1-[(3aR,4R,6R,6aR)-6-(hydroxymethyl)-2,2-dimethyl-3a,4,6,6a-tetrahydrofuro[3,4-d][1,3]dioxol-4-yl]-4-methyl-5-nitropyridin-2-one | 1053631-42-7

• 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-[(3aR,4R,6R,6aR)-6-(hydroxymethyl)-2,2-dimethyl-3a,4,6,6a-tetrahydrofuro[3,4-d][1,3]dioxol-4-yl]-4-methyl-5-nitropyridin-2-one
• CAS: 1053631-42-7
• 化学式: C₁₄H₁₈N₂O₇
• 分子量: 326.306
• InChiKey: CTSIKRQYMNRNAX-OJAKKHQRSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  -0.6
• 重原子数：
  23
• 可旋转键数：
  2
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.64
• 拓扑面积：
  114
• 氢给体数：
  1
• 氢受体数：
  7

反应信息

• 作为反应物：
  描述：

  1-[(3aR,4R,6R,6aR)-6-(hydroxymethyl)-2,2-dimethyl-3a,4,6,6a-tetrahydrofuro[3,4-d][1,3]dioxol-4-yl]-4-methyl-5-nitropyridin-2-one 在 吡啶 、 盐酸 、 sodium azide 作用下， 以 甲醇 、 二氯甲烷 、 N,N-二甲基甲酰胺 为溶剂， 反应 88.33h， 生成 6,9-Epoxy-5H,6H-1,2,5a,10a-tetraazacyclooct[cd]inden-5-one, 7,8,9,10-tetrahydro-7,8-dihydroxy-3-methyl-, (6R,7R,8S,9R)-
  参考文献：
  名称：

  Synthesis and Structure−Activity Relationships of Novel Anti-hepatitis C Agents: N³,5‘-Cyclo-4-(β-d-ribofuranosyl)-vic-triazolo[4,5-b]pyridin-5-one Derivatives

  摘要：

  Several 6- and 7-monosubstituted N-3 5'-cyclo-4-(beta-D-ribofuranosyl)-vic-triazolo[4,5-b]pyridin5-one derivatives as well as the 5-thiono analogue were synthesized, providing structure-anti-hepatitis C virus (HCV) activity relationships for the series. Among the compounds synthesized, the 6-bromo, 7-methylamino, and 5-thiono analogues exhibited more potent anti-HCV activity in an HCV subgenomic replicon cell based assay (EC90 = 1.9, 7.4, and 10.0 mu M, respectively) than the lead compound N-3, 5'-cyclo-4-(beta-D-ribofuranosyl)-vic-triazolo [4,5-b] pyridin-5-one (EC90 = 79.8 mu M).

  DOI：

  10.1021/jm058223t
• 作为产物：
  描述：

  1-乙酰基-三-苄氧基-罗伯糖 在 盐酸 、 硫酸氢铵 、 正丁胺 、 六甲基二硅氮烷 作用下， 以 甲醇 、 乙醚 为溶剂， 反应 69.0h， 生成 1-[(3aR,4R,6R,6aR)-6-(hydroxymethyl)-2,2-dimethyl-3a,4,6,6a-tetrahydrofuro[3,4-d][1,3]dioxol-4-yl]-4-methyl-5-nitropyridin-2-one
  参考文献：
  名称：

  Synthesis and Structure−Activity Relationships of Novel Anti-hepatitis C Agents: N³,5‘-Cyclo-4-(β-d-ribofuranosyl)-vic-triazolo[4,5-b]pyridin-5-one Derivatives

  摘要：

  Several 6- and 7-monosubstituted N-3 5'-cyclo-4-(beta-D-ribofuranosyl)-vic-triazolo[4,5-b]pyridin5-one derivatives as well as the 5-thiono analogue were synthesized, providing structure-anti-hepatitis C virus (HCV) activity relationships for the series. Among the compounds synthesized, the 6-bromo, 7-methylamino, and 5-thiono analogues exhibited more potent anti-HCV activity in an HCV subgenomic replicon cell based assay (EC90 = 1.9, 7.4, and 10.0 mu M, respectively) than the lead compound N-3, 5'-cyclo-4-(beta-D-ribofuranosyl)-vic-triazolo [4,5-b] pyridin-5-one (EC90 = 79.8 mu M).

  DOI：

  10.1021/jm058223t

文献信息

• Synthesis and Structure−Activity Relationships of Novel Anti-hepatitis C Agents: <i>N</i>³,5‘-Cyclo-4-(β-<scp>d</scp>-ribofuranosyl)-<i>vic</i>-triazolo[4,5-<i>b</i>]pyridin-5-one Derivatives
  作者：Peiyuan Wang、Jinfa Du、Suguna Rachakonda、Byoung-Kwon Chun、Phillip M. Tharnish、Lieven J. Stuyver、Michael J. Otto、Raymond F. Schinazi、Kyoichi A. Watanabe

  DOI：10.1021/jm058223t

  日期：2005.10.1

  Several 6- and 7-monosubstituted N-3 5'-cyclo-4-(beta-D-ribofuranosyl)-vic-triazolo[4,5-b]pyridin5-one derivatives as well as the 5-thiono analogue were synthesized, providing structure-anti-hepatitis C virus (HCV) activity relationships for the series. Among the compounds synthesized, the 6-bromo, 7-methylamino, and 5-thiono analogues exhibited more potent anti-HCV activity in an HCV subgenomic replicon cell based assay (EC90 = 1.9, 7.4, and 10.0 mu M, respectively) than the lead compound N-3, 5'-cyclo-4-(beta-D-ribofuranosyl)-vic-triazolo [4,5-b] pyridin-5-one (EC90 = 79.8 mu M).