Phenolic analogues of diastereoisomeric 2-methyl reversed esters of pethidine
- 1 March 1989
- journal article
- research article
- Published by Oxford University Press (OUP) in Journal of Pharmacy and Pharmacology
- Vol. 41 (3) , 209-211
- https://doi.org/10.1111/j.2042-7158.1989.tb06434.x
Abstract
The preparation and stereochemical characterization of α- and β-isomers of 1,2-dimethyl-4–m-hydroxyphenyl-4-propiony-loxypiperidine are described. Both the α (axial 4-aryl/chair) and β (equatorial 4-aryl/chair) isomers were of low potency or inactive in mice antinociceptive tests. Shortcomings of the α-isomer as a model for the 4-arylpiperidine moiety of morphine are discussed.This publication has 9 references indexed in Scilit:
- Rotational conformation of the phenyl moiety in geminally substituted phenylcyclohexanes with equatorial phenylThe Journal of Organic Chemistry, 1985
- Phenolic analogues of reversed esters of pethidineJournal of Pharmacy and Pharmacology, 1985
- A study of the biologically active conformers for prodine opiates and their derivativesJournal of Computational Chemistry, 1984
- Conformation activity study of 4-phenylpiperidine analgesicsJournal of Medicinal Chemistry, 1982
- Allylprodine analogs as receptor probes. Evidence that phenolic and nonphenolic ligands interact with different subsites on identical opioid receptorsJournal of Medicinal Chemistry, 1981
- Diastereoisomeric esters of 1,2-dimethyl-4-phenylpiperidin-4-ol and related compoundsJournal of the Chemical Society, Perkin Transactions 1, 1972
- Conformational analysis. LXXVIII. The conformation of phenylcyclohexane, and related molecules.Tetrahedron Letters, 1971
- Stereochemical aspects of the synthesis of 4-benzoyl-1,3-dimethyl-4-phenylpiperidine from 1,3-dimethyl-4-piperidoneCanadian Journal of Chemistry, 1970
- Synthetic analgesicsQuarterly Reviews, Chemical Society, 1948