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

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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 -opioid agonist character but in higher concentrations showed a non receptorial antagonist effect on isolated mouse vas deferens.

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

Document Type: Review Article

DOI: http://dx.doi.org/10.2174/0929867013373219

Publication date: May 1, 2001

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  • Current Medicinal Chemistry covers all the latest and outstanding developments in medicinal chemistry and rational drug design. Each issue contains a series of timely in-depth reviews written by leaders in the field covering a range of the current topics in medicinal chemistry. Current Medicinal Chemistry is an essential journal for every medicinal chemist who wishes to be kept informed and up-to-date with the latest and most important developments.
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