3 years ago

Synthesis, Pharmacology, and Molecular Docking Studies on 6-Desoxo-N-methylmorphinans as Potent μ-Opioid Receptor Agonists

Synthesis, Pharmacology, and Molecular Docking Studies on 6-Desoxo-N-methylmorphinans as Potent μ-Opioid Receptor Agonists
Tanila Ben Haddou, Helmut Schmidhammer, Stefan M. Noha, Elena Guerrieri, Mariana Spetea, Lea Schläfer, Maria Dumitrascuta
Position 6 of the morphinan skeleton plays a key role in the μ-opioid receptor (MOR) activity in vitro and in vivo. We describe the consequence of the 6-carbonyl group deletion in N-methylmorphinan-6-ones 14 on ligand–MOR interaction, signaling, and antinociception. While 6-desoxo compounds 1a, 2a, and 4a show similar profiles to their 6-keto counterparts, the 6-desoxo-14-benzyloxy substituted 3a displays significantly increased MOR binding and agonist potency and a distinct binding mode compared with its analogue 3.

Publisher URL: http://dx.doi.org/10.1021/acs.jmedchem.7b01363

DOI: 10.1021/acs.jmedchem.7b01363

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