Synthesis and cytotoxic activity of 7,4’-O-modified genistein amino acid derivatives

Abstract

Fifteen 7,4’- O-modified genistein amino acid derivatives are synthesized through nucleophilic substitution and hydrolysis, followed by condensation with diverse amino acid esters. The antiproliferative activity of all the synthesized compounds is evaluated against three cancer cell lines (MGC-803, HeLa, HCT-116) and one normal cell line (HUVEC) using 5-fluorouracil (5-Fu) as the positive control. The results show that methyl [2-({5-hydroxy-3-[4-(2-{[3-(4-hydroxyphenyl)-1-methoxy-1-oxopropan-2-yl]amino}-2-oxoethoxy)phenyl]-4-oxo-4 H-chromen-7-yl}oxy)acetyl] tyrosinate exhibits significant antiproliferative activity against the MGC-803 cell line with an IC50 value of 8.52 µM, and its inhibitory effects on HeLa and HCT-116 cancer cells are stronger than that of the positive control drug 5-Fu.