Structure‐Activity Relationship of Oxygenated Morphinans. V. Narcotic agonist and antagonist activity in the 14‐hydroxymorphinan series. Preliminary communication
- 16 December 1981
- journal article
- research article
- Published by Wiley in Helvetica Chimica Acta
- Vol. 64 (8) , 2540-2543
- https://doi.org/10.1002/hlca.19810640809
Abstract
The synthesis of several 14‐hydroxymorphinans, using oxymorphone (= 3, 14‐dihydroxy‐4,5‐epoxy‐N‐methylmorphinan‐6‐one, 1) as starting material, is described. The antinociceptive potency of the N‐methyl substituted 14‐hydroxy‐morphinans was determined. Thus, in order of antinociceptive potency, 14‐hydroxy‐4‐methoxy‐N‐methylmorphinan‐6‐one (5) >4,5‐epoxy‐14‐hydroxy‐N‐methyl‐morphinan‐6‐one (3)>4, 14‐dihydroxy‐N‐methylmorphinan‐6‐one (4)>14‐hydroxy‐4‐methoxy‐N‐methylmorphinan (11) ≈4, 14‐dihydroxy‐N‐methylmorphinan (12). The most potent compound in this series, 14‐hydroxy‐4‐methoxy‐N‐methyl‐morphinan‐6‐one (5), was found to have about six times the potency of morphine; it was equipotent with levorphanol.This publication has 6 references indexed in Scilit:
- Structure‐Activity Relationships of Oxygenated Morphinans. I. 4‐Mono‐ and 3,4‐dimethoxy‐N‐methylmorphinans and ‐N‐methyl‐morphinan‐6‐ones with unusually high antinociceptive potency. Preliminary communicationHelvetica Chimica Acta, 1981
- Long-acting opiate agonists and antagonists: 14-hydroxydihydromorphinone hydrazonesJournal of Medicinal Chemistry, 1980
- A stereoselective total synthesis of 14-hydroxymorphinans. Grewe approachJournal of the American Chemical Society, 1978
- Preparation and Analgesic Activity of Some 3,4-Disubstituted N-Methylmorphinans of the (-)-SeriesHETEROCYCLES, 1977
- Structures Related to Morphine. XXXI.1 2'-Substituted BenzomorphansJournal of Medicinal Chemistry, 1965
- SYNTHETIC ANALGESICS .2. DITHIENYLBUTENYLAMINES AND DITHIENYLBUTYLAMINES1953