Hexanoic acid ((E)-(1S,2R)-2-hydroxy-1-hydroxymethyl-undec-3-enyl)-amide | 241478-51-3

• 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: Hexanoic acid ((E)-(1S,2R)-2-hydroxy-1-hydroxymethyl-undec-3-enyl)-amide
• 英文别名: N-[(E,2S,3R)-1,3-dihydroxydodec-4-en-2-yl]hexanamide
• CAS: 241478-51-3
• 化学式: C₁₈H₃₅NO₃
• 分子量: 313.481
• InChiKey: XYHQCLGFWJDLCH-AONBVXOQSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  4.2
• 重原子数：
  22
• 可旋转键数：
  14
• 环数：
  0.0
• sp3杂化的碳原子比例：
  0.83
• 拓扑面积：
  69.6
• 氢给体数：
  3
• 氢受体数：
  3

反应信息

• 作为反应物：
  描述：

  Hexanoic acid ((E)-(1S,2R)-2-hydroxy-1-hydroxymethyl-undec-3-enyl)-amide 在 吡啶 、 4,4'-二氨基二苯乙烯-2,2'-二磺酸 作用下， 以 二氯甲烷 为溶剂， 反应 3.75h， 生成 (4S,5S)-5-[(E)-1-nonenyl]-2-pentyl-4-[(trityloxy)methyl]-4,5-dihydro-1,3-oxazole
  参考文献：
  名称：

  鞘氨醇部分具有取代芳环或烯丙基氟化物的神经酰胺类似物的合成和生物学评估。

  摘要：

  在海马神经元中研究了合成的神经酰胺类似物的生物活性，该神经酰胺类似物具有修饰的类神经鞘和N-酰基链以及在烯丙基位置的氟取代基。他们对轴突生长的影响与天然神经酰胺的C（6）-N-酰基类似物进行了比较。在鞘氨醇部分具有苯基且N-酰基链短的D-赤型神经酰胺能够逆转伏马菌素B（1）（FB（1））的抑制作用，但不能逆转D-threo-1-苯基的抑制作用-2-癸酰基氨基-3-吗啉代-1-丙醇（PDMP）对海马神经元轴突生长的促进作用。此外，我们证明了鞘氨醇部分中具有芳香环的神经酰胺类似物被葡糖神经酰胺合酶识别为底物，这表明观察到的生物学效应是通过糖基化激活神经酰胺类似物介导的。在鞘氨醇部分的苯环的对位引入甲基，戊基，氟或甲氧基取代基产生部分活性的化合物。同样，用苯环取代噻吩基并不能消除逆转FB（1）对轴突生长的抑制作用。具有烯丙基氟取代基的D-赤型和L-苏型神经酰胺类似物均部分逆转了FB（1）的抑制作

  DOI：

  10.1021/jm000939v
• 作为产物：
  描述：

  己酸 、 C12-鞘氨醇 在 1-羟基苯并三唑 、 达卡巴嗪 作用下， 以 二氯甲烷 为溶剂， 以81%的产率得到Hexanoic acid ((E)-(1S,2R)-2-hydroxy-1-hydroxymethyl-undec-3-enyl)-amide
  参考文献：
  名称：

  Effect of Aromatic Short-Chain Analogues of Ceramide on Axonal Growth in Hippocampal Neurons

  摘要：

  A series of D-erythro- and L-threo-ceramide analogues was synthesized and investigated for their ability to reverse the inhibitory effects of fumonisin B-1 (FB1) on axonal growth in hippocampal neurons. The analogues contained either a C-7 Side chain or a phenyl group substituted for the C-13 residue present in naturally occurring ceramides, while the N-acyl chain length was reduced from C-16-C-24 to C-2-C-8. D-erythro-Ceramide 18a with a C-7 Side chain and an N-acetyl residue and D-erythro-ceramide 20c with an aromatic side chain and an N-hexanoyl residue were most active in reversing the inhibitory effects of FB1 on axonal growth, although the mechanism remains unclear.

