11-Desacetoxy-11-oxo-wortmannin | 52041-40-4

• 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-Desacetoxy-11-oxo-wortmannin
• 英文别名: (1S,5S,9R,18S)-18-(methoxymethyl)-1,5-dimethyl-13,17-dioxapentacyclo[10.6.1.02,10.05,9.015,19]nonadeca-2(10),12(19),14-triene-3,6,11,16-tetrone
• CAS: 52041-40-4
• 化学式: C₂₁H₂₀O₇
• 分子量: 384.386
• InChiKey: MLTIJQJZGGGTFN-RUSAIQRGSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  1
• 重原子数：
  28
• 可旋转键数：
  2
• 环数：
  5.0
• sp3杂化的碳原子比例：
  0.52
• 拓扑面积：
  99.9
• 氢给体数：
  0
• 氢受体数：
  7

反应信息

• 作为产物：
  描述：

  11-O-desacetyl-20-(N,N-diethylimino)-20-desoxowortmannin 在 盐酸 、 重铬酸吡啶 作用下， 以 1,4-二氧六环 、 二氯甲烷 为溶剂， 反应 21.5h， 生成 11-Desacetoxy-11-oxo-wortmannin
  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

文献信息

• Synthesis and <i>in Vitro </i>Evaluation of New Wortmannin Esters:  Potent Inhibitors of Phosphatidylinositol 3-Kinase
  作者：Lawrence C. Creemer、Herbert A. Kirst、Chris J. Vlahos、Richard M. Schultz

  DOI：10.1021/jm960283z

  日期：1996.1.1

  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.