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Please use this identifier to cite or link to this item: http://hdl.handle.net/123456789/17104

Title: Stereochemical influences upon the opioid ligand activities of 4-alkyl-4-arylpiperidine derivatives
Authors: A. F. Casy
G. H. Dewar
Omar A.A. Al Deeb
Keywords: opioid ligand; 4-arylpiperidines; conformation, NMR
Issue Date: 1989
Publisher: Chirality
Abstract: The synthesis and stereochemistry (configuration and preferred solute conformation) of some 4-alkyl (methyl, n-propyl, isobutyl)-4-(3-hydrxyphenyl)-1-methylpiperidines and corresponding 3-methyl diastereoisomeric pairs are reported, together with their in vivo and in vitro activities as opioid ligands. All potent agonists exhibit a preference for axial 4-aryl chair conformations when protonated, and stereochemical analogies with rigid opioids of the benzomorphan class are discussed. Antagonist properties are found in compounds with preference for equatorial 4-aryl chairs, notably the cis 3,4-dimethyl derivative.
URI: http://hdl.handle.net/123456789/17104
Appears in Collections:College of Pharmacy

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