title: Synthesis and opioid activity of novel 6-ketolevorphanol derivatives.
abstract: Novel 6-ketolevorphanol analogs with diverse substitution patterns at ring C were synthesized and their binding affinities at the μ,δ and κ opioid receptors were investigated. The in vitro activity of the new analogs was then evaluated in the functional assay based on the electrically-stimulated contractions of the mouse ileum. It was shown that analogs with  Δ7,8 bond had no significant potency at any of the opioid receptor types. In contrast, analogs with the saturated ring C were either potent κ agonist or antagonist depending on the absence or presence of the hydroxyl group in position 14.
authors: Department of Organic Chemistry, University of Debrecen, Debrecen, Hungary.
authors: Zsuzsanna
authors: Z
authors: Gyulai
authors: Antal
authors: A
authors: Udvardy
authors: Attila
authors: A
authors: Cs Bényei
authors: Jakub
authors: J
authors: Fichna
authors: Katarzyna
authors: K
authors: Gach
authors: Martin
authors: M
authors: Storr
authors: Géza
authors: G
authors: Tóth
authors: Sándor
authors: S
authors: Antus
authors: Sándor
authors: S
authors: Berényi
authors: Anna
authors: A
authors: Janecka
authors: Attila
authors: A
authors: Sipos
mesh_terms: D000701:Analgesics, Opioid / Q000138:chemical synthesis* / Q000737:chemistry / Q000494:pharmacology*; D000818:Animals; D018360:Crystallography, X-Ray; D004305:Dose-Response Relationship, Drug; D007082:Ileum / Q000166:cytology / Q000187:drug effects; D007659:Ketones / Q000138:chemical synthesis / Q000737:chemistry / Q000494:pharmacology; D007981:Levorphanol / Q000138:chemical synthesis / Q000737:chemistry / Q000494:pharmacology; D008297:Male; D051379:Mice; D015394:Molecular Structure; D009119:Muscle Contraction / Q000187:drug effects*; D041701:Swiss 3T3 Cells
chemical_list: D000701:Analgesics, Opioid; D007659:Ketones; D007981:Levorphanol