6,7-seco-Discodermolide

• 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: 6,7-seco-Discodermolide
• 英文别名: [(3Z,5S,6S,7S,8R,9S,11Z,13S)-8-hydroxy-5,7,9,11-tetramethyl-13-[(2S,3S)-3-methyl-6-oxo-2,3-dihydropyran-2-yl]tetradeca-1,3,11-trien-6-yl] carbamate
• 化学式: C₂₅H₃₉NO₅
• 分子量: 433.588
• InChiKey: IWHUTUDZNNKLLU-OPRQYEGWSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  5.7
• 重原子数：
  31
• 可旋转键数：
  12
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.6
• 拓扑面积：
  98.8
• 氢给体数：
  2
• 氢受体数：
  5

反应信息

• 作为反应物：
  描述：

  6,7-seco-Discodermolide 在 titanium(IV) isopropylate 作用下， 以 二氯甲烷 为溶剂， 反应 336000.0h， 以0.6 mg的产率得到(2S,3S)-2-[(2S,3Z,6S,7R,8S,9S,10S,11Z)-7,9-dihydroxy-4,6,8,10-tetramethyltetradeca-3,11,13-trien-2-yl]-3-methyl-2,3-dihydropyran-6-one
  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：

  盘皮海绵内酯 在 manganese(IV) oxide 作用下， 以 乙酸乙酯 为溶剂， 反应 48.0h， 以3.4 mg的产率得到6,7-seco-Discodermolide
  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

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.

表征谱图