rac-1-O-hexadecyl-2-O-ethylglycero-3-phospho-N-isopropylethanolamine | 128723-54-6

• 分子结构分类: 有机化合物 - 脂质和类脂质分子 - 甘油磷脂
• 英文名称: rac-1-O-hexadecyl-2-O-ethylglycero-3-phospho-N-isopropylethanolamine
• 英文别名: 2-Ethoxy-3-(hexadecyloxy)propyl 2-[(propan-2-yl)amino]ethyl hydrogen phosphate；(2-ethoxy-3-hexadecoxypropyl) 2-(propan-2-ylamino)ethyl hydrogen phosphate
• CAS: 128723-54-6
• 化学式: C₂₆H₅₆NO₆P
• 分子量: 509.707
• InChiKey: QYZIFENMIRZXEQ-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  7.2
• 重原子数：
  34
• 可旋转键数：
  27
• 环数：
  0.0
• sp3杂化的碳原子比例：
  1.0
• 拓扑面积：
  93.7
• 氢给体数：
  1
• 氢受体数：
  6

反应信息

• 作为产物：
  描述：

  2-(异丙基氨)乙醇 、 3-(hexadecyloxy)-2-ethoxy-1-propanol 、 1,2-dimethylethenylene phosphorochloridate 在 三乙胺 作用下， 生成 rac-1-O-hexadecyl-2-O-ethylglycero-3-phospho-N-isopropylethanolamine
  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.