6801-26-9Relevant academic research and scientific papers
Synthesis, Pharmacology, and Molecular Docking Studies on 6-Desoxo-N-methylmorphinans as Potent μ-Opioid Receptor Agonists
Dumitrascuta, Maria,Ben Haddou, Tanila,Guerrieri, Elena,Noha, Stefan M.,Schl?fer, Lea,Schmidhammer, Helmut,Spetea, Mariana
, p. 9407 - 9412 (2017)
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 1-4 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.
Probes for narcotic receptor mediated phenomena. 24. synthesis, single crystal X-ray analyses, in vitro and in vivo properties of 6α-and 6β-IODO-3,14-dihydroxy-17-methyl-4,5α-epoxymorphinans
Kayakiri, Hiroshi,Jacobson, Arthur E.,Rice, Kenner C.,Rothman, Richard B.,Xu, Heng,Flippen-Anderson, Judith L.,George, Clifford,Aceto, Mario D.,Bowman, Edward R.,Harris, Louis S.,May, Everette L.,Partilla, John S.,Becketts, Karen
, p. 427 - 438 (2007/10/03)
The 6α- and 6β-iodo-3,14-dihydroxy-17-methyl-4,5α-epoxymorphinans, potential SPECT ligands, were synthesized and found to be μ-selective opioids, more potent in vitro and in vivo than their 6-hydroxy relatives. Single-crystal analysis showed that the 6α- and 6β-iodine atoms are spatially closely located although the C-ring conformations of these compounds are quite different (twist-boat form vs. chair). These epimeric conformational differences were not reflected in their binding affinities.
