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Hybridization of Aminoadamantanes with Cinnamic Acid Analogues and Elucidation of Their Antioxidant Profile

The result's identifiers

  • Result code in IS VaVaI

    <a href="https://www.isvavai.cz/riv?ss=detail&h=RIV%2F00216208%3A11310%2F22%3A10451906" target="_blank" >RIV/00216208:11310/22:10451906 - isvavai.cz</a>

  • Result on the web

    <a href="https://verso.is.cuni.cz/pub/verso.fpl?fname=obd_publikace_handle&handle=dLBZRN5SFU" target="_blank" >https://verso.is.cuni.cz/pub/verso.fpl?fname=obd_publikace_handle&handle=dLBZRN5SFU</a>

  • DOI - Digital Object Identifier

    <a href="http://dx.doi.org/10.1155/2022/7582587" target="_blank" >10.1155/2022/7582587</a>

Alternative languages

  • Result language

    angličtina

  • Original language name

    Hybridization of Aminoadamantanes with Cinnamic Acid Analogues and Elucidation of Their Antioxidant Profile

  • Original language description

    A series of seventeen cinnamic acid hybrids (4a(i)-c(i)) were obtained through an amidation of aminoadamantanes (amantadine, rimantadine, and memantine) with mixed anhydride generated from different substituted cinnamic acid and ethyl chloroformate. (1)H NMR, (13)C NMR, IR, and HRMS were used for the confirmation of the structures of the synthesized hybrids. Moreover, the antioxidant profiles of amides were estimated as per five different in vitro methods: 1,1-diphenyl-2-picrylhydrazyl (DPPH), 2,2&apos;-azinobis-3-ethylbenzothiazoline-6-sulfonic acid cation radical (ABTS+), ferric reducing antioxidant power (FRAP), cupric reducing antioxidant capacity (CUPRAC) assay, and inhibition of Fe(III)/asc induced lipid peroxidation (LP) in brain homogenate. For comparison, caffeic acid (CaffA), known as a potent naturally occurring antioxidant, was used as a reference compound in our study. The results revealed that the most prominent antioxidant activity was demonstrated by compound 4b(2), with excellent CUPRAC, FRAP, scavenging ABTS(+) potential, and inhibition of Fe/asc-induced LP, followed by 4c(6) &gt; 4a(6) &gt; CaffA &gt; 4c(5) and 4a(5) &gt; 4a(7). Overall, the results suggest that the hybrids (4b(2), 4c(6), and 4a(6)) consisting of a caffeoyl moiety and lipophilic adamantane core endow the molecules with the higher antioxidant activity than their parent compound (caffeic acid), especially against LP. Thus, these promising antioxidants could have beneficial effects in various pathological conditions, where oxidative stress is implicated.

  • Czech name

  • Czech description

Classification

  • Type

    J<sub>imp</sub> - Article in a specialist periodical, which is included in the Web of Science database

  • CEP classification

  • OECD FORD branch

    10401 - Organic chemistry

Result continuities

  • Project

  • Continuities

    I - Institucionalni podpora na dlouhodoby koncepcni rozvoj vyzkumne organizace

Others

  • Publication year

    2022

  • Confidentiality

    S - Úplné a pravdivé údaje o projektu nepodléhají ochraně podle zvláštních právních předpisů

Data specific for result type

  • Name of the periodical

    Journal of Chemistry

  • ISSN

    2090-9063

  • e-ISSN

    2090-9071

  • Volume of the periodical

    2022

  • Issue of the periodical within the volume

    November

  • Country of publishing house

    GB - UNITED KINGDOM

  • Number of pages

    11

  • Pages from-to

    7582587

  • UT code for WoS article

    000891078700001

  • EID of the result in the Scopus database

    2-s2.0-85143167668