5,6,7,8-tetrafluoro-4-oxo-1-(pentafluorophenyl)-1,4-dihydroquinoline-3-carboxylic acid | 119877-58-6

• 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: 5,6,7,8-tetrafluoro-4-oxo-1-(pentafluorophenyl)-1,4-dihydroquinoline-3-carboxylic acid
• 英文别名: 5,6,7,8-Tetrafluoro-4-oxo-1-(pentafluoro-phenyl)-1,4-dihydroquinoline-3-carboxylic acid；5,6,7,8-tetrafluoro-4-oxo-1-(2,3,4,5,6-pentafluorophenyl)quinoline-3-carboxylic acid
• CAS: 119877-58-6
• 化学式: C₁₆H₂F₉NO₃
• 分子量: 427.182
• InChiKey: PPSCWVMHYJJOBZ-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  4.4
• 重原子数：
  29
• 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：
  57.6
• 氢给体数：
  1
• 氢受体数：
  13

反应信息

• 作为产物：
  描述：

  2,3,4,5,6-五氟苯胺 在 硫酸 、 potassium carbonate 作用下， 以 乙醇 、 N,N-二甲基甲酰胺 为溶剂， 生成 5,6,7,8-tetrafluoro-4-oxo-1-(pentafluorophenyl)-1,4-dihydroquinoline-3-carboxylic acid
  参考文献：
  名称：

  Synthesis of novel 5-fluoro analogs of norfloxacin and ciprofloxacin

  摘要：

  A series of polyfluoro-3-quinolonecarboxylic acids have been synthesized and their in vitro antibacterial activity evaluated. The desired 7-(substituted amino) derivatives were prepared from the 5,6,7,8-tetrafluoroquinolone acids. Conversely, amine displacement occurred primarily at the 5-position when the ester was used. Structure-activity studies indicated that the antibacterial activity was greatest when the N-1 substituent was cyclopropyl and the 7-substituent was 4-methyl-1-piperazinyl. All 5-(substituted amino) derivatives showed poor in vitro activity.

  DOI：

  10.1021/jm00126a028

文献信息

• Inhibition of the Signal Transducer and Activator of Transcription-3 (STAT3) Signaling Pathway by 4-Oxo-1-Phenyl-1,4-Dihydroquinoline-3-Carboxylic Acid Esters
  作者：Jun Xu、Derek C. Cole、Chao-Pei Betty Chang、Ramzi Ayyad、Magda Asselin、Wenshan Hao、James Gibbons、Scott A. Jelinsky、Kathryn A. Saraf、Kaapjoo Park

  DOI：10.1021/jm701271y

  日期：2008.7.1

  The JAK-STAT3 pathway regulates genes that are important in cell proliferation and thus is a promising target for cancer therapy. A high-throughput screening (HTS) campaign using an Apo-ONE Homogenous Caspase 3/7 assay in U266 cells identified 4-oxo-1-phenyl-1,4-dihydroquinoline-3-carboxylicacid ethyl ester 4 as a potential STAT3 pathway inhibitor. Optimization of this HTS hit led to the identification of the 7-cyano analogue 8, which inhibited STAT3-Y705 phosphorylation with an EC(50) Of 170 nM. Compound 8 also inhibited cytokine induced JAK activation but did not inhibit BCR-ABL activated STAT5 phosphorylation in K562 cells.
• Synthesis of novel 5-fluoro analogs of norfloxacin and ciprofloxacin
  作者：Daniel B. Moran、Carl B. Ziegler、Theresa S. Dunne、Nydia A. Kuck、Yang I Lin

  DOI：10.1021/jm00126a028

  日期：1989.6

  A series of polyfluoro-3-quinolonecarboxylic acids have been synthesized and their in vitro antibacterial activity evaluated. The desired 7-(substituted amino) derivatives were prepared from the 5,6,7,8-tetrafluoroquinolone acids. Conversely, amine displacement occurred primarily at the 5-position when the ester was used. Structure-activity studies indicated that the antibacterial activity was greatest when the N-1 substituent was cyclopropyl and the 7-substituent was 4-methyl-1-piperazinyl. All 5-(substituted amino) derivatives showed poor in vitro activity.