3-(3-benzyl-3H-imidazo[4,5-b]pyridin-2-yl)propanoic acid

• 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: 3-(3-benzyl-3H-imidazo[4,5-b]pyridin-2-yl)propanoic acid
• 英文别名: 3-(3-benzylimidazo[4,5-b]pyridin-2-yl)propanoic acid
• 化学式: C₁₆H₁₅N₃O₂
• 分子量: 281.314
• InChiKey: OPWSWTXHMKHIHP-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.1
• 重原子数：
  21
• 可旋转键数：
  5
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.19
• 拓扑面积：
  68
• 氢给体数：
  1
• 氢受体数：
  4

反应信息

• 作为反应物：
  描述：

  3-(3-benzyl-3H-imidazo[4,5-b]pyridin-2-yl)propanoic acid 在 硫酸 、 potassium tert-butylate 作用下， 生成 3-(3-benzyl-3H-imidazo[4,5-b]pyridin-2-yl)-N-(4-methyl-benzyl)-propionamide
  参考文献：
  名称：

  Discovery of potent inhibitors of the lyso phospholipase autotaxin

  摘要：

  The autotaxin-lysophosphatidic acid (ATX-LPA) axis has been implicated in several disease conditions including inflammation, fibrosis and cancer. This makes ATX an attractive drug target and its inhibition may lead to useful therapeutic agents. Through a high throughput screen (HTS) we identified a series of small molecule inhibitors of ATX which have subsequently been optimized for potency, selectivity and developability properties. This has delivered drug-like compounds such as 9v (CRT0273750) which modulate LPA levels in plasma and are suitable for in vivo studies.)(Tray crystallography has revealed that these compounds have an unexpected binding mode in that they do not interact with the active site zinc ions but instead occupy the hydrophobic LPC pocket extending from the active site of ATX together with occupying the LPA 'exit' channel. (C) 2016 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.bmcl.2016.10.036
• 作为产物：
  描述：

  丁二酸酐 、 2-苄基氨基-3-氨基吡啶 以 1,4-二氧六环 为溶剂， 生成 3-(3-benzyl-3H-imidazo[4,5-b]pyridin-2-yl)propanoic acid
  参考文献：
  名称：

  Discovery of potent inhibitors of the lyso phospholipase autotaxin

  摘要：

  The autotaxin-lysophosphatidic acid (ATX-LPA) axis has been implicated in several disease conditions including inflammation, fibrosis and cancer. This makes ATX an attractive drug target and its inhibition may lead to useful therapeutic agents. Through a high throughput screen (HTS) we identified a series of small molecule inhibitors of ATX which have subsequently been optimized for potency, selectivity and developability properties. This has delivered drug-like compounds such as 9v (CRT0273750) which modulate LPA levels in plasma and are suitable for in vivo studies.)(Tray crystallography has revealed that these compounds have an unexpected binding mode in that they do not interact with the active site zinc ions but instead occupy the hydrophobic LPC pocket extending from the active site of ATX together with occupying the LPA 'exit' channel. (C) 2016 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.bmcl.2016.10.036