7-bromo-N-(2-methoxyphenyl)quinoline-4-carboxamide

• 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: 7-bromo-N-(2-methoxyphenyl)quinoline-4-carboxamide
• 化学式: C₁₇H₁₃BrN₂O₂
• 分子量: 357.206
• InChiKey: XNEGIDLVNLMKOM-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.7
• 重原子数：
  22
• 可旋转键数：
  3
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.06
• 拓扑面积：
  51.2
• 氢给体数：
  1
• 氢受体数：
  3

反应信息

• 作为产物：
  描述：

  6-溴靛红 在 1-[bis(dimethylamino)methylene]-1H-1,2,3-triazolo[4,5-b]pyridinium 3-oxid hexafluorophosphate 、 三乙胺 、 sodium hydroxide 作用下， 以 二氯甲烷 、 硝基苯 为溶剂， 反应 2.5h， 生成 7-bromo-N-(2-methoxyphenyl)quinoline-4-carboxamide
  参考文献：
  名称：

  Synthesis and biological evaluation of novel 2-oxo-1,2-dihydroquinoline-4-carboxamide derivatives for the treatment of esophageal squamous cell carcinoma

  摘要：

  No new and effective treatments have been approved for the treatment of esophageal squamous cell carcinoma (ESCC) in the past decade. Cisplatin and 5-fluoruracil are the most commonly used drugs for this disease. In order to develop a new class of drugs effective in our ESCC phenotypic screens, we began a systematic approach to generate novel compounds based on the 2-oxo-1,2-dihydroquinoline-4carboxamide fragment. Herein, we report on the synthesis and initial assessment of 55 new analogues in two ESCC cell lines. Some of the active analogues with 1050 values around 10 mu M were tested in three additional cell lines. Our structure-activity relationships revealed remarkable alterations in the anti proliferative activities upon modest chemical modifications and autophagy modulation is a suggested mechanism of action. (C) 2018 Elsevier Masson SAS. All rights reserved.

  DOI：

  10.1016/j.ejmech.2018.05.042

文献信息

• Synthesis and biological evaluation of novel 2-oxo-1,2-dihydroquinoline-4-carboxamide derivatives for the treatment of esophageal squamous cell carcinoma
  作者：Mai I. Shahin、Joyeeta Roy、Maha Hanafi、Dongyao Wang、Urarika Luesakul、Yifeng Chai、Nongnuj Muangsin、Deena S. Lasheen、Dalal A. Abou El Ella、Khaled A. Abouzid、Nouri Neamati

  DOI：10.1016/j.ejmech.2018.05.042

  日期：2018.7

  No new and effective treatments have been approved for the treatment of esophageal squamous cell carcinoma (ESCC) in the past decade. Cisplatin and 5-fluoruracil are the most commonly used drugs for this disease. In order to develop a new class of drugs effective in our ESCC phenotypic screens, we began a systematic approach to generate novel compounds based on the 2-oxo-1,2-dihydroquinoline-4carboxamide fragment. Herein, we report on the synthesis and initial assessment of 55 new analogues in two ESCC cell lines. Some of the active analogues with 1050 values around 10 mu M were tested in three additional cell lines. Our structure-activity relationships revealed remarkable alterations in the anti proliferative activities upon modest chemical modifications and autophagy modulation is a suggested mechanism of action. (C) 2018 Elsevier Masson SAS. All rights reserved.