(3R,4R)-4-[(3,4-dimethoxyphenyl)methyl]-3-[[4-hydroxy-3-(2-hydroxyethoxy)phenyl]methyl]oxolan-2-one | 1426297-67-7

• 分子结构分类: 有机化合物 - 木脂素、新木脂素和相关化合物 - 呋喃类木脂素
• 英文名称: (3R,4R)-4-[(3,4-dimethoxyphenyl)methyl]-3-[[4-hydroxy-3-(2-hydroxyethoxy)phenyl]methyl]oxolan-2-one
• CAS: 1426297-67-7
• 化学式: C₂₂H₂₆O₇
• 分子量: 402.444
• InChiKey: NNTYLIGLRNLRIY-DLBZAZTESA-N

物化性质

• 沸点：
  626.5±50.0 °C(Predicted)
• 密度：
  1.268±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  2.9
• 重原子数：
  29
• 可旋转键数：
  9
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.41
• 拓扑面积：
  94.4
• 氢给体数：
  2
• 氢受体数：
  7

反应信息

• 作为产物：
  描述：

  牛蒡子苷元 在 吡啶 、 aluminum (III) chloride 、 氢气 、 palladium(II) hydroxide 、 potassium carbonate 、 三苯基膦 、 potassium iodide 作用下， 以 甲醇 、 二氯甲烷 、 丙酮 为溶剂， 20.0 ℃ 、101.33 kPa 条件下， 反应 41.0h， 生成 (3R,4R)-4-[(3,4-dimethoxyphenyl)methyl]-3-[[4-hydroxy-3-(2-hydroxyethoxy)phenyl]methyl]oxolan-2-one
  参考文献：
  名称：

  Synthesis and antitumor evaluation of arctigenin derivatives based on antiausterity strategy

  摘要：

  A series of new (-)-arctigenin derivatives with variably modified O-alkyl groups were synthesized and their preferential cytotoxicity was evaluated against human pancreatic cancer cell line PANC-1 under nutrient-deprived conditions. The results showed that monoethoxy derivative 4i (PC50, 0.49 mu M), diethoxy derivative 4h (PC50, 0.66 mu M), and triethoxy derivative 4m (PC50, 0.78. mu M) showed the preferential cytotoxicities under nutrient-deprived conditions, which were identical to or more potent than (-)-arctigenin (1) (PC50, 0.80 mu M). Among them, we selected the triethoxy derivative 4m and examined its in vivo antitumor activity using a mouse xenograft model. Triethoxy derivative 4m exhibited also in vivo antitumor activity with the potency identical to or slightly more than (-)-arctigenin (1). These results would suggest that a modification of (-)-arctigenin structure could lead to a new drug based on the antiausterity strategy. (C) 2012 Elsevier Masson SAS. All rights reserved.

  DOI：

  10.1016/j.ejmech.2012.11.031