Scientific Reports (May 2017)

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

  • Anna Fantinati,
  • Sara Bianco,
  • Remo Guerrini,
  • Severo Salvadori,
  • Salvatore Pacifico,
  • Maria Camilla Cerlesi,
  • Girolamo Calo,
  • Claudio Trapella

DOI
https://doi.org/10.1038/s41598-017-02502-9
Journal volume & issue
Vol. 7, no. 1
pp. 1 – 7

Abstract

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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.