4-bromo-8-nitroquinolin-2(1H)-one

• 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-8-nitroquinolin-2(1H)-one
• 英文别名: 4-bromo-8-nitro-1H-quinolin-2-one
• 化学式: C₉H₅BrN₂O₃
• 分子量: 269.054
• InChiKey: VVLQVZTYWZIAEW-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  1.6
• 重原子数：
  15
• 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：
  74.9
• 氢给体数：
  1
• 氢受体数：
  3

反应信息

• 作为反应物：
  描述：

  4-bromo-8-nitroquinolin-2(1H)-one 在 ammonium hydroxide 作用下， 反应 5.0h， 以30%的产率得到4-amino-8-nitroquinolin-2(1H)-one
  参考文献：
  名称：

  Looking for new antileishmanial derivatives in 8-nitroquinolin-2(1H)-one series

  摘要：

  From a recently identified antileishmanial pharmacophore, a structure activity relationship study was conducted by introducing various aminated, phenoxy or thiophenoxy moieties at position 4 of the 8-nitroquinolin-2(1H)-one scaffold, using SNAr reactions. Thus a series of 47 derivatives was synthesized and evaluated in vitro on the promastigote stage of Leishmania donovani. In parallel, the cytotoxicity of the active molecules was tested on the human HepG2 cell line. The results we obtained showed that the introduction of a substituent at position 4 of the antileishmanial pharmacophore can either lead to inactive or active derivatives, depending on the nature of the substituent. Aminated moieties appear as very unfavorable toward antileishmanial activity, while phenoxy or thiophenoxy moieties were shown to maintain the in vitro antileishmanial profile, especially when the phenyl ring of these moieties was substituted at the para or ortho position by a halogen atom (except fluorine), a trifluoromethyl group or a methyl group. Most of these derivatives showed a lack of solubility in the culture media which hindered the in vitro determination of both their cytotoxicity and activity against the intracellular amastigoste stage of L. donovani. (C) 2014 Elsevier Masson SAS. All rights reserved.

  DOI：

  10.1016/j.ejmech.2014.12.056
• 作为产物：
  描述：

  2,4-二溴喹啉 在 高氯酸 、 硫酸 、 硝酸 作用下， 以 水 、 乙腈 为溶剂， 反应 3.0h， 生成 4-bromo-8-nitroquinolin-2(1H)-one
  参考文献：
  名称：

  新型8-硝基喹啉-2（1 H）-ones作为NTR-生物激活的抗动素体分子：合成，电化学和SAR研究

  摘要：

  为了研究抗寄生虫8-硝基喹啉-2（1 H）-一药效基团，以1-5个步骤合成了一系列31种衍生物，并在体外针对婴儿利什曼原虫和布鲁氏锥虫进行了评估。。并行地，通过循环伏安法测量所有分子的还原电势。构效关系首先表明，抗菌活性取决于内酰胺官能团与硝基之间的分子内氢键（通过X射线衍射描述），这是氧化还原电势（+0.3 V与氧化还原电势相比重要的变化）的重要原因。 8-硝基喹啉）。在计算化学的帮助下，设计了一组表现出大范围氧化还原电势（从-1.1至-0.45 V）的衍生物，并提供了一系列适合合成和测试的分子。该方法强调了在该系列中，只有氧化还原电势高于-0.6 V的底物才对婴儿乳杆菌具有活性。。然而，在T中未观察到氧化还原电势与体外抗寄生虫活性之间的这种关系。b。布鲁西。化合物22是该系列中的一种新型命中化合物，对人类HepG2细胞系既显示出抗疟原虫活性又具有抗锥虫活性，并且具有较低的细胞毒性。化合物22被L

  DOI：

  10.1016/j.ejmech.2018.06.001

文献信息

• Novel 8-nitroquinolin-2(1H)-ones as NTR-bioactivated antikinetoplastid molecules: Synthesis, electrochemical and SAR study
  作者：Julien Pedron、Clotilde Boudot、Sébastien Hutter、Sandra Bourgeade-Delmas、Jean-Luc Stigliani、Alix Sournia-Saquet、Alain Moreau、Elisa Boutet-Robinet、Lucie Paloque、Emmanuelle Mothes、Michèle Laget、Laure Vendier、Geneviève Pratviel、Susan Wyllie、Alan Fairlamb、Nadine Azas、Bertrand Courtioux、Alexis Valentin、Pierre Verhaeghe

  DOI：10.1016/j.ejmech.2018.06.001

  日期：2018.7

  important shift of the redox potential (+0.3 V in comparison with 8-nitroquinoline). With the assistance of computational chemistry, a set of derivatives presenting a large range of redox potentials (from −1.1 to −0.45 V) was designed and provided a list of suitable molecules to be synthesized and tested. This approach highlighted that, in this series, only substrates with a redox potential above −0.6 V

  为了研究抗寄生虫8-硝基喹啉-2（1 H）-一药效基团，以1-5个步骤合成了一系列31种衍生物，并在体外针对婴儿利什曼原虫和布鲁氏锥虫进行了评估。。并行地，通过循环伏安法测量所有分子的还原电势。构效关系首先表明，抗菌活性取决于内酰胺官能团与硝基之间的分子内氢键（通过X射线衍射描述），这是氧化还原电势（+0.3 V与氧化还原电势相比重要的变化）的重要原因。 8-硝基喹啉）。在计算化学的帮助下，设计了一组表现出大范围氧化还原电势（从-1.1至-0.45 V）的衍生物，并提供了一系列适合合成和测试的分子。该方法强调了在该系列中，只有氧化还原电势高于-0.6 V的底物才对婴儿乳杆菌具有活性。。然而，在T中未观察到氧化还原电势与体外抗寄生虫活性之间的这种关系。b。布鲁西。化合物22是该系列中的一种新型命中化合物，对人类HepG2细胞系既显示出抗疟原虫活性又具有抗锥虫活性，并且具有较低的细胞毒性。化合物22被L
• Looking for new antileishmanial derivatives in 8-nitroquinolin-2(1H)-one series
  作者：Charline Kieffer、Anita Cohen、Pierre Verhaeghe、Sébastien Hutter、Caroline Castera-Ducros、Michèle Laget、Vincent Remusat、Manel Kraiem M'Rabet、Sylvain Rault、Pascal Rathelot、Nadine Azas、Patrice Vanelle

  DOI：10.1016/j.ejmech.2014.12.056

  日期：2015.3

  From a recently identified antileishmanial pharmacophore, a structure activity relationship study was conducted by introducing various aminated, phenoxy or thiophenoxy moieties at position 4 of the 8-nitroquinolin-2(1H)-one scaffold, using SNAr reactions. Thus a series of 47 derivatives was synthesized and evaluated in vitro on the promastigote stage of Leishmania donovani. In parallel, the cytotoxicity of the active molecules was tested on the human HepG2 cell line. The results we obtained showed that the introduction of a substituent at position 4 of the antileishmanial pharmacophore can either lead to inactive or active derivatives, depending on the nature of the substituent. Aminated moieties appear as very unfavorable toward antileishmanial activity, while phenoxy or thiophenoxy moieties were shown to maintain the in vitro antileishmanial profile, especially when the phenyl ring of these moieties was substituted at the para or ortho position by a halogen atom (except fluorine), a trifluoromethyl group or a methyl group. Most of these derivatives showed a lack of solubility in the culture media which hindered the in vitro determination of both their cytotoxicity and activity against the intracellular amastigoste stage of L. donovani. (C) 2014 Elsevier Masson SAS. All rights reserved.