Pharmacy - Organic Chemistry

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
The 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)
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
Our 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.