2-[3-(8-Methoxy-5-methyl-6-oxophenanthridin-3-yl)propanoylamino]benzoic acid | 1146206-15-6

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 喹啉及其衍生物
• 英文名称: 2-[3-(8-Methoxy-5-methyl-6-oxophenanthridin-3-yl)propanoylamino]benzoic acid
• CAS: 1146206-15-6
• 化学式: C₂₅H₂₂N₂O₅
• 分子量: 430.46
• InChiKey: LQHCNQHTAOJTSL-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.8
• 重原子数：
  32
• 可旋转键数：
  6
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.16
• 拓扑面积：
  95.9
• 氢给体数：
  2
• 氢受体数：
  5

反应信息

• 作为反应物：
  描述：

  2-[3-(8-Methoxy-5-methyl-6-oxophenanthridin-3-yl)propanoylamino]benzoic acid 在 三溴化硼 、 水 作用下， 以 二氯甲烷 为溶剂， 以75%的产率得到2-(3-(8-Hydroxy-5-methyl-6-oxo-5,6-dihydrophenanthridin-3-yl)propanamido)benzoic 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：

  Methyl 3-[3-[(2-bromo-5-methoxybenzoyl)-methylamino]phenyl]propanoate 、 邻氨基苯甲酸 在 palladium diacetate 、 potassium carbonate 、 2-二苯基磷-2'-(N,N-二甲氨基)联苯 、 lithium hydroxide 作用下， 以 N,N-二甲基乙酰胺 、 四氢呋喃 、 甲醇 、 水 为溶剂， 反应 72.0h， 以3 mg的产率得到2-[3-(8-Methoxy-5-methyl-6-oxophenanthridin-3-yl)propanoylamino]benzoic 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