title: Cinnamoyl derivatives of 7alpha-aminomethyl-6,14-endo-ethanotetrahydrothebaine and 7alpha-aminomethyl-6,14-endo-ethanotetrahydrooripavine and related opioid ligands.
abstract: A new series of ligands has been synthesized where the cinnamoyl group of the 14-cinnamoylamino morphinones has been introduced to the 7alpha-substituent of the 6,14-bridged oripavine series. In vitro the compounds were mostly low efficacy partial agonists or antagonists with some selectivity for the mu opioid receptor, with evidence of micro efficacy in vivo. The similarity in SAR between these 6,14-bridged oripavines and the 14-cinnamoylamino series suggests a similar mode of interaction with the micro opioid receptor.
authors: Department of Pharmacy and Pharmacology, University of Bath, Bath, BA2 7AY, UK.
authors: David
authors: D
authors: Rennison
authors: Adrian P
authors: AP
authors: Neal
authors: Gerta
authors: G
authors: Cami-Kobeci
authors: Mario D
authors: MD
authors: Aceto
authors: Fernando
authors: F
authors: Martinez-Bermejo
authors: John W
authors: JW
authors: Lewis
authors: Stephen M
authors: SM
authors: Husbands
mesh_terms: D000700:Analgesics / Q000138:chemical synthesis* / Q000494:pharmacology; D000818:Animals; D001667:Binding, Competitive; D016466:CHO Cells; D002934:Cinnamates / Q000138:chemical synthesis* / Q000494:pharmacology; D006224:Cricetinae; D003412:Cricetulus; D006801:Humans; D008024:Ligands; D051379:Mice; D008968:Molecular Conformation; D009292:Narcotic Antagonists; D011869:Radioligand Assay; D011957:Receptors, Opioid / Q000819:agonists*; D017465:Receptors, Opioid, delta / Q000819:agonists / Q000037:antagonists & inhibitors; D017473:Receptors, Opioid, kappa / Q000819:agonists / Q000037:antagonists & inhibitors; D017450:Receptors, Opioid, mu / Q000819:agonists / Q000037:antagonists & inhibitors; D013329:Structure-Activity Relationship; D013797:Thebaine / Q000031:analogs & derivatives* / Q000138:chemical synthesis / Q000494:pharmacology
chemical_list: C524275:7-aminomethyl-6,14-ethanotetrahydrooripavine; C524274:7-aminomethyl-6,14-ethanotetrahydrothebaine; D000700:Analgesics; D002934:Cinnamates; D008024:Ligands; D009292:Narcotic Antagonists; D011957:Receptors, Opioid; D017465:Receptors, Opioid, delta; D017473:Receptors, Opioid, kappa; D017450:Receptors, Opioid, mu; D013797:Thebaine; C005283:oripavine