α2-Adrenoreceptors Profile Modulation. 3. (R)-(+)-m-Nitrobiphenyline, a New Efficient and α2C-Subtype Selective Agonist

To assess the stereochemical requirements for efficient α2C-adrenoreceptor activation, the enantiomeric forms of m-nitrobiphenyline [(±)-5] were prepared and tested on cells expressing the human α2-adrenoreceptor subtypes. The importance of chirality was confirmed, since the enantiomer (R)-(+)-5 was...

Full description

Saved in:
Bibliographic Details
Published in:Journal of medicinal chemistry 2007-08, Vol.50 (16), p.3964-3968
Main Authors: Crassous, Pierre-Antoine, Cardinaletti, Claudia, Carrieri, Antonio, Bruni, Bruno, Di Vaira, Massimo, Gentili, Francesco, Ghelfi, Francesca, Giannella, Mario, Paris, Hervé, Piergentili, Alessandro, Quaglia, Wilma, Schaak, Stéphane, Vesprini, Cristian, Pigini, Maria
Format: Article
Language:English
Subjects:
Biological and medical sciences
Catecholaminergic system
Medical sciences
Neuropharmacology
Neurotransmitters. Neurotransmission. Receptors
Pharmacology. Drug treatments
Online Access:Get full text
Tags: Add Tag
No Tags, Be the first to tag this record!
Description
Summary:To assess the stereochemical requirements for efficient α2C-adrenoreceptor activation, the enantiomeric forms of m-nitrobiphenyline [(±)-5] were prepared and tested on cells expressing the human α2-adrenoreceptor subtypes. The importance of chirality was confirmed, since the enantiomer (R)-(+)-5 was much more efficient than (S)-(−)-5 in producing α2C-activation. Surprising reversal of enantioselectivity was observed with respect to structurally similar biphenyline [(±)-1] whose (S)-(−)-form proved the preferred α2C-configuration.
ISSN:0022-2623
1520-4804
DOI:10.1021/jm061487a