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Stereochemical studies of the 4‐alkyl‐4‐arylpiperidine class of opioid ligand
Author(s) -
Casy A. F.,
Dewar G. H.,
AlDeeb Omar A. A.
Publication year - 1989
Publication title -
magnetic resonance in chemistry
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 0.483
H-Index - 72
eISSN - 1097-458X
pISSN - 0749-1581
DOI - 10.1002/mrc.1260271012
Subject(s) - chemistry , diastereomer , stereochemistry , aryl , piperidine , ligand (biochemistry) , agonist , alkyl , nmr spectra database , spectral line , receptor , organic chemistry , biochemistry , physics , astronomy
The 1 H (270, 400 MHz) and 13 C (67.5 MHz) NMR spectra of some 4‐methyl‐ (also 4‐ n ‐propyl‐ and ‐isobutyl)‐4‐(3‐hydroxy‐ and 3‐methoxy‐phenyl)piperidines and their 3‐methyl diastereoisomers are reported. Many of the compounds had opioid ligand activities. The data were analysed in terms of preferred conformation and configuration (3‐methyl derivatives). Only compounds with preference for axial 4‐aryl chair conformations displayed marked agonist properties and the one potent antagonist, cis ‐1,3,4‐trimethyl‐4‐(3‐hydroxyphenyl)piperidine, favoured an equatorial 4‐aryl chair.