(22β)-25β-hydroxy-27-nor-furost-5-en-3β-yl 3-acetate | 1620908-14-6

• 分子结构分类: 有机化合物 - 脂质和类脂质分子 - 类固醇和类固醇衍生物
• 英文名称: (22β)-25β-hydroxy-27-nor-furost-5-en-3β-yl 3-acetate
• CAS: 1620908-14-6
• 化学式: C₂₈H₄₄O₄
• 分子量: 444.655
• InChiKey: HKEXIXFKCRHUFJ-BICNDCGRSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  5.67
• 重原子数：
  32.0
• 可旋转键数：
  4.0
• 环数：
  5.0
• sp3杂化的碳原子比例：
  0.89
• 拓扑面积：
  55.76
• 氢给体数：
  1.0
• 氢受体数：
  4.0

反应信息

• 作为产物：
  描述：

  薯蓣皂素 在 吡啶 、 sodium tetrahydroborate 、 sodium cyanoborohydride 、 溶剂黄146 、 3,4,5-三甲氧基苯胺 、 pyridinium chlorochromate 作用下， 以 甲醇 、 乙醇 、 二氯甲烷 、 氯仿 为溶剂， 反应 9.5h， 生成 (22β)-25α-hydroxy-27-nor-furost-5-en-3β-yl 3-acetate 、 (22β)-25β-hydroxy-27-nor-furost-5-en-3β-yl 3-acetate
  参考文献：
  名称：

  Synthesis of novel anticancer agents through opening of spiroacetal ring of diosgenin

  摘要：

  Diosgenin has been modified to furostane derivatives after opening the F-spiroacetal ring. The aldehyde group at C26 in derivative 8 was unexpectedly transformed to the ketone 9. The structure of ketone 9 was confirmed by spectroscopy and finally by X-ray crystallography. Five of the diosgenin derivatives showed significant anticancer activity against human cancer cell lines. The most potent molecule of this series i.e. compound 7, inhibited cellular growth by arresting the population at G0/G1 phase of cell division cycle. Cells undergo apoptosis after exposure to the derivative 7 which was evident by increase in sub G0 population in cell cycle analysis. Docking experiments showed caspase-3 and caspase-9 as possible molecular targets for these compounds. This was further validated by cleavage of PARP, a caspase target in apoptotic pathway. Compound 7 was found non-toxic up to 1000mg/kg dose in acute oral toxicity in Swiss albino mice.

  DOI：

  10.1016/j.steroids.2014.05.025