(2R,3R,4R,5R)-5-(4-benzamido-2-oxopyrimidin-1(2H)-yl)-4-fluoro-2-(hydroxymethyl)tetrahydrofuran-3-yl benzoate | 1048374-12-4

• 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: (2R,3R,4R,5R)-5-(4-benzamido-2-oxopyrimidin-1(2H)-yl)-4-fluoro-2-(hydroxymethyl)tetrahydrofuran-3-yl benzoate
• 英文别名: [(2R,3R,4R,5R)-5-(4-benzamido-2-oxopyrimidin-1-yl)-4-fluoro-2-(hydroxymethyl)oxolan-3-yl] benzoate
• CAS: 1048374-12-4
• 化学式: C₂₃H₂₀FN₃O₆
• 分子量: 453.427
• InChiKey: SUHIBAMSHUKGLY-XLBJILASSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3
• 重原子数：
  33
• 可旋转键数：
  7
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.22
• 拓扑面积：
  118
• 氢给体数：
  2
• 氢受体数：
  7

反应信息

• 作为反应物：
  描述：

  (2R,3R,4R,5R)-5-(4-benzamido-2-oxopyrimidin-1(2H)-yl)-4-fluoro-2-(hydroxymethyl)tetrahydrofuran-3-yl benzoate 在 四溴化碳 、 三苯基膦 作用下， 以 二氯甲烷 为溶剂， 反应 48.0h， 以60%的产率得到(2S,3R,4R,5S)-5-(4-benzamido-2-oxopyrimidin-1(2H)-yl)-2-(bromomethyl)-4-fluorotetrahydrofuran-3-yl benzoate
  参考文献：
  名称：

  2'-Fluoronucleoside phosphonates as antiviral agents

  摘要：

  本发明涉及R-2'-氟核苷酸膦酸酯化合物和组合物，以及使用该化合物或组合物治疗HIV、HBV、HCV或异常细胞增殖的方法。

  公开号：

  US20070225249A1
• 作为产物：
  描述：

  在 溶剂黄146 作用下， 反应 48.0h， 生成 (2R,3R,4R,5R)-5-(4-benzamido-2-oxopyrimidin-1(2H)-yl)-4-fluoro-2-(hydroxymethyl)tetrahydrofuran-3-yl benzoate
  参考文献：
  名称：

  Evaluation of 2′-α-fluorine modified nucleoside phosphonates as potential inhibitors of HCV polymerase

  摘要：

  Ribonucleoside phosphonate analogues containing 2'-alpha-fluoro modifications were synthesized and their potency evaluated against HCV RNA polymerase. The diphosphophosphonate (triphosphate equivalent) adenine and cytidine analogues displayed potent inhibition of the HCV polymerase in the range of 1.9-2.1 mu M, but only modest cell-based activity in the HCV replicon. Pro- drugs of the parent nucleoside phosphonates improved the cell-based activity. (C) 2013 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.bmcl.2013.03.095

文献信息

• NUCLEOSIDE ANALOGS FOR ANTIVIRAL TREATMENT
  申请人：Chen James M.

  公开号：US20100104532A1

  公开（公告）日：2010-04-29

  The invention provides unsaturated phosphonates of Formula I or a tautomer or pharmaceutically accepatble salt thereof, as described herein, as well as pharmaceutical compositions comprising the compounds, and therapeutic methods comprising administering the compounds. The compounds have anti-viral properties and are useful for treating viral infections (e.g. HCV) in animals (e.g. humans).

  本发明提供了公式I或其互变异构体或药学上可接受的盐的不饱和膦酸酯，以及包含这些化合物的制药组合物和包括给予这些化合物的治疗方法。这些化合物具有抗病毒性质，适用于治疗动物（如人类）的病毒感染（例如HCV）。
• US8324179B2
  申请人：——

  公开号：US8324179B2

  公开（公告）日：2012-12-04
• [EN] NUCLEOSIDE ANALOGS FOR ANTIVIRAL TREATMENT<br/>[FR] ANALOGUES NUCLÉOSIDIQUES POUR TRAITEMENT ANTIVIRAL
  申请人：GILEAD SCIENCES INC

  公开号：WO2008100447A2

  公开（公告）日：2008-08-21

  [EN] The invention provides unsaturated phosphonates of Formula I or a tautomer or pharmaceutically accepatble salt thereof, as described herein, as well as pharmaceutical compositions comprising the compounds, and therapeutic methods comprising administering the compounds. The compounds have anti-viral properties and are useful for treating viral infections (e.g. HCV) in animals (e.g. humans).
  [FR] La présente invention concerne des phosphonates insaturés de formule (I) ou un tautomère ou un sel pharmaceutiquement acceptable de ceux-ci, ainsi que des compositions pharmaceutiques comportant les composés, et des procédés thérapeutiques comprenant l'administration des composés. Les composés présente des propriétés antivirales et sont utiles pour traiter des infections (par exemple, le VHC) chez des animaux (par exemple, des humains).
• Evaluation of 2′-α-fluorine modified nucleoside phosphonates as potential inhibitors of HCV polymerase
  作者：Jay P. Parrish、Sharon K. Lee、Constantine G. Boojamra、Hon Hui、Darius Babusis、Brandon Brown、I-hung Shih、Joy Y. Feng、Adrian S. Ray、Richard L. Mackman

  DOI：10.1016/j.bmcl.2013.03.095

  日期：2013.6

  Ribonucleoside phosphonate analogues containing 2'-alpha-fluoro modifications were synthesized and their potency evaluated against HCV RNA polymerase. The diphosphophosphonate (triphosphate equivalent) adenine and cytidine analogues displayed potent inhibition of the HCV polymerase in the range of 1.9-2.1 mu M, but only modest cell-based activity in the HCV replicon. Pro- drugs of the parent nucleoside phosphonates improved the cell-based activity. (C) 2013 Elsevier Ltd. All rights reserved.
• 2'-Fluoronucleoside phosphonates as antiviral agents
  申请人：Shi Junxing

  公开号：US20070225249A1

  公开（公告）日：2007-09-27

  The present invention includes compounds and compositions of R -2′-fluoronucleoside phosphonates, as well as methods to treat HIV, HBV, HCV or abnormal cellular proliferation comprising administering said compounds or compositions.

  本发明涉及R-2'-氟核苷酸膦酸酯化合物和组合物，以及使用该化合物或组合物治疗HIV、HBV、HCV或异常细胞增殖的方法。