISSN:
1860-7179
,
1860-7187
DOI:
10.1002/cmdc.201100283
Language:
English
Publisher:
Wiley
Publication Date:
2011
detail.hit.zdb_id:
2209649-8
SSG:
15,3
