3-(5-methyl-1-phenyl-1H-benzimidazol-2-yl)propanoic acid | 1613148-72-3

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 苯并咪唑类
• 英文名称: 3-(5-methyl-1-phenyl-1H-benzimidazol-2-yl)propanoic acid
• CAS: 1613148-72-3
• 化学式: C₁₇H₁₆N₂O₂
• 分子量: 280.326
• InChiKey: LDRHDNYZPFYNGG-UHFFFAOYSA-N

物化性质

• 沸点：
  520.2±52.0 °C(Predicted)
• 密度：
  1.21±0.1 g/cm3(Temp: 20 °C; Press: 760 Torr)(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  3.35
• 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：
  0.18
• 拓扑面积：
  55.12
• 氢给体数：
  1.0
• 氢受体数：
  3.0

反应信息

• 作为反应物：
  描述：

  3-(5-methyl-1-phenyl-1H-benzimidazol-2-yl)propanoic acid 在 N-溴代丁二酰亚胺(NBS) 、 1-丙基磷酸酐 作用下， 以 二氯甲烷 、 乙酸乙酯 、 乙腈 为溶剂， 反应 13.0h， 生成 5-bromo-7-[2-(5-methyl-1-phenyl-1H-benzimidazol-2-yl)ethyl]imidazo[1,5-b]pyridazine
  参考文献：
  名称：

  Novel benzimidazole derivatives as phosphodiesterase 10A (PDE10A) inhibitors with improved metabolic stability

  摘要：

  In this study, we report the identification of potent benzimidazoles as PDE10A inhibitors. We first identified imidazopyridine 1 as a high-throughput screening hit compound from an in-house library. Next, optimization of the imidazopyridine moiety to improve inhibitory activity gave imidazopyridinone 10b. Following further structure-activity relationship development by reducing lipophilicity and introducing substituents, we acquired 35, which exhibited both improved metabolic stability and reduced CYP3A4 time-dependent inhibition. (C) 2014 Published by Elsevier Ltd.

  DOI：

  10.1016/j.bmc.2014.04.023
• 作为产物：
  描述：

  methyl 3-(5-methyl-1-phenyl-1H-benzimidazol-2-yl)propanoate 在 水 、 sodium hydroxide 作用下， 反应 20.0h， 以81%的产率得到3-(5-methyl-1-phenyl-1H-benzimidazol-2-yl)propanoic acid
  参考文献：
  名称：

  Novel benzimidazole derivatives as phosphodiesterase 10A (PDE10A) inhibitors with improved metabolic stability

  摘要：

  In this study, we report the identification of potent benzimidazoles as PDE10A inhibitors. We first identified imidazopyridine 1 as a high-throughput screening hit compound from an in-house library. Next, optimization of the imidazopyridine moiety to improve inhibitory activity gave imidazopyridinone 10b. Following further structure-activity relationship development by reducing lipophilicity and introducing substituents, we acquired 35, which exhibited both improved metabolic stability and reduced CYP3A4 time-dependent inhibition. (C) 2014 Published by Elsevier Ltd.

  DOI：

  10.1016/j.bmc.2014.04.023