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Current Medicinal Chemistry


ISSN (Print): 0929-8673
ISSN (Online): 1875-533X

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 and S. Furst

Volume 8 , Issue 6 , 2001

Page: [621 - 626] Pages: 6

DOI: 10.2174/0929867013373219

Price: $65


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

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