Epiboxidine hydrochlorides (+)-2 and (-)-2, which are the structural analogs of the antipodes of epibatidine (±)-1, as well as the enantiomeric pairs (+)-3/(-)-3 and (+)-4/(-)-4 were synthesized and tested for binding affinity at α4β2 and α7 nicotinic acetylcholine receptor (nAChR) subtypes. Final derivatives were prepared through the condensation of racemic N-Boc-7-azabicyclo[2.2.1]heptane-2-one (±)-5 with the resolving agent (R)-(+)-2-methyl-2-propanesulfinamide. The pharmacological analysis carried out on the three new enantiomeric pairs evidenced an overall negligible degree of enantioselectivity at both nAChRs subtypes, a result similar to that reported for both natural and unnatural epibatidine enantiomers at the same investigated receptor subtypes. Chirality 24:543-551, 2012.
The enantiomers of epiboxidine and of two related analogs: Synthesis and estimation of their binding affinity at α4β2 and α7 neuronal nicotinic acetylcholine receptors / C.M.L. Dallanoce, C. Matera, M. DE AMICI, L. Rizzi, L. Pucci, C. Gotti, F. Clementi, C. DE MICHELI. - In: CHIRALITY. - ISSN 0899-0042. - 24:7(2012 Jul), pp. 543-551.
|Titolo:||The enantiomers of epiboxidine and of two related analogs: Synthesis and estimation of their binding affinity at α4β2 and α7 neuronal nicotinic acetylcholine receptors|
MATERA, CARLO (Secondo)
CLEMENTI, FRANCESCO (Penultimo)
DE MICHELI, CARLO (Ultimo)
|Settore Scientifico Disciplinare:||Settore CHIM/08 - Chimica Farmaceutica|
|Data di pubblicazione:||lug-2012|
|Digital Object Identifier (DOI):||http://dx.doi.org/10.1002/chir.22052|
|Appare nelle tipologie:||01 - Articolo su periodico|