(+/-)-3-(hexadecyloxy)-2-methoxypropylphosphonic acid | 131933-59-0

• 分子结构分类: 有机化合物 - 有机酸及其衍生物 - 有机膦酸及其衍生物
• 英文名称: (+/-)-3-(hexadecyloxy)-2-methoxypropylphosphonic acid
• 英文别名: rac-3-(hexadecyloxy)-2-methoxypropylphosphonic acid；(+/-)-3-Hexadecyloxy-2-methoxypropyl phosphonic acid；3-Hexadecyloxy-2-methoxypropyl phosphonic acid；(3-Hexadecoxy-2-methoxypropyl)phosphonic acid
• CAS: 131933-59-0
• 化学式: C₂₀H₄₃O₅P
• 分子量: 394.532
• InChiKey: YHTMCRFRVZQZKY-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  5.9
• 重原子数：
  26
• 可旋转键数：
  20
• 环数：
  0.0
• sp3杂化的碳原子比例：
  1.0
• 拓扑面积：
  76
• 氢给体数：
  2
• 氢受体数：
  5

反应信息

• 作为反应物：
  描述：

  1-(2-hydroxyethyl)pyridinium bromide 、 (+/-)-3-(hexadecyloxy)-2-methoxypropylphosphonic acid 在 吡啶 、 triisopropylbenzenesulfonyl chloride 作用下， 以52%的产率得到rac-2'-pyridylethyl 3-(hexadecyloxy)-2-methoxypropylphosphonate
  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：

  rac-dimethyl 3-(hexadecyloxy)-2-methoxypropylphosphonate 在 三甲基溴硅烷 作用下， 以 氯仿 为溶剂， 反应 1.0h， 以85%的产率得到(+/-)-3-(hexadecyloxy)-2-methoxypropylphosphonic acid
  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

• Synthesis and evaluation of novel ether lipid nucleoside conjugates for anti-HIV-1 activity
  作者：Claude Piantadosi、Canio J. Marasco、Susan L. Morris-Natschke、Karen L. Meyer、Fatma Gumus、Jefferson R. Surles、Khalid S. Ishaq、Louis S. Kucera、Nathan Iyer

  DOI：10.1021/jm00108a025

  日期：1991.4

  Combinations of an amidoalkylphosphocholine, 8, and AZT have been found to cause an apparent synergistic action in suppressing infectious HIV-1 replication. In addition, amidoalkyl, oxyalkyl, and thioalkyl ether lipids have been chemically linked to anti-HIV-1 nucleosides (AZT and DDI) through phosphate and phosphonate linkages. These conjugates have shown promising in vitro anti-HIV-1 activity. Also, the conjugates have a 5-10-fold reduction in cell cytotoxicity compared to AZT alone. The most active compound, an amidoalkyl ether lipid-AZT conjugate, 4A, was found to have a differential selectivity of 1793 in a syncytial plaque assay. In comparison, AZT alone has a value of 1281.
• 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：——
• PIANTADOSI, CLAUDE;MARASCO, CANIO J. (JR);MORRIS-NATACHKE, SUSAN L.;MEYER+, J. MED. CHEM., 34,(1991) N, C. 1408-1414
  作者：PIANTADOSI, CLAUDE、MARASCO, CANIO J. (JR)、MORRIS-NATACHKE, SUSAN L.、MEYER+

  DOI：——

  日期：——
• ETHER LIPID-NUCLEOSIDE COVALENT CONJUGATES
  申请人：WAKE FOREST UNIVERSITY

  公开号：EP0533825B1

  公开（公告）日：1996-04-24
• US5512671A
  申请人：——

  公开号：US5512671A

  公开（公告）日：1996-04-30