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[cyclohexanedihydropyrano[ 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.

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

FANTINATI, Anna
Primo
;
BIANCO, Sara;SALVADORI, Severo;PACIFICO, Salvatore;GUERRINI, Remo;CERLESI, Maria Camilla;TRAPELLA, Claudio
Ultimo
;
CALO', Girolamo
2017

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[cyclohexanedihydropyrano[ 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.
Fantinati, Anna; Bianco, Sara; Salvadori, Severo; Pacifico, Salvatore; Guerrini, Remo; Cerlesi, Maria Camilla; Trapella, Claudio; Calo', Girolamo
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Utilizza questo identificativo per citare o creare un link a questo documento: http://hdl.handle.net/11392/2371408
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