3-[4-[[2-(4-Fluorophenyl)imidazo[1,2-a]pyridin-6-yl]methoxy]phenyl]hex-4-ynoic 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-[4-[[2-(4-Fluorophenyl)imidazo[1,2-a]pyridin-6-yl]methoxy]phenyl]hex-4-ynoic acid
• 英文别名: 3-[4-[[2-(4-fluorophenyl)imidazo[1,2-a]pyridin-6-yl]methoxy]phenyl]hex-4-ynoic acid
• 化学式: C₂₆H₂₁FN₂O₃
• 分子量: 428.463
• InChiKey: VXTBZZIFZGIAOJ-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  5.3
• 重原子数：
  32.0
• 可旋转键数：
  7.0
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.15
• 拓扑面积：
  63.83
• 氢给体数：
  1.0
• 氢受体数：
  4.0

反应信息

• 作为产物：
  描述：

  6-氨基烟酸甲酯 在 lithium aluminium tetrahydride 、 氯化亚砜 、 苄基三乙基氯化铵 、 水 、 sodium carbonate 、 caesium carbonate 、 potassium iodide 、 lithium hydroxide 作用下， 以 四氢呋喃 、 甲醇 、 乙醇 、 二氯甲烷 、 乙酸乙酯 、 乙腈 为溶剂， 反应 20.0h， 生成 3-[4-[[2-(4-Fluorophenyl)imidazo[1,2-a]pyridin-6-yl]methoxy]phenyl]hex-4-ynoic acid
  参考文献：
  名称：

  Discovery of novel potent GPR40 agonists containing imidazo[1,2-a]pyridine core as antidiabetic agents

  摘要：

  Free fatty acid receptor 1 (FFA1 or GPR40) has been studied for many years as a target for the treatment of type 2 diabetes mellitus. In order to increase potency and reduce hepatotoxicity, a series of novel compounds containing imidazo[1,2-a]pyridine scaffold as GPR40 agonist were synthesized. Compound I-14 was identified as an effective agonist as shown by the conspicuous drop in blood glucose in normal and diabetic mice. It had no risk of hepatotoxicity compared with TAK-875. Moreover, good pharmacokinetic (PK) properties of I-14 were observed (CL = 27.26 ml/h/kg, t1/2 = 5.93 h). The results indicate that I-14 could serve as a possible candidate to treat diabetes.

  DOI：

  10.1016/j.bmc.2020.115574

文献信息

• Discovery of novel potent GPR40 agonists containing imidazo[1,2-a]pyridine core as antidiabetic agents
  作者：Zhiwen Ye、Chunxia Liu、Feng Zou、Yan Cai、Bin Chen、Yuxing Zou、Jiaxian Mo、Ting Han、Wenlong Huang、Qianqian Qiu、Hai Qian

  DOI：10.1016/j.bmc.2020.115574

  日期：2020.7

  Free fatty acid receptor 1 (FFA1 or GPR40) has been studied for many years as a target for the treatment of type 2 diabetes mellitus. In order to increase potency and reduce hepatotoxicity, a series of novel compounds containing imidazo[1,2-a]pyridine scaffold as GPR40 agonist were synthesized. Compound I-14 was identified as an effective agonist as shown by the conspicuous drop in blood glucose in normal and diabetic mice. It had no risk of hepatotoxicity compared with TAK-875. Moreover, good pharmacokinetic (PK) properties of I-14 were observed (CL = 27.26 ml/h/kg, t1/2 = 5.93 h). The results indicate that I-14 could serve as a possible candidate to treat diabetes.