[[(5R,6R,7R,9R)-9-(4-amino-2-oxo-pyrimidin-1-yl)-6-hydroxy-4,8-dioxaspiro[4.4]nonan-7-yl]methoxy-hydroxy-phosphoryl] phosphono hydrogen phosphate | 1378913-07-5

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: [[(5R,6R,7R,9R)-9-(4-amino-2-oxo-pyrimidin-1-yl)-6-hydroxy-4,8-dioxaspiro[4.4]nonan-7-yl]methoxy-hydroxy-phosphoryl] phosphono hydrogen phosphate
• 英文别名: [[(5R,6R,8R,9R)-6-(4-amino-2-oxopyrimidin-1-yl)-9-hydroxy-1,7-dioxaspiro[4.4]nonan-8-yl]methoxy-hydroxyphosphoryl] phosphono hydrogen phosphate
• CAS: 1378913-07-5
• 化学式: C₁₂H₂₀N₃O₁₄P₃
• 分子量: 523.224
• InChiKey: RYPTYZUODKSHPB-UGKPPGOTSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  -5.6
• 重原子数：
  32
• 可旋转键数：
  8
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.67
• 拓扑面积：
  257
• 氢给体数：
  6
• 氢受体数：
  14

反应信息

• 作为产物：
  描述：

  N-(2-oxo-1-((2R,6a'R,8'R,9a'R)-2',2',4',4'-tetraisopropyltetrahydro-3H,6'H,8'H-spiro[furan-2,9'-furo[3,2-f][1,3,5,2,4]trioxadisilocin]-8'-yl)-1,2-dihydropyrimidin-4-yl)benzamide 在 N,N-二甲基丙烯基脲 、 三正丁胺 、 四丁基氟化铵 、 氨 、 三丁基焦磷酸铵 、 三氯氧磷 作用下， 以 四氢呋喃 、 甲醇 为溶剂， 反应 21.0h， 生成 [[(5R,6R,7R,9R)-9-(4-amino-2-oxo-pyrimidin-1-yl)-6-hydroxy-4,8-dioxaspiro[4.4]nonan-7-yl]methoxy-hydroxy-phosphoryl] phosphono hydrogen phosphate
  参考文献：
  名称：

  Use of 2′-Spirocyclic Ethers in HCV Nucleoside Design

  摘要：

  Conformationally restricted 2'-spironucleosides and their prodrugs were synthesized as potential anti-HCV agents. Although the replicon activity of the new agents containing pyrimidine bases was modest, the triphosphate of a 2'-oxetane cytidine analogue demonstrated potent intrinsic biochemical activity against the NS5B polymerase, with IC50 = 8.48 mu M. Activity against NS5B bearing the S282T mutation was reduced. Phosphoramidate prodrugs of a 2'-oxetane 2-amino-6-O-methylpurine nucleoside demonstrated potent anti-HCV activity in vitro, and the corresponding triphosphate retained similar potent activity against both wild-type and S282T HCV NS5B polymerase.

  DOI：

  10.1021/jm401224y