1-(2,3-dideoxy-3-fluoro-β-D-xylofuranosyl)thymine

• 分子结构分类: 有机化合物 - 核苷、核苷酸和类似物 - 嘧啶核苷
• 英文名称: 1-(2,3-dideoxy-3-fluoro-β-D-xylofuranosyl)thymine
• 英文别名: 1-[(2R,4R,5R)-4-fluoro-5-(hydroxymethyl)oxolan-2-yl]-5-methylpyrimidine-2,4-dione
• 化学式: C₁₀H₁₃FN₂O₄
• 分子量: 244.223
• InChiKey: UXCAQJAQSWSNPQ-BWZBUEFSSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  -0.3
• 重原子数：
  17
• 可旋转键数：
  2
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.6
• 拓扑面积：
  78.9
• 氢给体数：
  2
• 氢受体数：
  5

反应信息

• 作为产物：
  描述：

  1,2-O-异丙基-α-D-呋喃核糖 在 吡啶 、 4-二甲氨基吡啶 、 二乙胺基三氟化硫 、 三氟甲磺酸三甲基硅酯 、 硫酸 、 2-(2-cyanopropan-2-yldiazenyl)-2-methylpropanenitrile 、 氨 、 三正丁基氢锡 、 一水合肼 、 溶剂黄146 、 牛血清白蛋白 作用下， 以 甲醇 、 二氯甲烷 、 甲苯 为溶剂， 反应 109.25h， 生成 1-(2,3-dideoxy-3-fluoro-β-D-xylofuranosyl)thymine
  参考文献：
  名称：

  1,2-Di-O-acetyl-5-O-benzoyl-3-deoxy-3-fluoro-d-xylofuranose. A versatile precursor for the synthesis of 3-deoxy-3-fluoro-β-d-xylofuranosyl nucleosides as potential antiviral agents

  摘要：

  The title compound has been synthesized from D-xylose for use in the preparation of 3-deoxy-3-fluoro-beta-D-xylofuranosyl nucleoside analogues and their 2-deoxy derivatives, as exemplified in the guanine and thymine series.

  DOI：

  10.1016/0008-6215(93)84056-c

文献信息

• Rapid synthesis of 2′,3′-dideoxy-3′β-fluoro-pyrimidine nucleosides from 2′-deoxypyrimidine nucleosides
  作者：Ahmed Khalil、Christophe Mathé、Christian Périgaud

  DOI：10.1016/j.bioorg.2010.08.003

  日期：2010.12

  A rapid synthesis of 2′,3′-dideoxy-3′-fluoro-β-d-threo-nucleosides bearing the pyrimidine canonical bases of nucleic acids has been developed in order to discover new nucleoside derivatives as potential antiviral drugs. However, when evaluated for their antiviral activity in cell culture experiments, none of these compounds showed any significant antiviral activity.

  为了发现新的核苷衍生物作为潜在的抗病毒药物，已经开发了带有核酸的嘧啶正典碱基的2'，3'-二脱氧-3'-氟-β- d-苏-核苷的快速合成。然而，当在细胞培养实验中评估其抗病毒活性时，这些化合物均未显示任何显着的抗病毒活性。
• SUBSTITUTED NUCLEOSIDE DERIVATIVES WITH ANTIVIRAL AND ANTIMICROBIAL PROPERTIES
  申请人：Eastern Virginia Medical School

  公开号：EP2175863B1

  公开（公告）日：2018-03-21
• Nucleoside based proliferation imaging markers
  申请人：Kolb Hartmuth C.

  公开号：US20090016958A1

  公开（公告）日：2009-01-15

  Disclosed herein are novel radiolabeled nucleosides and methods for detecting cellular proliferation in a mammal, the method comprising administrating an effective amount of a radiolabeled nucleoside; the method comprising: a) administering to the mammal a diagnostically effective amount of the nucleoside to the mammal; b) allowing the nucleoside to distribute into the effective tissue; and c) imaging the tissue, wherein an increase in binding of the compound to tissue compared to a normal control level of binding indicates that the mammal is suffering from a disease involving cellular proliferation.
• US7928210B2
  申请人：——

  公开号：US7928210B2

  公开（公告）日：2011-04-19
• 1,2-Di-O-acetyl-5-O-benzoyl-3-deoxy-3-fluoro-d-xylofuranose. A versatile precursor for the synthesis of 3-deoxy-3-fluoro-β-d-xylofuranosyl nucleosides as potential antiviral agents
  作者：Gilles Gosselin、Frédéric Puech、Corinne Génu-Dellac、Jean-Louis Imbach

  DOI：10.1016/0008-6215(93)84056-c

  日期：1993.10

  The title compound has been synthesized from D-xylose for use in the preparation of 3-deoxy-3-fluoro-beta-D-xylofuranosyl nucleoside analogues and their 2-deoxy derivatives, as exemplified in the guanine and thymine series.