RESUMO
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 mu-opioid agonist character but in higher concentrations showed a non receptorial antagonist effect on isolated mouse vas deferens.
Assuntos
Acetatos/química , Analgésicos Opioides/síntese química , Analgésicos Opioides/farmacologia , Iodobenzenos/química , Derivados da Morfina/síntese química , Derivados da Morfina/farmacologia , Animais , Relação Dose-Resposta a Droga , Feminino , Cobaias , Técnicas In Vitro , Espectroscopia de Ressonância Magnética , Masculino , Camundongos , Músculo Esquelético/efeitos dos fármacos , Músculo Esquelético/fisiologia , Músculo Liso/efeitos dos fármacos , Músculo Liso/fisiologia , Nociceptores/efeitos dos fármacos , Medição da Dor/efeitos dos fármacos , Ratos , Ratos Wistar , Ducto Deferente/efeitos dos fármacos , Ducto Deferente/fisiologiaRESUMO
The synthesis of the dansyl derivatives of the pharmacologically important 6,14-ethenomorphinans has not been reported. The authors realized the preparation of the dansyl derivatives (2a-i) of some 20-alkyl(aralkyl)-orvinols (1a-i). The authors unequivocally proved the structure of the parent compounds, and their dansyl derivatives. The authors also investigated certain analitical characteristics (thin-layer chromatography, UV-spectral data and reversed-phase HPLC purity tests) for the detection if necessary of these compound in biological fluid. Namely, due to the fluorescent properties of the dansyl derivatives, the sensitivity and selectivity of the analytical determinations of the parent compounds are significantly enhanced.
