ethyl 2-(5,7-dibromoquinolin-8-yloxy)acetate | 131924-26-0

• 分子结构分类: 有机化合物 - 苯类化合物 - 苯和取代衍生物
• 英文名称: ethyl 2-(5,7-dibromoquinolin-8-yloxy)acetate
• 英文别名: Ethyl 2-(5,7-dibromoquinolin-8-yl)oxyacetate
• CAS: 131924-26-0
• 化学式: C₁₃H₁₁Br₂NO₃
• mdl: MFCD00990619
• 分子量: 389.043
• InChiKey: SEQKUEZKCMGCGE-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.8
• 重原子数：
  19
• 可旋转键数：
  5
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.23
• 拓扑面积：
  48.4
• 氢给体数：
  0
• 氢受体数：
  4

反应信息

• 作为反应物：
  描述：

  ethyl 2-(5,7-dibromoquinolin-8-yloxy)acetate 在 一水合肼 、 溶剂黄146 作用下， 以 乙醇 为溶剂， 反应 8.0h， 生成 2-(5,7-dibromoquinolin-8-yloxy)-N'-(4-hydroxy-3-methoxybenzylidene)acetohydrazide
  参考文献：
  名称：

  Synthesis and in vitro antiproliferative effect of novel quinoline-based potential anticancer agents

  摘要：

  Several derivatives with a quinoline scaffold and a flexible, semi-flexible or rigid side chains at position 8 of the quinoline ring were synthesized and assessed for their in vitro activity versus the human colon cancer cell line HT29 and the human breast cancer cell line MDA-MB231. The HT29 cell line was more refractory to the cytotoxic activity of some compounds, meanwhile all the quinoline derivatives except one displayed high to moderate activity against MDA-MB231 with IC50 values ranging between 4.6 and 48.2 mu M. The most active derivative in this study against both tested cell lines was the Schiff's base 4e with IC50 of 4.7 and 4.6 mu M against HT29 and MDA-MB231, respectively. (C) 2013 Elsevier Masson SAS. All rights reserved.

  DOI：

  10.1016/j.ejmech.2013.03.008
• 作为产物：
  描述：

  5,7-二溴-8-羟基喹啉 、 氯乙酸乙酯 在 potassium carbonate 作用下， 以 N,N-二甲基甲酰胺 为溶剂， 反应 6.0h， 以84%的产率得到ethyl 2-(5,7-dibromoquinolin-8-yloxy)acetate
  参考文献：
  名称：

  Synthesis and in vitro antiproliferative effect of novel quinoline-based potential anticancer agents

  摘要：

  Several derivatives with a quinoline scaffold and a flexible, semi-flexible or rigid side chains at position 8 of the quinoline ring were synthesized and assessed for their in vitro activity versus the human colon cancer cell line HT29 and the human breast cancer cell line MDA-MB231. The HT29 cell line was more refractory to the cytotoxic activity of some compounds, meanwhile all the quinoline derivatives except one displayed high to moderate activity against MDA-MB231 with IC50 values ranging between 4.6 and 48.2 mu M. The most active derivative in this study against both tested cell lines was the Schiff's base 4e with IC50 of 4.7 and 4.6 mu M against HT29 and MDA-MB231, respectively. (C) 2013 Elsevier Masson SAS. All rights reserved.

  DOI：

  10.1016/j.ejmech.2013.03.008

文献信息

• Facile Synthesis of Tricyclic Oxazino- or Oxazepino-Fused Tetrahydroquinolines via Intramolecular Reductive Amidation
  作者：Nirup Mondal、Shyamal Mondal、Arindam Maity、Subhendu Naskar、Rupankar Paira、Abhijit Hazra、Krishnendu Sahu、Pritam Saha、Saktipada Das、Sukdeb Banerjee

  DOI：10.1055/s-0030-1260056

  日期：2011.7

  Reductive cyclization of ω-(8-quinolyloxy)alkyl esters by zinc in acetic acid is shown to constitute a convenient methodology for the synthesis of oxazino- or oxazepino-fused tetrahydroquinolines. It is operationally simple, requires a short reaction time, and provides excellent yields.

  乙酸中锌促进的（8-喹啉氧基）烷基酯还原环化反应被证明是一种便捷的方法，用于合成含氧杂环或氧杂环并环的氢化喹啉类化合物。该方法操作简单，反应时间短，并能提供优异的产率。
• Synthesis and in vitro antiproliferative effect of novel quinoline-based potential anticancer agents
  作者：Reem K. Arafa、Gehan H. Hegazy、Gary A. Piazza、Ashraf H. Abadi

  DOI：10.1016/j.ejmech.2013.03.008

  日期：2013.5

  Several derivatives with a quinoline scaffold and a flexible, semi-flexible or rigid side chains at position 8 of the quinoline ring were synthesized and assessed for their in vitro activity versus the human colon cancer cell line HT29 and the human breast cancer cell line MDA-MB231. The HT29 cell line was more refractory to the cytotoxic activity of some compounds, meanwhile all the quinoline derivatives except one displayed high to moderate activity against MDA-MB231 with IC50 values ranging between 4.6 and 48.2 mu M. The most active derivative in this study against both tested cell lines was the Schiff's base 4e with IC50 of 4.7 and 4.6 mu M against HT29 and MDA-MB231, respectively. (C) 2013 Elsevier Masson SAS. All rights reserved.