The Enantiomers of Epiboxidine and of Two Related Analogs: Synthesis and Estimation of Their Binding Affinity at α4β2 and α7 Neuronal Nicotinic Acetylcholine Receptors

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The Enantiomers of Epiboxidine and of Two Related Analogs: Synthesis and Estimation of Their Binding Affinity at α4β2 and α7 Neuronal Nicotinic Acetylcholine Receptors

The Enantiomers of Epiboxidine and of Two Related Analogs: Synthesis and Estimation of Their Binding Affinity at α4β2 and α7 Neuronal Nicotinic Acetylcholine Receptors

Clelia Dallanoce, Carlo Matera, Marco De Amici, Luca Rizzi, Luca Pucci, Cecilia Gotti, Francesco Clementi, Carlo De Micheli

Chirality. 2012 Jul;24(7):543-51.

PMID: 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 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.

Chemicals Related in the Paper:

Catalog Number	Product Name	Structure	CAS Number	Price
AP188895967	Epiboxidine hydrochloride		188895-96-7	Price

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