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 H-1 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-I, with unit cell dimensions a=0.9222(2) nm, b=0.9732(2) nm, c=10127(2) nm, alpha=88.920(4)degrees, beta=75 672(3)degrees, gamma=62.404(3)degrees, V=0.7755(3) nm(3), Z=2 D-c= 1.329 Mg.m(-3), mu=0.097 mm(-1), F(000)=324. The final R=0.0590, wR=0 1841.