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Open AccessArticle

Investigation of Anti-Inflammatory Potential of N-Arylcinnamamide Derivatives

1
Division of Biologically Active Complexes and Molecular Magnets, Regional Centre of Advanced Technologies and Materials, Faculty of Science, Palacký University, Šlechtitelů 27, 78371 Olomouc, Czech Republic
2
Faculty of Pharmacy, Comenius University, Odbojárov 10, 83232 Bratislava, Slovakia
3
Department of Analytical Chemistry, Faculty of Natural Sciences, Comenius University, Ilkovičova 6, 84215 Bratislava, Slovakia
*
Authors to whom correspondence should be addressed.
Molecules 2019, 24(24), 4531; https://doi.org/10.3390/molecules24244531
Received: 18 November 2019 / Revised: 9 December 2019 / Accepted: 10 December 2019 / Published: 11 December 2019
(This article belongs to the Special Issue Facing Novel Challenges in Drug Discovery)
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)ʹ or C(2,6)ʹ positions of the anilide core by rather lipophilic and bulky moieties seems to be preferable for the anti-inflammatory potential of these compounds. View Full-Text
Keywords: cinnamamides; X-ray structure; polypharmacology; anti-inflammatory potential cinnamamides; X-ray structure; polypharmacology; anti-inflammatory potential
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MDPI and ACS Style

Hošek, J.; Kos, J.; Strhársky, T.; Černá, L.; Štarha, P.; Vančo, J.; Trávníček, Z.; Devínsky, F.; Jampílek, J. Investigation of Anti-Inflammatory Potential of N-Arylcinnamamide Derivatives. Molecules 2019, 24, 4531.

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