Structure-activity study of retinoid agonists bearing substituted dicarba-closo-dodecaborane. Relation between retinoidal activity and conformation of two aromatic nuclei

Citation
Y. Endo et al., Structure-activity study of retinoid agonists bearing substituted dicarba-closo-dodecaborane. Relation between retinoidal activity and conformation of two aromatic nuclei, BIOORG MED, 11(10), 2001, pp. 1307-1311
Citations number
28
Language
INGLESE
art.tipo
Article
Categorie Soggetti
Chemistry & Analysis
Journal title
BIOORGANIC & MEDICINAL CHEMISTRY LETTERS
ISSN journal
0960-894X → ACNP
Volume
11
Issue
10
Year of publication
2001
Pages
1307 - 1311
Database
ISI
SICI code
0960-894X(20010521)11:10<1307:SSORAB>2.0.ZU;2-J
Abstract
We have investigated the structure-activity relationships of the potent ret inoid agonist, 4-[4-(2-propyl-1,2-dicarba-closo-dodecaboran-1-yl)phenylamin o]benzoic acid (BR403), which we have previously reported. Substitution of a methyl group on the aromatic nucleus or a methyl group on the nitrogen at om, or replacement of the amino group with ether, methylene, carboxyl or 1, 1-ethylene greatly decreased the activity. The relatively planar conformati on at the phenyl-N-phenyl moiety seems to play a critical role in the appea rance of the biological activity. (C) 2001 Elsevier Science Ltd. All rights reserved.