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  • 1
    Electronic Resource
    Electronic Resource
    Stereoselectivity in central analgesic action of tocainide and its analogs (1993)
    New York, NY [u.a.] : Wiley-Blackwell
    Chirality 5 (1993), S. 135-142 
    Details
    ISSN: 0899-0042
    Keywords: antiarrhythmic drug ; tocainide ; antinociceptive activity ; chiral analogs ; presynaptic receptor ; Chemistry ; Organic Chemistry
    Source: Wiley InterScience Backfile Collection 1832-2000
    Topics: Chemistry and Pharmacology
    Notes: The antiarrhythmic drug tocainide (5a) and some related chiral α-amino and α-imino anilides (5b-e) were synthesized in optically active form. The antinociceptive effects of the different stereoisomers of these compounds were examined and it was found that the analgesic effect of tocainide is due only to its (-)-(R)-enantiomer. Benzyl replacement for methyl group at the stereogenic centre of tocainide causes loss of activity while both enantiomers of the αiminoxilidide 5e and of the strictly related tocainide analog 5d produce an analgesic effect without any stereoselectivity. Pharmacological tests and [3H] quinuclidinyl benzilate ([3H]QNB) binding assay, taken together, seem to show that the antinociceptive effect of (-)-(R)-tocainide, like the analgesia induced by lidocaine, procaine, and mexiletine, is due to a central presynaptic cholinergic mechanism of action. © 1993 Wiley-Liss, Inc.
    Additional Material: 2 Ill.
    Type of Medium: Electronic Resource
    URL: http://dx.doi.org/10.1002/chir.530050306
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  • 2
    Electronic Resource
    Electronic Resource
    Stereospecific synthesis and absolute configuration of mexiletine (1994)
    New York, NY [u.a.] : Wiley-Blackwell
    Chirality 6 (1994), S. 590-595 
    Details
    ISSN: 0899-0042
    Keywords: antiarrhythmic drug ; mexiletine ; absolute configuration ; X-ray analysis ; Chemistry ; Organic Chemistry
    Source: Wiley InterScience Backfile Collection 1832-2000
    Topics: Chemistry and Pharmacology
    Notes: Data on the absolute configuration of mexiletine (MEX) do not appear to have been published, although in several published reports the configuration is referred to as (-)-(R) and (+)-(S), based on information from manufactures providing the drug stereoisomers. We demonstrate that (-)-MEX has the (R)-configuration by mean of a new stereospecific synthesis. X-Ray analysis of an optical active sample of (+)-MEX as its hydrobromide salt, obtained from chemical resolution of the racemic mixture, was carried out in order to obtain precise information on bond lengths and angles, useful for studies on structure-activity relationships. We also report the NMR analysis in presence of Eu(hfc)3 as shift reagent, which represents a simple method for the determination of enantiomeric excess (ee) in addition to the well-known chiral HPLC methods. © 1994 Wiley-Liss, Inc.
    Additional Material: 1 Ill.
    Type of Medium: Electronic Resource
    URL: http://dx.doi.org/10.1002/chir.530060713
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