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

Abstract

Enantiomers of N-substituted benzofuro[2,3-c]pyridin-6-ols have been synthesized, and the subnanomolar affinity and potent agonist activity of the known racemic N-phenethyl substituted benzofuro[2,3-c]pyridin-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 benzofuro[2,3-c]pyridin-6-ols were compared to provide the rationale for their binding affinity.

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Document Details

Document Type
Technical Report
Publication Date
Jan 01, 2009
Accession Number
ADA513105

Entities

People

  • Arthur E. Jacobson
  • Christina M. Dersch
  • Jeffrey R. Deschamps
  • Kenner C. Rice
  • Richard B. Rothman
  • Yi Zhang
  • Yong S. Lee

Organizations

  • National Institutes of Health

Tags

Communities of Interest

  • Biomedical

DTIC Thesaurus Topics

  • 1-Ring Heterocyclic Compounds
  • Alcohols
  • Alkanes
  • Bromine Compounds
  • Chemical Shifts
  • Chemical Synthesis
  • Chemistry
  • Chromatography
  • Column Chromatography
  • Crystallization
  • Crystals
  • Drug Abuse
  • Geometry
  • High Vacuum
  • Materials
  • Organic Chemistry
  • X Rays

Fields of Study

  • Chemistry

Readers

  • Neurotoxicology
  • Organic Chemistry