β-11-O-desacetyl-11-O-propionyl-17-dihydrowortmannin | 174304-96-2

• 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: β-11-O-desacetyl-11-O-propionyl-17-dihydrowortmannin
• 英文别名: [(1R,3R,5S,6S,9R,18S)-6-hydroxy-18-(methoxymethyl)-1,5-dimethyl-11,16-dioxo-13,17-dioxapentacyclo[10.6.1.02,10.05,9.015,19]nonadeca-2(10),12(19),14-trien-3-yl] propanoate
• CAS: 174304-96-2
• 化学式: C₂₄H₂₈O₈
• 分子量: 444.482
• InChiKey: WVFPGSZMUCKPKZ-GAOXGZQTSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2
• 重原子数：
  32
• 可旋转键数：
  5
• 环数：
  5.0
• sp3杂化的碳原子比例：
  0.62
• 拓扑面积：
  112
• 氢给体数：
  1
• 氢受体数：
  8

反应信息

• 作为反应物：
  描述：

  N,N,N'-三甲基乙二胺 、 β-11-O-desacetyl-11-O-propionyl-17-dihydrowortmannin 以 二氯甲烷 为溶剂， 以100%的产率得到propionic acid 4-{[(2-dimethylamino-ethyl)-methyl-amino]-methylene}-6,17-dihydroxy-1-methoxymethyl-10,13-dimethyl-3,7-dioxo-1,3,4,7,10,11,12,13,14,15,16,17-dodecahydro-2-oxa-cyclopenta[a]phenanthren-11-yl ester
  参考文献：
  名称：

  WO2006/44453

  摘要：

  公开号：
• 作为产物：
  描述：

  11-O-desacetyl-20-(N,N-diethylimino)-20-desoxowortmannin 在 吡啶 、 盐酸 、 diborane(6) 作用下， 以 四氢呋喃 、 1,4-二氧六环 为溶剂， 反应 49.5h， 生成 β-11-O-desacetyl-11-O-propionyl-17-dihydrowortmannin
  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

• WO2006/44453
  申请人：——

  公开号：——

  公开（公告）日：——
• 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.