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化学学报
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化学学报 ›› 2009, Vol. 67 ›› Issue (22): 2597-2606. 上一篇    下一篇

研究论文

呋喃并呫吨酮衍生物的合成与生物活性研究

覃江克a，韩留玉a，兰文丽a，唐煌a，苏桂发*,a，戴支凯b，徐庆b   

  1. (a广西师范大学化学化工学院 药用资源化学与药物分子工程教育部重点实验室 桂林 541004) (b桂林医学院药理实验中心 桂林541004)
  • 投稿日期:2009-04-09 修回日期:2009-06-09 发布日期:2009-07-23
  • 通讯作者: 苏桂发 E-mail:edward_su75@163.com
  • 基金资助:

    广西科技开发计划应用基础研究专项、广西师大科研基金资助项目

Synthesis and Bioactivity of Furoxanthone Derivatives

Qin, Jiangkea，Han, Liuyua，Lan, Wenlia，Tang, Huanga ，Su, Guifa*,a，Dai, Zhikaib，Xu, Qingb   

  1. (a Key Laboratory for the Chemistry and Molecular Engineering of Medicinal Resources of State Education Ministry, College of Chemistry & Chemical Engineering, Guangxi Normal University, Guilin 541004) (b Pharmacological Experiment Center, Guilin Medical College, Guilin 541004)
  • Received:2009-04-09 Revised:2009-06-09 Published:2009-07-23

PDF

2043

被引次数

7

以水杨酸、间苯三酚为原料合成了1,3-二羟基呫吨酮, 经醚化、环化反应得到1-羟基呋喃并呫吨酮3a和3b, 再经Mannich反应合成了10个呋喃并呫吨酮衍生物4和5, 接着通过季铵化反应得到相应的10个季铵盐6和7. 运用IR、一维和二维NMR、MS、元素分析等对化合物进行了结构表征, 考察了化合物4～7对乙酰胆碱酯酶的抑制作用及化合物6, 7的抗癌活性. 结果表明: 化合物4～7对乙酰胆碱酯酶具有较好的抑制活性, IC50＝2.0～12.4 μmol/L; 化合物6, 7对肝癌(HepG2)、肺癌(SPC-A)、口腔上皮癌(KB)、乳腺癌(MCF-7)这四种癌细胞株的增殖均有抑制作用, 其中化合物6c对癌细胞株HepG2、化合物7d对癌细胞株MCF-7的抑制作用最强, IC50分别为0.82和0.77 μmol/L.

关键词: 呫吨酮, 呋喃并呫吨酮衍生物, 合成, 胆碱酯酶, 抗癌活性

The linearly and angularly isomeric furoxanthones 3a, 3b were synthesized by etherification and cyclization of 1,3-dihydroxylxanthone, which was synthesized from salicylic acid and phloroglucinol; then ten furoxanthone derivatives 4 and 5 were prepared via Mannich reaction of 3a, 3b, respectively, finally the ten corresponding quaternary ammonium salts 6 and 7 were obtained by quaternization of 4 and 5; the structures of the synthesized compounds were confirmed by IR, NMR, MS and elemental analysis. Acetylcholinesterase (AChE) inhibitory activities of compounds 4～7 and anti-cancer activities of compounds 6, 7 were also investigated. The results indicated that compounds 4～7 were capable of inhibiting AChE in vitro with moderate to good activities, IC50＝2.0～12.4 μmol/L. MTT assay indicated that compounds 6, 7 possessed effectively inhibitory activity against the proliferation of four cancer cells, including HepG2 (liver cancer), SPC-A (lung cancer), KB (oral epithelial carcinoma) and MCF-7 (galactophore cancer), among which 6c against HepG2 and 7d against MCF-7 had the highest inhibitory activities, with the IC50 being 0.82 and 0.77 μmol/L, respectively.

Key words: xanthone, furoxanthone derivative, synthesis, cholinesterase, anti-cancer activity