6-chloro-7-propylamine-5,8-quinolinedione | 1609167-87-4

• 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-chloro-7-propylamine-5,8-quinolinedione
• 英文别名: 6-chloro-7-propylaminoquinoline-5,8-dione；6-Chloro-7-(propylamino)quinoline-5,8-dione
• CAS: 1609167-87-4
• 化学式: C₁₂H₁₁ClN₂O₂
• 分子量: 250.685
• InChiKey: HGFMTFBSHWSREJ-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.6
• 重原子数：
  17
• 可旋转键数：
  3
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.25
• 拓扑面积：
  59.1
• 氢给体数：
  1
• 氢受体数：
  4

反应信息

• 作为产物：
  描述：

  8-羟基喹啉 在 盐酸 、 sodium chlorate 作用下， 以 水 为溶剂， 反应 7.0h， 生成 6-chloro-7-propylamine-5,8-quinolinedione 、 7-chloro-6-propylamine-5,8-quinolinedione
  参考文献：
  名称：

  The synthesis and evaluation of quinolinequinones as anti-mycobacterial agents

  摘要：

  A library of thirty-two quinolinequinones (QQs) with various amine substituents at the 6- and 7-positions were synthesised efficiently and in good yields for evaluation as potential anti-tuberculosis agents. Mycobacterium tuberculosis growth inhibition assays demonstrated that QQs bearing moderate length alkyl chains (i.e. heptyl-phenylamino-and octylamino-QQs), and aryl groups (i.e. phenylethylamino-and benzylamino-QQs) exhibited encouraging inhibitory activity, while QQ analogue 7-chloro-6-propargylamino-quinoline-5,8-dione (16b) had excellent inhibitory activity (MIC=8 mu M). The cLogP values and redox activities of the QQs were determined, and neither readout correlated with the anti-mycobacterial activities of the compounds. Notwithstanding, mode of action studies of 16b revealed that treatment of M. tuberculosis with this compound led to activation of NADH-dependent oxygen consumption suggesting a redox cycling mechanism. To this end, the promising anti-mycobacterial activity of several QQs and their ability to perturb oxygen management leading to an uncontrolled respiratory burst, as identified in this work and by others, demonstrates the merit of further optimising the anti-mycobacterial activity of this readily synthesised class of compound.

  DOI：

  10.1016/j.bmc.2019.06.002

文献信息

• Synthesis, crystal structure and infrared spectra of new 6- and 7-propylamine-5,8-quinolinediones
  作者：Maria Jastrzebska、Stanisław Boryczka、Monika Kadela、Roman Wrzalik、Joachim Kusz、Maria Nowak

  DOI：10.1016/j.molstruc.2014.03.031

  日期：2014.6

  observed. The studied compounds were also analyzed due to their interesting carbonyl stretching bands in the infrared spectra. Considerable changes in the frequency separation of the carbonyl stretching bands for different positions of the propylamine chain were found. Correlation between frequency separation of the carbonyl bands and the nature and position of the 6- and 7-substituents may provide

  摘要 我们合成了6-氯-7-丙胺-5,8-喹啉二酮和7-氯-6-丙胺-5,8-喹啉二酮，并通过X 射线衍射和红外光谱技术以及DFT 计算对这些新化合物进行了表征。进行分析时特别注意由所研究的 6- 和 7-丙胺-5,8-喹啉二酮中丙胺链的不同位置引起的结构变化。发现标题化合物在强烈影响氢键形成的晶体结构上有显着差异。对 6- 和 7- 取代基以及起始化合物 6,7-二氯-5,8-喹啉二酮的晶体结构中的 H 键进行了详细分析。发现晶体结构主要由NH⋯O、CH⋯O和CH⋯N型氢键稳定。对于 7-取代 5，观察到 8-喹啉二酮丙胺链与环平面（接近 90°）发生强烈扭曲，导致 H 键形成发生变化。还分析了研究的化合物，因为它们在红外光谱中具有有趣的羰基伸缩带。发现丙胺链不同位置的羰基伸缩带的频率分离发生了相当大的变化。羰基带的频率分离与 6 和 7 取代基的性质和位置之间的相关性可能为使用红外光谱