(R,E)-N-(1-hydroxyoctadec-3-en-2-yl)octanamide | 1155206-42-0

• 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: (R,E)-N-(1-hydroxyoctadec-3-en-2-yl)octanamide
• CAS: 1155206-42-0
• 化学式: C₂₆H₅₁NO₂
• 分子量: 409.696
• InChiKey: OENMVUVLLDDCEX-XOGSUGJCSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  7.47
• 重原子数：
  29.0
• 可旋转键数：
  22.0
• 环数：
  0.0
• sp3杂化的碳原子比例：
  0.88
• 拓扑面积：
  49.33
• 氢给体数：
  2.0
• 氢受体数：
  2.0

反应信息

• 作为反应物：
  描述：

  (R,E)-N-(1-hydroxyoctadec-3-en-2-yl)octanamide 在 palladium 10% on activated carbon 、 氢气 作用下， 以 甲醇 为溶剂， 20.0 ℃ 、101.33 kPa 条件下， 反应 24.0h， 以90%的产率得到(R)-N-(1-hydroxyoctadecan-2-yl)octanamide
  参考文献：
  名称：

  Cytotoxicity and acid ceramidase inhibitory activity of 2-substituted aminoethanol amides

  摘要：

  The acid ceramidase (AC) inhibitory activity of octanoylamides, p-tert-butylbenzamides and pivaloylamides of several 2-substituted aminoethanols is reported. All the aminoethanol amides bearing a hexadecyl substituent (C16), as well as (S)-N-(1-(hexadecylthio)-3-hydroxypropan-2-yl)pivaloylamide (SC16-tb)were inhibitory in cell lysates overexpressing AC, while all other compounds were not inhibitors. Kinetic experiments with (R,E)-N-(1-hydroxyoctadec-3-en-2-yl)pivaloylamide(E-tb)and SC16-tb showed that inhibition was competitive, with K-I Values of 34 and 94.0 mu M, respectively. None of the compounds inhibited neutral ceramidase. Compounds E-tb and E-c7 (the octanoylamide of the unsaturated base E), which elicited a dose-response inhibition with IC50 values around 15 mu M, were the only AC inhibitors in intact cells. Both compounds were toxic to A549 cells with LD50 values nearly 40 mu M. Flow cytometry Studies with E-tb evidence that this compound induced a concentration-dependent cell cycle arrest at G(l) and a 20-25% apoptosis/late apoptosis/necrosis after a 24-h incubation at 50 mu M. In agreement with its activity as acidic ceramidase inhibitor, this effect was accompanied with an increase in the amounts of C14. C16 and C18 ceramides (LC-MS analyses), which suggested that these lipids may be responsible for the cytotoxic activity of E-tb. (c) 2008 Elsevier Ireland Ltd. All rights reserved,

  DOI：

  10.1016/j.chemphyslip.2008.07.012
• 作为产物：
  描述：

  辛酰氯 、 (2R,3E)-2-aminooctadec-3-en-1-ol 在 sodium acetate 作用下， 以 四氢呋喃 、 水 为溶剂， 反应 0.25h， 以92%的产率得到(R,E)-N-(1-hydroxyoctadec-3-en-2-yl)octanamide
  参考文献：
  名称：

  Cytotoxicity and acid ceramidase inhibitory activity of 2-substituted aminoethanol amides

  摘要：

  The acid ceramidase (AC) inhibitory activity of octanoylamides, p-tert-butylbenzamides and pivaloylamides of several 2-substituted aminoethanols is reported. All the aminoethanol amides bearing a hexadecyl substituent (C16), as well as (S)-N-(1-(hexadecylthio)-3-hydroxypropan-2-yl)pivaloylamide (SC16-tb)were inhibitory in cell lysates overexpressing AC, while all other compounds were not inhibitors. Kinetic experiments with (R,E)-N-(1-hydroxyoctadec-3-en-2-yl)pivaloylamide(E-tb)and SC16-tb showed that inhibition was competitive, with K-I Values of 34 and 94.0 mu M, respectively. None of the compounds inhibited neutral ceramidase. Compounds E-tb and E-c7 (the octanoylamide of the unsaturated base E), which elicited a dose-response inhibition with IC50 values around 15 mu M, were the only AC inhibitors in intact cells. Both compounds were toxic to A549 cells with LD50 values nearly 40 mu M. Flow cytometry Studies with E-tb evidence that this compound induced a concentration-dependent cell cycle arrest at G(l) and a 20-25% apoptosis/late apoptosis/necrosis after a 24-h incubation at 50 mu M. In agreement with its activity as acidic ceramidase inhibitor, this effect was accompanied with an increase in the amounts of C14. C16 and C18 ceramides (LC-MS analyses), which suggested that these lipids may be responsible for the cytotoxic activity of E-tb. (c) 2008 Elsevier Ireland Ltd. All rights reserved,

  DOI：

  10.1016/j.chemphyslip.2008.07.012