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Digitale Medien

Stereochemical influences upon the opioid ligand activities of 4-alkyl-4-arylpiperidine derivatives (1989)

Casy, A. F. ; Dewar, G. H. ; Al Deeb, Omar A.A.

New York, NY [u.a.] : Wiley-Blackwell

Chirality 1 (1989), S. 202-208

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ISSN: 0899-0042

Schlagwort(e): opioid ligand ; 4-arylpiperidines ; conformation, NMR ; Chemistry ; Organic Chemistry

Quelle: Wiley InterScience Backfile Collection 1832-2000

Thema: Chemie und Pharmazie

Notizen: 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.

Zusätzliches Material: 3 Tab.

Materialart: Digitale Medien

URL: http://dx.doi.org/10.1002/chir.530010305

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Digitale Medien

Stereochemistry of diastereoisomeric propionyl esters of 4-(2-furyl)-3-methyl-1-phenethyl-piperidin-4-ols and the analgesic ether derived from their acid-catalysed ethanolysis (1983)

Casy, A. F. ; Dewar, G. H. ; Pascoe, R. A.

Chichester : Wiley-Blackwell

Organic Magnetic Resonance 21 (1983), S. 137-139

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ISSN: 0030-4921

Schlagwort(e): Chemistry ; Analytical Chemistry and Spectroscopy

Quelle: Wiley InterScience Backfile Collection 1832-2000

Thema: Chemie und Pharmazie

Notizen: The stereochemistry of diastereoisomeric propionyl esters of 4-(2-furyl)-3-methyl-1-phenethylpiperidin-4-ols has been established by 13C NMR analysis. Both isomers, after acid-catalysed ethanolysis, are converted to the corresponding 4-ethoxy derivative of configuration (t-3-Me, r-4-OEt) that correlates with its analgesic properties.

Zusätzliches Material: 1 Tab.

Materialart: Digitale Medien

URL: http://dx.doi.org/10.1002/omr.1270210212

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Digitale Medien

Stereochemical studies of the 4-alkyl-4-arylpiperidine class of opioid ligand (1989)

Casy, A. F. ; Dewar, G. H. ; Al-Deeb, Omar A. A.

Chichester : Wiley-Blackwell

Organic Magnetic Resonance 27 (1989), S. 964-972

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ISSN: 0749-1581

Schlagwort(e): 4-Alkyl-4-arylpiperidines ; Opioid ligands ; 1H NMR ; 13C NMR ; Stereochemistry ; Conformational analysis ; Chemistry ; Analytical Chemistry and Spectroscopy

Quelle: Wiley InterScience Backfile Collection 1832-2000

Thema: Chemie und Pharmazie

Notizen: The 1H (270, 400 MHz) and 13C (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.

Zusätzliches Material: 2 Ill.

Materialart: Digitale Medien

URL: http://dx.doi.org/10.1002/mrc.1260271012

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