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Title: Biological activities and ADMET-related properties of novel set of cinnamanilides
Authors: Kos, Jiri
Bąk, Andrzej
Kozik, Violetta
Jankech, Timotiej
Strharsky, Tomas
Świetlicka, Aleksandra
Michnova, Hana
Hosek, Jana
Smoliński, Adam
Oravec, Michal
Devinsky, Ferdinand
Hutta, Milan
Jampilek, Josef
Keywords: cinnamamides; synthesis; antistaphylococcal activity; MTT assay; cytotoxicity; lipophilicity; PCA; IVE-PLS; quantitative structure-property relationships
Issue Date: 2020
Citation: "Molecules (Basel)" (2020) Iss. 18, art. no. 4121
Abstract: A series of nineteen novel ring-substituted N-arylcinnamanilides was synthesized and characterized. All investigated compounds were tested against Staphylococcus aureus as the reference strain, two clinical isolates of methicillin-resistant S. aureus (MRSA), and Mycobacterium 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 M) againstMRSAisolates than the commonly used ampicillin (MIC 45.8 M). The screening of the cell viability was performed using THP1-Blue NF- B cells and, except for (2E)-N-(4-bromo-3-chlorophenyl)-3-phenylprop-2-enamide (IC50 6.5 M), none of the discussed compounds showed any significant cytotoxic e ect up to 20 M. Moreover, all compounds were tested for their anti-inflammatory potential; several compounds attenuated the lipopolysaccharide-induced NF- 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 pKa 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.
DOI: 10.3390/molecules25184121
ISSN: 1420-3049
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