ingenol-5β,20-O,O-isopropylidene-3β-O-palmitate

• 分子结构分类: 有机化合物 - 脂质和类脂质分子 - 脂肪酰基
• 英文名称: ingenol-5β,20-O,O-isopropylidene-3β-O-palmitate
• 英文别名: [(1S,4S,5S,6R,13S,14R,16R,18R)-5-hydroxy-3,8,8,15,15,18-hexamethyl-19-oxo-7,9-dioxapentacyclo[11.5.1.01,5.06,11.014,16]nonadeca-2,11-dien-4-yl] hexadecanoate
• 化学式: C₃₉H₆₂O₆
• 分子量: 626.918
• InChiKey: FGFHNMBIMRVWIW-FQBABPJXSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  9.1
• 重原子数：
  45
• 可旋转键数：
  16
• 环数：
  5.0
• sp3杂化的碳原子比例：
  0.85
• 拓扑面积：
  82.1
• 氢给体数：
  1
• 氢受体数：
  6

反应信息

• 作为反应物：
  描述：

  ingenol-5β,20-O,O-isopropylidene-3β-O-palmitate 在 盐酸 作用下， 以 水 为溶剂， 生成 ingenol-3-palmitate
  参考文献：
  名称：

  Syntheses, biological evaluation and SAR of ingenol mebutate analogues for treatment of actinic keratosis and non-melanoma skin cancer

  摘要：

  Ingenol mebutate is the active ingredient in Picato (R) a new drug for the treatment of actinic keratosis. A number of derivatives related to ingenol mebutate were prepared by chemical synthesis from ingenol with the purpose of investigating the SAR and potency in assays relating to pro-inflammatory effects (induction of PMN oxidative burst and keratinocyte cytokine release), the potential of cell death induction, as well as the chemical stability. By modifications of the ingenol scaffold several prerequisites for activity were identified. The chemical stability of the compounds could be linked to an acyl migration mechanism. We were able to find analogues of ingenol mebutate with comparable in vitro properties. Some key features for potent and more stable ingenol derivatives have been identified. (C) 2013 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.bmcl.2013.08.038
• 作为产物：
  描述：

  ingenol-5,20-acetonide 、 棕榈酰氯 在 4-二甲氨基吡啶 作用下， 以 甲苯 为溶剂， 反应 2.0h， 生成 ingenol-5β,20-O,O-isopropylidene-3β-O-palmitate
  参考文献：
  名称：

  Sorg, Bernd; Hecker, Erich, Zeitschrift fur Naturforschung, Teil B: Anorganische Chemie, Organische Chemie, 1982, vol. 37, # 6, p. 748 - 756

  摘要：

  DOI：

文献信息

• New diterpenoids from the roots of<i>Euphorbia ebracteolata</i>Hayata
  作者：Bin Deng、Shu-Zhen Mu、Jian-Xin Zhang、Xiao-Jiang Hao

  DOI：10.1080/14786410903388017

  日期：2010.10.10

  Three new diterpenoids, ingenol-5,20-O,O-isopropylidene-3-palmitate (1), ingenol-5,20-O,O-isopropylidene-3-myristinate (2) and 3,19-dihydroxy-1(10),15-rosadien-2-one (3), were isolated from the roots of Euphorbia ebracteolata Hayata. Their structures were deduced by spectroscopic means and analytic techniques.
• Syntheses, biological evaluation and SAR of ingenol mebutate analogues for treatment of actinic keratosis and non-melanoma skin cancer
  作者：Xifu Liang、Gunnar Grue-Sørensen、Kristoffer Månsson、Per Vedsø、Anke Soor、Martin Stahlhut、Malene Bertelsen、Karen Margrethe Engell、Thomas Högberg

  DOI：10.1016/j.bmcl.2013.08.038

  日期：2013.10

  Ingenol mebutate is the active ingredient in Picato (R) a new drug for the treatment of actinic keratosis. A number of derivatives related to ingenol mebutate were prepared by chemical synthesis from ingenol with the purpose of investigating the SAR and potency in assays relating to pro-inflammatory effects (induction of PMN oxidative burst and keratinocyte cytokine release), the potential of cell death induction, as well as the chemical stability. By modifications of the ingenol scaffold several prerequisites for activity were identified. The chemical stability of the compounds could be linked to an acyl migration mechanism. We were able to find analogues of ingenol mebutate with comparable in vitro properties. Some key features for potent and more stable ingenol derivatives have been identified. (C) 2013 Elsevier Ltd. All rights reserved.
• Sorg, Bernd; Hecker, Erich, Zeitschrift fur Naturforschung, Teil B: Anorganische Chemie, Organische Chemie, 1982, vol. 37, # 6, p. 748 - 756
  作者：Sorg, Bernd、Hecker, Erich

  DOI：——

  日期：——