Design, synthesis, characterization of ferulic acid and p-coumaric acid amide derivatives as an antibacterial/antioxidant agent

设计、合成和表征阿魏酸和对香豆酸酰胺衍生物作为抗菌/抗氧化剂

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Abstract

Ferulic acid and p-coumaric acid, cinnamic derivatives of phenolic acid, have antibacterial, prooxidant, and antioxidant effects. In this study ferulic acid and p-coumaric acid amide derivatives were investigated for their antibacterial and antioxidant properties are described in this communication. The most effective conjugates against B subtilis were 5b (IC(50): 215 ​± ​1.3 ​μM) and 4d (IC(50): 336 ​± ​2.7 ​μM) and against P. aeruginosa were 4b (IC(50): 365 ​± ​2.8 ​μM) and 5b (IC(50): 341 ​± ​3.6 ​μM), whereas the none of conjugates were more effective against E. coli than reference Kanamycin. Conjugates 5b was the most effective against B subtilis of all the synthesized conjugates, with IC(50) values of (IC(50): 215 ​± ​1.3 ​μM). The free radical scavenging capacity of each compound was determined using the DPPH and ABTS assays. Conjugates 4b (IC(50): 53 ​± ​3.6 ​μM), 4c (IC(50): 58 ​± ​1.3 ​μM), 4d (IC(50): 57 ​± ​2.5 ​μM), 5b (IC(50): 29 ​± ​1.5 ​μM) and 4a (IC(50): 56 ​± ​4.3 ​μM) have greater antioxidant capacity than ferulic acid and ascorbic acid in the DPPH assay. Whereas in the ABTS assay, compounds 4b (IC(50): 7 ​± ​1.8 ​μM), 5b (IC(50): 5 ​± ​0.7 ​μM), 4a (IC(50): 9 ​± ​3.2 ​μM), 4g (IC(50): 7 ​± ​2.3 ​μM), and 5a (IC(50): 8 ​± ​4.3 ​μM) showed more antioxidant activity than ferulic acid, p-coumaric acid and ascorbic acid. Thus, a large library of compounds derived from bile acid can be easily synthesized for extensive structure-activity relationship studies in order to identify the most appropriate antibacterial and antioxidant agents.

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