1,4-二氢-4-beta-D-呋喃核糖基-5H-1,2,3-三唑并[4,5-b]吡啶-5-酮 | 59892-40-9

• 分子结构分类: 有机化合物 - 有机氧化合物
• 中文名称: 1,4-二氢-4-beta-D-呋喃核糖基-5H-1,2,3-三唑并[4,5-b]吡啶-5-酮
• 中文别名: 4-(Β-D-呋喃核糖基)-维克-三唑并[4,5-Β]吡啶-5-酮；4-(&Beta-D-呋喃核糖基)-维克-三唑并[4,5-&Beta]吡啶-5-酮
• 英文名称: 4-(β-D-ribofuranosyl)-vic-triazolo[4,5-b]pyridin-5-one
• 英文别名: 4-β-D-ribofuranosyl-1,4-dihydro-[1,2,3]triazolo[4,5-b]pyridin-5-one；4-(b-D-Ribofuranosyl)-vic-triazolo[4,5-b]pyridin-5-one；4-[(2R,3R,4S,5R)-3,4-dihydroxy-5-(hydroxymethyl)oxolan-2-yl]-2H-triazolo[4,5-b]pyridin-5-one
• CAS: 59892-40-9
• 化学式: C₁₀H₁₂N₄O₅
• 分子量: 268.229
• InChiKey: NEJMHPHGOOTALN-VPCXQMTMSA-N

物化性质

• 沸点：
  631.1±55.0 °C(Predicted)
• 密度：
  1.814±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  -2
• 重原子数：
  19
• 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：
  132
• 氢给体数：
  4
• 氢受体数：
  7

反应信息

• 作为反应物：
  描述：

  1,4-二氢-4-beta-D-呋喃核糖基-5H-1,2,3-三唑并[4,5-b]吡啶-5-酮 在 盐酸 、 溴 、 对甲苯磺酸 、 三苯基膦 、 丙酮 、 偶氮二甲酸二乙酯 作用下， 以 1,4-二氧六环 、 水 、 N,N-二甲基甲酰胺 为溶剂， 反应 12.0h， 生成 6,9-Epoxy-5H,6H-1,2,5a,10a-tetraazacyclooct[cd]inden-5-one, 4-bromo-7,8,9,10-tetrahydro-7,8-dihydroxy-, (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：

  2-羟基-5-硝基吡啶 在 ammonium sulfate 、 sodium azide 、 氨 、 四氯化锡 作用下， 以 甲醇 、 二氯甲烷 、 1,2-二氯乙烷 、 N,N-二甲基甲酰胺 为溶剂， 反应 30.0h， 生成 1,4-二氢-4-beta-D-呋喃核糖基-5H-1,2,3-三唑并[4,5-b]吡啶-5-酮
  参考文献：
  名称：

  Synthesis of N³,5‘-Cyclo-4-(β-d-ribofuranosyl)-vic-triazolo[4,5-b]pyridin-5-one, a Novel Compound with Anti-Hepatitis C Virus Activity

  摘要：

  A novel anti-hepatitis C virus (HCV) agent, N-3,5'-cyclo-4-(beta-D-ribofuranosyl)-vic-triazolo[4,5-b]pyridinin-5-one, was identified, and the structure was confirmed by chemical synthesis from 2-hydroxy-5-nitropyridine.

  DOI：

  10.1021/jm0401210

文献信息

• SYNTHESIS OF N³,5′-CYCLO-4-(β-D-RIBOFURANOSYL)-<i>VIC</i>-TRIAZOLO[4,5-<i>b</i>]PYRIDIN-5-ONE AND ITS 3′-DEOXYSUGAR ANALOGUE AS POTENTIAL ANTI-HEPATITIS C VIRUS AGENTS
  作者：Peiyuan Wang、Laurent Hollecker、Krzysztof W. Pankiewicz、Steven E. Patterson、Tony Whitaker、Tamara R. McBrayer、Phillip M. Tharnish、Lieven J. Stuyver、Raymond F. Schinazi、Michael J. Otto、Kyoichi A. Watanabe

  DOI：10.1081/ncn-200059314

  日期：2005.4.1

  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.
• Synthesis of <i>N</i>³,5‘-Cyclo-4-(β-<scp>d</scp>-ribofuranosyl)-<i>v</i><i>ic</i>-triazolo[4,5-<i>b</i>]pyridin-5-one, a Novel Compound with Anti-Hepatitis C Virus Activity
  作者：Peiyuan Wang、Laurent Hollecker、Krzysztof W. Pankiewicz、Steven E. Patterson、Tony Whitaker、Tamara R. McBrayer、Phillip M. Tharnish、Robert W. Sidwell、Lieven J. Stuyver、Michael J. Otto、Raymond F. Schinazi、Kyoichi A. Watanabe

  DOI：10.1021/jm0401210

  日期：2004.11.1

  A novel anti-hepatitis C virus (HCV) agent, N-3,5'-cyclo-4-(beta-D-ribofuranosyl)-vic-triazolo[4,5-b]pyridinin-5-one, was identified, and the structure was confirmed by chemical synthesis from 2-hydroxy-5-nitropyridine.
• 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).