  DOI：

  10.1021/jm990091e

文献信息

• Synthesis and apoptogenic activity of fluorinated ceramide and dihydroceramide analogues
  作者：Steven De Jonghe、Ilse Van Overmeire、Johan Gunst、André De Bruyn、Chris Hendrix、Serge Van Calenbergh、Roger Busson、Denis De Keukeleire、Jan Philippé、Piet Herdewijn

  DOI：10.1016/s0960-894x(99)00553-3

  日期：1999.11

  Short-chain 3-fluoro-(dihydro)ceramide analogues are synthesized from L-serine using diethylaminosulfur trifluoride (DAST) as fluorinating agent. The apoptogenic activity of these compounds was measured in three different cell lines and compared with their hydroxylated counterparts. (C) 1999 Elsevier Science Ltd. All rights reserved.
• Synthesis and Biological Evaluation of Ceramide Analogues with Substituted Aromatic Rings or an Allylic Fluoride in the Sphingoid Moiety
  作者：Ilse Van Overmeire、Swetlana A. Boldin、Krishnan Venkataraman、Rivka Zisling、Steven De Jonghe、Serge Van Calenbergh、Denis De Keukeleire、Anthony H. Futerman、Piet Herdewijn

  DOI：10.1021/jm000939v

  日期：2000.11.1

  The biological activity of synthetic ceramide analogues, having modified sphingoid and N-acyl chains, as well as fluorine substituents in the allylic position, was investigated in hippocampal neurons. Their influence on axonal growth was compared to that of C(6)-N-acyl analogues of natural ceramides. D-erythro-Ceramides with a phenyl group in the sphingoid moiety and a short N-acyl chain were able

  在海马神经元中研究了合成的神经酰胺类似物的生物活性，该神经酰胺类似物具有修饰的类神经鞘和N-酰基链以及在烯丙基位置的氟取代基。他们对轴突生长的影响与天然神经酰胺的C（6）-N-酰基类似物进行了比较。在鞘氨醇部分具有苯基且N-酰基链短的D-赤型神经酰胺能够逆转伏马菌素B（1）（FB（1））的抑制作用，但不能逆转D-threo-1-苯基的抑制作用-2-癸酰基氨基-3-吗啉代-1-丙醇（PDMP）对海马神经元轴突生长的促进作用。此外，我们证明了鞘氨醇部分中具有芳香环的神经酰胺类似物被葡糖神经酰胺合酶识别为底物，这表明观察到的生物学效应是通过糖基化激活神经酰胺类似物介导的。在鞘氨醇部分的苯环的对位引入甲基，戊基，氟或甲氧基取代基产生部分活性的化合物。同样，用苯环取代噻吩基并不能消除逆转FB（1）对轴突生长的抑制作用。具有烯丙基氟取代基的D-赤型和L-苏型神经酰胺类似物均部分逆转了FB（1）的抑制作
• Effect of Aromatic Short-Chain Analogues of Ceramide on Axonal Growth in Hippocampal Neurons
  作者：Ilse Van Overmeire、Swetlana A. Boldin、Filip Dumont、Serge Van Calenbergh、Guido Slegers、Denis De Keukeleire、Anthony H. Futerman、Piet Herdewijn

  DOI：10.1021/jm990091e

  日期：1999.7.1

  A series of D-erythro- and L-threo-ceramide analogues was synthesized and investigated for their ability to reverse the inhibitory effects of fumonisin B-1 (FB1) on axonal growth in hippocampal neurons. The analogues contained either a C-7 Side chain or a phenyl group substituted for the C-13 residue present in naturally occurring ceramides, while the N-acyl chain length was reduced from C-16-C-24 to C-2-C-8. D-erythro-Ceramide 18a with a C-7 Side chain and an N-acetyl residue and D-erythro-ceramide 20c with an aromatic side chain and an N-hexanoyl residue were most active in reversing the inhibitory effects of FB1 on axonal growth, although the mechanism remains unclear.