Synthesis, opioid receptor binding, and functional activity of 5′-substituted 17-cyclopropylmethylpyrido[2′,3′:6,7]morphinans

Subramaniam Ananthan, Hollis S. Kezar, Surendra K. Saini, Naveen K. Khare, Peg Davis, Christina M. Dersch, Frank Porreca, Richard B. Rothman

Research output: Contribution to journalArticle

14 Scopus citations

Abstract

A series of naltrexone-derived pyridomorphinans possessing various substituents at the 5′-position on the pyridine ring were synthesized and evaluated for opioid receptor binding in rodent brain membranes and functional activity in smooth muscle preparations. While the introduction of aromatic 1-pyrrolyl group (6h) improved the δ affinity and δ antagonist potency of the parent compound (3), the introduction of guanidine group (6i) transformed it to a κ selective ligand in opioid receptor binding and [35S]GTP-γ-S functional assays.

Original languageEnglish (US)
Pages (from-to)529-532
Number of pages4
JournalBioorganic and Medicinal Chemistry Letters
Volume13
Issue number3
DOIs
StatePublished - Feb 1 2003

ASJC Scopus subject areas

  • Biochemistry
  • Molecular Medicine
  • Molecular Biology
  • Pharmaceutical Science
  • Drug Discovery
  • Clinical Biochemistry
  • Organic Chemistry

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