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  • 11
    Electronic Resource
    Electronic Resource
    Studies in Alkyl-Oxygen Heterolysis. Some 4-Alkoxypiperidines Related to Reversed Esters of Pethidine (1965)
    s.l. : American Chemical Society
    Journal of medicinal chemistry 8 (1965), S. 57-61 
    Details
    ISSN: 1520-4804
    Source: ACS Legacy Archives
    Topics: Chemistry and Pharmacology
    Type of Medium: Electronic Resource
    URL: http://dx.doi.org/10.1021/jm00325a014
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  • 12
    Electronic Resource
    Electronic Resource
    Stereochemistry of Certain Analgesics (1954)
    [s.l.] : Nature Publishing Group
    Nature 173 (1954), S. 1231-1232 
    Details
    ISSN: 1476-4687
    Source: Nature Archives 1869 - 2009
    Topics: Biology , Chemistry and Pharmacology , Medicine , Natural Sciences in General , Physics
    Notes: [Auszug] We have established that the analgesically active isomers '(-)-methadone' ((-)-6-dimethylamino-4: 4-diphenylheptan-3-one), (-)-ethyl-l: l-diphenyl-3-di-methylaminobutyl sulphone, and (+)-3-dimethyl-amino-1: l-(2'-thienyl)-but-l-ene, possess identical configurations which are related to ...
    Type of Medium: Electronic Resource
    URL: http://dx.doi.org/10.1038/1731231a0
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  • 13
    Electronic Resource
    Electronic Resource
    Ketal formation in 4-piperidones (1964)
    Springer
    Cellular and molecular life sciences 20 (1964), S. 437-438 
    Details
    ISSN: 1420-9071
    Source: Springer Online Journal Archives 1860-2000
    Topics: Biology , Medicine
    Notes: Zusammenfassung Die Reaktion gewisser heterocyclischer Ketone mit Äthanol in Gegenwart von Säure ist abhängig von der Ringgrösse und wird plötzlich durch die Wechselwirkung von 1,2-cis- oder 1,3-diaxalen Substituenten beeinflusst.
    Type of Medium: Electronic Resource
    URL: http://dx.doi.org/10.1007/BF02152135
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  • 14
    Electronic Resource
    Electronic Resource
    Stereochemical influences upon the opioid ligand activities of 4-alkyl-4-arylpiperidine derivatives (1989)
    New York, NY [u.a.] : Wiley-Blackwell
    Chirality 1 (1989), S. 202-208 
    Details
    ISSN: 0899-0042
    Keywords: opioid ligand ; 4-arylpiperidines ; conformation, NMR ; Chemistry ; Organic Chemistry
    Source: Wiley InterScience Backfile Collection 1832-2000
    Topics: Chemistry and Pharmacology
    Notes: 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.
    Additional Material: 3 Tab.
    Type of Medium: Electronic Resource
    URL: http://dx.doi.org/10.1002/chir.530010305
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  • 15
    Electronic Resource
    Electronic Resource
    PMR studies of the deuteration and hydration of 4-piperidones (1969)
    Chichester : Wiley-Blackwell
    Organic Magnetic Resonance 1 (1969), S. 389-399 
    Details
    ISSN: 0030-4921
    Keywords: Chemistry ; Analytical Chemistry and Spectroscopy
    Source: Wiley InterScience Backfile Collection 1832-2000
    Topics: Chemistry and Pharmacology
    Notes: PMR spectra of substituted 4-piperidones in base and salt forms in D2O, water and other solvents are reported, and spectral characteristics interpreted in terms of equilibria between free ketone and 4,4-dideuteroxy (or hydroxy) forms. It is shown that 1-mono and 1,3-disubstituted-4-piperidones exist extensively as the corresponding dideuteroxy (or hydrated) species in D2O (or H2O) provided the ring nitrogen atom is positively charged, and that 3-substituents decrease the population of these forms. The facile D/H exchange of α-protons in the piperidone bases is also demonstrated.
    Additional Material: 3 Ill.
    Type of Medium: Electronic Resource
    URL: http://dx.doi.org/10.1002/mrc.1270010506
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  • 16
    Electronic Resource
    Electronic Resource
    Conformational analysis of the tropane analogue of pethidine and related compounds by 1H NMR spectroscopy (1974)
    Chichester : Wiley-Blackwell
    Organic Magnetic Resonance 6 (1974), S. 441-444 
    Details
    ISSN: 0030-4921
    Keywords: Chemistry ; Analytical Chemistry and Spectroscopy
    Source: Wiley InterScience Backfile Collection 1832-2000
    Topics: Chemistry and Pharmacology
    Notes: The preferred solute conformation of ethyl 3α-phenyltropane-3β-carboxylate hydrochloride, the tropane analogue of pethidine, is shown to be a piperidine chair with an axial 3-phenyl substituent by analysis of its 1H NMR characteristics and spectral comparisons with model compounds. Conformational studies of synthetic intermediates are also reported and favoured boat forms identified for 3α-diphenylhydroxymethyl-3β-tropanol and 3α-phenyl-3β-tropanyl phenyl ketone. In the hot-plate test for analgesia performed on mice, ethyl 3α-phenyltropane-3β-carboxylate is about 1·5 times as effective as pethidine.
