The enantiomers of epiboxidine and of two related analogs: synthesis and estimation of their binding affinity at α4ß2 and α7 neuronal nicotinic acetylcholine receptors.
Chirality
; 24(7): 543-51, 2012 Jul.
Article
en En
| MEDLINE
| ID: mdl-22566097
ABSTRACT
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 α4ß2 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.
Texto completo:
1
Colección:
01-internacional
Banco de datos:
MEDLINE
Asunto principal:
Receptores Nicotínicos
/
Isoxazoles
/
Neuronas
Límite:
Animals
Idioma:
En
Revista:
Chirality
Asunto de la revista:
BIOLOGIA MOLECULAR
/
QUIMICA
Año:
2012
Tipo del documento:
Article
País de afiliación:
Italia