Discodermolide-3,7,11-triacetate

• 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-triacetate
• 英文别名: [(2S,3S,4S,5R)-2-[(2S,3Z,5S,6S,7S,8Z,11S,12R,13S,14S,15S,16Z)-2,6-diacetyloxy-14-carbamoyloxy-12-hydroxy-5,7,9,11,13,15-hexamethylnonadeca-3,8,16,18-tetraenyl]-3,5-dimethyl-6-oxooxan-4-yl] acetate
• 化学式: C₃₉H₆₁NO₁₁
• 分子量: 719.913
• InChiKey: RUYVGMQDCWIODV-IORCPSHDSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  7.2
• 重原子数：
  51
• 可旋转键数：
  23
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.67
• 拓扑面积：
  178
• 氢给体数：
  2
• 氢受体数：
  11

反应信息

• 作为反应物：
  描述：

  Discodermolide-3,7,11-triacetate 在 sodium carbonate 作用下， 以 乙醇 为溶剂， 反应 24.0h， 以1.5 mg的产率得到Acetic acid (3Z,11Z)-(1S,2S,6S,7R,8S,9S,10S)-9-carbamoyloxy-1-[(Z)-(1S,4S)-5-((2S,3R)-3,5-dimethyl-6-oxo-3,6-dihydro-2H-pyran-2-yl)-4-hydroxy-1-methyl-pent-2-enyl]-7-hydroxy-2,4,6,8,10-pentamethyl-tetradeca-3,11,13-trienyl ester
  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.