(6-allyloxy-naphthalen-2-yl)-pyridin-4-yl-methanone | 1143573-58-3

• 分子结构分类: 有机化合物 - 苯类化合物 - 萘
• 英文名称: (6-allyloxy-naphthalen-2-yl)-pyridin-4-yl-methanone
• CAS: 1143573-58-3
• 化学式: C₁₉H₁₅NO₂
• 分子量: 289.334
• InChiKey: KNVYUFJUKJTUSG-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  4.03
• 重原子数：
  22.0
• 可旋转键数：
  5.0
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.05
• 拓扑面积：
  39.19
• 氢给体数：
  0.0
• 氢受体数：
  3.0

反应信息

• 作为反应物：
  描述：

  (6-allyloxy-naphthalen-2-yl)-pyridin-4-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 (6-hydroxy-5-propyl-naphthalen-2-yl)-pyridin-4-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
• 作为产物：
  描述：

  4-吡啶甲醛 、 6-Bromo-2-(2-propenyloxy)naphthalene 在 碘 、 magnesium 、 重铬酸吡啶 作用下， 以 四氢呋喃 、 二氯甲烷 为溶剂， 反应 8.0h， 生成 (6-allyloxy-naphthalen-2-yl)-pyridin-4-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