5-((5,7-dibromoquinolin-8-yloxy)methyl)-4-phenyl-4H-1,2,4-triazol-3-ol | 1443108-36-8

• 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: 5-((5,7-dibromoquinolin-8-yloxy)methyl)-4-phenyl-4H-1,2,4-triazol-3-ol
• 英文别名: 3-[(5,7-dibromoquinolin-8-yl)oxymethyl]-4-phenyl-1H-1,2,4-triazol-5-one
• CAS: 1443108-36-8
• 化学式: C₁₈H₁₂Br₂N₄O₂
• 分子量: 476.127
• InChiKey: MMBHXQZYIZMLDQ-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  4.3
• 重原子数：
  26
• 可旋转键数：
  4
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.06
• 拓扑面积：
  66.8
• 氢给体数：
  1
• 氢受体数：
  4

反应信息

• 作为产物：
  描述：

  5,7-二溴-8-羟基喹啉 在 potassium carbonate 、 一水合肼 、 溶剂黄146 、 sodium hydroxide 作用下， 以 乙醇 、 N,N-二甲基甲酰胺 为溶剂， 反应 24.5h， 生成 5-((5,7-dibromoquinolin-8-yloxy)methyl)-4-phenyl-4H-1,2,4-triazol-3-ol
  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

• 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.