C12-鞘氨醇 | 128427-86-1

• 分子结构分类: 有机化合物 - 有机氮化合物
• 中文名称: C12-鞘氨醇
• 英文名称: (2S,3R,4E)-2-amino-4-dodecene-1,3-diol
• 英文别名: D-erythro-sphingosine；(E,2S,3R)-2-aminododec-4-ene-1,3-diol
• CAS: 128427-86-1
• 化学式: C₁₂H₂₅NO₂
• 分子量: 215.336
• InChiKey: NCNKWPUJUUMFNR-VDTGWRSZSA-N

物化性质

• 沸点：
  364.8±42.0 °C(Predicted)
• 密度：
  0.980±0.06 g/cm3(Predicted)
• 溶解度：
  DMF：10mg/mL； DMSO：2mg/mL；乙醇：可混溶

计算性质

• 辛醇/水分配系数(LogP)：
  2
• 重原子数：
  15
• 可旋转键数：
  9
• 环数：
  0.0
• sp3杂化的碳原子比例：
  0.83
• 拓扑面积：
  66.5
• 氢给体数：
  3
• 氢受体数：
  3

制备方法与用途

C12鞘氨醇是一种短链鞘氨醇同系物，能够抑制原代培养小脑细胞中的丝氨酸棕榈酰转移酶活性。

反应信息

• 作为反应物：
  描述：

  C12-鞘氨醇 在 吡啶 、 sodium hydroxide 、 四溴化碳 作用下， 以 1,4-二氧六环 为溶剂， 生成 [(E)-(1S,2R)-1-(Dimethoxy-phosphoryloxymethyl)-2-hydroxy-undec-3-enyl]-carbamic acid tert-butyl ester
  参考文献：
  名称：

  Syntheses of sphingosine-1-phosphate analogues and their interaction with EDG/S1P receptors

  摘要：

  Sphingosine-I-phosphate (SIP) is an important regulator of a wide variety of biological processes acting as an endogenous ligand to EDG/S1P receptors. In an effort to establish structure-activity relationship between EDG/S1P and ligands, we report herein homology modeling study of EDG-1/S1P(1), syntheses of S I P analogues, and cell based binding affinity study for EDG/S1P receptors. (C) 2004 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.bmcl.2004.03.001
• 作为产物：
  描述：

  (E)-(S)-1-(tert-Butyl-dimethyl-silanyloxy)-2-(trityl-amino)-dodec-4-en-3-one 在 盐酸 、 zinc(II) tetrahydroborate 作用下， 以 四氢呋喃 、 甲醇 为溶剂， 生成 C12-鞘氨醇
  参考文献：
  名称：

  Syntheses of sphingosine-1-phosphate analogues and their interaction with EDG/S1P receptors

  摘要：

  Sphingosine-I-phosphate (SIP) is an important regulator of a wide variety of biological processes acting as an endogenous ligand to EDG/S1P receptors. In an effort to establish structure-activity relationship between EDG/S1P and ligands, we report herein homology modeling study of EDG-1/S1P(1), syntheses of S I P analogues, and cell based binding affinity study for EDG/S1P receptors. (C) 2004 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.bmcl.2004.03.001

文献信息

• 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.
• USE OF SPHINGOID LONG CHAIN BASES AND THEIR ANALOGS IN TREATING AND PREVENTING BACTERIAL INFECTIONS
  申请人：YEDA RESEARCH AND DEVELOPMENT CO. LTD.

  公开号：US20150258043A1

  公开（公告）日：2015-09-17

  Methods of preventing or treating bacterial infections, including but not limited to Pseudomonas aeruginosa infections, by administering sphingoid long chain bases (LCB) are provided. The invention further relates to the use of sphingoid long chain bases, or pharmaceutical composition comprising same, for the treatment of lung diseases or disorders such as cystic fibrosis and chronic obstructive pulmonary disease.