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  • 2-Amino-5-alkylidenethiazol-4-ones as promising lipid peroxidation inhibitors
    Zvezdanović, Jelena, farmacevtka ...
    2-Amino-5-alkylidenethiazol-4-one represents a promising scaffold in medicinal chemistry and drug discovery. In the present study the antioxidant activity of 30 diverse ... 2-amino-5-alkylidenethiazol-4-ones was screened using a lipid peroxidation (LP) method. All compounds under study showed activity regardless of the substituent nature. However, several compounds exhibited a significant LP inhibition effect, which was in the range of that obtained with standard antioxidants. Compounds containing an (indol-3-yl)methylene group at position 5 of thiazol-4-one moiety and a six-membered ring as the 2-amino substituent showed inhibitory effects higher than 60 %. The most active compound, 5-benzylidene-2-morpholinothiazol-4(5H)-one, was investigated by means of ab initio calculations in order to clarify the most probable mechanism of antioxidant action. These calculations imply that electron transfer from the 2-amino-5-alkylidenethiazol-4-ones to the lipid alkoxyl, lipid peroxyl, or hydroxyl radicals could produce radical cations able to scavenge the lipid radicals and produce adducts, and ultimately terminate the reaction by proton transfer. Thus we propose the electron transfer (SET) mechanism as the most probable one that explains the observed inhibition of LP.
    Source: Monatshefte für Chemie = Chemical Monthly. - ISSN 0026-9247 (Vol. 145, issue 6, 2014, str. 945-952)
    Type of material - article, component part
    Publish date - 2014
    Language - english
    COBISS.SI-ID - 3588465

    Link(s):

    http://link.springer.com/article/10.1007/s00706-014-1162-4
    DOI

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