[(2R,3R,4R,5R)-5-(6-benzamidopurin-9-yl)-4-fluoro-2-(hydroxymethyl)oxolan-3-yl] benzoate | 1048373-86-9

• 分子结构分类: 有机化合物 - 核苷、核苷酸和类似物 - 嘌呤核苷
• 英文名称: [(2R,3R,4R,5R)-5-(6-benzamidopurin-9-yl)-4-fluoro-2-(hydroxymethyl)oxolan-3-yl] benzoate
• CAS: 1048373-86-9
• 化学式: C₂₄H₂₀FN₅O₅
• 分子量: 477.452
• InChiKey: MHHMJUPMCPQYPO-ZLFGVDQTSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.6
• 重原子数：
  35
• 可旋转键数：
  7
• 环数：
  5.0
• sp3杂化的碳原子比例：
  0.21
• 拓扑面积：
  129
• 氢给体数：
  2
• 氢受体数：
  9

反应信息

• 作为反应物：
  描述：

  [(2R,3R,4R,5R)-5-(6-benzamidopurin-9-yl)-4-fluoro-2-(hydroxymethyl)oxolan-3-yl] benzoate 在 2,6-二甲基吡啶 、 ammonium hydroxide 、 三正丁胺 、 三甲基溴硅烷 、 三氟乙酸吡啶 、 N,N'-二环己基碳二亚胺 、 N,N'-羰基二咪唑 作用下， 以 二甲基亚砜 、 N,N-二甲基甲酰胺 、 乙腈 为溶剂， 反应 55.0h， 生成 (2-((2R,3R,4R,5R)-5-(6-amino-9H-purin-9-yl)-4-fluoro-3-hydroxytetrahydrofuran-2-yl)vinyl)phosphonic diphosphoric anhydride
  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
• 作为产物：
  描述：

  2'-氟-2'-脱氧腺苷 在 吡啶 、 potassium carbonate 、 溶剂黄146 作用下， 以 甲醇 为溶剂， 反应 86.0h， 生成 [(2R,3R,4R,5R)-5-(6-benzamidopurin-9-yl)-4-fluoro-2-(hydroxymethyl)oxolan-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
• 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.