新型含氟姜黄素类似物的合成、晶体结构及抗肿瘤活性

采用活性基团拼接法将含氟苯甲醛与酮反应, 合成了5个含氟单羰基姜黄素类似物, 结构经IR, ¹H NMR及ESI-MS确认. 对所合成的化合物进行了抗肿瘤活性测试(MTT法), 结果表明, 部分化合物对肿瘤细胞有较强的选择性抑制活性, 其中2,6-二(4-氟亚苯基)环己酮(3a)和2,6-二(2-氟亚苯基)环己酮(3b)的抗肿瘤谱广, 活性较好, 就此对化合物3b作了单晶培养, 并就晶体结构进行了X衍射分析. 结构表明化合物3b属三斜晶系, 空间群 P-1. 晶胞参数 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, D_c＝1.329 Mg?m^－3, μ＝0.097 mm^－1, F(000)＝324, 最终偏离因子R＝0.0590, wR＝0.1841.

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

Five fluorine-containing eurcumin 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 ex-hibit anti-proliferative activities against selected tumor cells. Among the presented compounds, the cyclo-hexanone-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. D_c= 1.329 Mg·m~(-3), μ=0.097 mm~(-1), F(000)=324. The final R=0.0590, wR=0.1841.