4-(2-chlorophenoxy)-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-(2-chlorophenoxy)-8-nitroquinolin-2(1H)-one
• 英文别名: 4-(2-chlorophenoxy)-8-nitro-1H-quinolin-2-one
• 化学式: C₁₅H₉ClN₂O₄
• 分子量: 316.7
• InChiKey: PHZNFNVRHCPKAS-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3
• 重原子数：
  22
• 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：
  84.2
• 氢给体数：
  1
• 氢受体数：
  4

反应信息

• 作为产物：
  描述：

  2,4-二溴喹啉 在 高氯酸 、 硫酸 、 硝酸 、 sodium hydride 作用下， 以 二甲基亚砜 、 乙腈 为溶剂， 反应 6.0h， 生成 4-(2-chlorophenoxy)-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

文献信息

• 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.