title: Synthesis and characterization of thiazolo- and thiazinomorphinans and their intermediate products as novel opioid-active derivatives.
abstract: A new procedure was elaborated for the synthesis of potentially opioid-active thiazolo- and thiazinomorphinans. These derivatives and some intermediates related with the synthesis were tested in opioid receptor binding studies. Two compounds showed remarkable µ opioid activities and specificities. The ligand-stimulated [(35) S]GTPγS assays confirmed for both compounds the potent full agonist profile at the µ receptor and for the benzothiazinomorphinan derivative also the δ receptor full agonist character. The structures of these remarkably effective compounds were analyzed with the aid of computational chemistry calculations.
authors.affiliation: Department of Pharmaceutical Chemistry, Institute of Pharmacy, and Center for Molecular Biosciences Innsbruck, University of Innsbruck, Innsbruck, Austria. sipos.attila@pharm.unideb.hu
authors.forename: Attila
authors.initials: A
authors.lastname: Sipos
authors.forename: Valeria
authors.initials: V
authors.lastname: Follia
authors.forename: Sándor
authors.initials: S
authors.lastname: Berényi
authors.forename: Sándor
authors.initials: S
authors.lastname: Antus
authors.forename: Helmut
authors.initials: H
authors.lastname: Schmidhammer
authors.forename: Mariana
authors.initials: M
authors.lastname: Spetea
mesh_terms: D000701:Analgesics, Opioid / Q000138:chemical synthesis / Q000737:chemistry / Q000494:pharmacology*; D000818:Animals; D006168:Guinea Pigs; D008024:Ligands; D009019:Morphinans / Q000138:chemical synthesis / Q000737:chemistry / Q000494:pharmacology*; D051381:Rats; D017207:Rats, Sprague-Dawley; D017465:Receptors, Opioid, delta / Q000187:drug effects* / Q000378:metabolism; D017450:Receptors, Opioid, mu / Q000187:drug effects* / Q000378:metabolism; D013329:Structure-Activity Relationship
chemical_list: D000701:Analgesics, Opioid; D008024:Ligands; D009019:Morphinans; D017465:Receptors, Opioid, delta; D017450:Receptors, Opioid, mu