(2-((2R,3R,4R,5R)-5-(6-amino-9H-purin-9-yl)-4-fluoro-3-hydroxytetrahydrofuran-2-yl)vinyl)phosphonic diphosphoric anhydride | 1048373-94-9

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 咪唑并嘧啶类
• 英文名称: (2-((2R,3R,4R,5R)-5-(6-amino-9H-purin-9-yl)-4-fluoro-3-hydroxytetrahydrofuran-2-yl)vinyl)phosphonic diphosphoric anhydride
• CAS: 1048373-94-9
• 化学式: C₁₁H₁₅FN₅O₁₁P₃
• 分子量: 505.187
• InChiKey: WBNLPRDUAFJVPC-HUKYDQBMSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  -0.07
• 重原子数：
  31.0
• 可旋转键数：
  7.0
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.36
• 拓扑面积：
  249.67
• 氢给体数：
  6.0
• 氢受体数：
  12.0

反应信息

• 作为反应物：
  描述：

  (2-((2R,3R,4R,5R)-5-(6-amino-9H-purin-9-yl)-4-fluoro-3-hydroxytetrahydrofuran-2-yl)vinyl)phosphonic diphosphoric anhydride 在 palladium 10% on activated carbon 、 氢气 作用下， 以 水 为溶剂， 反应 0.5h， 以69%的产率得到2-[(2R,3R,4R,5R)-5-(6-aminopurin-9-yl)-4-fluoro-3-hydroxyoxolan-2-yl]ethyl-[hydroxy(phosphonooxy)phosphoryl]oxyphosphinic acid
  参考文献：
  名称：

  Evaluation of 2′-α-fluorine modified nucleoside phosphonates as potential inhibitors of HCV polymerase

  摘要：

  Ribonucleoside phosphonate analogues containing 2'-alpha-fluoro modifications were synthesized and their potency evaluated against HCV RNA polymerase. The diphosphophosphonate (triphosphate equivalent) adenine and cytidine analogues displayed potent inhibition of the HCV polymerase in the range of 1.9-2.1 mu M, but only modest cell-based activity in the HCV replicon. Pro- drugs of the parent nucleoside phosphonates improved the cell-based activity. (C) 2013 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.bmcl.2013.03.095
• 作为产物：
  描述：

  (2R,3R,4R,5R)-5-(6-benzamido-9H-purin-9-yl)-2-(2-(dimethoxyphosphoryl)vinyl)-4-fluorotetrahydrofuran-3-yl benzoate 在 2,6-二甲基吡啶 、 ammonium hydroxide 、 三正丁胺 、 三甲基溴硅烷 、 N,N'-羰基二咪唑 作用下， 以 N,N-二甲基甲酰胺 、 乙腈 为溶剂， 反应 36.0h， 生成 (2-((2R,3R,4R,5R)-5-(6-amino-9H-purin-9-yl)-4-fluoro-3-hydroxytetrahydrofuran-2-yl)vinyl)phosphonic diphosphoric anhydride
  参考文献：
  名称：

  Evaluation of 2′-α-fluorine modified nucleoside phosphonates as potential inhibitors of HCV polymerase

  摘要：

  Ribonucleoside phosphonate analogues containing 2'-alpha-fluoro modifications were synthesized and their potency evaluated against HCV RNA polymerase. The diphosphophosphonate (triphosphate equivalent) adenine and cytidine analogues displayed potent inhibition of the HCV polymerase in the range of 1.9-2.1 mu M, but only modest cell-based activity in the HCV replicon. Pro- drugs of the parent nucleoside phosphonates improved the cell-based activity. (C) 2013 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.bmcl.2013.03.095