Novel opiates and antagonists. 6. 7-Alkyl-6,7-didehydromorphinans

A method for preparing a variety of 7-alkyl-6,7- didehydromorphinans from the corresponding 6- morphinanones is described. The key intermediates in this sequence are the 7-formyl derivatives. The two epimeric B/C-trans-7-(1- hydroxypentyl ) morphinans ( 16a ,b) are stereochemically similar to the en...

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Bibliographic Details
Published in:Journal of medicinal chemistry 1984-05, Vol.27 (5), p.632-637
Main Authors: Quick, James, Herlihy, Patricia, Howes, John F
Format: Article
Language:English
Subjects:
Analgesia
Animals
Biological Assay
Indicators and Reagents
Magnetic Resonance Spectroscopy
Mice
Morphinans - chemical synthesis
Morphinans - pharmacology
Narcotic Antagonists - chemical synthesis
Narcotic Antagonists - pharmacology
Narcotics - chemical synthesis
Narcotics - pharmacology
Rats
Structure-Activity Relationship
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Description
Summary:A method for preparing a variety of 7-alkyl-6,7- didehydromorphinans from the corresponding 6- morphinanones is described. The key intermediates in this sequence are the 7-formyl derivatives. The two epimeric B/C-trans-7-(1- hydroxypentyl ) morphinans ( 16a ,b) are stereochemically similar to the endo- ethanotetrahydrooripavines and are extremely potent in the mouse writhing test. The corresponding B/C-cis -7-(1- hydroxypentyl ) morphinans are inactive in this test.
ISSN:0022-2623
1520-4804
DOI:10.1021/jm00371a013