A diastereoselective synthesis of Cebranopadol, a novel analgesic showing NOP/mu mixed agonism
Abstract 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 ch...
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Nature Portfolio
2017
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oai:doaj.org-article:f9793336055c4632b76511f6e31645712021-12-02T12:30:24ZA diastereoselective synthesis of Cebranopadol, a novel analgesic showing NOP/mu mixed agonism10.1038/s41598-017-02502-92045-2322https://doaj.org/article/f9793336055c4632b76511f6e31645712017-05-01T00:00:00Zhttps://doi.org/10.1038/s41598-017-02502-9https://doaj.org/toc/2045-2322Abstract 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.Anna FantinatiSara BiancoRemo GuerriniSevero SalvadoriSalvatore PacificoMaria Camilla CerlesiGirolamo CaloClaudio TrapellaNature PortfolioarticleMedicineRScienceQENScientific Reports, Vol 7, Iss 1, Pp 1-7 (2017) |
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Medicine R Science Q |
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Medicine R Science Q Anna Fantinati Sara Bianco Remo Guerrini Severo Salvadori Salvatore Pacifico Maria Camilla Cerlesi Girolamo Calo Claudio Trapella A diastereoselective synthesis of Cebranopadol, a novel analgesic showing NOP/mu mixed agonism |
| description |
Abstract 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. |
| format |
article |
| author |
Anna Fantinati Sara Bianco Remo Guerrini Severo Salvadori Salvatore Pacifico Maria Camilla Cerlesi Girolamo Calo Claudio Trapella |
| author_facet |
Anna Fantinati Sara Bianco Remo Guerrini Severo Salvadori Salvatore Pacifico Maria Camilla Cerlesi Girolamo Calo Claudio Trapella |
| author_sort |
Anna Fantinati |
| title |
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_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_sort |
diastereoselective synthesis of cebranopadol, a novel analgesic showing nop/mu mixed agonism |
| publisher |
Nature Portfolio |
| publishDate |
2017 |
| url |
https://doaj.org/article/f9793336055c4632b76511f6e3164571 |
| work_keys_str_mv |
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1718394432885096448 |