7-苯胺基-6-氯喹啉-5,8-二酮 | 61431-04-7

• 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
• 中文名称: 7-苯胺基-6-氯喹啉-5,8-二酮
• 英文名称: 6-chloro-7-phenylaminoquinoline-5,8-dione
• 英文别名: 7-anilino-6-chloro-quinoline-5,8-dione；7-Anilino-6-chloroquinoline-5,8-dione
• CAS: 61431-04-7
• 化学式: C₁₅H₉ClN₂O₂
• 分子量: 284.702
• InChiKey: BOMIBDRSQWKVIF-UHFFFAOYSA-N

物化性质

• 沸点：
  430.4±45.0 °C(Predicted)
• 密度：
  1.45±0.1 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  3.3
• 重原子数：
  20
• 可旋转键数：
  2
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.0
• 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-phenylamino-7-chloro-5,8-quinolinedione 、 7-苯胺基-6-氯喹啉-5,8-二酮
  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

• The synthesis and evaluation of quinolinequinones as anti-mycobacterial agents
  作者：Kristiana T. Santoso、Ayana Menorca、Chen-Yi Cheung、Gregory M. Cook、Bridget L. Stocker、Mattie S.M. Timmer

  DOI：10.1016/j.bmc.2019.06.002

  日期：2019.8

  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.