Synthesis, Crystal Structure and Anti-tumor Properties of Fluorine-Containing Curcumin Analogues

Five fluorine-containing curcumin analogues were synthesized by the aldol condensation of fluorine-containing benzaldehyde with ketones. Their structures were characterized by 1 H 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) nm 3 , Z=2. Dc=1.329 Mg•m -3 , μ=0.097 mm -1 , F(000)=324. The final R=0.0590, wR=0.1841 .