6,7-dichloro-1-(2,3,5-tri-O-benzoyl-β-D-ribofuranosyl)-4-(2,3,5-tri-O-benzoyl-β-D-ribofuranosyl)imidazo<4,5-b>quinolin-2-one | 224635-92-1

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: 6,7-dichloro-1-(2,3,5-tri-O-benzoyl-β-D-ribofuranosyl)-4-(2,3,5-tri-O-benzoyl-β-D-ribofuranosyl)imidazo<4,5-b>quinolin-2-one
• 英文别名: [(2R,3R,4R,5R)-3,4-dibenzoyloxy-5-[6,7-dichloro-1-[(2R,3R,4R,5R)-3,4-dibenzoyloxy-5-(benzoyloxymethyl)oxolan-2-yl]-2-oxoimidazo[4,5-b]quinolin-4-yl]oxolan-2-yl]methyl benzoate
• CAS: 224635-92-1
• 化学式: C₆₂H₄₅Cl₂N₃O₁₅
• 分子量: 1142.96
• InChiKey: LXFYLAPCYRHTSU-MCKGLLGGSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  11.8
• 重原子数：
  82
• 可旋转键数：
  22
• 环数：
  11.0
• sp3杂化的碳原子比例：
  0.16
• 拓扑面积：
  212
• 氢给体数：
  0
• 氢受体数：
  15

反应信息

• 作为反应物：
  描述：

  6,7-dichloro-1-(2,3,5-tri-O-benzoyl-β-D-ribofuranosyl)-4-(2,3,5-tri-O-benzoyl-β-D-ribofuranosyl)imidazo<4,5-b>quinolin-2-one 在 三氟甲磺酸三甲基硅酯 、 氨 作用下， 以 甲醇 、 1,2-二氯乙烷 、 乙腈 为溶剂， 反应 29.0h， 生成 6,7-dichloro-1-(β-D-ribofuranosyl)imidazo<4,5-b>quinolin-2-one
  参考文献：
  名称：

  Synthesis and Regioselective Ribosylation of 6,7-Dichloroimidazo[4,5-b]quinolin-2-one

  摘要：

  The polyhalogenated benzimidazole nucleosides 2,5,6-trichloro-1-(beta-D-ribofuranosyl)benzimidazole (TCRB) and the 2-bromo analogue (BDCRB) were synthesized in our laboratory and established as potent and selective antiviral agents against human cytomegalovirus (HCMV) with a novel mode of action. In an effort to study the behavior of the key substructure of these analogues in a dimensionally stretched-out manner and probe the spatial limitation of the target enzyme(s), a series of N1- and N3-ribonucleosides of imidazo[4,5-b]quinolines were designed as linear dimensional analogues. The nucleosides 6,7-dichloro-1-(beta-D-ribofuranosyl)imidazo[4,5-b]quinolin-2-one and 6,7-dichloro-3-(beta-D-ribofuranosyl)imidazo[4,5-b]quinolin-2-one were selected and prepared as the key intermediates in this study. During this study, a novel photoassisted annulation was developed for the synthesis of 6,7-dichloroimidazo[4,5-b]quinolin-2-one, which overcame several problems that were encountered with the literature annulation method. Regioselective ribosylations of this heterocycle were developed and gave both the N1 and the N3 isomers in high yield.

  DOI：

  10.1021/jo982084o
• 作为产物：
  描述：

  1-O-acetyl-2,3,5-tri-O-benzoyl-α-D-ribofuranose 、 6,7-dichloro-4-(2,3,5-tri-O-benzoyl-β-D-ribofuranosyl)imidazo<4,5-b>quinolin-2-one 在 苯磺酰胺 、 三氟甲磺酸三甲基硅酯 作用下， 生成 6,7-dichloro-1-(2,3,5-tri-O-benzoyl-β-D-ribofuranosyl)imidazo<4,5-b>quinolin-2-one 、 6,7-dichloro-1-(2,3,5-tri-O-benzoyl-β-D-ribofuranosyl)-4-(2,3,5-tri-O-benzoyl-β-D-ribofuranosyl)imidazo<4,5-b>quinolin-2-one
  参考文献：
  名称：

  Synthesis and Regioselective Ribosylation of 6,7-Dichloroimidazo[4,5-b]quinolin-2-one

  摘要：

  The polyhalogenated benzimidazole nucleosides 2,5,6-trichloro-1-(beta-D-ribofuranosyl)benzimidazole (TCRB) and the 2-bromo analogue (BDCRB) were synthesized in our laboratory and established as potent and selective antiviral agents against human cytomegalovirus (HCMV) with a novel mode of action. In an effort to study the behavior of the key substructure of these analogues in a dimensionally stretched-out manner and probe the spatial limitation of the target enzyme(s), a series of N1- and N3-ribonucleosides of imidazo[4,5-b]quinolines were designed as linear dimensional analogues. The nucleosides 6,7-dichloro-1-(beta-D-ribofuranosyl)imidazo[4,5-b]quinolin-2-one and 6,7-dichloro-3-(beta-D-ribofuranosyl)imidazo[4,5-b]quinolin-2-one were selected and prepared as the key intermediates in this study. During this study, a novel photoassisted annulation was developed for the synthesis of 6,7-dichloroimidazo[4,5-b]quinolin-2-one, which overcame several problems that were encountered with the literature annulation method. Regioselective ribosylations of this heterocycle were developed and gave both the N1 and the N3 isomers in high yield.

  DOI：

  10.1021/jo982084o

文献信息

• Synthesis and Regioselective Ribosylation of 6,7-Dichloroimidazo[4,5-<i>b</i>]quinolin-2-one
  作者：Zhijian Zhu、Blaise Lippa、Leroy B. Townsend

  DOI：10.1021/jo982084o

  日期：1999.5.1

  The polyhalogenated benzimidazole nucleosides 2,5,6-trichloro-1-(beta-D-ribofuranosyl)benzimidazole (TCRB) and the 2-bromo analogue (BDCRB) were synthesized in our laboratory and established as potent and selective antiviral agents against human cytomegalovirus (HCMV) with a novel mode of action. In an effort to study the behavior of the key substructure of these analogues in a dimensionally stretched-out manner and probe the spatial limitation of the target enzyme(s), a series of N1- and N3-ribonucleosides of imidazo[4,5-b]quinolines were designed as linear dimensional analogues. The nucleosides 6,7-dichloro-1-(beta-D-ribofuranosyl)imidazo[4,5-b]quinolin-2-one and 6,7-dichloro-3-(beta-D-ribofuranosyl)imidazo[4,5-b]quinolin-2-one were selected and prepared as the key intermediates in this study. During this study, a novel photoassisted annulation was developed for the synthesis of 6,7-dichloroimidazo[4,5-b]quinolin-2-one, which overcame several problems that were encountered with the literature annulation method. Regioselective ribosylations of this heterocycle were developed and gave both the N1 and the N3 isomers in high yield.