2-amino-6-[N-(t-butyloxycarbonyl)aminoxy]-9-(2'-C-methyl-β-D-ribofuranosyl)-9H-purine

• 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: 2-amino-6-[N-(t-butyloxycarbonyl)aminoxy]-9-(2'-C-methyl-β-D-ribofuranosyl)-9H-purine
• 英文别名: tert-butyl N-[2-amino-9-[(2R,3R,4R,5R)-3,4-dihydroxy-5-(hydroxymethyl)-3-methyloxolan-2-yl]purin-6-yl]oxycarbamate
• 化学式: C₁₆H₂₄N₆O₇
• 分子量: 412.403
• InChiKey: AMXUALYPCXHJBK-CEVPSZDGSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  -0.5
• 重原子数：
  29
• 可旋转键数：
  6
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.62
• 拓扑面积：
  187
• 氢给体数：
  5
• 氢受体数：
  11

反应信息

• 作为反应物：
  描述：

  2-amino-6-[N-(t-butyloxycarbonyl)aminoxy]-9-(2'-C-methyl-β-D-ribofuranosyl)-9H-purine 、 (2S)-2-((氯(苯氧基)膦)氨基)丙酸乙酯 在 N-甲基咪唑 作用下， 以 四氢呋喃 、 乙腈 为溶剂， 反应 3.0h， 以72%的产率得到ethyl ((((2R,3R,4R,5R)-5-(2-amino-6-(((tert-butoxycarbonyl)amino)oxy)-9H-purin-9-yl)-3,4-dihydroxy-4-methyltetrahydrofuran-2-yl)methoxy)(phenoxy)phosphoryl)-L-alaninate
  参考文献：
  名称：

  Synthesis and Evaluation of 2,6-Modified Purine 2′-C-Methyl Ribonucleosides as Inhibitors of HCV Replication

  摘要：

  A variety of 2,6-modified purine 2'-C-methylribonucleosides and their phosphoramidate prodrugs were synthesized and evaluated for inhibition of HCV RNA replication in Huh-7 cells and for cytotoxicity in various cell lines. Cellular pharmacology and HCV polymerase incorporation studies on the most potent and selective compound are reported.

  DOI：

  10.1021/acsmedchemlett.5b00402
• 作为产物：
  描述：

  N-羟基氨基甲酸叔丁酯 、 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， 反应 3.17h， 以69%的产率得到2-amino-6-[N-(t-butyloxycarbonyl)aminoxy]-9-(2'-C-methyl-β-D-ribofuranosyl)-9H-purine
  参考文献：
  名称：

  Synthesis and Evaluation of 2,6-Modified Purine 2′-C-Methyl Ribonucleosides as Inhibitors of HCV Replication

  摘要：

  A variety of 2,6-modified purine 2'-C-methylribonucleosides and their phosphoramidate prodrugs were synthesized and evaluated for inhibition of HCV RNA replication in Huh-7 cells and for cytotoxicity in various cell lines. Cellular pharmacology and HCV polymerase incorporation studies on the most potent and selective compound are reported.

  DOI：

  10.1021/acsmedchemlett.5b00402

文献信息

• Synthesis and Evaluation of 2,6-Modified Purine 2′-<i>C</i>-Methyl Ribonucleosides as Inhibitors of HCV Replication
  作者：Longhu Zhou、Hongwang Zhang、Sijia Tao、Maryam Ehteshami、Jong Hyun Cho、Tamara R. McBrayer、Philip Tharnish、Tony Whitaker、Franck Amblard、Steven J. Coats、Raymond F. Schinazi

  DOI：10.1021/acsmedchemlett.5b00402

  日期：2016.1.14

  A variety of 2,6-modified purine 2'-C-methylribonucleosides and their phosphoramidate prodrugs were synthesized and evaluated for inhibition of HCV RNA replication in Huh-7 cells and for cytotoxicity in various cell lines. Cellular pharmacology and HCV polymerase incorporation studies on the most potent and selective compound are reported.