3-(β-D-ribofuranosyl)-6-hydroxymethyl-2,3-dihydrofurano[2,3-d]pyrimidin-2-one | 1058167-74-0

• 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
• 英文别名: 3-((2R,3R,4S,5R)-3,4-Dihydroxy-5-(hydroxymethyl)tetrahydrofuran-2-yl)-6-(hydroxymethyl)furo[2,3-d]pyrimidin-2(3H)-one；3-[(2R,3R,4S,5R)-3,4-dihydroxy-5-(hydroxymethyl)oxolan-2-yl]-6-(hydroxymethyl)furo[2,3-d]pyrimidin-2-one
• CAS: 1058167-74-0
• 化学式: C₁₂H₁₄N₂O₇
• 分子量: 298.252
• InChiKey: RAVVHPSRJRETBQ-TURQNECASA-N

计算性质

• 辛醇/水分配系数(LogP)：
  -2.4
• 重原子数：
  21
• 可旋转键数：
  3
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.5
• 拓扑面积：
  132
• 氢给体数：
  4
• 氢受体数：
  7

反应信息

• 作为反应物：
  描述：

  3-(β-D-ribofuranosyl)-6-hydroxymethyl-2,3-dihydrofurano[2,3-d]pyrimidin-2-one 在 ammonium hydroxide 作用下， 以 甲醇 为溶剂， 反应 20.0h， 生成
  参考文献：
  名称：

  呋喃和吡咯 [2,3-D] 嘧啶核苷及其 5'-O-三磷酸酯：合成和酶活性

  摘要：

  合成了一系列双环 [2,3-d] 呋喃和吡咯并嘧啶核糖核苷，并将其化学转化为相应的 5'-O-三磷酸。报道了三磷酸盐对某些 RNA 和 DNA 聚合酶的底物特性

  DOI：

  10.1080/15257770701516250
• 作为产物：
  描述：

  3-(β-D-ribofuranosyl)-6-trytyloxymethyl-2,3-dihydrofurano[2,3-d]pyrimidin-2-one 在 水 、 溶剂黄146 作用下， 反应 12.0h， 以87%的产率得到3-(β-D-ribofuranosyl)-6-hydroxymethyl-2,3-dihydrofurano[2,3-d]pyrimidin-2-one
  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