1-((2R,3S,4R,5R)-5-azido-3-fluoro-4-hydroxy-5-(hydroxymethyl)tetrahydrofuran-2-yl)-4-((3-hydroxypropyl)amino)pyrimidin-2(1H)-one | 1360458-97-4

• 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-((2R,3S,4R,5R)-5-azido-3-fluoro-4-hydroxy-5-(hydroxymethyl)tetrahydrofuran-2-yl)-4-((3-hydroxypropyl)amino)pyrimidin-2(1H)-one
• 英文别名: 1-[(2R,3S,4R,5R)-5-azido-3-fluoro-4-hydroxy-5-(hydroxymethyl)tetrahydrofuran-2-yl]-4-(3-hydroxypropylamino)pyrimidin-2-one；1-[(2R,3S,4R,5R)-5-azido-3-fluoro-4-hydroxy-5-(hydroxymethyl)oxolan-2-yl]-4-(3-hydroxypropylamino)pyrimidin-2-one
• CAS: 1360458-97-4
• 化学式: C₁₂H₁₇FN₆O₅
• 分子量: 344.303
• InChiKey: ZTZLNNCJGOFNFQ-UXCLJVHYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  -0.2
• 重原子数：
  24
• 可旋转键数：
  7
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.67
• 拓扑面积：
  129
• 氢给体数：
  4
• 氢受体数：
  8

反应信息

• 作为产物：
  描述：

  在 氨 作用下， 以 甲醇 为溶剂， 生成 1-((2R,3S,4R,5R)-5-azido-3-fluoro-4-hydroxy-5-(hydroxymethyl)tetrahydrofuran-2-yl)-4-((3-hydroxypropyl)amino)pyrimidin-2(1H)-one
  参考文献：
  名称：

  Design, synthesis, and biological evaluation of new N 4 -Substituted 2′-deoxy-2′-fluoro-4′-azido cytidine derivatives as potent anti-HBV agents

  摘要：

  A series of new 2'-deoxy-2'-beta-fluoro-4'-azido-B-D-arabinofuranosyl cytidine derivatives bearing heteroatom-containing N-4-substituents were designed and synthesized. Antiviral screening in HepG2.2.15 cells identified three analogs (1a, 1d & 1g) with good anti-HBV activity and low cytotoxicty. Of them, compound 1g exhibited significant inhibitory activity on both HBV antigens secretion (EC50, HBsAg = 9 HM, EC50, HBeAg = 0.25 mu M) and viral DNA replication (intracellular, EC50 = 0.099 mu M; extracellular, EC50 < 0.01 mu M). (C) 2015 Elsevier Masson SAS. All rights reserved.

  DOI：

  10.1016/j.ejmech.2015.06.030