title: Access to 7β-analogs of codeine with mixed μ/δ agonist activity via 6,7-α-epoxide opening.
abstract: (-)-Codeine 1 was converted into previously unknown 7β-methyl-7,8-dihydrocodeine/morphine derivatives such as 13 via classical diaxial opening of α-epoxide 3. Several analogs exhibited dual μ/δ-agonist activity.
authors.affiliation: Department of Chemistry and Biochemistry, University of Texas at Austin, 1 University Station A5300, Austin, TX 78712, United States.
authors.forename: Philip
authors.initials: P
authors.lastname: Magnus
authors.forename: Bahman
authors.initials: B
authors.lastname: Ghavimi
authors.forename: Jotham W
authors.initials: JW
authors.lastname: Coe
mesh_terms: D000818:Animals; D003061:Codeine / Q000031:analogs & derivatives* / Q000494:pharmacology*; D004852:Epoxy Compounds / Q000737:chemistry / Q000494:pharmacology; D006801:Humans; D051379:Mice; D008958:Models, Molecular; D009019:Morphinans / Q000737:chemistry / Q000494:pharmacology; D017465:Receptors, Opioid, delta / Q000819:agonists* / Q000378:metabolism; D017450:Receptors, Opioid, mu / Q000819:agonists* / Q000378:metabolism
chemical_list: D004852:Epoxy Compounds; D009019:Morphinans; D017465:Receptors, Opioid, delta; D017450:Receptors, Opioid, mu; C046877:metopon; D003061:Codeine
keywords: 6,7-α-Epoxide; Metopon; Mixed μ/δ agonist; Opioid