2-(hexadecylthio)ethylphosphocholine | 131933-54-5

• 分子结构分类: 有机化合物 - 有机氮化合物
• 英文名称: 2-(hexadecylthio)ethylphosphocholine
• 英文别名: 2-Hexadecylthioethyl phosphocholine；2-hexadecylsulfanylethyl 2-(trimethylazaniumyl)ethyl phosphate
• CAS: 131933-54-5
• 化学式: C₂₃H₅₀NO₄PS
• 分子量: 467.694
• InChiKey: QMZUWVWTSXKAJU-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  7.4
• 重原子数：
  30
• 可旋转键数：
  23
• 环数：
  0.0
• sp3杂化的碳原子比例：
  1.0
• 拓扑面积：
  83.9
• 氢给体数：
  0
• 氢受体数：
  5

反应信息

• 作为产物：
  描述：

  溴代十六烷 在 氢氧化钾 、 三乙胺 作用下， 以 乙醇 、 水 为溶剂， 反应 24.0h， 生成 2-(hexadecylthio)ethylphosphocholine
  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：——
• (PHOSPHO)LIPIDS FOR COMBATTING HEPATITIS B VIRUS INFECTION
  申请人：WAKE FOREST UNIVERSITY

  公开号：EP0702556A1

  公开（公告）日：1996-03-27
• US5770584A
  申请人：——

  公开号：US5770584A

  公开（公告）日：1998-06-23
• US6030960A
  申请人：——

  公开号：US6030960A

  公开（公告）日：2000-02-29
• [EN] (PHOSPHO)LIPIDS FOR COMBATTING HEPATITIS B VIRUS INFECTION<br/>[FR] (PHOSPHO)LIPIDES CONTRE L'INFECTION A VIRUS DE L'HEPATITE B
  申请人：——

  公开号：WO1994028908A2

  公开（公告）日：1994-12-22

  [EN] A method of treating hepatitis B virus is disclosed. The method comprises administering to a subject in need of such treatment a hepatitis B combatting amount of alkyl ether phospholipids and alkyl ether phospholipid derivatives.
  [FR] L'invention concerne un procédé de traitement du virus de l'hépatite B. Le procédé consiste à administrer à un sujet nécessitant ce traitement une dose de phospholipides d'alkyle éther et de dérivés de phospholipides d'alkyle éther efficace pour combattre le virus de l'hépatite B.