L-sphingine | 250789-26-5

• 分子结构分类: 有机化合物 - 有机氮化合物
• 英文名称: L-sphingine
• 英文别名: L-Sphingin；(2S)-2-aminooctadecan-1-ol
• CAS: 250789-26-5
• 化学式: C₁₈H₃₉NO
• 分子量: 285.514
• InChiKey: DHDQQXZPXPREBK-SFHVURJKSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  7
• 重原子数：
  20
• 可旋转键数：
  16
• 环数：
  0.0
• sp3杂化的碳原子比例：
  1.0
• 拓扑面积：
  46.2
• 氢给体数：
  2
• 氢受体数：
  2

反应信息

• 作为反应物：
  描述：

  L-sphingine 在 吡啶 、 水 、 potassium carbonate 作用下， 以 乙醇 为溶剂， 生成 (2S)-2-(acetylamino)octadecan-1-ol
  参考文献：
  名称：

  (3Z)-2-Acetylamino-3-octadecen-1-ol as a potent apoptotic agent against HL-60 cells

  摘要：

  （2R,3Z）-，（2R,3E）-，（2S,3Z）和（2S,3E）-2-乙酰氨基-3-十八烯-1-醇，以及（2R）和（2S）-2-乙酰氨基-十八烷-1-醇是通过加纳尔醛（N-Boc-N,O-异丙叉-L-或D-丝氨酸）的维蒂格反应由L-或D-丝氨酸制备的。使用MTT检测法，在人白血病HL-60细胞中测试了这些饱和和不饱和2-乙酰氨基醇的凋亡活性。在新合成的化合物中，顺式异构体的活性最强。尽管它们的结构简单，（2R,3Z）-和（2S,3Z）-2-乙酰氨基-3-十八烯-1-醇的凋亡活性与N-乙酰基-D-赤型鞘氨醇（D-e-C2-Cer，一种已知的凋亡诱导剂）相比仍然很高且相当。它们的凋亡活性顺序为：D-e-C2-Cer≈L-e-C2-Cer≈（2R,3Z）≈（2S,3Z）> (2R,3E）≈（2S,3E⇒(2R））≈（2S）-衍生物。通过琼脂糖凝胶电泳对这些化合物引起的DNA片段化进行了定性分析，发现（2R,3Z）和（2S,3Z）异构体如C2-Cer会引起典型的DNA片段化，而反式和饱和异构体则不会。这些化合物诱导的细胞死亡通过外观特征、促凋性半胱氨酸蛋白酶-3的加工和多聚ADP核糖聚合酶（PARP）的切割进一步确认为凋亡。这些观察结果表明，新合成的化合物（3Z）-2-乙酰氨基-3-十八烯-1-醇在HL-60细胞中具有与C2-Cer相似的特性和诱导凋亡的活性。© 2003 Elsevier Ltd. 保留所有权利。

  DOI：

  10.1016/j.bmc.2003.10.040
• 作为产物：
  描述：

  1-acetoxy-octadecan-2-one 在 lithium aluminium tetrahydride 、 乙醚 、 乙醇 、 盐酸羟胺 、 sodium acetate 作用下， 生成 L-sphingine
  参考文献：
  名称：

  Studies in the Sphingolipids Series. II. Synthesis of Enantiomeric Sphingines

  摘要：

  DOI：

  10.1021/jo50017a011

文献信息

• Sphingoid compounds for prophylaxis and/or therapy of a viral infection
  申请人：Harbins Ruhr Bioscience, Inc.

  公开号：US10688065B2

  公开（公告）日：2020-06-23

  Provided are processes for the prevention or treatment of viral infection in a subject. Some aspects provide administration of a sphingoid compound, optionally sphingosine, an active ingredient that activates generation of a sphingoid base, optionally of sphingosine; or an active agent that inhibits the degradation of a sphingoid base, optionally of sphingosine, to a subject such as a human. By increasing the local concentration of sphingosine in a subject or an area of a subject to which the composition is administered such as the nose or interior of the nose or portion thereof, the ability of viruses to infect the subject or cells thereof is reduced thereby treating of preventing infection by the virus.

  本文提供了预防或治疗受试者病毒感染的方法。某些方面提供了向人等受试者施用鞘氨醇化合物（可选鞘氨醇）、激活生成鞘氨醇基（可选鞘氨醇）的活性成分；或抑制鞘氨醇基（可选鞘氨醇）降解的活性剂。通过增加施用组合物的受试者或受试者的局部（如鼻子或鼻子内部或其部分）的鞘氨醇浓度，可降低病毒感染受试者或其细胞的能力，从而达到预防病毒感染的目的。
• Sphingoid compounds for prophylaxis and/or therapy of coronaviridae infection
  申请人：Harbins Ruhr Bioscience, Inc.

