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Synthesis and biological evaluation of 14‐alkoxymorphinans. Part 7. 14,14′‐dimethoxy analogues of norbinaltorphimine: Synthesis and determination of their χ opioid antagonist selectivity
Author(s) -
Schmidhammer Helmut,
Ganglbauer Ernst,
Mitterdorfer Jörg,
Rollinger Judith M.,
Smith Colin F. C.
Publication year - 1990
Publication title -
helvetica chimica acta
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 0.74
H-Index - 82
eISSN - 1522-2675
pISSN - 0018-019X
DOI - 10.1002/hlca.19900730622
Subject(s) - chemistry , selectivity , antagonist , combinatorial chemistry , stereochemistry , opioid receptor , receptor , pharmacology , organic chemistry , biochemistry , catalysis , medicine
The bimorphinans 6 and 7 have been prepared from 14 ‐ O ‐methylnaloxone ( 2 ) and 14‐ O ‐methylnaltrexone ( 3 ), respectively. The known compounds 2 and 3 were synthesized by a different route than the route described. Bimorphinan 7 possessed a similar χ receptor affinity to norbinaltorphimine ( 1 ) but had a reduced selectivity due to marked increases in μ and δ receptor affinity. Bimorphinan 6 was both a less selective and less potent χ antagonist than 1 .