(2s,3r,4r,5r)-2-(4-Aminopyrazolo[1,5-a][1,3,5]triazin-8-yl)-5-(hydroxymethyl)-3-methyl-tetrahydrofuran-3,4-diol | 622380-97-6

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: (2s,3r,4r,5r)-2-(4-Aminopyrazolo[1,5-a][1,3,5]triazin-8-yl)-5-(hydroxymethyl)-3-methyl-tetrahydrofuran-3,4-diol
• 英文别名: (2S,3R,4R,5R)-2-(4-aminopyrazolo[1,5-a][1,3,5]triazin-8-yl)-5-(hydroxymethyl)-3-methyloxolane-3,4-diol
• CAS: 622380-97-6
• 化学式: C₁₁H₁₅N₅O₄
• 分子量: 281.271
• InChiKey: YPIBKPYMFSUDOU-HGIWHZBTSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  -1.9
• 重原子数：
  20
• 可旋转键数：
  2
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.55
• 拓扑面积：
  139
• 氢给体数：
  4
• 氢受体数：
  8

反应信息

• 作为产物：
  描述：

  在 palladium 10% on activated carbon 、 氢气 、 sodium acetate 作用下， 以 甲醇 为溶剂， 反应 3.5h， 以78%的产率得到(2s,3r,4r,5r)-2-(4-Aminopyrazolo[1,5-a][1,3,5]triazin-8-yl)-5-(hydroxymethyl)-3-methyl-tetrahydrofuran-3,4-diol
  参考文献：
  名称：

  Discovery and Synthesis of C-Nucleosides as Potential New Anti-HCV Agents

  摘要：

  Nucleoside analogues have long been recognized as prospects for the discovery of direct acting antivirals (DAM) to treat hepatitis C virus because they have generally exhibited cross-genotype activity and a high barrier to resistance. C-Nucleosides have the potential for improved metabolism and pharmacokinetic properties over their N-nucleoside counterparts due to the presence of a strong carbon carbon glycosidic bond and a non-natural heterocyclic base. Three 2'CMe-C-adenosine analogues and two 2'CMe-guanosine analogues were synthesized and evaluated for their these analogues were found to inhibit the NS5B polymerase, and pharmacokinetic properties demonstrating the potential of this drug anti-HCV efficacy. The nucleotide triphosphates of four of adenosine analogue 1 was discovered to have excellent class.

  DOI：

  10.1021/ml500077j

文献信息

• Nucleoside derivatives for treating hepatitis C virus infection
  申请人：——

  公开号：US20040063658A1

  公开（公告）日：2004-04-01

  Disclosed are compounds, compositions and methods for treating hepatitis C virus infections.

  本发明涉及用于治疗丙型肝炎病毒感染的化合物、组合物和方法。
• METHODS FOR THE PREPARATION OF 9-DEAZAPURINE DERIVATIVES
  申请人：Chand Pooran

  公开号：US20100093991A1

  公开（公告）日：2010-04-15

  Methods for the preparation of the β isomer of a 9-deazapurine derivatives using benzyl protecting groups as the protecting groups for the 2 and 3 hydroxyl groups in ribose are provided.

  本文提供了一种使用苄基保护基作为核糖中2和3羟基的保护基来制备9-脱氮嘌呤衍生物β异构体的方法。
• NUCLEOSIDE DERIVATIVES FOR TREATING HEPATITIS C VIRUS INFECTION
  申请人：GENELABS TECHNOLOGIES, INC.

  公开号：EP1501850A2

  公开（公告）日：2005-02-02
• PYRAZOLOTRIAZOLYL NUCLEOSIDE ANALOGUES AND OLIGONUCLEOTIDES COMPRISING THEM
  申请人：Bio-lab Ltd.

  公开号：EP2854813A1

  公开（公告）日：2015-04-08
• US8344132B2
  申请人：——

  公开号：US8344132B2

  公开（公告）日：2013-01-01