Design, synthesis and biological activity of phenolic derivatives of oat active constituents (RSPOC 2.2)

Abstract

aCaffeic aacid is a aphenolic acompound awhich acan aoccur anaturally in aplants asuch as aoat, afruit ,avegetable and acoffee abean and acan abe aobtained by aextraction amethod from it or be asynthesized by atwo aroutes afirst athe areaction of aHorner–Wadsworth–Emmons(HWE) 4 aThe asecond aachieves aKnoevenagel and aaldol ashortenings. aIt ahas a avariety of aactivity asuch aas aantimicrobial , aanti-inflammatory , aanti-viral , aantioxidant and aanticancer aactivity. It is amainly aused in the aester form to give the aanticancer aactivity asuch as acaffeic acid phenyl ester (CAPE) 1 in the form of aester, it acan treat many atypes of acancer such as alung ,acolon , aprostate, aleukemia and amelanoma , ait aacts as antioxidant by atwo amechanisms afree Aradical ascavengers and asometimes as metal chelators and as aanticancer by ainhibiting the anucleotide aturn over Asalvage pathway , addition of aperoxide to alipid, astrand of DNA abreak, adivisions of protein and it ainhibits 5-lipoxygenase aenzyme by a awhole anon-competitive mechanism 3 aOur aim is to adesign new aderivatives of acaffeic acid, asynthesis of derivative of acaffeic aacid and atest the abiological aactivity of the anewly synthesized acompounds against acancer acell alines. aCaffeic aamide aderivatives were aexpected to be asynthesized athrough aformation of the aacid achloride ausing POCl3 afollowed by aamide aformation awith the ahelp of the arespective aamine. Due to the ainsolubility aof the aformed caffeic acid achloride another aamethod was devised using DCC to adirectly aacouple the aamine with caffeic acid.4-hydroxyanaline, P-toluidine, Cyclohexyl amine and M-toluidine amines used to asynthesis adifferent amide aderivatives of caffeic acid which achemopreventive anti-tumor aagents.