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Biological Activities and ADMET-Related Properties of Novel Set of Cinnamanilides dagger
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SYSNO ASEP 0536266 Document Type J - Journal Article R&D Document Type Journal Article Subsidiary J Článek ve WOS Title Biological Activities and ADMET-Related Properties of Novel Set of Cinnamanilides dagger Author(s) Kos, J. (CZ)
Bak, A. (PL)
Kozik, V. (PL)
Jankech, T. (SK)
Strharsky, T. (CZ)
Swietlicka, A. (PL)
Michnova, H. (CZ)
Hošek, J. (CZ)
Smolinski, A. (PL)
Oravec, Michal (UEK-B) RID, ORCID, SAI
Devinsky, F. (SK)
Hutta, M. (SK)
Jampílek, J. (SK)Number of authors 13 Article number 4121 Source Title Molecules. - : MDPI
Roč. 25, č. 18 (2020)Number of pages 23 s. Language eng - English Country CH - Switzerland Keywords molecular lipophilicity ; drug discovery ; log-p ; som-4d-qsar ; prediction ; hybrids ; agents ; pk(a) ; dye ; cinnamamides ; synthesis ; antistaphylococcal activity ; MTT assay ; cytotoxicity ; lipophilicity ; pca ; ive-pls ; quantitative structure-property relationships Subject RIV AO - Sociology, Demography OECD category Demography R&D Projects EF16_019/0000797 GA MŠMT - Ministry of Education, Youth and Sports (MEYS) Method of publishing Open access Institutional support UEK-B - RVO:86652079 UT WOS 000580723700001 EID SCOPUS 85090844501 DOI 10.3390/molecules25184121 Annotation A series of nineteen novel ring-substitutedN-arylcinnamanilides was synthesized and characterized. All investigated compounds were tested againstStaphylococcus aureusas the reference strain, two clinical isolates of methicillin-resistantS. aureus(MRSA), andMycobacterium tuberculosis. (2E)-N-[3-Fluoro-4-(trifluoromethyl)phenyl]-3-phenylprop-2-enamide showed even better activity (minimum inhibitory concentration (MIC) 25.9 and 12.9 mu M) against MRSA isolates than the commonly used ampicillin (MIC 45.8 mu M). The screening of the cell viability was performed using THP1-Blue (TM) NF-kappa B cells and, except for (2E)-N-(4-bromo-3-chlorophenyl)-3-phenylprop-2-enamide (IC(50)6.5 mu M), none of the discussed compounds showed any significant cytotoxic effect up to 20 mu M. Moreover, all compounds were tested for their anti-inflammatory potential, several compounds attenuated the lipopolysaccharide-induced NF-kappa B activation and were more potent than the parental cinnamic acid. The lipophilicity values were specified experimentally as well. In addition, in silico approximation of the lipophilicity values was performed employing a set of free/commercial clogP estimators, corrected afterwards by the corresponding pK(a)calculated at physiological pH and subsequently cross-compared with the experimental parameters. The similarity-driven property space evaluation of structural analogs was carried out using the principal component analysis, Tanimoto metrics, and Kohonen mapping. Workplace Global Change Research Institute Contact Nikola Šviková, svikova.n@czechglobe.cz, Tel.: 511 192 268 Year of Publishing 2021 Electronic address https://www.mdpi.com/1420-3049/25/18/4121
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