Novel delta-opioid-receptor-selective ligands in the 14-alkoxy-substituted indolo- and benzofuromorphinan series

Dauren Biyashev, Krisztina Monory, Sandor Benyhe, Johannes Schütz, Martin Koch, Helmut Schmidhammer, Anna Borsodi

Research output: Contribution to journalArticle

9 Citations (Scopus)

Abstract

Several new indolo- and benzofuromorphinans substituted at the positions 5 and 14 were prepared and tested in vitro by means of opioid-receptor binding and functional ([35S]GTPγS binding) assays. All compounds 1-11 displayed high affinity for δ opioid-binding sites (Table 1). Compound 4 proved to be an agonist, and all other compounds were antagonists. The presence of a Me group at position 5 induced no change in δ affinity (see 1 vs. 3), but decreased the μ and κ affinities. An EtO group at position 14 conferred a very high affinity and also high selectivity to δ opioid receptors (see 2 and 10). Chain elongation of the 14-alkoxy group resulted in compounds with reduced δ affinity and selectivity (see 4 and 11 and also 5-9). The results of the present study indicate that the 5- and 14-positions of indolo- and benzofuromorphinans represent critical sites that could be a trigger to develop new compounds with increased δ affinity and/or selectivity.

Original languageEnglish
Pages (from-to)2015-2021
Number of pages7
JournalHelvetica Chimica Acta
Volume84
Issue number7
DOIs
Publication statusPublished - Sep 11 2001

ASJC Scopus subject areas

  • Catalysis
  • Biochemistry
  • Drug Discovery
  • Physical and Theoretical Chemistry
  • Organic Chemistry
  • Inorganic Chemistry

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