有机化学 ›› 2010, Vol. 30 ›› Issue (02): 289-294. 上一篇    下一篇

研究简报

新型含氟姜黄素类似物的合成、晶体结构及抗肿瘤活性

赵承光,杨菊,梁栋楼,唐琴琴,张翼,梁广*,李校堃   

  1. (温州医学院药学院 浙江省生物技术制药工程重点实验室 温州 325035)
  • 收稿日期:2009-03-23 修回日期:2009-08-20 发布日期:2010-02-20
  • 通讯作者: 梁广 E-mail:wzmcliangguang@163.com
  • 基金资助:

    浙江省教育厅;温州市科技局;国家级.国家自然科学基金

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

Zhao Chengguang Yang Ju Liang Donglou Tang Qinqin Zhang Yi Liang Guang* Li Xiaokun   

  1. (Zhejiang Provincial Key Laboratory of Biotechnology Pharmaceutical Engineering, School of Pharmacy, Wenzhou Medicinal College, Wenzhou 325035)
  • Received:2009-03-23 Revised:2009-08-20 Published:2010-02-20

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, Dc=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.

关键词: 姜黄素类似物, 合成, 晶体结构, 抗肿瘤活性

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 cyclo-hexanone-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 Mg•m-3, μ=0.097 mm-1, F(000)=324. The final R=0.0590, wR=0.1841 .

Key words: curcumin analogue, synthesis, crystal structure, anti-tumor property