Discodermolide-3,7,11,17-tetraacetate | 299173-77-6

• 分子结构分类: 有机化合物 - 脂质和类脂质分子 - 异戊烯醇脂质
• 英文名称: Discodermolide-3,7,11,17-tetraacetate
• 英文别名: [(3R,4S,5S,6S)-3,5-dimethyl-2-oxo-6-[(2S,3Z,5S,6S,7S,8Z,11S,12R,13S,14S,15S,16Z)-2,6,12-triacetyloxy-14-carbamoyloxy-5,7,9,11,13,15-hexamethylnonadeca-3,8,16,18-tetraenyl]oxan-4-yl] acetate
• CAS: 299173-77-6
• 化学式: C₄₁H₆₃NO₁₂
• 分子量: 761.951
• InChiKey: PWBSZAOOBIXHLV-BLNDBFJPSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  7.7
• 重原子数：
  54
• 可旋转键数：
  25
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.66
• 拓扑面积：
  184
• 氢给体数：
  1
• 氢受体数：
  12

反应信息

• 作为反应物：
  描述：

  Discodermolide-3,7,11,17-tetraacetate 在 吡啶 、 sodium carbonate 作用下， 以 乙醇 为溶剂， 反应 2.0h， 生成 [(2S,3Z,5S,6S,7S,8Z,11S,12R,13S,14S,15S,16Z)-6,12-diacetyloxy-14-carbamoyloxy-1-[(2S,3R)-3,5-dimethyl-6-oxo-2,3-dihydropyran-2-yl]-5,7,9,11,13,15-hexamethylnonadeca-3,8,16,18-tetraen-2-yl] acetate
  参考文献：
  名称：

  Semisynthetic Analogues of the Microtubule-Stabilizing Agent Discodermolide:  Preparation and Biological Activity

  摘要：

  A series of 12 semisynthetic discodermolide analogues, 2-13, have been prepared using natural (+)discodermolide (1) and evaluated for in vitro cytotoxicity against cultured murine P-388 leukemia and A-549 human adenocarcinoma cells. These semisynthetic analogues showed a significant variation of cytotoxicity and confirmed the importance of the C-7 through C-19 molecular fragment for potency. Specifically, these analogues suggested the importance of the C-11 and C-17 hydroxyl groups and the C-13 double bond for the potency of discodermolide. The preparation, structure elucidation, and biological activity of these new analogues are described.

  DOI：

  10.1021/np0203234
• 作为产物：
  描述：

  乙酸酐 、 盘皮海绵内酯 在 吡啶 作用下， 以3.5 mg的产率得到Discodermolide-3,7,11,17-tetraacetate
  参考文献：
  名称：

  Acetylated Analogues of the Microtubule-Stabilizing Agent Discodermolide:  Preparation and Biological Activity

  摘要：

  A series of eight discodermolide acetates have been prepared using natural (+)-discodermolide and evaluated for in vitro cytotoxicity against the cultured murine P-388 leukemia cells. The acetylated analogues showed a significant variation of cytotoxicity and suggested the importance of C-11 and C-17 hydroxyl groups for potency. The preparation and structure elucidation of the new analogues are described.

  DOI：

  10.1021/np000423e

文献信息

• Semisynthetic Analogues of the Microtubule-Stabilizing Agent Discodermolide:  Preparation and Biological Activity
  作者：Sarath P. Gunasekera、Ross E. Longley、Richard A. Isbrucker

  DOI：10.1021/np0203234

  日期：2002.12.1

  A series of 12 semisynthetic discodermolide analogues, 2-13, have been prepared using natural (+)discodermolide (1) and evaluated for in vitro cytotoxicity against cultured murine P-388 leukemia and A-549 human adenocarcinoma cells. These semisynthetic analogues showed a significant variation of cytotoxicity and confirmed the importance of the C-7 through C-19 molecular fragment for potency. Specifically, these analogues suggested the importance of the C-11 and C-17 hydroxyl groups and the C-13 double bond for the potency of discodermolide. The preparation, structure elucidation, and biological activity of these new analogues are described.
• Acetylated Analogues of the Microtubule-Stabilizing Agent Discodermolide:  Preparation and Biological Activity
  作者：Sarath P. Gunasekera、Ross E. Longley、Richard A. Isbrucker

  DOI：10.1021/np000423e

  日期：2001.2.1

  A series of eight discodermolide acetates have been prepared using natural (+)-discodermolide and evaluated for in vitro cytotoxicity against the cultured murine P-388 leukemia cells. The acetylated analogues showed a significant variation of cytotoxicity and suggested the importance of C-11 and C-17 hydroxyl groups for potency. The preparation and structure elucidation of the new analogues are described.