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Synthesis and opioid‐receptor binding of novel amino‐substituted morphan analogues
Author(s) -
Höfner Georg,
Streicher Benedikt,
Wünsch Bernhard
Publication year - 2001
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 - 10.1002/1521-4184(200109)334:8/9<284::aid-ardp284>3.0.co;2-b
Subject(s) - chemistry , stereochemistry , moiety , receptor , intramolecular force , aryl , bromide , acetal , chemical synthesis , in vitro , biochemistry , organic chemistry , alkyl
Starting with methyl 4,6‐ O ‐benzylidene‐α‐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 μ‐receptors than for κ‐receptors. The most μ‐active compound 18b (K i = 14 nM) contains two aryl substituents, which presumably may occupy both aryl binding sites of μ‐receptors.