Reactions of Morphine Derivatives with Phenyliodo(III)Diacetate (PIDA) Synthesis of New Morphine Analogues+,++

Author(s): S. Garadnay, P. Herczegh, S. Makleit, T. Friedmann, P. Riba, S. Furst.

Journal Name: Current Medicinal Chemistry

Volume 8 , Issue 6 , 2001

Become EABM
Become Reviewer


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.

Keywords: Morphine, Phenyliodo(III)Diacetate, Morphine Analogues, GPI, Mouse vas deferens MVD

Rights & PermissionsPrintExport Cite as

Article Details

Year: 2001
Page: [621 - 626]
Pages: 6
DOI: 10.2174/0929867013373219
Price: $58

Article Metrics

PDF: 1