7-氟-2-氧代-1,2-二氢喹啉-4-羧酸 | 1227465-79-3

• 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
• 中文名称: 7-氟-2-氧代-1,2-二氢喹啉-4-羧酸
• 英文名称: 7-fluoro-2-oxo-1,2-dihydroquinoline-4-carboxylic acid
• 英文别名: 7-fluoro-2-oxo-1H-quinoline-4-carboxylic acid
• CAS: 1227465-79-3
• 化学式: C₁₀H₆FNO₃
• mdl: MFCD15527354
• 分子量: 207.161
• InChiKey: JNJDJHAPAYHLSZ-UHFFFAOYSA-N

物化性质

• 沸点：
  380.9±42.0 °C(Predicted)
• 密度：
  1.517±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  0.7
• 重原子数：
  15
• 可旋转键数：
  1
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.0
• 拓扑面积：
  66.4
• 氢给体数：
  2
• 氢受体数：
  4

安全信息

• 海关编码：
  2933790090

反应信息

• 作为反应物：
  描述：

  7-氟-2-氧代-1,2-二氢喹啉-4-羧酸 在 tris-(dibenzylideneacetone)dipalladium(0) 、 1-[bis(dimethylamino)methylene]-1H-1,2,3-triazolo[4,5-b]pyridinium 3-oxid hexafluorophosphate 、 三乙胺 、 sodium t-butanolate 、 2-二环己基磷-2,4,6-三异丙基联苯 作用下， 以 1,4-二氧六环 、 二氯甲烷 为溶剂， 反应 16.5h， 生成 N-(4-((5-(diethylamino)pentan-2-yl)amino)-3-fluorophenyl)-7-fluoro-2-oxo-1,2-dihydroquinoline-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
• 作为产物：
  描述：

  6-氟吲哚 在 aluminum (III) chloride 、 silica gel 、 溶剂黄146 、 pyridinium chlorochromate 作用下， 生成 7-氟-2-氧代-1,2-二氢喹啉-4-羧酸
  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

• [EN] COMPOSITIONS AND METHODS OF TREATMENT FOR TUMORS IN THE NERVOUS SYSTEM<br/>[FR] COMPOSITIONS ET PROCÉDÉS DE TRAITEMENT DE TUMEURS DANS LE SYSTÈME NERVEUX
  申请人：UNIV GEORGETOWN

  公开号：WO2011156632A2

  公开（公告）日：2011-12-15

  The invention provides compounds, compositions and methods for preventing and treating tumors of the nervous system, by means of compounds that inhibit or modulate p75 neurotrophic receptors. Compounds of the invention have structures of the form G-H-I, wherein G is a small ring system reminiscent of redox-mediating moieties in metabolism, H is a linker of up to 8 atoms in length, and I is a simple end group such as a lower alkyl or small heteroaryl or heterocyclic ring system.
• 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.