furan-3-yl-(6-hydroxy-5-propyl-naphthalen-2-yl)-methanone | 1143573-45-8

• 分子结构分类: 有机化合物 - 苯类化合物 - 萘
• 英文名称: furan-3-yl-(6-hydroxy-5-propyl-naphthalen-2-yl)-methanone
• CAS: 1143573-45-8
• 化学式: C₁₈H₁₆O₃
• 分子量: 280.323
• InChiKey: JUNGTMXXLKJFIM-UHFFFAOYSA-N

物化性质

• 沸点：
  458.6±30.0 °C(predicted)
• 密度：
  1.207±0.06 g/cm3(Temp: 20 °C; Press: 760 Torr)(predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  4.32
• 重原子数：
  21.0
• 可旋转键数：
  4.0
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.17
• 拓扑面积：
  50.44
• 氢给体数：
  1.0
• 氢受体数：
  3.0

反应信息

• 作为反应物：
  描述：

  ethyl 2-[1-(3-chloropropyl)-1H-indol-5-yloxy]-2-methylpropionate 、 furan-3-yl-(6-hydroxy-5-propyl-naphthalen-2-yl)-methanone 在 potassium carbonate 、 potassium iodide 、 lithium hydroxide 作用下， 以 N,N-二甲基甲酰胺 、 甲醇 、 水 为溶剂， 反应 4.0h， 以70%的产率得到2-(1-{3-[6-(furan-3-carbonyl)-1-propyl-naphthalen-2-yloxy]-propyl}-1H-indol-5-yloxy)-2-methyl-propionic acid
  参考文献：
  名称：

  Design and Structural Analysis of Novel Pharmacophores for Potent and Selective Peroxisome Proliferator-activated Receptor γ Agonists

  摘要：

  Utilizing medicinal chemistry design strategies such as benzo splitting and ring expansion, we converted PPARalpha/gamma dual agonist 1 to selective PPARgamma agonists 19 and 20. Compounds 19 and 20 were 2- to 4-fold better than rosiglitazone at PPARgamma receptor, with 80- to 100-fold PPARgamma selectivity over PPARalpha receptor. X-ray cocrystal studies in PPARgamma and modeling studies in PPARalpha give molecular insights for the improved PPARgamma potency and selectivity for 19 when compared to 1.

  DOI：

  10.1021/jm801594x
• 作为产物：
  描述：

  (6-allyloxy-naphthalen-2-yl)-furan-3-yl-methanone 在 N,N-二甲基苯胺 、 5%-palladium/activated carbon 、 氢气 作用下， 以 乙酸乙酯 为溶剂， 200.0 ℃ 、303.99 kPa 条件下， 反应 4.5h， 生成 furan-3-yl-(6-hydroxy-5-propyl-naphthalen-2-yl)-methanone
  参考文献：
  名称：

  Design and Structural Analysis of Novel Pharmacophores for Potent and Selective Peroxisome Proliferator-activated Receptor γ Agonists

  摘要：

  Utilizing medicinal chemistry design strategies such as benzo splitting and ring expansion, we converted PPARalpha/gamma dual agonist 1 to selective PPARgamma agonists 19 and 20. Compounds 19 and 20 were 2- to 4-fold better than rosiglitazone at PPARgamma receptor, with 80- to 100-fold PPARgamma selectivity over PPARalpha receptor. X-ray cocrystal studies in PPARgamma and modeling studies in PPARalpha give molecular insights for the improved PPARgamma potency and selectivity for 19 when compared to 1.

  DOI：

  10.1021/jm801594x