2,2-dimethylpropyl (2S)-2-[[[(2R,3R,4R,5R)-5-[2-amino-6-(3-methoxypropoxy)purin-9-yl]-3,4-dihydroxy-4-methyl-tetrahydrofuran-2-yl]methoxy-(1-naphthyloxy)phosphoryl]amino]propanoate | 1338700-50-7

• 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: 2,2-dimethylpropyl (2S)-2-[[[(2R,3R,4R,5R)-5-[2-amino-6-(3-methoxypropoxy)purin-9-yl]-3,4-dihydroxy-4-methyl-tetrahydrofuran-2-yl]methoxy-(1-naphthyloxy)phosphoryl]amino]propanoate
• 英文别名: 2,2-dimethylpropyl (2S)-2-[[[(2R,3R,4R,5R)-5-[2-amino-6-(3-methoxypropoxy)purin-9-yl]-3,4-dihydroxy-4-methyloxolan-2-yl]methoxy-naphthalen-1-yloxyphosphoryl]amino]propanoate
• CAS: 1338700-50-7
• 化学式: C₃₃H₄₅N₆O₁₀P
• 分子量: 716.728
• InChiKey: XJFPOPKEGFOBOF-BAAFVKSTSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.1
• 重原子数：
  50
• 可旋转键数：
  17
• 环数：
  5.0
• sp3杂化的碳原子比例：
  0.52
• 拓扑面积：
  212
• 氢给体数：
  4
• 氢受体数：
  15

反应信息

• 作为产物：
  描述：

  6-氯-9-(2-C-甲基-beta-D-呋喃核糖基)-9H-嘌呤-2-胺 在 sodium hydride 作用下， 以 四氢呋喃 为溶剂， 生成 2,2-dimethylpropyl (2S)-2-[[[(2R,3R,4R,5R)-5-[2-amino-6-(3-methoxypropoxy)purin-9-yl]-3,4-dihydroxy-4-methyl-tetrahydrofuran-2-yl]methoxy-(1-naphthyloxy)phosphoryl]amino]propanoate
  参考文献：
  名称：

  Dual pro-drugs of 2′-C-methyl guanosine monophosphate as potent and selective inhibitors of hepatitis C virus

  摘要：

  We have previously reported the power of combining a 5'-phosphoramidate ProTide, phosphate prodrug, motif with a 6-methoxy purine pro-drug entity to generate highly potent anti-HCV agents, leading to agents in clinical trial. We herein extend this work with the disclosure that a variety of alternative 6-substituents are tolerated. Several compounds exceed the potency of the prior 6-methoxy leads, and in almost every case the ProTide is several orders of magnitude more potent than the parent nucleoside. We also demonstrate that these agents act as pro-drugs of 2'-C-methyl guanosine monophosphate. We have also reported the novel use of hepatocyte cell lysate as an ex vivo model for ProTide metabolism. (C) 2011 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.bmcl.2011.06.013