  公开号：US11298412B2

  公开（公告）日：2022-04-12

  Provided are processes for the prevention or treatment of infection by SARS-CoV-2. Some aspects provide administration of a sphingoid compound, optionally sphingosine, an active ingredient that activates generation of a sphingoid base, optionally of sphingosine; or an active agent that inhibits the degradation of a sphingoid base, optionally of sphingosine, to a subject such as a human. By increasing the local concentration of sphingosine in a subject or an area of a subject to which the composition is administered such as the airways, nose or interior of the nose or portion thereof, the ability or SARS-CoV-2 to infect the subject or cells thereof is reduced thereby treating of preventing infection by the virus.

  本文提供了预防或治疗 SARS-CoV-2 感染的方法。某些方面提供了对人等受试者施用鞘氨醇化合物（可选鞘氨醇）、激活鞘氨醇基（可选鞘氨醇）生成的活性成分；或抑制鞘氨醇基（可选鞘氨醇）降解的活性剂。通过增加受试者或受试者施用组合物的部位（如呼吸道、鼻腔或鼻腔内部或其部分）的鞘氨醇的局部浓度，可降低 SARS-CoV-2 感染受试者或其细胞的能力，从而起到预防病毒感染的作用。
• SPHINGOID COMPOUNDS FOR PROPHYLAXIS AND/OR THERAPY OF A VIRAL INFECTION
  申请人：Harbins Ruhr Bioscience, Inc.

  公开号：US20200113850A1

  公开（公告）日：2020-04-16

  Provided are processes for the prevention or treatment of viral infection in a subject. Some aspects provide administration of a sphingoid compound, optionally sphingosine, an active ingredient that activates generation of a sphingoid base, optionally of sphingosine; or an active agent that inhibits the degradation of a sphingoid base, optionally of sphingosine, to a subject such as a human. By increasing the local concentration of sphingosine in a subject or an area of a subject to which the composition is administered such as the nose or interior of the nose or portion thereof, the ability of viruses to infect the subject or cells thereof is reduced thereby treating of preventing infection by the virus.
• SPHINGOID COMPOUNDS FOR PROPHYLAXIS AND/OR THERAPY OF CORONAVIRIDAE INFECTION
  申请人：Harbins Ruhr Bioscience, Inc.

  公开号：US20220016222A1

  公开（公告）日：2022-01-20

  Provided are processes for the prevention or treatment of infection by SARS-CoV-2. Some aspects provide administration of a sphingoid compound, optionally sphingosine, an active ingredient that activates generation of a sphingoid base, optionally of sphingosine; or an active agent that inhibits the degradation of a sphingoid base, optionally of sphingosine, to a subject such as a human. By increasing the local concentration of sphingosine in a subject or an area of a subject to which the composition is administered such as the airways, nose or interior of the nose or portion thereof, the ability or SARS-CoV-2 to infect the subject or cells thereof is reduced thereby treating of preventing infection by the virus.
• [DE] PSEUDO-CERAMIDE<br/>[EN] PSEUDOCERAMIDES<br/>[FR] PSEUDO-CERAMIDES
  申请人：MAX PLANCK GESELLSCHAFT

  公开号：WO2000021919A1

  公开（公告）日：2000-04-20

  Neue Pseudoceramid-Verbindungen der allgemeinen Formel (Ia), oder (Ib), worin x = 9 bis 17; y = 4 bis 34; R1 = H, OR4; R2 = H, CH3, C2H5, (CH2-CHOH-CH2O)zH; R3 = H, (CH2-CHOH-CH2O)z'H, R4 = H, OOC-(CH2)w-CH3; z und z' = 1 bis 6; w = 2 bis 34 bedeuten, und R2 und R3 nicht gleichzeitig die Strukturelemente (CH2-CHOH-CH2O)zH bzw. (CH2-CHOH-CH2O)z'H, darstellen, lassen sich aus den zugrundeliegenden Aminen durch Umsetzung mit einem entsprechenden Säurehalogenid unter Bildung des Säureamids herstellen. Aufgrund ihrer hautschützenden Eigenschaften sind sie für Wasch- und Pflegemittel interessant.