5-硝基-1-(2,3,5-三-O-苯甲酰基-beta-D-呋喃核糖基)-2(1H)-吡啶酮 | 59892-37-4

• 分子结构分类: 有机化合物 - 有机氧化合物
• 中文名称: 5-硝基-1-(2,3,5-三-O-苯甲酰基-beta-D-呋喃核糖基)-2(1H)-吡啶酮
• 英文名称: 1-(2,3,5-tri-O-benzoyl-β-D-ribofuranosyl)-5-nitropyridine-2(1H)-one
• 英文别名: 1-(2,3,5-tri-O-benzoyl-β-D-ribofuranosyl)-5-nitropyridin-2-one；5-nitro-1-(2,3,5-tri-O-benzoyl-β-D-ribofuranosyl)-2-pyridone；(2R,3R,4R,5R)-2-((Benzoyloxy)methyl)-5-(5-nitro-2-oxopyridin-1(2H)-yl)tetrahydrofuran-3,4-diyl dibenzoate；[(2R,3R,4R,5R)-3,4-dibenzoyloxy-5-(5-nitro-2-oxopyridin-1-yl)oxolan-2-yl]methyl benzoate
• CAS: 59892-37-4
• 化学式: C₃₁H₂₄N₂O₁₀
• 分子量: 584.539
• InChiKey: IEZNOQUIRFRCMT-YULOIDQLSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  4.6
• 重原子数：
  43
• 可旋转键数：
  11
• 环数：
  5.0
• sp3杂化的碳原子比例：
  0.16
• 拓扑面积：
  154
• 氢给体数：
  0
• 氢受体数：
  10

反应信息

• 作为反应物：
  描述：

  5-硝基-1-(2,3,5-三-O-苯甲酰基-beta-D-呋喃核糖基)-2(1H)-吡啶酮 在 盐酸 、 sodium azide 、 氨 、 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 、 甲醇 、 水 、 N,N-二甲基甲酰胺 为溶剂， 反应 36.0h， 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 、 四氯化锡 作用下， 以 二氯甲烷 、 1,2-二氯乙烷 为溶剂， 反应 6.0h， 生成 5-硝基-1-(2,3,5-三-O-苯甲酰基-beta-D-呋喃核糖基)-2(1H)-吡啶酮
  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

• Compounds with the bicyclo[4.2.1]nonane system for the treatment of flavivridae infections
  申请人：——

  公开号：US20040082574A1

  公开（公告）日：2004-04-29

  The disclosed invention is a bicyclo[4.2.1]nonane and its pharmaceutically acceptable salt or prodrug, and its composition and method of use to treat Flaviviridae (Hepacivirus, Flavivirus, and Pestivirus) infections in a host, including animals, and especially humans.

  本公开发明涉及一种双环[4.2.1]壬烷及其药用可接受的盐或前药，以及其组合物和治疗宿主（包括动物，特别是人类）的黄病毒科（肝病毒、黄病毒和瘟疫病毒）感染的方法。
• Compounds with the bicyclo[4.2.1]nonane system for the treatment of Flaviviridae infections
  申请人：Pharmasset, Inc.

  公开号：US08093380B2

  公开（公告）日：2012-01-10

  The disclosed invention is a bicyclo[4.2.1]nonane and its pharmaceutically acceptable salt or prodrug, and its composition and method of use to treat Flaviviridae (Hepacivirus, Flavivirus, and Pestivirus) infections in a host, including animals, and especially humans.

  所披露的发明是一种双环[4.2.1]壬烷及其药学上可接受的盐或前药，以及其组合物和使用方法，用于治疗宿主中的黄病毒科（肝病病毒、黄病毒和瘟疫病毒）感染，包括动物，尤其是人类。
• 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.
• COMPOUNDS WITH THE BICYCLO 4.2.1 NONANE SYSTEM FOR THE TREATMENT OF i FLAVIVIRIDAE /i INFECTIONS
  申请人：Pharmasset, Inc.

  公开号：EP1545545A2

  公开（公告）日：2005-06-29
• EP1545545A4
  申请人：——

  公开号：EP1545545A4

  公开（公告）日：2008-09-03