4-(benzyloxy)-7-((2S,3S,4R,5R)-3,4-bis(benzyloxy)-5-((benzyloxy)methyl)-3-methyltetrahydrofuran-2-yl)-2-chloropyrrolo[2,1-f][1,2,4]triazine | 1591741-96-6

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: 4-(benzyloxy)-7-((2S,3S,4R,5R)-3,4-bis(benzyloxy)-5-((benzyloxy)methyl)-3-methyltetrahydrofuran-2-yl)-2-chloropyrrolo[2,1-f][1,2,4]triazine
• CAS: 1591741-96-6
• 化学式: C₄₀H₃₈ClN₃O₅
• 分子量: 676.212
• InChiKey: LLRHSVXGEJBJPH-XAKWVJTLSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  8.18
• 重原子数：
  49.0
• 可旋转键数：
  14.0
• 环数：
  7.0
• sp3杂化的碳原子比例：
  0.25
• 拓扑面积：
  76.34
• 氢给体数：
  0.0
• 氢受体数：
  8.0

反应信息

• 作为反应物：
  描述：

  4-(benzyloxy)-7-((2S,3S,4R,5R)-3,4-bis(benzyloxy)-5-((benzyloxy)methyl)-3-methyltetrahydrofuran-2-yl)-2-chloropyrrolo[2,1-f][1,2,4]triazine 在 tris-(dibenzylideneacetone)dipalladium(0) 、 sodium methylate 、 caesium carbonate 、 4,5-双二苯基膦-9,9-二甲基氧杂蒽 作用下， 以 1,4-二氧六环 为溶剂， 20.0~130.0 ℃ 、101.33 kPa 条件下， 反应 83.17h， 生成 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
• 作为产物：
  描述：

  2,4-二氯吡咯并[2,1-f][1,2,4]三嗪 在 三乙基硅烷 、 N-溴代丁二酰亚胺(NBS) 、 正丁基锂 、 三氟化硼乙醚 作用下， 以 四氢呋喃 、 二氯甲烷 为溶剂， 反应 3.83h， 生成 4-(benzyloxy)-7-((2S,3S,4R,5R)-3,4-bis(benzyloxy)-5-((benzyloxy)methyl)-3-methyltetrahydrofuran-2-yl)-2-chloropyrrolo[2,1-f][1,2,4]triazine
  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