1-((2R,3S,4R,5R)-5-azido-3-fluoro-4-hydroxy-5-(hydroxymethyl)tetrahydrofuran-2-yl)-4-(ethylamino)pyrimidin-2(1H)-one | 1360458-83-8

• 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-(ethylamino)pyrimidin-2(1H)-one
• 英文别名: 1-[(2R,3S,4R,5R)-5-azido-3-fluoro-4-hydroxy-5-(hydroxymethyl)oxolan-2-yl]-4-(ethylamino)pyrimidin-2-one
• CAS: 1360458-83-8
• 化学式: C₁₁H₁₅FN₆O₄
• 分子量: 314.276
• InChiKey: JIVVDZNKZVXBCQ-WYOJIJJFSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  0
• 重原子数：
  22
• 可旋转键数：
  5
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.64
• 拓扑面积：
  109
• 氢给体数：
  3
• 氢受体数：
  7

反应信息

• 作为产物：
  描述：

  1-(4-azido-2-deoxy-2-fluoro-3-O-benzoyl-5-O-(3-chlorobenzoyl)-β-D-arabinofuranosyl)uracil 在 4-二甲氨基吡啶 、 N,N-二异丙基乙胺 作用下， 以 二氯甲烷 、 N,N-二甲基甲酰胺 为溶剂， 反应 35.5h， 生成 1-((2R,3S,4R,5R)-5-azido-3-fluoro-4-hydroxy-5-(hydroxymethyl)tetrahydrofuran-2-yl)-4-(ethylamino)pyrimidin-2(1H)-one
  参考文献：
  名称：

  NUCLEOSIDE DERIVATIVES, SYNTHESIS METHODS AND USES THEREOF FOR PREPARING ANTI-TUMOR AND ANTI-VIRUS MEDICAMENTS

  摘要：

  公开号：

  EP2615101B1

文献信息

• Synthesis and Biological Evaluation of 4-Substituted Fluoronucleoside Analogs for the Treatment of Hepatitis B Virus Infection
  作者：Qinghua Yang、Jinfeng Kang、Liyun Zheng、Xue-Jun Wang、Na Wan、Jie Wu、Yan Qiao、Pengfei Niu、Sheng-Qi Wang、Youmei Peng、Qingduan Wang、Wenquan Yu、Junbiao Chang

  DOI：10.1021/jm5012963

  日期：2015.5.14

  A series of 4-substituted fluoronucleosides have been synthesized in order to address the toxicity issue of the parent compound 7, and after in vitro evaluation, the cyclopropylamino analog 1f was selected for in vivo study. In mice, this compound exhibited a significantly improved toxicity profile. Administered orally, compound 1f was well-tolerated at a dose up to 3 g/kg and showed insignificant toxicity on white blood cells and a low mutagenic effect at dosages up to 80 mg/kg (single) or 20 mg/kg/day (5 days). In duck HBV (DHBV)-infected duck models, both the serum and liver DHBV DNA levels (74.2 and 82.1%, respectively) were markedly reduced by the treatment of 1f at a dose of 1 mg/kg/day for 10 days. In addition, both the viral DNA levels had a lower degree of recovery after withdrawal of the test compound for 3 days.
• NUCLEOSIDE DERIVATIVES, SYNTHESIS METHODS AND USES THEREOF FOR PREPARING ANTI-TUMOR AND ANTI-VIRUS MEDICAMENTS
  申请人：High & New Technology Research Center, Henan Academy of Sciences

  公开号：EP2615101B1

  公开（公告）日：2018-10-17