Phenolic analogues of diastereoisomeric 2-methyl reversed esters of pethidine.
The preparation and stereochemical characterization of alpha- and beta-isomers of 1,2-dimethyl-4-m-hydroxyphenyl-4-propionyloxypiperidine are described. Both the alpha (axial 4-aryl/chair) and beta (equatorial 4-aryl/chair) isomers were of low potency or inactive in mice antinociceptive tests. Shortcomings of the alpha-isomer as a model for the 4-arylpiperidine moiety of morphine are discussed.
Casy
A F
AF
School of Pharmacy and Pharmacology, University of Bath, UK.
Dewar
G H
GH
Pascoe
R A
RA
D000700:Analgesics; D000818:Animals; D009682:Magnetic Resonance Spectroscopy; D008614:Meperidine / Q000031:analogs & derivatives* / Q000378:metabolism / Q000494:pharmacology; D051379:Mice; D009020:Morphine / Q000494:pharmacology; D010636:Phenols / Q000378:metabolism; D013237:Stereoisomerism
D000700:Analgesics; D010636:Phenols; D009020:Morphine; D008614:Meperidine