294177-64-3Relevant academic research and scientific papers
Tyrosinase inhibitory effects and antioxidative activities of novel cinnamoyl amides with amino acid ester moiety
Fan, Qian,Jiang, Hong,Yuan, Er-Dong,Zhang, Jian-Xun,Ning, Zheng-Xiang,Qi, Sui-Jian,Wei, Qing-Yi
, p. 1081 - 1087 (2012)
Nine cinnamoyl amides with amino acid ester (CAAE) moiety were synthesized by the conjugation of the corresponding cinnamic acids (cinnamic acid, 4-hydroxy cinnamic acid, ferulic acid and caffeic acid) with amino acid esters, and their inhibitory effects on the activities of mushroom tyrosinase were investigated, using l-3,4-dihydroxyl-phenylalanine (l-DOPA) as the substrate. Among these CAAE amides, ethyl N-[3-(4-hydroxy-3-methoxyphenyl)-1-oxo-2-propen-1-yl]-l- phenylalaninate (b4) showed the strongest inhibitory activity; the IC50 was 0.18 μM. The IC50 values, inhibition types, inhibition mechanisms and kinetics of all these CAAE amides were evaluated. A structure-activity relationship (SAR) study found that the inhibitory effects were potentiated with the increasing length of hydrocarbon chains at the amino acid esters and also influenced by the substituents at the styrene groups. Furthermore, the hydroxyl radical scavenging and anti-lipid peroxidation activities of four CAAE derivatives were also investigated. Among these compounds, b3 (ethyl N-[3-(3,4-dihydroxyphenyl)-1-oxo-2-propen-1-yl]- l-phenylalaninate) and b4 exhibited potential antioxidant activities.
Antimicrobial activities of the cinnamoyl amide of amino acid derivatives
Wei,Jiang,Zhang,Zhang,Guo
experimental part, p. 2383 - 2388 (2012/09/07)
Cinnamic acid derivatives are well known natural antimicrobial compounds. In present studies, 23 cinnamoyl amides of amino acid derivatives were synthesized and their antimicrobial activities against Bacillus subtilis, Escherichia coli and Saccharomyces cerevisiae were evaluated with benzoic acid as a reference. Most of the synthesized compounds were more active in inhibiting bacterial growth and all of them were more sensitive in controlling the growth of yeast Saccharomyces cerevisiae than cinnamic acid. Moreover, some of them such as cinnamoyl butyl glycinate(compound 4) were more active than benzoic acid. The pH value influence on the antimicrobial activities of compound 4 was also investigated. Compared to benzoic acid, compound 4 was much more active when pH value was up to 7 and 7.5. These results gives us useful information for food preservatives.
