3-[2-(5-methoxy-1-phenyl-1H-benzimidazol-2-yl)ethyl]-1-methyl-1,3-dihydro-2H-imidazo[4,5-b]pyridin-2-one | 1613148-98-3

• 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-[2-(5-methoxy-1-phenyl-1H-benzimidazol-2-yl)ethyl]-1-methyl-1,3-dihydro-2H-imidazo[4,5-b]pyridin-2-one
• 英文别名: 3-[2-(5-Methoxy-1-phenylbenzimidazol-2-yl)ethyl]-1-methylimidazo[4,5-b]pyridin-2-one；3-[2-(5-methoxy-1-phenylbenzimidazol-2-yl)ethyl]-1-methylimidazo[4,5-b]pyridin-2-one
• CAS: 1613148-98-3
• 化学式: C₂₃H₂₁N₅O₂
• 分子量: 399.452
• InChiKey: QMXCWRCTPGEKMX-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.3
• 重原子数：
  30
• 可旋转键数：
  5
• 环数：
  5.0
• sp3杂化的碳原子比例：
  0.17
• 拓扑面积：
  63.5
• 氢给体数：
  0
• 氢受体数：
  4

反应信息

• 作为产物：
  描述：

  1,3-二氢-1-甲基-2H-咪唑并[4,5-b]吡啶-2-酮 在 1-[bis(dimethylamino)methylene]-1H-1,2,3-triazolo[4,5-b]pyridinium 3-oxid hexafluorophosphate 、 水 、 1,8-二氮杂双环[5.4.0]十一碳-7-烯 、 N,N-二异丙基乙胺 、 sodium hydroxide 作用下， 以 乙醇 、 二氯甲烷 为溶剂， 反应 40.0h， 生成 3-[2-(5-methoxy-1-phenyl-1H-benzimidazol-2-yl)ethyl]-1-methyl-1,3-dihydro-2H-imidazo[4,5-b]pyridin-2-one
  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