2-octadecanamidoethylphosphocholine | 82755-92-8

• 分子结构分类: 有机化合物 - 有机氮化合物
• 英文名称: 2-octadecanamidoethylphosphocholine
• 英文别名: 2-Octadecanamidoethyl phosphocholine；2-(octadecanoylamino)ethyl 2-(trimethylazaniumyl)ethyl phosphate
• CAS: 82755-92-8
• 化学式: C₂₅H₅₃N₂O₅P
• 分子量: 492.68
• InChiKey: YUPOCVFDWNKTCJ-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  6.7
• 重原子数：
  33
• 可旋转键数：
  24
• 环数：
  0.0
• sp3杂化的碳原子比例：
  0.96
• 拓扑面积：
  87.7
• 氢给体数：
  1
• 氢受体数：
  5

反应信息

• 作为产物：
  描述：

  十八烷酰氯 在 吡啶 、 silver carbonate 作用下， 以 乙醚 、 氯仿 、 水 、 N,N-二甲基甲酰胺 、 异丙醇 为溶剂， 反应 12.5h， 生成 2-octadecanamidoethylphosphocholine
  参考文献：
  名称：

  In vitro evaluation of phosphocholine and quaternary ammonium containing lipids as novel anti-HIV agents

  摘要：

  A series of synthetic lipids containing a two- or three-carbon backbone substituted with a thio, oxy, or amidoalkyl functionality and either a phosphocholine or quaternary ammonium moiety was evaluated as potential anti-HIV-1 agents. Several analogues were identified as possessing activity with the most promising compound being rac-3-octadecanamido-2-ethoxypropylphosphocholine (8). Compound 8 exhibited an IC50 for the inhibition of plaque formation of 0.16-mu-M which was 84-fold lower than the IC50 value determined for CEM-SS cell growth inhibition. Initial mechanistic studies have indicated that these compounds, unlike AZT, are not reverse transcriptase (RT) inhibitors, but instead appear to inhibit a late step in HIV replication involving virus assembly and infectious virus production. Since these lipids are acting via a different mechanism, they represent an alternative approach to the chemotherapeutic treatment of AIDS as well as candidates for combination therapy with AZT.

  DOI：

  10.1021/jm00108a021

文献信息

• MEYER, KAREN L.;MARASCO, CANIO J. (JR);MORRIS-NATSCHKE, SUSAN L.;ISHAQ, K+, J. MED. CHEM., 34,(1991) N, C. 1377-1383
  作者：MEYER, KAREN L.、MARASCO, CANIO J. (JR)、MORRIS-NATSCHKE, SUSAN L.、ISHAQ, K+

  DOI：——

  日期：——
• In vitro evaluation of phosphocholine and quaternary ammonium containing lipids as novel anti-HIV agents
  作者：Karen L. Meyer、Canino J. Marasco、Susan L. Morris-Natschke、Khalid S. Ishaq、Claude Piantadosi、Louis S. Kucera

  DOI：10.1021/jm00108a021

  日期：1991.4

  A series of synthetic lipids containing a two- or three-carbon backbone substituted with a thio, oxy, or amidoalkyl functionality and either a phosphocholine or quaternary ammonium moiety was evaluated as potential anti-HIV-1 agents. Several analogues were identified as possessing activity with the most promising compound being rac-3-octadecanamido-2-ethoxypropylphosphocholine (8). Compound 8 exhibited an IC50 for the inhibition of plaque formation of 0.16-mu-M which was 84-fold lower than the IC50 value determined for CEM-SS cell growth inhibition. Initial mechanistic studies have indicated that these compounds, unlike AZT, are not reverse transcriptase (RT) inhibitors, but instead appear to inhibit a late step in HIV replication involving virus assembly and infectious virus production. Since these lipids are acting via a different mechanism, they represent an alternative approach to the chemotherapeutic treatment of AIDS as well as candidates for combination therapy with AZT.