1-(4'-azido-3'-deoxy-3'-fluoro-β-D-xylofuranosyl)cytosine | 1145869-40-4

• 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-(4'-azido-3'-deoxy-3'-fluoro-β-D-xylofuranosyl)cytosine
• 英文别名: 4-amino-1-[(2R,3S,4R,5R)-5-azido-4-fluoro-3-hydroxy-5-(hydroxymethyl)oxolan-2-yl]pyrimidin-2-one
• CAS: 1145869-40-4
• 化学式: C₉H₁₁FN₆O₄
• 分子量: 286.223
• InChiKey: PCPGVUKMIADCCP-JXOAFFINSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  -1.4
• 重原子数：
  20
• 可旋转键数：
  3
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.56
• 拓扑面积：
  123
• 氢给体数：
  3
• 氢受体数：
  7

反应信息

• 作为产物：
  描述：

  1-(4'-azido-3'-deoxy-3'-fluoro-2',5'-di-O-trityl-β-D-xylofuranosyl)cytosine 在 氨 作用下， 以 甲醇 、 乙醇 为溶剂， 反应 3.0h， 以47%的产率得到1-(4'-azido-3'-deoxy-3'-fluoro-β-D-xylofuranosyl)cytosine
  参考文献：
  名称：

  The Design, Synthesis, and Antiviral Activity of Monofluoro and Difluoro Analogues of 4′-Azidocytidine against Hepatitis C Virus Replication: The Discovery of 4′-Azido-2′-deoxy-2′-fluorocytidine and 4′-Azido-2′-dideoxy-2′,2′-difluorocytidine

  摘要：

  The discovery of 4'-azidocytidine (3) (R1479) (J. Biol. Chem. 2006, 281, 3793; Bioorg. Med. Chem. Lett. 2007, 17, 2570) as a potent inhibitor of RNA synthesis by NS5B (EC50 = 1.28 mu M), the RNA polymerase encoded by hepatitis C virus (HCV), has led to the synthesis and biological evaluation of several monofluoro and difluoro derivatives of 4'-azidocytidine. The most potent compounds in this series were 4'-azido-2'-deoxy-2',2'-difluorocytidine and 4'-azido-2'-deoxy-2'-fluoroarabinocytidine with antiviral EC50 of 66 nM and 24 nM in the HCV replicon system, respectively. The structure-activity relationships within this series were discussed. which led to the discovery of these novel nucleoside analogues with the most potent compound, showing more than a 50-fold increase in antiviral potency as compared to 4'-azidocytidine (3).

  DOI：

  10.1021/jm801595c