1-(3-hydroxy-5-hydroxymethyl-tetrahydro-furan-2-yl)-5-nitro-1H-pyridin-2-one | 909722-38-9

• 分子结构分类: 有机化合物 - 有机1,3-偶极化合物 - 烯丙基型1,3-偶极有机化合物
• 英文名称: 1-(3-hydroxy-5-hydroxymethyl-tetrahydro-furan-2-yl)-5-nitro-1H-pyridin-2-one
• CAS: 909722-38-9
• 化学式: C₁₀H₁₂N₂O₆
• 分子量: 256.215
• InChiKey: KXDJIWCPPBDANP-QXFUBDJGSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  -0.6
• 重原子数：
  18.0
• 可旋转键数：
  3.0
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.5
• 拓扑面积：
  114.83
• 氢给体数：
  2.0
• 氢受体数：
  7.0

反应信息

• 作为反应物：
  描述：

  1-(3-hydroxy-5-hydroxymethyl-tetrahydro-furan-2-yl)-5-nitro-1H-pyridin-2-one 在 吡啶 、 sodium azide 作用下， 以 N,N-二甲基甲酰胺 为溶剂， 反应 96.0h， 生成 (6R,7R,9S)-5-oxo-7,8,9,10-tetrahydro-5H,6H-11-oxa-1,2,5a,10a-tetraaza-6,9-methanocycloocta[cd]inden-7-yl benzoate
  参考文献：
  名称：

  SYNTHESIS OF N³,5′-CYCLO-4-(β-D-RIBOFURANOSYL)-VIC-TRIAZOLO[4,5-b]PYRIDIN-5-ONE AND ITS 3′-DEOXYSUGAR ANALOGUE AS POTENTIAL ANTI-HEPATITIS C VIRUS AGENTS

  摘要：

  We recently discovered a novel compound, identified as N-3,5'-cyclo-4-(beta-D-ribofuranosyl)-victriazolo[4,5-b]pyridinin-5-one, with anti-hepatitis C virus (HCV) activity in vitro. The structure was confirmed by chemical synthesis from 2-hydroxy-5-nitropyridine. It showed anti-HCV activity with EC50 = 19.7 mu M in replicon cells. Its 3'-deoxy sugar analogue was also synthesized, but was inactive against HCV in vitro.

  DOI：

  10.1081/ncn-200059314
• 作为产物：
  描述：

  1,2-di-O-acetyl-5-O-(methoxycarbonyl)-3-deoxy-D-erythro-pentofuranose 在 甲醇 、 silylating reagent 、 sodium methylate 作用下， 生成 1-(3-hydroxy-5-hydroxymethyl-tetrahydro-furan-2-yl)-5-nitro-1H-pyridin-2-one
  参考文献：
  名称：

  SYNTHESIS OF N³,5′-CYCLO-4-(β-D-RIBOFURANOSYL)-VIC-TRIAZOLO[4,5-b]PYRIDIN-5-ONE AND ITS 3′-DEOXYSUGAR ANALOGUE AS POTENTIAL ANTI-HEPATITIS C VIRUS AGENTS

  摘要：

  We recently discovered a novel compound, identified as N-3,5'-cyclo-4-(beta-D-ribofuranosyl)-victriazolo[4,5-b]pyridinin-5-one, with anti-hepatitis C virus (HCV) activity in vitro. The structure was confirmed by chemical synthesis from 2-hydroxy-5-nitropyridine. It showed anti-HCV activity with EC50 = 19.7 mu M in replicon cells. Its 3'-deoxy sugar analogue was also synthesized, but was inactive against HCV in vitro.

  DOI：

  10.1081/ncn-200059314