benzyl ((((3a'S,4'R,6'R,6a'R)-4'-azido-6'-(6-oxo-1,6-dihydro-9H-purin-9-yl)tetrahydrospiro[cyclopentane-1,2'-furo[3,4-d][1,3]dioxol]-4'-yl)methoxy)(phenoxy)phosphoryl)-L-alaninate | 1170666-24-6

• 分子结构分类: 有机化合物 - 有机酸及其衍生物 - 羧酸及其衍生物
• 英文名称: benzyl ((((3a'S,4'R,6'R,6a'R)-4'-azido-6'-(6-oxo-1,6-dihydro-9H-purin-9-yl)tetrahydrospiro[cyclopentane-1,2'-furo[3,4-d][1,3]dioxol]-4'-yl)methoxy)(phenoxy)phosphoryl)-L-alaninate
• CAS: 1170666-24-6
• 化学式: C₃₁H₃₃N₈O₉P
• 分子量: 692.625
• InChiKey: HJIVUHTWXAAZKY-JRPOWUSYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  4.63
• 重原子数：
  49.0
• 可旋转键数：
  12.0
• 环数：
  7.0
• sp3杂化的碳原子比例：
  0.42
• 拓扑面积：
  213.88
• 氢给体数：
  2.0
• 氢受体数：
  13.0

反应信息

• 作为反应物：
  描述：

  benzyl ((((3a'S,4'R,6'R,6a'R)-4'-azido-6'-(6-oxo-1,6-dihydro-9H-purin-9-yl)tetrahydrospiro[cyclopentane-1,2'-furo[3,4-d][1,3]dioxol]-4'-yl)methoxy)(phenoxy)phosphoryl)-L-alaninate 在 甲酸 、 水 作用下， 反应 5.0h， 以70%的产率得到benzyl (2S)-2-[[[(2R,3S,4R,5R)-2-azido-3,4-dihydroxy-5-(6-oxo-1H-purin-9-yl)oxolan-2-yl]methoxy-phenoxyphosphoryl]amino]propanoate
  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：

  2',3'-O-cyclopentandienide-4'-azidoinosine 、 phenyl(benzyloxy-L-alaninyl)phosphorochloridate 在 magnesium,2-methylpropane,bromide 作用下， 以 四氢呋喃 为溶剂， 反应 17.0h， 以57%的产率得到benzyl ((((3a'S,4'R,6'R,6a'R)-4'-azido-6'-(6-oxo-1,6-dihydro-9H-purin-9-yl)tetrahydrospiro[cyclopentane-1,2'-furo[3,4-d][1,3]dioxol]-4'-yl)methoxy)(phenoxy)phosphoryl)-L-alaninate
  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