Referenced in: none

Automatically associated channels: Kir2.3

Title: Synthesis and alpha4beta2 nicotinic affinity of unichiral 5-(2-pyrrolidinyl)oxazolidinones and 2-(2-pyrrolidinyl)benzodioxanes.

Authors: Marco Pallavicini, Barbara Moroni, Cristiano Bolchi, Antonio Cilia, Francesco Clementi, Laura Fumagalli, Cecilia Gotti, Fiorella Meneghetti, Loredana Riganti, Giulio Vistoli, Ermanno Valoti

Journal, date & volume: Bioorg. Med. Chem. Lett., 2006 Nov 1 , 16, 5610-5

PubMed link: http://www.ncbi.nlm.nih.gov/pubmed/16942873

Abstract
The RS and SR enantiomers of 2-oxazolidinone and 1,4-benzodioxane bearing a 2-pyrrolidinyl substituent at the 5- and 2-position, respectively, were synthesized as candidate nicotinoids. One of the two benzodioxane stereoisomers reasonably fits the pharmacophore elements of (S)-nicotine and binds at alpha4beta2 nicotinic acetylcholine receptor with submicromolar affinity. Interestingly, both the synthesized pyrrolidinylbenzodioxanes exhibit analogous affinity at alpha(2) adrenergic receptor resembling the behaviour of some known alpha(2)-AR ligands recently proved to possess neuronal nicotinic affinity.