    Additional Material: 1 Tab.
    Type of Medium: Electronic Resource
    URL: http://dx.doi.org/10.1002/mrc.1270060809
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  • 17
    Electronic Resource
    Electronic Resource
    Conformationally dependent influence of 3-substituents on the observable magnetic non-equivalence of benzylic methylene protons in N-benzylpiperidines (1975)
    Chichester : Wiley-Blackwell
    Organic Magnetic Resonance 7 (1975), S. 544-547 
    Details
    ISSN: 0030-4921
    Keywords: Chemistry ; Analytical Chemistry and Spectroscopy
    Source: Wiley InterScience Backfile Collection 1832-2000
    Topics: Chemistry and Pharmacology
    Notes: Examples are given of the conformationally dependent influence of 3-substituents (methyl, n-propyl, allyl, aryl, hydroxy and acyloxy) on the magnetic non-equivalence of the benzylic methylene protons (NCH2Ph) of N-benzylpiperidine as observable by 1H NMR. The results, together with data already reported, emphasise the value of 1H NMR studies of N-benzyl derivatives in stereochemical investigations of substituted piperidines.
    Additional Material: 1 Tab.
    Type of Medium: Electronic Resource
    URL: http://dx.doi.org/10.1002/mrc.1270071105
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  • 18
    Electronic Resource
    Electronic Resource
    PMR studies of N-substituted-2,5-dimethyl-4-piperidones (1970)
    Chichester : Wiley-Blackwell
    Organic Magnetic Resonance 2 (1970), S. 197-208 
    Details
    ISSN: 0030-4921
    Keywords: Chemistry ; Analytical Chemistry and Spectroscopy
    Source: Wiley InterScience Backfile Collection 1832-2000
    Topics: Chemistry and Pharmacology
    Notes: PMR characteristics of some isomeric 1-substituted-2,5-dimethyl-4-piperidones are reported and major isomers shown to have a trans 2,5-dimethyl configuration. Differences between benzylic methylene signals of isomeric 1-benzyl analogs provide evidence of the preferred conformation of the cis derivative. Evidence of the D/H exchange of α-protons in 1,2,5-trimethyl-4-piperidone base and of addition of D2O to the carbonyl group of the corresponding hydrochloride and methiodide salts is also demonstrated. The effect of a 2-methyl substituent upon the chemical shifts of N-methyl groups in some piperidine methiodides is discussed.
    Additional Material: 3 Ill.
    Type of Medium: Electronic Resource
    URL: http://dx.doi.org/10.1002/mrc.1270020213
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  • 19
    Electronic Resource
    Electronic Resource
    Configurational and conformational studies of N,N-dimethylpiperidinium derivatives by 13C and 1H NMR spectroscopy (1982)
    Chichester : Wiley-Blackwell
    Organic Magnetic Resonance 18 (1982), S. 171-175 
    Details
    ISSN: 0030-4921
    Keywords: Chemistry ; Analytical Chemistry and Spectroscopy
    Source: Wiley InterScience Backfile Collection 1832-2000
    Topics: Chemistry and Pharmacology
    Notes: The 13C and 1H NMR spectra of a series of methiodides of mono- and di-C-methyl derivatives of 1-methyl-4-phenyl-4-piperidinols are reported and chemical shift data analysed in terms of configurations and conformations of isomeric sets. Results demondtrate the value of quaternary salt NMR data as an aid to configurational assignment, and the evaluation of non-bonded interactions governing conformational equilibria in piperidine derivatives.
    Additional Material: 2 Tab.
    Type of Medium: Electronic Resource
    URL: http://dx.doi.org/10.1002/mrc.1270180312
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  • 20
    Electronic Resource
    Electronic Resource
    Stereochemical studies of substituted 6,7- benzomorphan derivatives by 13C and 1H NMR spectroscopy (1982)
    Chichester : Wiley-Blackwell
    Organic Magnetic Resonance 20 (1982), S. 254-259 
    Details
    ISSN: 0030-4921
    Keywords: Chemistry ; Analytical Chemistry and Spectroscopy
    Source: Wiley InterScience Backfile Collection 1832-2000
    Topics: Chemistry and Pharmacology
    Notes: The 13C NMR spectra of a series of 6,7-benzomorphan derivatives variously substituted at C-5 and C-9 by methyl and at C-3 by cyano, alkyl and aralkyl groups, together with certain 3-cyano, 3-allyl or benzyl congeners, are reported and chemical shift data analysed in terms of the configuration of isomeric pairs and compounds isolated as single diastereoisomers. Special attention is given to the consequences of γ-shielding interactions, the effects of the nitrogen lone-pair orbital and anisotropic shielding by the aromatic region of the molecule. Deductions of stereochemistry are supported by 1H NMR data and the NMR features of the corresponding methiodide salts.
    Additional Material: 2 Tab.
    Type of Medium: Electronic Resource
    URL: http://dx.doi.org/10.1002/mrc.1270200413
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