6-amino-7,8-dichloroquinoline | 261764-94-7

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 喹啉及其衍生物
• 英文名称: 6-amino-7,8-dichloroquinoline
• 英文别名: 7,8-Dichloroquinolin-6-amine
• CAS: 261764-94-7
• 化学式: C₉H₆Cl₂N₂
• 分子量: 213.066
• InChiKey: CJNGLNDGLKKZCA-UHFFFAOYSA-N

物化性质

• 沸点：
  378.0±37.0 °C(Predicted)
• 密度：
  1.490±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  2.8
• 重原子数：
  13
• 可旋转键数：
  0
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.0
• 拓扑面积：
  38.9
• 氢给体数：
  1
• 氢受体数：
  2

反应信息

• 作为反应物：
  描述：

  6-amino-7,8-dichloroquinoline 在 palladium on activated charcoal 氨 、 一水合肼 、 三氯氧磷 作用下， 以 乙醇 为溶剂， 反应 153.0h， 生成 [4,7]phenanthrolin-1-ylamine
  参考文献：
  名称：

  Design, synthesis, and preliminary in vitro and in silico antiviral activity of [4,7]phenantrolines and 1-oxo-1,4-dihydro-[4,7]phenantrolines against single-stranded positive-sense RNA genome viruses

  摘要：

  Following the antiviral screening of a wide series of new angular and linear N-tricyclic systems both in silico and in vitro, the [4,7]phenantroline nucleus emerged as a new ring system endowed with activity against viruses containing single-stranded, positive-sense RNA genomes (ssRNA(+)). Here, we report our new pathway to the synthesis of this nucleus and of several related derivatives, as well as the results of both cell-based antiviral assays and molecular dynamics simulations. In the antiviral screening, several compounds (9 and 16-20) showed to be fairly active against BVDV, CVB-2, and Polio I (EC50, 6-25 mu M). According to molecular dynamics simulations, compounds (15) and (17) emerged for its potency against the HCV NS5B, with a calculated IC50 of 11-12 mu M. (c) 2007 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.bmc.2007.01.005
• 作为产物：
  描述：

  2,3-二氯苯胺 在 arsenic pentoxide hydrate 、 硫酸 、 potassium nitrate 、 甲基肼 作用下， 以 乙醇 为溶剂， 反应 74.0h， 生成 6-amino-7,8-dichloroquinoline
  参考文献：
  名称：

  Design, synthesis, and preliminary in vitro and in silico antiviral activity of [4,7]phenantrolines and 1-oxo-1,4-dihydro-[4,7]phenantrolines against single-stranded positive-sense RNA genome viruses

  摘要：

  Following the antiviral screening of a wide series of new angular and linear N-tricyclic systems both in silico and in vitro, the [4,7]phenantroline nucleus emerged as a new ring system endowed with activity against viruses containing single-stranded, positive-sense RNA genomes (ssRNA(+)). Here, we report our new pathway to the synthesis of this nucleus and of several related derivatives, as well as the results of both cell-based antiviral assays and molecular dynamics simulations. In the antiviral screening, several compounds (9 and 16-20) showed to be fairly active against BVDV, CVB-2, and Polio I (EC50, 6-25 mu M). According to molecular dynamics simulations, compounds (15) and (17) emerged for its potency against the HCV NS5B, with a calculated IC50 of 11-12 mu M. (c) 2007 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.bmc.2007.01.005

文献信息

• Synthesis of Substituted Aminoquinolines as Useful Intermediates for Preparation of Aromatic N-Tricyclic Systems
  作者：Antonio Carta、Michele Palomba、Paola Corona

  DOI：10.3987/com-06-10782

  日期：——

  An effective approach for the synthesis of new substituted mono and diaminoquinolines is described. Two known quinolines 7,8-dichloro-6-nitroquinoline (1) and 7,8-dichloro-6-nitrohydroquinolin-4-one (9) were used as key intermediates.

  描述了一种合成新的取代单和二氨基喹啉的有效方法。两种已知的喹啉 7,8-二氯-6-硝基喹啉 (1) 和 7,8-二氯-6-硝基氢喹啉-4-酮 (9) 被用作关键中间体。
• Synthesis of Two Novel Tricyclic Rings: Triazolo[4,5-g]quinolines and Pyrido[2,3-g]quinoxalines Derived from 6,7-Diaminoquinolines
  作者：Paolo Sanna、Antonio Carta、Giuseppe Paglietti

  DOI：10.3987/com-99-8766

  日期：——

  A general simple route for the synthesis of triazolo[4,5-g]quinolines and pyrido[2,3-g]quinoxalines is described. The heterocycles obtained were fully characterised by their spectroscopical properties. A revision of the nitration of the 2,3-dichloroacetanilide is also discussed, since it afforded the request nitro derivative to build up the key intermediate 6,7-diaminoquinolines.