(E)-2-(5-fluoro-1-(quinoxalin-6-ylmethylene)-1H-inden-3-yl)-ethanoic acid | 1049800-43-2

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 二氮杂萘
• 英文名称: (E)-2-(5-fluoro-1-(quinoxalin-6-ylmethylene)-1H-inden-3-yl)-ethanoic acid
• 英文别名: 2-[(3E)-6-fluoro-3-(quinoxalin-6-ylmethylidene)inden-1-yl]acetic acid
• CAS: 1049800-43-2
• 化学式: C₂₀H₁₃FN₂O₂
• 分子量: 332.334
• InChiKey: KKLVWUGQXKYUGT-NTUHNPAUSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.7
• 重原子数：
  25
• 可旋转键数：
  3
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.05
• 拓扑面积：
  63.1
• 氢给体数：
  1
• 氢受体数：
  5

反应信息

• 作为产物：
  描述：

  ethyl 2-(5-fluoro-1H-inden-3-yl)acetate 、 喹喔啉-6-甲醛 在 sodium hydroxide 、 水 作用下， 以 甲醇 为溶剂， 生成 (E)-2-(5-fluoro-1-(quinoxalin-6-ylmethylene)-1H-inden-3-yl)-ethanoic acid
  参考文献：
  名称：

  Sulindac Derivatives That Activate the Peroxisome Proliferator-activated Receptor γ but Lack Cyclooxygenase Inhibition

  摘要：

  A series of novel derivatives of the nonsteroidal anti-inflammatory drug (NSAID) sulindac sulfide were synthesized as potential agonists of the peroxisome proliferator-activated receptor gamma (PPAR gamma). Nonpolar and aromatic substitutions oil the benzylidene ring as well as retention of the carboxylic acid side chain were required for optimal activity. Compound 24 was as potent a compound as my other in the series with,in EC(50) Of 0-1 mu M for the induction of peroxisome proliferator response element (PPRE)-luciferase activity. Direct binding of compound 24 to PPAR gamma was demonstrated by the displacement of I. 3 H]troglitazone, a PPAR gamma agonist, in a scintillation proximity assay. Compound 24 also stimulated the binding of PPAR gamma to a PPRE-containing oligonucleotide and induced expression of liver fatty-acid binding protein (L-FABP) and adipocyte fatty acid-binding protein (aP2), two established PPAR gamma target genes. Taken together, these compounds represent potential leads in the development of novel PPAR gamma agonists.

  DOI：

  10.1021/jm700969c

文献信息

• Sulindac Derivatives That Activate the Peroxisome Proliferator-activated Receptor γ but Lack Cyclooxygenase Inhibition
  作者：Andrew S. Felts、Brianna S. Siegel、Shiu M. Young、Christopher W. Moth、Terry P. Lybrand、Andrew J. Dannenberg、Lawrence J. Marnett、Kotha Subbaramaiah

  DOI：10.1021/jm700969c

  日期：2008.8.1

  A series of novel derivatives of the nonsteroidal anti-inflammatory drug (NSAID) sulindac sulfide were synthesized as potential agonists of the peroxisome proliferator-activated receptor gamma (PPAR gamma). Nonpolar and aromatic substitutions oil the benzylidene ring as well as retention of the carboxylic acid side chain were required for optimal activity. Compound 24 was as potent a compound as my other in the series with,in EC(50) Of 0-1 mu M for the induction of peroxisome proliferator response element (PPRE)-luciferase activity. Direct binding of compound 24 to PPAR gamma was demonstrated by the displacement of I. 3 H]troglitazone, a PPAR gamma agonist, in a scintillation proximity assay. Compound 24 also stimulated the binding of PPAR gamma to a PPRE-containing oligonucleotide and induced expression of liver fatty-acid binding protein (L-FABP) and adipocyte fatty acid-binding protein (aP2), two established PPAR gamma target genes. Taken together, these compounds represent potential leads in the development of novel PPAR gamma agonists.