4-bromo-6-nitro-1H-quinolin-2-one | 934687-49-7

• 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: 4-bromo-6-nitro-1H-quinolin-2-one
• CAS: 934687-49-7
• 化学式: C₉H₅BrN₂O₃
• 分子量: 269.054
• InChiKey: JDLDGLHKEWHVTA-UHFFFAOYSA-N

物化性质

• 沸点：
  469.0±45.0 °C(Predicted)
• 密度：
  1.839±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  2.61
• 重原子数：
  15.0
• 可旋转键数：
  1.0
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.0
• 拓扑面积：
  76.26
• 氢给体数：
  1.0
• 氢受体数：
  4.0

反应信息

• 作为反应物：
  描述：

  4-bromo-6-nitro-1H-quinolin-2-one 在 palladium on activated charcoal 氢气 作用下， 生成 6-Amino-4-bromoquinolin-2(1H)-one
  参考文献：
  名称：

  Novel selective androgen receptor modulators: SAR studies on 6-bisalkylamino-2-quinolinones

  摘要：

  A series of selective androgen receptor modulators (SARMs) with a wide spectrum of receptor modulating activities was developed based on optimization of the 4-substituted 6-bisalkylamino-2-quinolinones (3). Significance of the trifluoromethyl group on the side chains and its interactions with amino acid residues within the androgen receptor (AR) ligand binding domain are discussed. A representative analog (9) was tested orally in a rodent model of hypogonadism and demonstrated desirable tissue selectivity. (c) 2007 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.bmcl.2007.01.001
• 作为产物：
  描述：

  4-溴喹啉-2(1H)-酮 在 硫酸 、 硝酸 作用下， 反应 0.33h， 生成 4-bromo-6-nitro-1H-quinolin-2-one
  参考文献：
  名称：

  Novel selective androgen receptor modulators: SAR studies on 6-bisalkylamino-2-quinolinones

  摘要：

  A series of selective androgen receptor modulators (SARMs) with a wide spectrum of receptor modulating activities was developed based on optimization of the 4-substituted 6-bisalkylamino-2-quinolinones (3). Significance of the trifluoromethyl group on the side chains and its interactions with amino acid residues within the androgen receptor (AR) ligand binding domain are discussed. A representative analog (9) was tested orally in a rodent model of hypogonadism and demonstrated desirable tissue selectivity. (c) 2007 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.bmcl.2007.01.001

文献信息

• The discovery of quinoline derivatives, as NF-κB inducing kinase (NIK) inhibitors with anti-inflammatory effects in vitro, low toxicities against T cell growth
  作者：Jianing Song、Yuqin Zhu、Weidong Zu、Chunqi Duan、Junyu Xu、Fei Jiang、Xinren Wang、Shuwen Li、Chenhe Liu、Qianqian Gao、Hongmei Li、Yanmin Zhang、Weifang Tang、Tao Lu、Yadong Chen

  DOI：10.1016/j.bmc.2020.115856

  日期：2021.1

  are faced by the current inhibitor research to a certain extent. Besides, the compound's toxicity against the growth of T cells under non-stress conditions was evaluated, for the first time, as an indicator for the investigation to avoid potential safety risks. Pharmacokinetic properties evaluation of the less toxic compound 24c confirmed its good metabolic behavior (especially oral properties, F% = 21

  NIK是非经典NF-kB通路的关键调节蛋白，其激活失调已被证明是多种自身免疫性疾病和炎症性疾病的致病因素之一。然而，其相应的抑制剂开发面临诸多障碍，包括已知抑制剂结构类型的缺乏、化合物体外活性评价方法不成熟等。本研究通过合理设计和化学合成得到了一系列喹啉衍生物。其中，代表性化合物17c和24c对LPS诱导的巨噬细胞（J774）一氧化氮释放和抗Con A刺激的原代T细胞增殖具有优异的抑制活性。该评价方法具有良好的普适性，在一定程度上克服了当前抑制剂研究面临的上述障碍。此外，首次评估了该化合物在非应激条件下对T细胞生长的毒性，作为研究的指标，以避免潜在的安全风险。对毒性较小的化合物24c的药代动力学性质评价证实了其良好的代谢行为（尤其是口服性质，F% = 21.7%）以及后续的开发价值。