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

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

Volume: 8 Issue: 6

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

Affiliation:

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

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.

Cite this article as:

Garadnay S., Herczegh P., Makleit S., Friedmann T., Riba P. and Furst S., Reactions of Morphine Derivatives with Phenyliodo(III)Diacetate (PIDA) Synthesis of New Morphine Analogues+,++, Current Medicinal Chemistry 2001; 8 (6) . https://dx.doi.org/10.2174/0929867013373219