(8R,8'R)-3,3'-dimethoxy-9a,9b,9c,9d-tetrahomolignane-4,4'-diol | 1612227-20-9

• 分子结构分类: 有机化合物 - 苯类化合物 - 酚类
• 英文名称: (8R,8'R)-3,3'-dimethoxy-9a,9b,9c,9d-tetrahomolignane-4,4'-diol
• CAS: 1612227-20-9
• 化学式: C₂₄H₃₄O₄
• 分子量: 386.532
• InChiKey: QBFUHNOJLUKHEW-YLJYHZDGSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  5.73
• 重原子数：
  28.0
• 可旋转键数：
  11.0
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.5
• 拓扑面积：
  58.92
• 氢给体数：
  2.0
• 氢受体数：
  4.0

反应信息

• 作为产物：
  描述：

  在 六甲基磷酰三胺 、 sodium tetrahydroborate 、 palladium on activated charcoal 、 氢气 、 三乙胺 、 pyridinium chlorochromate 作用下， 以 四氢呋喃 、 二氯甲烷 、 乙酸乙酯 为溶剂， 反应 20.5h， 生成 (8R,8'R)-3,3'-dimethoxy-9a,9b,9c,9d-tetrahomolignane-4,4'-diol
  参考文献：
  名称：

  Cytotoxic Activity of Dietary Lignan and Its Derivatives: Structure–Cytotoxic Activity Relationship of Dihydroguaiaretic Acid

  摘要：

  Cytotoxic activities of synthesized lignan derivatives were estimated by WST-8 reduction assay against HL-60 and HeLa cells to show the structure-activity relationship. The activities of some effective compounds were examined against Colon 26 and Vero cells. Dietary secoisolariciresinol (SECO, 1) and its metabolite, 9,9'-anhydrosecoisolariciresinol (2), did not show the cytotoxic activity. On the other hand, all stereoisomers of dihydroguaiaretic acid (DGA, 9,9'-dehydroxysecoisolariciresinol, 3-5) exhibited the activity (IC50: around 30 mu M). The IC50 value of (8R,8'R)-9-butyl DGA derivative 13 was around 6 mu M. This fact means that the hydrophobic group was advantageous for higher activity at 9- and 9'-positions. By the evaluation of the effect of 7and 7'-aryl group on the activity, we discovered the highest activity of (8R,8'R)-7-(3-hydroxy-4-methoxyphenyl)-7'-(2-ethoxyphenyl) DGA derivative 47 showing around 1 mu M of IC50 value, which is about 24-fold higher activity than that of natural (8R,8'R)-DGA. The derivative of dietary lignan showed the high cytotoxic activity.

  DOI：

  10.1021/jf5010572