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
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author Fantinati, Anna
Bianco, Sara
Guerrini, Remo
Salvadori, Severo
Pacifico, Salvatore
Cerlesi, Maria Camilla
Calo, Girolamo
Trapella, Claudio
author_facet Fantinati, Anna
Bianco, Sara
Guerrini, Remo
Salvadori, Severo
Pacifico, Salvatore
Cerlesi, Maria Camilla
Calo, Girolamo
Trapella, Claudio
author_sort Fantinati, Anna
collection PubMed
description 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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spelling pubmed-54450672017-05-26 A diastereoselective synthesis of Cebranopadol, a novel analgesic showing NOP/mu mixed agonism Fantinati, Anna Bianco, Sara Guerrini, Remo Salvadori, Severo Pacifico, Salvatore Cerlesi, Maria Camilla Calo, Girolamo Trapella, Claudio Sci Rep Article 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. Nature Publishing Group UK 2017-05-25 /pmc/articles/PMC5445067/ /pubmed/28546566 http://dx.doi.org/10.1038/s41598-017-02502-9 Text en © The Author(s) 2017 Open Access This article is licensed under a Creative Commons Attribution 4.0 International License, which permits use, sharing, adaptation, distribution and reproduction in any medium or format, as long as you give appropriate credit to the original author(s) and the source, provide a link to the Creative Commons license, and indicate if changes were made. The images or other third party material in this article are included in the article’s Creative Commons license, unless indicated otherwise in a credit line to the material. If material is not included in the article’s Creative Commons license and your intended use is not permitted by statutory regulation or exceeds the permitted use, you will need to obtain permission directly from the copyright holder. To view a copy of this license, visit http://creativecommons.org/licenses/by/4.0/.
spellingShingle Article
Fantinati, Anna
Bianco, Sara
Guerrini, Remo
Salvadori, Severo
Pacifico, Salvatore
Cerlesi, Maria Camilla
Calo, Girolamo
Trapella, Claudio
A diastereoselective synthesis of Cebranopadol, a novel analgesic showing NOP/mu mixed agonism
title A diastereoselective synthesis of Cebranopadol, a novel analgesic showing NOP/mu mixed agonism
title_full A diastereoselective synthesis of Cebranopadol, a novel analgesic showing NOP/mu mixed agonism
title_fullStr A diastereoselective synthesis of Cebranopadol, a novel analgesic showing NOP/mu mixed agonism
title_full_unstemmed A diastereoselective synthesis of Cebranopadol, a novel analgesic showing NOP/mu mixed agonism
title_short A diastereoselective synthesis of Cebranopadol, a novel analgesic showing NOP/mu mixed agonism
title_sort diastereoselective synthesis of cebranopadol, a novel analgesic showing nop/mu mixed agonism
topic Article
url 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
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