2',3'-O-cyclopentandienide-4'-azidoinosine | 926309-62-8

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 咪唑并嘧啶类
• 英文名称: 2',3'-O-cyclopentandienide-4'-azidoinosine
• 英文别名: 2',3'-O-cyclopentylidene-4'-azidoinosine
• CAS: 926309-62-8
• 化学式: C₁₅H₁₇N₇O₅
• 分子量: 375.344
• InChiKey: YSILCOKQZPSJOF-YJKIEOBBSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  0.7
• 重原子数：
  27.0
• 可旋转键数：
  3.0
• 环数：
  5.0
• sp3杂化的碳原子比例：
  0.67
• 拓扑面积：
  160.25
• 氢给体数：
  2.0
• 氢受体数：
  9.0

反应信息

• 作为反应物：
  描述：

  α-naphthyl(tert-butyloxy-L-alaninyl) phosphorochloridate 、 2',3'-O-cyclopentandienide-4'-azidoinosine 在 magnesium,2-methylpropane,bromide 作用下， 以 四氢呋喃 为溶剂， 反应 17.0h， 以100%的产率得到
  参考文献：
  名称：

  The application of the phosphoramidate ProTide approach confers micromolar potency against Hepatitis C virus on inactive agent 4′-azidoinosine: Kinase bypass on a dual base/sugar modified nucleoside

  摘要：

  Novel phosphoramidate ProTides derived from 4'-azidoinosine have been prepared and evaluated in the replicon assay against hepatitis C Virus (HCV). The parent nucleoside analogue is inactive in this assay, while the ProTides are active at low mu M levels in some cases. This is a rare example of an inosine nucleoside analogue with potent antiviral activity and further supports the notion of ProTides as a drug discovery motif. (C) 2009 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.bmcl.2009.03.138
• 作为产物：
  描述：

  4'-azidoinosine 、 1,1-二甲氧基环戊烷 在 对甲苯磺酸 作用下， 反应 2.0h， 以70%的产率得到2',3'-O-cyclopentandienide-4'-azidoinosine
  参考文献：
  名称：

  The application of the phosphoramidate ProTide approach confers micromolar potency against Hepatitis C virus on inactive agent 4′-azidoinosine: Kinase bypass on a dual base/sugar modified nucleoside

  摘要：

  Novel phosphoramidate ProTides derived from 4'-azidoinosine have been prepared and evaluated in the replicon assay against hepatitis C Virus (HCV). The parent nucleoside analogue is inactive in this assay, while the ProTides are active at low mu M levels in some cases. This is a rare example of an inosine nucleoside analogue with potent antiviral activity and further supports the notion of ProTides as a drug discovery motif. (C) 2009 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.bmcl.2009.03.138

文献信息

• Antiviral phosphoramidates
  申请人：Klumpp Klaus

  公开号：US20070042988A1

  公开（公告）日：2007-02-22

  The invention provides novel nucleoside compounds of formula I wherein R 1 , R 2a , R 2b , R 3 , R 4 , R 5 , R 6 , R 8a , R 9 and R 10 are as defined herein which are useful for the treatment of Hepatitis C Virus (HCV) mediated diseases. The invention further provides methods for treatment or prophylaxis of HCV mediated diseases with compounds of formula I and pharmaceutical compositions comprising these compounds,

  该发明提供了一种新颖的核苷类化合物，其化学式为I，其中R1、R2a、R2b、R3、R4、R5、R6、R8a、R9和R10如本文所定义，这些化合物对治疗由丙型肝炎病毒（HCV）介导的疾病是有用的。该发明还提供了使用化合物I的方法进行治疗或预防HCV介导的疾病，以及包含这些化合物的药物组合物。