Design, synthesis and biological activity of semisynthetic phenolic acid analogues (RSPOC 2.5)

Abstract

Ferulic acid (4- hydroxy-3-methoxycinnamic acid) is derived from natural source, consequently it has low Toxicity. It is one of the most abundant phenolic acids in plants. Ferulic acid has shown anticancer activity in various types of cancers. Large amounts of hydrogen peroxide are produced and secreted by tumour cells, which are responsible for spreading and invasion of the tumour. Anti-cancer activity of Ferulic Acid is related to its antioxidant property by inhibition of oxidative enzyme, enhancement of cytoprotective enzymes and acting as free radical scavenger. Ferulic acid structure has phenolic ring which act as free radical scavenger by its hydrogen donating ability. The presence of p-hydroxyl groups in aromatic ring, meta methoxy group and conjugated double bond are essential for activity. The aim of the project is to design and synthetize ferulic acid derivatives with potential anticancer activity. The amide derivatives of ferulic acid were synthetized by the reaction between ferulic acid and the different amines using DCC and THF. Purification of the compounds was done using column chromatography which is conducted by the pharmacognosy department and characterization was done using IR spectroscopy and proton NMR. Compounds were screened for anticancer activity against caco cell lines where they showed a significant anticancer activity.