6,7-dichloro-3-(2,3,5-tri-O-benzoyl-β-D-ribofuranosyl)imidazo<4,5-b>quinolin-2-one | 177980-41-5

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: 6,7-dichloro-3-(2,3,5-tri-O-benzoyl-β-D-ribofuranosyl)imidazo<4,5-b>quinolin-2-one
• 英文别名: 6,7-dichloro-3-(2,3,5-tri-O-benzoyl-β-D-ribofuranosyl)imidazo[4,5-b]quinolin-2-one；[(2R,3R,4R,5R)-3,4-dibenzoyloxy-5-(6,7-dichloro-2-oxo-1H-imidazo[4,5-b]quinolin-3-yl)oxolan-2-yl]methyl benzoate
• CAS: 177980-41-5
• 化学式: C₃₆H₂₅Cl₂N₃O₈
• 分子量: 698.516
• InChiKey: KXHMZGWMOKCGMR-PBAMLIMUSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  7.2
• 重原子数：
  49
• 可旋转键数：
  11
• 环数：
  7.0
• sp3杂化的碳原子比例：
  0.14
• 拓扑面积：
  133
• 氢给体数：
  1
• 氢受体数：
  9

反应信息

• 作为反应物：
  描述：

  6,7-dichloro-3-(2,3,5-tri-O-benzoyl-β-D-ribofuranosyl)imidazo<4,5-b>quinolin-2-one 在 四氯化碳 、 4 A molecular sieve 、 硫化氢 、 氨 、 氯 、 三乙胺 、 三氯氧磷 作用下， 以 甲醇 、 二氯甲烷 、 乙腈 为溶剂， 反应 122.5h， 生成 6,7-dichloro-2-cyclopropylamino-3-(β-D-ribofuranosyl)imidazo[4,5-b]quinoline
  参考文献：
  名称：

  三环核苷（尺寸探针）作为某些抗病毒多卤代苯并咪唑核糖核苷类似物的设计，合成和生物学评估。

  摘要：

  在我们的实验室中合成了多卤代苯并咪唑核苷2,5、6-三氯-1-（β-D-呋喃呋喃糖基）苯并咪唑（TCRB）和2-溴类似物（BDCRB），并将其作为人巨细胞病毒的有效和选择性抑制剂（ HCMV）具有新颖的作用方式。为了研究关键亚结构的行为，在尺寸上扩展并探究目标酶的空间限制，一系列了2-取代的6、7-二氯-1-（β-D-呋喃呋喃糖基）制备了萘酚，2,3-二咪唑和2-取代的6,7-二氯咪唑-4、5-喹啉的N1-和N3-核糖核苷。核苷6、7-二氯-1-（β-D-呋喃呋喃糖基）咪唑4,5-bquinolin-2-one和6,7-二氯-3-（β-D-核呋喃糖基）咪唑-4,5-选择了bquinolin-2-one，并将其用作咪唑4的关键合成中间体，5-喹啉系列。对化合物针对HCMV和1型单纯疱疹病毒的活性进行评估后发现，TCRB的三氯类似物（2a，3a）对HCMV的活性与TCRB几乎相同，但具有更高的

  DOI：

  10.1021/jm990290y
• 作为产物：
  描述：

  4,5-二氯-2-硝基苯胺 在 ammonium hydroxide 、 sodium hydroxide 、 亚硝酸特丁酯 、 硼烷四氢呋喃络合物 、 三氟化硼乙醚 、 四氯化锡 、 铁粉 、 copper(II) sulfate 、 iron(II) sulfate 、 溶剂黄146 、 三乙胺 、 pyridinium chlorochromate 、 sodium nitrite 作用下， 以 四氢呋喃 、 甲醇 、 二氯甲烷 、 水 、 溶剂黄146 、 乙腈 为溶剂， 反应 77.58h， 生成 6,7-dichloro-3-(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

• Regioselective ribosylation of 6,7-dichloroimidazo[4,5-b]quinolin-2-one
  作者：Zhijian Zhu、Leroy B. Townsend

  DOI：10.1016/0040-4039(96)00529-1

  日期：1996.5

  Regioselective ribosylation conditions were established which gave both 6,7-dichloro-1-(2,3,5-tri-O-benzoyl-β-D-ribofuranosyl)imidazo[4,5-b]quinolin-2-one (4) and 6,7-dichloro-3-(2,3,5-tri-O-benzoyl-β-D-ribofuranosyl)imidazo [4,5-b]quinolin-2-one (5), respectively, in high yield from 6,7-dichloroimidazo[4,5-b]quinolin-2-one (6). The distributions of the sites of ribosylation under a variety of conditions

  建立了区域选择性核糖基化条件，该条件可同时生成6,7-二氯-1-（2,3,5-三-O-苯甲酰基-β-D-核呋喃呋喃糖基）咪唑并[4,5 - b ]喹啉-2-酮（4）和6,7-二氯-3-（2,3,5-三- ø -苯甲酰-β-d-D-呋喃核糖基）咪唑并[4,5-b]喹啉-2-酮（5），分别在高由6，7-二氯咪唑并[4，5- b ]喹啉-2-酮（6）得到。讨论了在各种条件下核糖基化位点的分布。
• 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.
• Design, Synthesis, and Biological Evaluation of Tricyclic Nucleosides (Dimensional Probes) as Analogues of Certain Antiviral Polyhalogenated Benzimidazole Ribonucleosides
  作者：Zhijian Zhu、Blaise Lippa、John C. Drach、Leroy B. Townsend

  DOI：10.1021/jm990290y

  日期：2000.6.1

  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 inhibitors of human cytomegalovirus (HCMV) with a novel mode of action. In an effort to study the behavior of the key substructure in a dimensionally extended manner and probe the spatial

  在我们的实验室中合成了多卤代苯并咪唑核苷2,5、6-三氯-1-（β-D-呋喃呋喃糖基）苯并咪唑（TCRB）和2-溴类似物（BDCRB），并将其作为人巨细胞病毒的有效和选择性抑制剂（ HCMV）具有新颖的作用方式。为了研究关键亚结构的行为，在尺寸上扩展并探究目标酶的空间限制，一系列了2-取代的6、7-二氯-1-（β-D-呋喃呋喃糖基）制备了萘酚，2,3-二咪唑和2-取代的6,7-二氯咪唑-4、5-喹啉的N1-和N3-核糖核苷。核苷6、7-二氯-1-（β-D-呋喃呋喃糖基）咪唑4,5-bquinolin-2-one和6,7-二氯-3-（β-D-核呋喃糖基）咪唑-4,5-选择了bquinolin-2-one，并将其用作咪唑4的关键合成中间体，5-喹啉系列。对化合物针对HCMV和1型单纯疱疹病毒的活性进行评估后发现，TCRB的三氯类似物（2a，3a）对HCMV的活性与TCRB几乎相同，但具有更高的