(1'R,2'Z)-N-[1-(hydroxymethyl)heptadec-2-enyl]-2,2-dimethylpropionamide | 1001429-49-7

• 分子结构分类: 有机化合物 - 有机酸及其衍生物 - 羧酸及其衍生物
• 英文名称: (1'R,2'Z)-N-[1-(hydroxymethyl)heptadec-2-enyl]-2,2-dimethylpropionamide
• 英文别名: (2r,3z)-N-(1-hydroxyoctadec-3-en-2-yl)pivalamide；N-[(Z,2R)-1-hydroxyoctadec-3-en-2-yl]-2,2-dimethylpropanamide
• CAS: 1001429-49-7
• 化学式: C₂₃H₄₅NO₂
• 分子量: 367.616
• InChiKey: XLKVHEHEFPYLAG-IGCQWYOMSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  8.1
• 重原子数：
  26
• 可旋转键数：
  17
• 环数：
  0.0
• sp3杂化的碳原子比例：
  0.87
• 拓扑面积：
  49.3
• 氢给体数：
  2
• 氢受体数：
  2

反应信息

• 作为反应物：
  描述：

  (1'R,2'Z)-N-[1-(hydroxymethyl)heptadec-2-enyl]-2,2-dimethylpropionamide 、 辛酰氯 在 sodium acetate 作用下， 以 四氢呋喃 、 水 为溶剂， 以84%的产率得到(R)-N-(1-hydroxyoctadecan-2-yl)pivalamide
  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：

  三甲基乙酰氯 、 (2R,3Z)-2-aminooctadec-3-en-1-ol 在 sodium acetate 作用下， 以 四氢呋喃 为溶剂， 反应 20.0h， 生成 (1'R,2'Z)-N-[1-(hydroxymethyl)heptadec-2-enyl]-2,2-dimethylpropionamide
  参考文献：
  名称：

  Synthesis and preliminary antifungal evaluation of a library of phytosphingolipid analogues

  摘要：

  已制备出一个由64种植物鞘氨醇类类似物组成的库，这些类似物是通过系统改变植物鞘氨醇（PHS）的C1、C3、C4和N-酰基基团而获得的，采用了源自手性池和Sharpless不对称二醇化反应的公共骨架。该库的成员作为酵母酿酒酵母（Saccaromyces cerevisiae）的生长抑制剂进行了评估。此外，还测试了1-氨基-N-哌喹酰PHS类似物，作为IPC合成酶抑制剂，并与天然产物khafrefungin进行比较。

  DOI：

  10.1039/b709421c

文献信息

• Cytotoxicity and acid ceramidase inhibitory activity of 2-substituted aminoethanol amides
  作者：Carmen Bedia、Daniel Canals、Xavier Matabosch、Youssef Harrak、Josefina Casas、Amadeu Llebaria、Antonio Delgado、Gemma Fabriás

  DOI：10.1016/j.chemphyslip.2008.07.012

  日期：2008.11

  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,
• Synthesis and preliminary antifungal evaluation of a library of phytosphingolipid analogues
  作者：David Mormeneo、Josefina Casas、Amadeu Llebaria、Antonio Delgado

  DOI：10.1039/b709421c

  日期：——

  A library of 64 phytosphingolipid analogues resulting from the systematic variation of the C1, C3, C4, and the N-acyl moiety of phytosphingosine (PHS) has been prepared from common scaffolds derived from the chiral pool and Sharpless asymmetric dihydroxylation reactions. Library members have been evaluated as growth inhibitors of the yeast Saccaromyces cerevisiae. In addition, 1-amino-N-pivaloyl PHS analogues were also tested as IPC synthase inhibitors, in comparison with the natural product khafrefungin.

  已制备出一个由64种植物鞘氨醇类类似物组成的库，这些类似物是通过系统改变植物鞘氨醇（PHS）的C1、C3、C4和N-酰基基团而获得的，采用了源自手性池和Sharpless不对称二醇化反应的公共骨架。该库的成员作为酵母酿酒酵母（Saccaromyces cerevisiae）的生长抑制剂进行了评估。此外，还测试了1-氨基-N-哌喹酰PHS类似物，作为IPC合成酶抑制剂，并与天然产物khafrefungin进行比较。