3-(7-hydroxynaphtho[2,1-d]isoxazol-3-yl)propanoic acid | 1146206-26-9

• 分子结构分类: 有机化合物 - 苯类化合物 - 萘
• 英文名称: 3-(7-hydroxynaphtho[2,1-d]isoxazol-3-yl)propanoic acid
• CAS: 1146206-26-9
• 化学式: C₁₄H₁₁NO₄
• 分子量: 257.246
• InChiKey: RLUDNTVPSYNMJG-UHFFFAOYSA-N

物化性质

• 沸点：
  547.0±35.0 °C(predicted)
• 密度：
  1.461±0.06 g/cm3(Temp: 20 °C; Press: 760 Torr)(predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  2.7
• 重原子数：
  19.0
• 可旋转键数：
  3.0
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.14
• 拓扑面积：
  83.56
• 氢给体数：
  2.0
• 氢受体数：
  4.0

反应信息

• 作为反应物：
  描述：

  3-(7-hydroxynaphtho[2,1-d]isoxazol-3-yl)propanoic acid 在 N-氯代丁二酰亚胺 作用下， 以 N,N-二甲基甲酰胺 为溶剂， 反应 2.0h， 以69%的产率得到3-(6-chloro-7-hydroxynaphtho[2,1-d]isoxazol-3-yl)propanoic acid
  参考文献：
  名称：

  Discovery of Novel Tricyclic Full Agonists for the G-Protein-Coupled Niacin Receptor 109A with Minimized Flushing in Rats

  摘要：

  Tricyclic analogues were rationally designed as the high affinity niacin receptor G-protein-coupled receptor 109A (GPR109A) agonists by overlapping three lead structures. Various tricyclic anthranilide and cycloalkene carboxylic acid full agonists were discovered with excellent in vitro activity. Compound 2g displayed a good therapeutic index regarding free fatty acids (FFA) reduction and vasodilation effects in rats, with very weak cytochrome P450 2C8 (CYP2C8) and cytochrome P450 2C9 (CYP2C9) inhibition, and a good mouse pharmacokinetics (PK) profile.

  DOI：

  10.1021/jm900151e
• 作为产物：
  描述：

  3-(7-hydroxynaphtho[2,1-d]isoxazol-3-yl)acrylic acid 在 palladium 10% on activated carbon 、 氢气 作用下， 以 甲醇 为溶剂， 反应 1.0h， 以75%的产率得到3-(7-hydroxynaphtho[2,1-d]isoxazol-3-yl)propanoic acid
  参考文献：
  名称：

  Discovery of Novel Tricyclic Full Agonists for the G-Protein-Coupled Niacin Receptor 109A with Minimized Flushing in Rats

  摘要：

  Tricyclic analogues were rationally designed as the high affinity niacin receptor G-protein-coupled receptor 109A (GPR109A) agonists by overlapping three lead structures. Various tricyclic anthranilide and cycloalkene carboxylic acid full agonists were discovered with excellent in vitro activity. Compound 2g displayed a good therapeutic index regarding free fatty acids (FFA) reduction and vasodilation effects in rats, with very weak cytochrome P450 2C8 (CYP2C8) and cytochrome P450 2C9 (CYP2C9) inhibition, and a good mouse pharmacokinetics (PK) profile.

  DOI：

  10.1021/jm900151e