Synthesis, crystal structure and anti-tumor properties of fluorine-containing curcumin analogues

Abstract

Five fluorine-containing curcumin analogues were synthesized by the aldol condensation of fluorine-containing benzaldehyde with ketones. Their structures were characterized by 1H NMR, IR and ESI-MS techniques. The anti-tumor activities of the mono-carbonyl analogues were evaluated against seven different tumor cell lines by an MTT assay. The results suggest that the fluorine-containing compounds exhibit anti-proliferative activities against selected tumor cells. Among the presented compounds, the cyclohexanone- containing analogues exhibited better anti-tumor properties in wider spectrum than acetone and cyclopentanone-containing analogues did. Therefore, one of cyclohexanone-containing compounds 3b was further determined and analyzed using X-ray single-crystal diffraction. The crystal of compound 3b belongs to triclinic, space group P-1, with unit cell dimensions a=0.9222(2) nm, b=0.9732(2) nm, c= 1.0127(2) nm, α=88.920(4)°, β=75.672(3)°, γ=62.404(3)°, V=0.7755(3) nm3, Z=2. Dc= 1.329 Mġm-3, μ=0.097 mm-1, F(000)=324. The final R=0.0590, wR=0.1841.