Accession Number:

ADA513105

Title:

Probes for Narcotic Receptor Mediated Phenomena. 39. Enantiomeric N-Substituted Benzofuro[2,3-c]pyridin-6-ols: Synthesis and Topological Relationship to Oxide-Bridged Phenylmorphans

Descriptive Note:

Journal article

Corporate Author:

NATIONAL INSTITUTES OF HEALTH BETHESDA MD

Report Date:

2009-01-01

Pagination or Media Count:

11.0

Abstract:

Enantiomers of N-substituted benzofuro2,3-cpyridin-6-ols have been synthesized, and the subnanomolar affinity and potent agonist activity of the known racemic N-phenethyl substituted benzofuro2,3-cpyridin-6-ol can now be ascribed to the 4aS,9aR enantiomer. The energy-minimized structures suggest that the active enantiomer bears a greater three-dimensional resemblance to morphine than to an ostensibly structurally similar oxide-bridged phenylmorphan. Structural features of the conformers of N-substituted benzofuro2,3-cpyridin-6-ols were compared to provide the rationale for their binding affinity.

Subject Categories:

  • Biochemistry
  • Physical Chemistry

Distribution Statement:

APPROVED FOR PUBLIC RELEASE