A diastereoselective synthesis of Cebranopadol, a novel analgesic showing NOP/mu mixed agonism

A diastereoselective synthesis of the title compound as a single E diastereomer has been efficiently accomplished by assembling the featured pyrano-indole scaffold of the spiro[cyclohexane-dihydropyrano[3,4-b]-indole]-amine framework through an oxa-Pictet-Spengler reaction, promoted by a cheap and g...

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Detalles Bibliográficos
Autores principales: Fantinati, Anna, Bianco, Sara, Guerrini, Remo, Salvadori, Severo, Pacifico, Salvatore, Cerlesi, Maria Camilla, Calo, Girolamo, Trapella, Claudio
Formato: Online Artículo Texto
Lenguaje:English
Publicado: Nature Publishing Group UK 2017
Materias:
Article
Acceso en línea:https://www.ncbi.nlm.nih.gov/pmc/articles/PMC5445067/
https://www.ncbi.nlm.nih.gov/pubmed/28546566
http://dx.doi.org/10.1038/s41598-017-02502-9
Descripción
Sumario:A diastereoselective synthesis of the title compound as a single E diastereomer has been efficiently accomplished by assembling the featured pyrano-indole scaffold of the spiro[cyclohexane-dihydropyrano[3,4-b]-indole]-amine framework through an oxa-Pictet-Spengler reaction, promoted by a cheap and green Zeolite catalyst. Basic pharmacological experiments demonstrate that Cebranopadol acts as a mixed nociception/orphanin FQ (NOP) and mu (MOP) opioid receptor agonist useful for treatment of chronic pain.

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