11-O-desacetyl-20-(N,N-diethylimino)-20-desoxowortmannin | 58053-89-7

• 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: 11-O-desacetyl-20-(N,N-diethylimino)-20-desoxowortmannin
• 英文别名: (3aR,9S,9aR,10R,11aS)-6-(diethylaminomethylidene)-5,10-dihydroxy-9-(methoxymethyl)-9a,11a-dimethyl-2,3,3a,9,10,11-hexahydroindeno[4,5-h]isochromene-1,4,7-trione
• CAS: 58053-89-7
• 化学式: C₂₅H₃₃NO₇
• 分子量: 459.54
• InChiKey: BNPXTRYFFAASKQ-JDQULTIISA-N

物化性质

• 沸点：
  633.3±55.0 °C(Predicted)
• 密度：
  1.31±0.1 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  2.23
• 重原子数：
  33.0
• 可旋转键数：
  5.0
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.64
• 拓扑面积：
  113.37
• 氢给体数：
  2.0
• 氢受体数：
  8.0

反应信息

• 作为反应物：
  描述：

  11-O-desacetyl-20-(N,N-diethylimino)-20-desoxowortmannin 在 盐酸 作用下， 以 1,4-二氧六环 为溶剂， 反应 19.0h， 生成 11-desacetylwortmannin
  参考文献：
  名称：

  Synthesis and in Vitro Evaluation of New Wortmannin Esters:  Potent Inhibitors of Phosphatidylinositol 3-Kinase

  摘要：

  New C-11 esters of the fermentation product wortmannin have been synthesized, with some of them further derivatized at C-17. The new esters show greater inhibition of isolated phosphatidylinositol 3-kinase and increased cell cytotoxicity in a rapidly proliferating leukemia cell line, when compared to wortmannin. Reduction of the C-17 ketone caused a slight increase in activity, while acylation of this new alcohol caused severe loss of activity. With their increased activity, the new C-11 esters may be good candidates to explore the in vivo antitumor effects of phosphatidylinositol 3-kinase inhibitors.

  DOI：

  10.1021/jm960283z
• 作为产物：
  描述：

  二乙胺 、 渥曼青霉素 以 甲醇 为溶剂， 反应 22.0h， 生成 11-O-desacetyl-20-(N,N-diethylimino)-20-desoxowortmannin
  参考文献：
  名称：

  Synthesis and in Vitro Evaluation of New Wortmannin Esters:  Potent Inhibitors of Phosphatidylinositol 3-Kinase

  摘要：

  New C-11 esters of the fermentation product wortmannin have been synthesized, with some of them further derivatized at C-17. The new esters show greater inhibition of isolated phosphatidylinositol 3-kinase and increased cell cytotoxicity in a rapidly proliferating leukemia cell line, when compared to wortmannin. Reduction of the C-17 ketone caused a slight increase in activity, while acylation of this new alcohol caused severe loss of activity. With their increased activity, the new C-11 esters may be good candidates to explore the in vivo antitumor effects of phosphatidylinositol 3-kinase inhibitors.

  DOI：

  10.1021/jm960283z