2',3'-dideoxyuridin-5'-yl H-phosphonate triethylammonium salt | 156714-00-0

• 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: 2',3'-dideoxyuridin-5'-yl H-phosphonate triethylammonium salt
• 英文别名: triethylammonium 2',3'-dideoxyuridin-5'-yl phosphonate
• CAS: 156714-00-0
• 化学式: C₆H₁₅N*C₉H₁₃N₂O₆P
• 分子量: 377.378
• InChiKey: RTGOKUFECLQEGJ-QDOHZIMISA-N

计算性质

• 辛醇/水分配系数(LogP)：
  0.96
• 重原子数：
  25.0
• 可旋转键数：
  7.0
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.73
• 拓扑面积：
  113.86
• 氢给体数：
  2.0
• 氢受体数：
  7.0

反应信息

• 作为反应物：
  描述：

  2',3'-dideoxyuridin-5'-yl H-phosphonate triethylammonium salt 在 吡啶 、 碘 、 氯磷酸二苯酯 作用下， 以 吡啶 、 二氯甲烷 为溶剂， 反应 0.24h， 生成 triethylammonium 2',3'-dideoxyuridin-5'-yl [N-(4-methylthiazol-2-yl)]phosphoramidate
  参考文献：
  名称：

  Aryl H-Phosphonates 18. Synthesis, properties, and biological activity of 2′,3′-dideoxynucleoside (N-heteroaryl)phosphoramidates of increased lipophilicity

  摘要：

  Recently, AZT (N-pyridyl)phosphoramidates were reported as a new type of potential anti-HIV therapeutics. In continuation of that work, here we present new (N-heteroaryl)phosphoramidate derivatives of antiviral 2',3'-dideoxynucleosides containing other types of N-heteroaryl moieties, particularly those with higher lipophilicity. The present studies comprise mechanistic investigations using P-31 NMR correlation analysis, which permitted improvements in the synthetic procedures. The obtained compounds were tested in biological systems to establish their cytotoxicity and anti-HIV activity. The results were analyzed with respect to possible correlations between biological and physico-chemical properties of the phosphoramidates studied, to get some,insight into their antiviral mode of action. (C) 2015 Elsevier Masson SAS. All rights reserved.

  DOI：

  10.1016/j.ejmech.2015.06.004
• 作为产物：
  描述：

  (9H-fluoren-9-yl)methyl (((2S,5R)-5-(2,4-dioxo-3,4-dihydropyrimidin-1(2H)-yl)tetrahydrofuran-2-yl)methyl) phosphonate 在 三乙胺 作用下， 以 乙腈 为溶剂， 反应 0.33h， 生成 2',3'-dideoxyuridin-5'-yl H-phosphonate triethylammonium salt
  参考文献：
  名称：

  一种新的、有效的非亲脂性 H-膦酸酯单酯的进入——抗 HIV 核苷酸类似物的制备

  摘要：

  结晶 (9H-芴-9-基) 甲基 H-膦酸铵是通过一种新的、简单的方法制备的，它被用作将 H-膦酸单酯官能团引入非亲脂性抗 HIV 核苷的首选试剂类似物。

  DOI：

  10.2174/157017809789124821