PhosphonorylLipid-AZT | 131933-68-1

• 分子结构分类: 有机化合物 - 核苷、核苷酸和类似物 - 嘧啶核苷
• 英文名称: PhosphonorylLipid-AZT
• 英文别名: sodium;[(2S,3S,5R)-3-azido-5-(5-methyl-2,4-dioxopyrimidin-1-yl)oxolan-2-yl]methoxy-(3-hexadecoxy-2-methoxypropyl)phosphinate
• CAS: 131933-68-1
• 化学式: C₃₀H₅₃N₅O₈P*Na
• 分子量: 665.743
• InChiKey: MXWVDUGITADCSX-MTJYKNDWSA-M

计算性质

• 辛醇/水分配系数(LogP)：
  2.9
• 重原子数：
  45
• 可旋转键数：
  25
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.87
• 拓扑面积：
  141
• 氢给体数：
  1
• 氢受体数：
  10

反应信息

• 作为产物：
  描述：

  rac-dimethyl 3-(hexadecyloxy)-2-methoxypropylphosphonate 在 三甲基溴硅烷 、 2,3-二脱氧胞啶 作用下， 以 氯仿 为溶剂， 反应 97.0h， 生成 PhosphonorylLipid-AZT
  参考文献：
  名称：

  Synthesis and evaluation of novel ether lipid nucleoside conjugates for anti-HIV-1 activity

  摘要：

  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.

  DOI：

  10.1021/jm00108a025

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.