Synthesis of a novel series of (E, E)-4,6-bis(styryl)-2-O-glucopyranosyl- pyrimidines and their potent multidrug resistance (MDR) reversal activity against cancer cells

A novel series of methoxy or benzyloxy substituted (E,E)-4,6-bis(styryl)-2- O-glucopyranosyl-pyrimidines as curcuminoid analogs were synthesized in four steps with total yields of 21.5% to 33.9%. A549 and HL60 cells were employed for the anticancer activity testing. The results demonstrated that 5a, 5c, and 5e have some inhibitory activity against the HL-60 cell line. Unfortunately, no compound displayed inhibitory activity against A549 except for 5c. MDR reversal activity results demonstrated that compounds 4a (RF = 12.3) and 4b (RF = 18.5) showed strong reversal activity to the P-gp-mediated LCC6MDR cells compared to verapamil (RF = 3.2) and no cytotoxicity to cancer or normal cell lines even at a high concentrations (100M).