(2S,4E)-2-acetylamino-3-oxo-4-octadecen-1-ol

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: (2S,4E)-2-acetylamino-3-oxo-4-octadecen-1-ol
• 英文别名: N-acetyl-(S,E)-2-amino-1-oxy-octadec-4-ene-3-one；3-Oxo-1-hydroxy-2-acetamido-4-octadecen；N-[(E,2S)-1-hydroxy-3-oxooctadec-4-en-2-yl]acetamide
• 化学式: C₂₀H₃₇NO₃
• 分子量: 339.519
• InChiKey: WOJNREJLOHSMIT-VVLLFNJHSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  5.9
• 重原子数：
  24
• 可旋转键数：
  16
• 环数：
  0.0
• sp3杂化的碳原子比例：
  0.8
• 拓扑面积：
  66.4
• 氢给体数：
  2
• 氢受体数：
  3

反应信息

• 作为产物：
  描述：

  十四醇 在 三氟乙酸 、 2-碘酰基苯甲酸 作用下， 以 四氢呋喃 、 二氯甲烷 、 乙酸乙酯 为溶剂， 反应 14.0h， 生成 (2S,4E)-2-acetylamino-3-oxo-4-octadecen-1-ol
  参考文献：
  名称：

  Flexible, polymer-supported synthesis of sphingosine derivatives provides ceramides with enhanced biological activity

  摘要：

  A polymer-supported route for the synthesis of sphingosine derivatives is presented based on the C-acylation of polymeric phosphoranylidene acetates with an Fmoc-protected amino acid. The approach enables the flexible variation of the sphingosine tail through a deprotection-decarboxylation sequence followed by E-selective Wittig olefination cleavage. d-Erythro-sphingosine analogs have been synthesized by diastereoselective reduction of the keto group employing LiAlH(O-tBu)3 as reducing agent. The effect of ceramides and keto-ceramides on the proliferation of three cancer cell lines HEP G-2, PC-12 and HL-60 was investigated and a ceramide containing an aromatic sphingosine tail was identified as being most active.

  DOI：

  10.1016/j.bmc.2014.07.024

文献信息

• Short-chain 3-ketoceramides, strong apoptosis inducers against human leukemia HL-60 cells
  作者：Hideki Azuma、So Ijichi、Mayuko Kataoka、Akira Masuda、Takayuki Izumi、Tetsuya Yoshimoto、Taro Tachibana

  DOI：10.1016/j.bmc.2007.02.008

  日期：2007.4

  leukemia HL-60 cells. In particular, the two monoenoic compounds, A and C, are far more powerful than the corresponding alcoholic analogue, N-acetyl-D-erythro-sphingosine. Observations of DNA fragmentation, caspase-3 activation, and cytochrome c release from mitochondria provide substantiated evidence for mitochondrial apoptosis and the effects of exogenous glutathione on these phenomena are also discussed

  神经酰胺充当凋亡信号传导过程的第二信使。包含C-3，C-4和C-5碳的烯丙醇部分对于此功能至关重要。已经提出该醇部分在线粒体中被氧化成羰基部分，并产生活性氧。然而，对于这样推测的3-酮神经酰胺的细胞凋亡性能尚无确定的先例。在这项工作中，我们合成了三种不同类型的短链3-酮神经酰胺，即（2S，4E）-2-乙酰氨基-3-氧代-4-十八烯-1-醇（A），（2S，4E ，6E）-2-乙酰氨基-3-oxo-4,6-octadecadien-1-ol（B）和（2S，4E）-2-乙酰氨基-1-甲氧基-3-oxo-4-octadecene（C）并证明这些3-酮神经酰胺能够诱导人白血病HL-60细胞有效凋亡。特别是两种单烯化合物 A和C比相应的醇类似物N-乙酰基-D-赤型-鞘氨醇强得多。DNA片段化，caspase-3激活和线粒体细胞色素c释放的观察提供了线粒体凋亡的确凿证据，并且还讨论了外源性谷胱甘肽对这些现象的影响。
• Chemistry and Metabolism of Sphingolipids. 3-Oxo Derivatives of N-Acetylsphingosine and N-Acetyldihydrosphingosine
  作者：Robert C. Gaver、Charles C. Sweeley

  DOI：10.1021/ja00967a032

  日期：1966.8
• Flexible, polymer-supported synthesis of sphingosine derivatives provides ceramides with enhanced biological activity
  作者：Adeeb El-Dahshan、Samer I. Al-Gharabli、Silke Radetzki、Taleb H. Al-Tel、Pradeep Kumar、Jörg Rademann

  DOI：10.1016/j.bmc.2014.07.024

  日期：2014.10

  A polymer-supported route for the synthesis of sphingosine derivatives is presented based on the C-acylation of polymeric phosphoranylidene acetates with an Fmoc-protected amino acid. The approach enables the flexible variation of the sphingosine tail through a deprotection-decarboxylation sequence followed by E-selective Wittig olefination cleavage. d-Erythro-sphingosine analogs have been synthesized by diastereoselective reduction of the keto group employing LiAlH(O-tBu)3 as reducing agent. The effect of ceramides and keto-ceramides on the proliferation of three cancer cell lines HEP G-2, PC-12 and HL-60 was investigated and a ceramide containing an aromatic sphingosine tail was identified as being most active.