Extension of the Nenitzescu reaction to simple ketones provides an efficient route to 1′-alkyi-5′-hydroxynaltrindole analogues, potent and selective δ-opioid receptor antagonists

Shefali, Sanjay K. Srivastava, Stephen M. Husbands, John W. Lewis

Research output: Contribution to journalArticlepeer-review

20 Citations (SciVal)

Abstract

The well-established Nenitzescu reaction of imines of β-dicarbonyl systems, as their enamine tautomers, with benzoquinone has been applied to a wide range of such imines to give 5-hydroxyindoles, some of which are of significant biological importance. This reaction has now been extended to the benzylimines of simple ketones, including those of the potent μ-opioid receptor antagonists naltrexone and naloxone. The products of the latter reactions, 1′-benzyl-5′-hydroxyindolomorphinans (7), are potent δ-opioid receptor (DOR) antagonists, confirming the enhancement of DOR antagonist potency and selectivity resulting from the introduction of the 1′-benzyl group.

Original languageEnglish
Pages (from-to)635-638
Number of pages4
JournalJournal of Medicinal Chemistry
Volume48
Issue number2
DOIs
Publication statusPublished - 31 Dec 2004

ASJC Scopus subject areas

  • Molecular Medicine
  • Drug Discovery

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