sodium;[(2S,3S,5R)-3-azido-5-(5-methyl-2,4-dioxopyrimidin-1-yl)oxolan-2-yl]methyl (3-hexadecylsulfanyl-2-methoxypropyl) phosphate | 131933-71-6

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 二嗪类
• 英文名称: sodium;[(2S,3S,5R)-3-azido-5-(5-methyl-2,4-dioxopyrimidin-1-yl)oxolan-2-yl]methyl (3-hexadecylsulfanyl-2-methoxypropyl) phosphate
• CAS: 131933-71-6
• 化学式: C₃₀H₅₃N₅O₈PS*Na
• 分子量: 697.809
• InChiKey: DOFYBSBTOUPWRJ-MTJYKNDWSA-M

计算性质

• 辛醇/水分配系数(LogP)：
  3.55
• 重原子数：
  46
• 可旋转键数：
  26
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.87
• 拓扑面积：
  166
• 氢给体数：
  1
• 氢受体数：
  11

反应信息

• 作为产物：
  描述：

  1-S-hexadecyl-2-O-methyl-rac-thioglycerol 在 三乙胺 、 2,3-二脱氧胞啶 、 三氯氧磷 作用下， 以 正己烷 、 甲苯 为溶剂， 反应 96.0h， 生成 sodium;[(2S,3S,5R)-3-azido-5-(5-methyl-2,4-dioxopyrimidin-1-yl)oxolan-2-yl]methyl (3-hexadecylsulfanyl-2-methoxypropyl) phosphate
  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

• 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：——