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Structure-Activity Relationship of Oxygenated Morphinans. VII. 5-Methylated and 14-Hydroxy-substituted Agonists and Antagonists of the 4-Hydroxy- and 3, 4-Dioxygenated 6-Morphinanone Series

✍ Scribed by Arnold Brossi; Louise Atwell; Arthur E. Jacobson; Maria D. Rozwadowska; Helmut Schmidhammer; Judith L. Flippen-Anderson; Richard Gilardi

Book ID: 102857961
Publisher: John Wiley and Sons
Year: 1982
Tongue: German
Weight: 716 KB
Volume: 65
Category: Article
ISSN: 0018-019X
DOI: 10.1002/hlca.19820650804

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✦ Synopsis

Abstract

Several morphinanone agonists differently substituted at C(3), C(4), C(5) and C (14) and antagonists of the 4‐hydroxy and 3, 4‐dimethoxy series were prepared by conventional chemistry. It was demonstrated that the oxygenation pattern in the bay‐area, encompassing C(3) and C(4), is important. Alkylation at C(5) or hydroxylation at C(14) lowered the potency of the compounds. The most potent agonist was found to be the N‐phenethyl‐substituted ketone 27, which was six times more potent than morphine in the hot‐plate assay. The 3, 4‐methylenedioxy‐substituted ketone 9 was about 20 times less potent than its 3, 4‐dimethoxy congener. An X‐ray analysis of 9 and a representative agonist showed that the stereochemical features in the bay‐area were similar and could not be used to explain this difference.

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