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Synthesis and Characterization of Thiazolo‐ and Thiazinomorphinans and Their Intermediate Products as Novel Opioid‐Active Derivatives
Author(s) -
Sipos Attila,
Follia Valeria,
Berényi Sándor,
Antus Sándor,
Schmidhammer Helmut,
Spetea Mariana
Publication year - 2012
Publication title -
archiv der pharmazie
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 0.468
H-Index - 61
eISSN - 1521-4184
pISSN - 0365-6233
DOI - 10.1002/ardp.201200176
Subject(s) - chemistry , agonist , stereochemistry , opioid receptor , ligand (biochemistry) , opioid , chemical synthesis , derivative (finance) , receptor , combinatorial chemistry , biochemistry , in vitro , economics , financial economics
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]GTP γ S 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.