2-amino-7-[(2S,3R,4R,5R)-3,4-dihydroxy-5-(hydroxymethyl)-3-methyl-tetrahydrofuran-2-yl]-3H-pyrrolo[2,1-f][1,2,4]triazin-4-one | 1591741-23-9

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: 2-amino-7-[(2S,3R,4R,5R)-3,4-dihydroxy-5-(hydroxymethyl)-3-methyl-tetrahydrofuran-2-yl]-3H-pyrrolo[2,1-f][1,2,4]triazin-4-one
• 英文别名: 2-amino-7-[(2S,3R,4R,5R)-3,4-dihydroxy-5-(hydroxymethyl)-3-methyloxolan-2-yl]-3H-pyrrolo[2,1-f][1,2,4]triazin-4-one
• CAS: 1591741-23-9
• 化学式: C₁₂H₁₆N₄O₅
• 分子量: 296.283
• InChiKey: SWTWCEVQPINDJY-KZFFXBSXSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  -2
• 重原子数：
  21
• 可旋转键数：
  2
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.5
• 拓扑面积：
  142
• 氢给体数：
  5
• 氢受体数：
  6

反应信息

• 作为产物：
  描述：

  在 sodium methylate 作用下， 反应 1.67h， 以71%的产率得到2-amino-7-[(2S,3R,4R,5R)-3,4-dihydroxy-5-(hydroxymethyl)-3-methyl-tetrahydrofuran-2-yl]-3H-pyrrolo[2,1-f][1,2,4]triazin-4-one
  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