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  • 1
    Electronic Resource
    Electronic Resource
    Springer
    Pharmaceutical research 7 (1990), S. 91-95 
    ISSN: 1573-904X
    Keywords: malaria ; drug metabolism ; deuterium isotope effect ; cytotoxicity, quinocide
    Source: Springer Online Journal Archives 1860-2000
    Topics: Chemistry and Pharmacology
    Notes: Abstract The substitution of two deuterium atoms on the α-carbon of the primaquine side chain was found to produce a sevenfold decrease in the rate of conversion of primaquine to carboxyprimaquine by enzymatic oxidative deamination, but the deuterium substitution was found to have no significant effect on the in vitro antimalarial activity or on in vitro hepatocyte toxicity. Placing a single methyl group on the α-carbon was found to produce only a slight decrease in the rate of oxidative deamination. Although metabolic attack occurred adjacent to either the aniline nitrogen or the aliphatic amine, metabolic attack occurred primarily adjacent to the more basic nitrogen at the l′-position, even when this position bore a methyl substituent. Primaquine, the α-dideutero analogue, and the α-methyl analogue were all found to have about the same in vitro antimalarial activity as determined in the liver hepatocyte assay.
    Type of Medium: Electronic Resource
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  • 2
    Electronic Resource
    Electronic Resource
    s.l. : American Chemical Society
    Journal of natural products 47 (1984), S. 439-444 
    ISSN: 1520-6025
    Source: ACS Legacy Archives
    Topics: Chemistry and Pharmacology
    Type of Medium: Electronic Resource
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  • 3
    Electronic Resource
    Electronic Resource
    s.l. : American Chemical Society
    Journal of natural products 50 (1987), S. 434-441 
    ISSN: 1520-6025
    Source: ACS Legacy Archives
    Topics: Chemistry and Pharmacology
    Type of Medium: Electronic Resource
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  • 4
    Electronic Resource
    Electronic Resource
    Chichester : Wiley-Blackwell
    Biological Mass Spectrometry 15 (1988), S. 211-222 
    ISSN: 0887-6134
    Keywords: Chemistry ; Analytical Chemistry and Spectroscopy
    Source: Wiley InterScience Backfile Collection 1832-2000
    Topics: Chemistry and Pharmacology
    Notes: Steviol (ent-13-hydroxykaur-16-en-19-oic acid), the aglycone of various plant-derived glycoside sweeteners consumed by human populations, is known to be mutagenic toward Salmonella typhimurium strain TM677 when metabolically activated using a 9000 × g supernatant fraction derived from the liver of Aroclor 1254-pretreated rats. Mass spectral analysis of this diterpenoid and some analogs revealed characteristic patterns reflecting differential stereochemistry at the C/D rings and variations in the nature of the substituents present. Such information has been used to help identify several in vitro metabolites of steviol in conditions known to produce a mutagenic response, when analyzed by human populations, is known to be mutagenic toward Salmonella typhimurium strain TM677 when metabolically be allylic oxidation and epoxidation. 15-Oxosteviol, a product of oxidation of the major steviol metabolite, 15α-hydroxysteviol, was found to be a direct-acting mutagen.
    Additional Material: 10 Ill.
    Type of Medium: Electronic Resource
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