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Published on: July 3, 2015
Synthesis and opioid-receptor binding of novel amino-substituted morphan analogues
G Höfner1, B Streicher, B Wünsch
1Institut für Pharmazie-Zentrum für Pharmaforschung, Universität München, Butenandt Str. 5-13, D-81377 München, Germany.
Abstract:
Starting with methyl 4,6-O-benzylidene-alpha-D-glucopyranoside (4), an optimized procedure is reported for preparation of the bromide 7, which is transformed into the N-acylated heptopyranosamine 9. After introduction of an axially positioned azido moiety in position 3 intramolecular N/O-acetal formation succeeds to provide the morphan analogue 17. In receptor binding studies with radioligands the amines 18b-18d reveal higher affinity for mu-receptors than for kappa-receptors. The most mu-active compound 18b (Ki = 14 nM) contains two aryl substituents, which presumably may occupy both aryl binding sites of mu-receptors.
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