N-benzyl-3-(3-benzylimidazo[4,5-b]pyridin-2-yl)propanamide

• 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-benzyl-3-(3-benzylimidazo[4,5-b]pyridin-2-yl)propanamide
• 化学式: C₂₃H₂₂N₄O
• 分子量: 370.454
• InChiKey: YSMOOBCKCPXXSC-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.3
• 重原子数：
  28
• 可旋转键数：
  7
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.17
• 拓扑面积：
  59.8
• 氢给体数：
  1
• 氢受体数：
  3

反应信息

• 作为产物：
  描述：

  2-苄基氨基-3-氨基吡啶 在 硫酸 、 potassium tert-butylate 作用下， 以 1,4-二氧六环 为溶剂， 生成 N-benzyl-3-(3-benzylimidazo[4,5-b]pyridin-2-yl)propanamide
  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

文献信息

• Discovery of potent inhibitors of the lyso phospholipase autotaxin
  作者：Pritom Shah、Anne Cheasty、Caroline Foxton、Tony Raynham、Muddasar Farooq、Irene Farre Gutierrez、Aurore Lejeune、Michelle Pritchard、Andrew Turnbull、Leon Pang、Paul Owen、Susan Boyd、Alexandra Stowell、Allan Jordan、Niall M. Hamilton、James R. Hitchin、Martin Stockley、Ellen MacDonald、Mar Jimenez Quesada、Elisabeth Trivier、Jana Skeete、Huib Ovaa、Wouter H. Moolenaar、Hamish Ryder

  DOI：10.1016/j.bmcl.2016.10.036

  日期：2016.11

  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.