Synthesis and biological evaluation of 14-alkoxymorphinans. 16. 14-O-alkylderivatives of the mu opioid receptor antagonist cyprodime

Authors
Schmidhammer, H Krassnig, R Greiner, E Traynor, JR
Citation
H. Schmidhammer et al., Synthesis and biological evaluation of 14-alkoxymorphinans. 16. 14-O-alkylderivatives of the mu opioid receptor antagonist cyprodime, HETEROCYCLE, 49, 1998, pp. 489-497
Citations number
9
Categorie Soggetti
Organic Chemistry/Polymer Science
Journal title
HETEROCYCLES
ISSN journal
03855414 → ACNP
Volume
49
Year of publication
1998
Pages
489 - 497
Database
ISI
SICI code
0385-5414(199812)49:<489:SABEO1>2.0.ZU;2-4
Abstract
The 14-O-benzyl derivatives of cyprodime and 3-hydroxycyprodime (compounds (5) and (6), respectively) were synthesized in several steps from 3-desoxyn altrexone (2a) and naltrexone (2), respectively. In the mouse vas deferens preparation it was found that a 14-O-benzyl group could enhance mu opioid r eceptor affinity in cyprodime while the mu affinity of 3-hydroxycyprodime w as not changed.