Reactions of morphine derivatives with phenyliodo(III)diacetate (PIDA): Synthesis of new morphine analogues+,++

S. Garadnay, P. Herczegh, S. Makleit, T. Friedmann, P. Riba, S. Fürst

Research output: Contribution to journalArticle

2 Citations (Scopus)

Abstract

The reactions of morphine and its derivatives with phenyliodo(III)diacetate (PIDA) have been studied. This methodology has not been introduced to morphine alkaloids, despite the fact that such a strategy would ensure dearomatization of the electrophilic aromatic ring of morphine derivatives leading to nucleophilic ortho-quinoidal structures with potential pharmacological interest. The products, formed in regio- and diastereoselective or diastereospecific reactions, carry mixed-acetal or 1,3-dioxolane moieties. At low concentrations 6a has μ-opioid agonist character but in higher concentrations showed a non receptorial antagonist effect on isolated mouse vas deferens.

Original languageEnglish
Pages (from-to)621-626
Number of pages6
JournalCurrent medicinal chemistry
Volume8
Issue number6
DOIs
Publication statusPublished - Jan 1 2001

ASJC Scopus subject areas

  • Biochemistry
  • Molecular Medicine
  • Pharmacology
  • Drug Discovery
  • Organic Chemistry

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