1-[2-(phosphonomethoxy)ethyl]-5-(3-thienyl)uracil | 937805-23-7

• 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: 1-[2-(phosphonomethoxy)ethyl]-5-(3-thienyl)uracil
• 英文别名: 2-(2,4-Dioxo-5-thiophen-3-ylpyrimidin-1-yl)ethoxymethylphosphonic acid
• CAS: 937805-23-7
• 化学式: C₁₁H₁₃N₂O₆PS
• 分子量: 332.274
• InChiKey: LUHUQIJQRYTIIX-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  -1.4
• 重原子数：
  21
• 可旋转键数：
  6
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.27
• 拓扑面积：
  144
• 氢给体数：
  3
• 氢受体数：
  7

反应信息

• 作为产物：
  描述：

  5-(3-thienyl)-1-[2-(diisopropoxyphosphoryl)ethyl]uracil 在 三甲基溴硅烷 作用下， 以 乙腈 、 水 为溶剂， 反应 1.0h， 以75%的产率得到1-[2-(phosphonomethoxy)ethyl]-5-(3-thienyl)uracil
  参考文献：
  名称：

  Use of Pd-catalyzed Suzuki–Miyaura coupling reaction in the rapid synthesis of 5-aryl-6-(phosphonomethoxy)uracils and evaluation of their inhibitory effect towards human thymidine phosphorylase

  摘要：

  A number of new 5-aryl substituted pyrimidine acyclic nucleoside phosphonates were synthesized and tested for their ability to inhibit human TP. Their rapid synthesis using Pd-catalyzed Suzuki-Miyaura coupling reactions of various arylboronic acids with 5-bromo-4-(phosphonomethoxy)-2,6-dibutoxypyrimidine was successfully applied. For a series of 5-aryl-6-phosphonomethoxyuracils, an increased inhibitory effect was determined. This effect is supported by the results found for 4-fluorophenyl (K-i(dThd)=4.89 +/- 0.62) and 3-nitrophenyl (K-i(dThd)=3.98 +/- 0.46) substituents. (C) 2009 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.tet.2009.08.039