ethyl 2-cyano-3-(4-(pyridin-2-yl)phenyl)acrylate | 773091-68-2

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 吡啶及其衍生物
• 英文名称: ethyl 2-cyano-3-(4-(pyridin-2-yl)phenyl)acrylate
• CAS: 773091-68-2
• 化学式: C₁₇H₁₄N₂O₂
• 分子量: 278.31
• InChiKey: SFZNDAOOEFBUKG-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.22
• 重原子数：
  21.0
• 可旋转键数：
  4.0
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.12
• 拓扑面积：
  62.98
• 氢给体数：
  0.0
• 氢受体数：
  4.0

反应信息

• 作为反应物：
  描述：

  ethyl 2-cyano-3-(4-(pyridin-2-yl)phenyl)acrylate 、 间苯二酚 在 哌啶 作用下， 以 乙醇 为溶剂， 反应 24.0h， 以43%的产率得到ethyl 2-amino-7-hydroxy-4-(4-pyridin-2-ylphenyl)-4H-chromene-3-carboxylate
  参考文献：
  名称：

  Synthesis, Structure–Activity Relationships and Brain Uptake of a Novel Series of Benzopyran Inhibitors of Insulin-Regulated Aminopeptidase

  摘要：

  Peptide inhibitors of insulin-regulated aminopeptidase (IRAP) enhance fear avoidance and spatial memory and accelerate spatial learning in a number of memory paradigms. Using a virtual screening approach, a series of benzopyran compounds was identified that inhibited the catalytic activity of IRAP, ultimately resulting in the identification of potent and specific inhibitors. The present study describes the medicinal chemistry campaign that led to the development of the lead candidate, 3, highlighting the key structural features considered as critical for binding. Furthermore, the in vivo pharmacokinetics and brain uptake of compounds (1 and 3) were assessed in rats and were complemented with in vitro human and rat microsomal stability studies. Following intravenous administration to rodents, 3 exhibits brain exposure, albeit it is rapidly converted to 1, a compound which also exhibits potent inhibition of IRAP.

  DOI：

  10.1021/jm401540f
• 作为产物：
  描述：

  4-(2-吡啶基)-苯甲醛 、 氰乙酸乙酯 在 哌啶 作用下， 以 乙醇 为溶剂， 反应 24.0h， 以74%的产率得到ethyl 2-cyano-3-(4-(pyridin-2-yl)phenyl)acrylate
  参考文献：
  名称：

  Synthesis, Structure–Activity Relationships and Brain Uptake of a Novel Series of Benzopyran Inhibitors of Insulin-Regulated Aminopeptidase

  摘要：

  Peptide inhibitors of insulin-regulated aminopeptidase (IRAP) enhance fear avoidance and spatial memory and accelerate spatial learning in a number of memory paradigms. Using a virtual screening approach, a series of benzopyran compounds was identified that inhibited the catalytic activity of IRAP, ultimately resulting in the identification of potent and specific inhibitors. The present study describes the medicinal chemistry campaign that led to the development of the lead candidate, 3, highlighting the key structural features considered as critical for binding. Furthermore, the in vivo pharmacokinetics and brain uptake of compounds (1 and 3) were assessed in rats and were complemented with in vitro human and rat microsomal stability studies. Following intravenous administration to rodents, 3 exhibits brain exposure, albeit it is rapidly converted to 1, a compound which also exhibits potent inhibition of IRAP.

  DOI：

  10.1021/jm401540f