4-(2,3,5-tri-O-benzoyl-β-D-ribofuranosyl)-vic-triazolo[4,5-b]pyridin-5-one | 59892-42-1

• 分子结构分类: 有机化合物 - 核苷、核苷酸和类似物
• 英文名称: 4-(2,3,5-tri-O-benzoyl-β-D-ribofuranosyl)-vic-triazolo[4,5-b]pyridin-5-one
• 英文别名: 4-(tri-O-benzoyl-β-D-ribofuranosyl)-1,4-dihydro-[1,2,3]triazolo[4,5-b]pyridin-5-one
• CAS: 59892-42-1
• 化学式: C₃₁H₂₄N₄O₈
• 分子量: 580.554
• InChiKey: NCOYQJOKJBUBLZ-GTVIQNQPSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.33
• 重原子数：
  43.0
• 可旋转键数：
  8.0
• 环数：
  6.0
• sp3杂化的碳原子比例：
  0.16
• 拓扑面积：
  151.7
• 氢给体数：
  1.0
• 氢受体数：
  11.0

反应信息

• 作为产物：
  描述：

  1-乙酰基-三-苄氧基-罗伯糖 在 sodium azide 、 四氯化锡 作用下， 以 1,2-二氯乙烷 、 N,N-二甲基甲酰胺 为溶剂， 反应 24.0h， 生成 4-(2,3,5-tri-O-benzoyl-β-D-ribofuranosyl)-vic-triazolo[4,5-b]pyridin-5-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

文献信息

• 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.