benzyl (2S)-2-[[[(2R,3S,4R,5R)-5-(4-amino-2-oxopyrimidin-1-yl)-2-azido-3,4-dihydroxyoxolan-2-yl]methoxy-(2-methylphenoxy)phosphoryl]amino]propanoate | 1186412-33-8

• 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 (2S)-2-[[[(2R,3S,4R,5R)-5-(4-amino-2-oxopyrimidin-1-yl)-2-azido-3,4-dihydroxyoxolan-2-yl]methoxy-(2-methylphenoxy)phosphoryl]amino]propanoate
• CAS: 1186412-33-8
• 化学式: C₂₆H₃₀N₇O₉P
• 分子量: 615.539
• InChiKey: AMUGZVQGSPNJDS-ZPHJKGPLSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  1.3
• 重原子数：
  43
• 可旋转键数：
  13
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.35
• 拓扑面积：
  197
• 氢给体数：
  4
• 氢受体数：
  12

反应信息

• 作为产物：
  描述：

  benzyl ((((3aS,4R,6R,6aR)-6-(4-amino-2-oxopyrimidin-1(2H)-yl)-4-azido-2,2-dimethyltetrahydrofuro[3,4-d][1,3]dioxol-4-yl)methoxy)(o-tolyloxy)phosphoryl)-L-alaninate 在 水 、 溶剂黄146 作用下， 生成 benzyl (2S)-2-[[[(2R,3S,4R,5R)-5-(4-amino-2-oxopyrimidin-1-yl)-2-azido-3,4-dihydroxyoxolan-2-yl]methoxy-(2-methylphenoxy)phosphoryl]amino]propanoate
  参考文献：
  名称：

  The application of phosphoramidate ProTide technology to the potent anti-HCV compound 4′-azidocytidine (R1479)

  摘要：

  We report the design, synthesis and evaluation of a family of ca 50 phosphoramidate ProTides of the potent anti-HCV compound 4 '-azidocytidine (R1479), with variation on the ester, amino acid and aryl moiety of the ProTide. Sub-mu M inhibitors of HCV emerge. The compounds are all non-cytotoxic in the replicon assay. We herein report detailed SARs for each of the regions of the ProTide. (C) 2009 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.bmcl.2009.05.099

文献信息

• The application of phosphoramidate ProTide technology to the potent anti-HCV compound 4′-azidocytidine (R1479)
  作者：Christopher McGuigan、Mary Rose Kelleher、Plinio Perrone、Sinead Mulready、Giovanna Luoni、Felice Daverio、Sonal Rajyaguru、Sophie Le Pogam、Isabel Najera、Joseph A. Martin、Klaus Klumpp、David B. Smith

  DOI：10.1016/j.bmcl.2009.05.099

  日期：2009.8

  We report the design, synthesis and evaluation of a family of ca 50 phosphoramidate ProTides of the potent anti-HCV compound 4 '-azidocytidine (R1479), with variation on the ester, amino acid and aryl moiety of the ProTide. Sub-mu M inhibitors of HCV emerge. The compounds are all non-cytotoxic in the replicon assay. We herein report detailed SARs for each of the regions of the ProTide. (C) 2009 Elsevier Ltd. All rights reserved.