benzyl 1-(4-cyano-2,3,5,6-tetrafluorophenyl)-6,7,8-trifluoro-4-oxo-1,4-dihydroquinoline-3-carboxylate | 1041438-69-0

• 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: benzyl 1-(4-cyano-2,3,5,6-tetrafluorophenyl)-6,7,8-trifluoro-4-oxo-1,4-dihydroquinoline-3-carboxylate
• 英文别名: benzyl 1-(4-cyano-2,3,5,6-tetrafluorophenyl)-6,7,8-trifluoro-4-oxoquinoline-3-carboxylate
• CAS: 1041438-69-0
• 化学式: C₂₄H₉F₇N₂O₃
• 分子量: 506.336
• InChiKey: RHAHUACACWLHCL-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  5.2
• 重原子数：
  36
• 可旋转键数：
  5
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.04
• 拓扑面积：
  70.4
• 氢给体数：
  0
• 氢受体数：
  12

反应信息

• 作为产物：
  描述：

  、 4-氨基-2,3,5,6-四氟苯甲腈 在 sodium hydride 作用下， 以 四氢呋喃 、 mineral oil 为溶剂， 生成 benzyl 1-(4-cyano-2,3,5,6-tetrafluorophenyl)-6,7,8-trifluoro-4-oxo-1,4-dihydroquinoline-3-carboxylate
  参考文献：
  名称：

  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

  摘要：

  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.

  DOI：

  10.1021/jm701271y

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.