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Stereochemical studies of the 4-alkyl-4-arylpiperidine class of opioid ligand

✍ Scribed by A. F. Casy; G. H. Dewar; Omar A. A. Al-Deeb

Publisher: John Wiley and Sons
Year: 1989
Tongue: English
Weight: 551 KB
Volume: 27
Category: Article
ISSN: 0749-1581
DOI: 10.1002/mrc.1260271012

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✦ Synopsis

The 'H (270,400 MHz) and I3C (67.5 MHz) NMR spectra of some 4-methyl-(also 4-n-propyl-and -isobutyl)-4-(Ihydroxy-and 3-methoxy-pheny1)pipridines and their Imethyl diastereoisomers are reported. Many of the compounds had opioid ligand activities. The data were analysed in terms of preferred conformation and configuration (>methyl derivatives). Only compounds with preference for axial Caryl chair conformations displayed marked agonist properties and the one potent antagonist, cis-1,3,4-trimethyl-4-(3-hydroxyphenyl)piperidine, favoured an equatorial Qaryl chair.

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