6-nitro-2-(trichloromethyl)quinoline

• 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-nitro-2-(trichloromethyl)quinoline
• 英文别名: 6-nitro-2-trichloromethylquinoline
• 化学式: C₁₀H₅Cl₃N₂O₂
• 分子量: 291.521
• InChiKey: XVMMYPXUAOJBCG-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.7
• 重原子数：
  17
• 可旋转键数：
  0
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.1
• 拓扑面积：
  58.7
• 氢给体数：
  0
• 氢受体数：
  3

反应信息

• 作为反应物：
  描述：

  6-nitro-2-(trichloromethyl)quinoline 、 2-硝基丙烷 在 四丁基氢氧化铵 作用下， 以 二氯甲烷 、 水 为溶剂， 反应 5.0h， 以95%的产率得到2-(1-chloro-2-methylprop-1-enyl)-6-nitroquinoline
  参考文献：
  名称：

  Discovery of a new antileishmanial hit in 8-nitroquinoline series

  摘要：

  A series of nitrated 2-substituted-quinolines was synthesized and evaluated in vitro toward Leishmania donovani promastigotes. In parallel, the in vitro cytotoxicity of these molecules was assessed on the murine J774 and human HepG2 cell lines. Thus, a very promising antileishmanial hit molecule was identified (compound 21), displaying an IC50 value of 6.6 mu M and CC50 values >= 100 mu M, conferring quite good selectivity index to this molecule, in comparison with 3 drug-compounds of reference (amphotericin B, miltefosine and pentamidine). Compound 21 also appears as an efficient in vitro antileishmanial molecule against both Leishmania infantum promastigotes and the intracellular L. donovani amastigotes (respective IC50 = 7.6 and 6.5 mu M). Moreover, hit quinoline 21 does not show neither significant antiplasmodial nor antitoxoplasmic in vitro activity and though, presents a selective antileishmanial activity. Finally, a structure activity relationships study enabled to define precisely the antileishmanial pharmacophore based on this nitroquinoline scaffold: 2-hydroxy-8-nitroquinoline. (C) 2012 Elsevier Masson SAS. All rights reserved.

  DOI：

  10.1016/j.ejmech.2012.04.029
• 作为产物：
  描述：

  2-甲基-6-硝基喹啉 在 五氯化磷 、 三氯氧磷 作用下， 反应 0.33h， 以83%的产率得到6-nitro-2-(trichloromethyl)quinoline
  参考文献：
  名称：

  Highly efficient microwave assisted α-trichlorination reaction of α-methylated nitrogen containing heterocycles

  摘要：

  A new methodology permitting the chlorination of different alpha-methylated nitrogen containing heterocycles into N-alpha-trichloromethylated derivatives is described here. The combination of microwave technology with a PCl5/POCl3 protocol has allowed to reach trichloromethyl derivatives with high yields in a few minutes. (c) 2006 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.tet.2006.05.081

文献信息

• Highly efficient microwave assisted α-trichlorination reaction of α-methylated nitrogen containing heterocycles
  作者：Pierre Verhaeghe、Pascal Rathelot、Armand Gellis、Sylvain Rault、Patrice Vanelle

  DOI：10.1016/j.tet.2006.05.081

  日期：2006.8

  A new methodology permitting the chlorination of different alpha-methylated nitrogen containing heterocycles into N-alpha-trichloromethylated derivatives is described here. The combination of microwave technology with a PCl5/POCl3 protocol has allowed to reach trichloromethyl derivatives with high yields in a few minutes. (c) 2006 Elsevier Ltd. All rights reserved.
• Nitrated isomers of 2-(trichloromethyl)quinoline
  作者：Jana Sopková-de Oliveira Santos、Pierre Verhaeghe、Jean-François Lohier、Pascal Rathelot、Patrice Vanelle、Sylvain Rault

  DOI：10.1107/s0108270108020374

  日期：2008.8.15

  In the closely related quinoline compounds 8-nitro-2-(trichloromethyl) quinoline, (I), 6-nitro-2-(trichloromethyl) quinoline, (II), and 5-nitro-2-(trichloromethyl) quinoline, (III), all C10H5Cl3N2O2, which are of both reactivity and pharmacological interest, and for which the biological activity and cytotoxicity appear to be based on the positions of the CCl3 and nitro substituents, the nitro group is only coplanar with its aromatic substrate in (II). The deviation of the nitro group from coplanarity is concluded to be a function of both its position with respect to the trichloromethyl group and the intermolecular contacts in which it participates. The discrepancies between the crystal structures and the molecular shapes predicted by ab initio calculations are also explained in these terms. The quinoline ring is not rigorously planar in any of the structures, which may be explained by stress produced by the CCl3 substituent.
• Discovery of a new antileishmanial hit in 8-nitroquinoline series
  作者：Lucie Paloque、Pierre Verhaeghe、Magali Casanova、Caroline Castera-Ducros、Aurélien Dumètre、Litaty Mbatchi、Sébastien Hutter、Manel Kraiem-M'Rabet、Michèle Laget、Vincent Remusat、Sylvain Rault、Pascal Rathelot、Nadine Azas、Patrice Vanelle

  DOI：10.1016/j.ejmech.2012.04.029

  日期：2012.8

  A series of nitrated 2-substituted-quinolines was synthesized and evaluated in vitro toward Leishmania donovani promastigotes. In parallel, the in vitro cytotoxicity of these molecules was assessed on the murine J774 and human HepG2 cell lines. Thus, a very promising antileishmanial hit molecule was identified (compound 21), displaying an IC50 value of 6.6 mu M and CC50 values >= 100 mu M, conferring quite good selectivity index to this molecule, in comparison with 3 drug-compounds of reference (amphotericin B, miltefosine and pentamidine). Compound 21 also appears as an efficient in vitro antileishmanial molecule against both Leishmania infantum promastigotes and the intracellular L. donovani amastigotes (respective IC50 = 7.6 and 6.5 mu M). Moreover, hit quinoline 21 does not show neither significant antiplasmodial nor antitoxoplasmic in vitro activity and though, presents a selective antileishmanial activity. Finally, a structure activity relationships study enabled to define precisely the antileishmanial pharmacophore based on this nitroquinoline scaffold: 2-hydroxy-8-nitroquinoline. (C) 2012 Elsevier Masson SAS. All rights reserved.