26080-07-9Relevant academic research and scientific papers
Biological Activities and ADMET-Related Properties of Novel Set of Cinnamanilides ?
Bak, Andrzej,Devinsky, Ferdinand,Hosek, Jan,Hutta, Milan,Jampilek, Josef,Jankech, Timotej,Kos, Jiri,Kozik, Violetta,Michnova, Hana,Oravec, Michal,Smolinski, Adam,Strharsky, Tomas,Swietlicka, Aleksandra
, (2020)
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 μM) against MRSA isolates than the commonly used ampicillin (MIC 45.8 μM). The screening of the cell viability was performed using THP1-Blue NF-κB cells and, except for (2E)-N-(4-bromo-3-chlorophenyl)-3-phenylprop-2-enamide (IC50 6.5 μM), none of the discussed compounds showed any significant cytotoxic effect up to 20 μM. Moreover, all compounds were tested for their anti-inflammatory potential; several compounds attenuated the lipopolysaccharide-induced NF-κB 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.
5,6,8-Trichloro-4-phenyl-3,4-dihydroquinolin-2(1H)-one
Thirumurugan,Shanmuga Sundara Raj,Murugan,Ramakrishnan,Chacko
, p. 1862 - 1864 (2007/10/03)
In the quinolone ring system of the title compound, C15H10Cl3NO, the pyridone moiety assumes a slightly twisted boat conformation. The plane of the benzene ring is twisted at an angle of 11.9(1)° with respect to the pyridone ring, indicating the slight non-planarity of the system. The molecules are stabilized by N-H...-O-type hydrogen bonds in addition to van der Waals interactions.
