2-octadecanamidoethyl 2'-bromoethyl phosphate | 131933-62-5

• 分子结构分类: 有机化合物 - 有机酸及其衍生物 - 有机磷酸及其衍生物
• 英文名称: 2-octadecanamidoethyl 2'-bromoethyl phosphate
• 英文别名: 2-bromoethyl 2-(octadecanoylamino)ethyl hydrogen phosphate
• CAS: 131933-62-5
• 化学式: C₂₂H₄₅BrNO₅P
• 分子量: 514.481
• InChiKey: HRBFLFMXWQYVNS-UHFFFAOYSA-N

物化性质

• 密度：
  1.155±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  6.89
• 重原子数：
  30.0
• 可旋转键数：
  23.0
• 环数：
  0.0
• sp3杂化的碳原子比例：
  0.95
• 拓扑面积：
  84.86
• 氢给体数：
  2.0
• 氢受体数：
  4.0

反应信息

• 作为反应物：
  描述：

  2-octadecanamidoethyl 2'-bromoethyl phosphate 、 三甲胺 在 silver carbonate 作用下， 以 氯仿 、 水 、 N,N-二甲基甲酰胺 、 异丙醇 为溶剂， 反应 6.0h， 以62.6%的产率得到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
• 作为产物：
  描述：

  十八烷酰氯 在 吡啶 作用下， 以 乙醚 、 水 、 N,N-二甲基甲酰胺 为溶剂， 反应 6.5h， 生成 2-octadecanamidoethyl 2'-bromoethyl phosphate
  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：——