Abstract
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.
Highlights
Inflammation is physiological immune reaction against infectious agents or injury, and its main role is to eradicate the noxious agent and to restore tissue homeostasis [1]
Chronic inflammation is a hallmark of many diseases, including atherosclerosis [2], rheumatoid arthritis [3], psoriasis [4], cancer [5], chronic respiratory diseases [6,7], and type 2 diabetes mellitus [8]
Our results showed no effect of compounds 17, 8, and cinnamic acid (CA) on the IκBα levels and
Summary
Inflammation is physiological immune reaction against infectious agents or injury, and its main role is to eradicate the noxious agent and to restore tissue homeostasis [1]. CA and its natural and many interesting biological effects, as antimicrobial [12,13], anticancer anti-oxidant [13], synthetic derivatives possess manysuch interesting biological effects, such as [14], antimicrobial [12,13], and anti-inflammatory activities anticancer [14], anti-oxidant [13],[15]. Chemistry series of N-arylcinnamide derivatives this work was previously tested for their anti-microbial activity [25,26], presented in this work was previously tested for their anti-microbial activity N-arylcinnamanilides was chosen for the their ability to above-mentioned a group of eighteen N-arylcinnamanilides wasscreening chosen forofthe screening of moderate thetoinflammation-like reaction in vitro Their ability moderate the inflammation-like reaction in vitro
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