N-[N-(cyclobutyl)piperidin-4-ylmethyl]-3-isopropyl-imidazo[1,5-a]pyridine-1-carboxamide

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 咪唑并吡啶类
• 英文名称: N-[N-(cyclobutyl)piperidin-4-ylmethyl]-3-isopropyl-imidazo[1,5-a]pyridine-1-carboxamide
• 英文别名: N-[(1-cyclobutylpiperidin-4-yl)methyl]-3-propan-2-ylimidazo[1,5-a]pyridine-1-carboxamide
• 化学式: C₂₁H₃₀N₄O
• 分子量: 354.495
• InChiKey: MKAHOPLIAPPZBH-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  4.3
• 重原子数：
  26
• 可旋转键数：
  5
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.62
• 拓扑面积：
  49.6
• 氢给体数：
  1
• 氢受体数：
  3

反应信息

• 作为反应物：
  描述：

  L-酒石酸 、 N-[N-(cyclobutyl)piperidin-4-ylmethyl]-3-isopropyl-imidazo[1,5-a]pyridine-1-carboxamide 以 异丙醇 为溶剂， 反应 1.0h， 生成 N-[N-(cyclobutyl)piperidin-4-ylmethyl]-3-isopropyl-imidazo[1,5-a]pyridine-1-carboxamide L(+)-tartarate
  参考文献：
  名称：

  Synthesis and SAR of Imidazo[1,5-a]pyridine derivatives as 5-HT4 receptor partial agonists for the treatment of cognitive disorders associated with Alzheimer's disease

  摘要：

  Alzheimer's disease (AD) is a neurodegenerative disease which has a higher prevalence and incidence in older people. The need for improved AD therapies is unmet. The 5-hydroxytryptamine(4) receptor (5-HT4R) partial agonists may be of benefit for both the symptomatic and disease-modifying treatment of cognitive disorders associated with AD. Herein, we report the design, synthesis and SAR of imidazo [1,5-a] pyridine derivatives as 5-HT4R partial agonists. The focused SAR, optimization of ADME properties resulted the discovery of compound 5a as potent, selective, brain penetrant 5-HT4 partial agonist as a lead compound with good ADME properties and efficacy in both symptomatic and disease modifying animal models of cognition. (C) 2015 Elsevier Masson SAS. All rights reserved.

  DOI：

  10.1016/j.ejmech.2015.08.051
• 作为产物：
  描述：

  2-氨基-2-(2-吡啶)乙酸乙酯 在 盐酸 、 三乙酰氧基硼氢化钠 、 溶剂黄146 、 N,N-二异丙基乙胺 、 sodium hydroxide 、 三氯氧磷 作用下， 以 乙醇 、 二氯甲烷 、 水 、 1,2-二氯乙烷 、 异丙醇 、 甲苯 为溶剂， 反应 20.58h， 生成 N-[N-(cyclobutyl)piperidin-4-ylmethyl]-3-isopropyl-imidazo[1,5-a]pyridine-1-carboxamide
  参考文献：
  名称：

  Synthesis and SAR of Imidazo[1,5-a]pyridine derivatives as 5-HT4 receptor partial agonists for the treatment of cognitive disorders associated with Alzheimer's disease

  摘要：

  Alzheimer's disease (AD) is a neurodegenerative disease which has a higher prevalence and incidence in older people. The need for improved AD therapies is unmet. The 5-hydroxytryptamine(4) receptor (5-HT4R) partial agonists may be of benefit for both the symptomatic and disease-modifying treatment of cognitive disorders associated with AD. Herein, we report the design, synthesis and SAR of imidazo [1,5-a] pyridine derivatives as 5-HT4R partial agonists. The focused SAR, optimization of ADME properties resulted the discovery of compound 5a as potent, selective, brain penetrant 5-HT4 partial agonist as a lead compound with good ADME properties and efficacy in both symptomatic and disease modifying animal models of cognition. (C) 2015 Elsevier Masson SAS. All rights reserved.

  DOI：

  10.1016/j.ejmech.2015.08.051