[(2S,3S,5R)-3-叠氮基-5-(5-甲基-2,4-二氧代嘧啶-1-基)四氢呋喃-2-基]甲基[2-乙氧基-3-(十八碳酰氨基)丙基]磷酸酯钠盐 | 131933-67-0

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 二嗪类
• 中文名称: [(2S,3S,5R)-3-叠氮基-5-(5-甲基-2,4-二氧代嘧啶-1-基)四氢呋喃-2-基]甲基[2-乙氧基-3-(十八碳酰氨基)丙基]磷酸酯钠盐
• 英文名称: 3'-azido-3'-deoxy-5'-(3-octadecanamido-2-ethoxypropyl)phosphothymidine
• 英文别名: Sodium 1-{3-azido-2,3-dideoxy-5-O-[{2-ethoxy-3-[(1-oxidanidyloctadecylidene)amino]propoxy}(hydroxy)phosphoryl]pentofuranosyl}-4-hydroxy-5-methylpyrimidin-2(1H)-one；sodium;N-[3-[[(2S,3S,5R)-3-azido-5-(5-methyl-2,4-dioxopyrimidin-1-yl)oxolan-2-yl]methoxy-hydroxyphosphoryl]oxy-2-ethoxypropyl]octadecanimidate
• CAS: 131933-67-0
• 化学式: C₃₃H₅₈N₆O₉P*Na
• 分子量: 736.822
• InChiKey: BAPXDLATVJKKRD-ZIYRSEDISA-M

计算性质

• 辛醇/水分配系数(LogP)：
  3.1
• 重原子数：
  50
• 可旋转键数：
  28
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.85
• 拓扑面积：
  170
• 氢给体数：
  2
• 氢受体数：
  11

反应信息

• 作为产物：
  描述：

  (+/-)-3-octadecanamido-2-ethoxy-1-propanol 在 platinum(IV) oxide 吡啶 、 氢气 、 2,3-二脱氧胞啶 作用下， 以 乙醚 、 乙醇 为溶剂， 25.0~52.0 ℃ 、99.98 kPa 条件下， 反应 100.67h， 生成 [(2S,3S,5R)-3-叠氮基-5-(5-甲基-2,4-二氧代嘧啶-1-基)四氢呋喃-2-基]甲基[2-乙氧基-3-(十八碳酰氨基)丙基]磷酸酯钠盐
  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：——
• 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.