3-(β-D-ribofuranosyl)-6-hydroxymethyl-2,3-dihydrofurano[2,3-d]pyrimidin-2-one 5'-triphosphate | 1132792-81-4

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: 3-(β-D-ribofuranosyl)-6-hydroxymethyl-2,3-dihydrofurano[2,3-d]pyrimidin-2-one 5'-triphosphate
• CAS: 1132792-81-4
• 化学式: C₁₂H₁₇N₂O₁₆P₃
• 分子量: 538.192
• InChiKey: XYNFCJMGYYESHP-TURQNECASA-N

物化性质

• 沸点：
  927.5±75.0 °C(predicted)
• 密度：
  2.45±0.1 g/cm3(Temp: 20 °C; Press: 760 Torr)(predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  -1.56
• 重原子数：
  33.0
• 可旋转键数：
  9.0
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.5
• 拓扑面积：
  277.77
• 氢给体数：
  7.0
• 氢受体数：
  14.0

反应信息

• 作为产物：
  描述：

  3-(β-D-ribofuranosyl)-6-hydroxymethyl-2,3-dihydrofurano[2,3-d]pyrimidin-2-one 在 磷酸三乙酯 、 1,8-双二甲氨基萘 、 三氯氧磷 、 三正丁胺 、 三丁基焦磷酸铵 、 水 作用下， 以 甲苯 、 N,N-二甲基甲酰胺 为溶剂， 反应 2.33h， 以14%的产率得到3-(β-D-ribofuranosyl)-6-hydroxymethyl-2,3-dihydrofurano[2,3-d]pyrimidin-2-one 5'-triphosphate
  参考文献：
  名称：

  New furano- and pyrrolo[2,3-d]pyrimidine nucleosides and their 5′-O-triphosphates: Synthesis and biological properties

  摘要：

  Bicyclic furano[2,3-d]pyrimidine ribonucleosides were synthesized by Pd(0)-and CuI-catalyzed coupling of 5-iodouridine with terminal alkynes. The treatment of the resulting nucleosides with ammonia or methylamine solution in aqueous alcohol resulted in pyrrolo-and N-7-methylpyrrolo[2,3-d]pyrimidine nucleosides. 5'-O-Triphosphates of bicyclic nucleosides were obtained by the treatment of the nucleosides with POCl3 in the presence of a "proton sponge." The 5'-O-triphosphates are not substrates for HCV RNA-dependent RNA polymerase, but are effective substrates for HCV RNA helicase/NTPase and did not inhibit ATP hydrolysis. Only 3-(beta-D-ribofuranosyl)-6-decyl-2,3-dihydrofuro-[2,3-d]pyrimidin-2-one showed a moderate anti-HCV activity in the HCV replicon system and efficiently inhibited replication of bovine viral diarrhea virus (BVDV) in KCT-cells, other compounds being inactive. None of the compounds were cytotoxic within the tested range of concentrations.

  DOI：

  10.1134/s1068162008050099