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Investigation of Anti-Inflammatory Potential of N-Arylcinnamamide Derivatives

The result's identifiers

  • Result code in IS VaVaI

    <a href="https://www.isvavai.cz/riv?ss=detail&h=RIV%2F61989592%3A15310%2F19%3A73596653" target="_blank" >RIV/61989592:15310/19:73596653 - isvavai.cz</a>

  • Result on the web

    <a href="https://www.mdpi.com/1420-3049/24/24/4531/pdf" target="_blank" >https://www.mdpi.com/1420-3049/24/24/4531/pdf</a>

  • DOI - Digital Object Identifier

    <a href="http://dx.doi.org/10.3390/molecules24244531" target="_blank" >10.3390/molecules24244531</a>

Alternative languages

  • Result language

    angličtina

  • Original language name

    Investigation of Anti-Inflammatory Potential of N-Arylcinnamamide Derivatives

  • Original language description

    A series of sixteen ring-substituted N-arylcinnamanilides, previously described as highly antimicrobially effective against a wide spectrum of bacteria and fungi, together with two new derivatives from this group were prepared and characterized. Moreover, the molecular structure of (2E)-N-(2-bromo-5-fluorophenyl)-3-phenylprop-2-enamide as a model compound was determined using single-crystal X-ray analysis. All the compounds were tested for their anti-inflammatory potential, and most tested compounds significantly attenuated the lipopolysaccharide-induced NF-κB activation and were more potent than the parental cinnamic acid. (2E)-N-[2-Chloro-5-(trifluoromethyl)phenyl]-3-phenylprop-2-enamide, (2E)-N-(2,6-dibromophenyl)-3-phenylprop-2-enamide, and (2E)-N-(2,5-dichlorophenyl)-3-phenylprop-2-enamide demonstrated the highest inhibition effect on transcription factor NF-κB at the concentration of 2 µM and showed a similar effectiveness as the reference drug prednisone. Several compounds also decreased the level of TNF-α. Nevertheless, subsequent tests showed that the investigated compounds affect neither IκBα level nor MAPKs activity, which suggests that the N-arylcinnamanilides may have a different mode of action to prednisone. The modification of the C(2,5) 0 or C(2,6) 0 positions of the anilide core by rather lipophilic and bulky moieties seems to be preferable for the anti-inflammatory potential of these compounds.

  • 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

    30107 - Medicinal chemistry

Result continuities

  • Project

    <a href="/en/project/LO1305" target="_blank" >LO1305: Development of the center of advanced technologies and materials</a><br>

  • Continuities

    P - Projekt vyzkumu a vyvoje financovany z verejnych zdroju (s odkazem do CEP)

Others

  • Publication year

    2019

  • Confidentiality

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

Data specific for result type

  • Name of the periodical

    MOLECULES

  • ISSN

    1420-3049

  • e-ISSN

  • Volume of the periodical

    24

  • Issue of the periodical within the volume

    DEC

  • Country of publishing house

    CH - SWITZERLAND

  • Number of pages

    15

  • Pages from-to

    "4531-1"-"4531-15"

  • UT code for WoS article

    000507299600109

  • EID of the result in the Scopus database

    2-s2.0-85076457671