methyl 3-[4-(methylsulfanyl)phenyl]imidazo[1,2-a]pyridine-6-carboxylate | 1191885-70-7

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 唑类
• 英文名称: methyl 3-[4-(methylsulfanyl)phenyl]imidazo[1,2-a]pyridine-6-carboxylate
• 英文别名: Methyl 3-(4-methylsulfanylphenyl)imidazo[1,2-a]pyridine-6-carboxylate
• CAS: 1191885-70-7
• 化学式: C₁₆H₁₄N₂O₂S
• 分子量: 298.365
• InChiKey: FFYQSUAMVKTOEO-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.8
• 重原子数：
  21
• 可旋转键数：
  4
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.12
• 拓扑面积：
  68.9
• 氢给体数：
  0
• 氢受体数：
  4

反应信息

• 作为反应物：
  描述：

  methyl 3-[4-(methylsulfanyl)phenyl]imidazo[1,2-a]pyridine-6-carboxylate 在 一水合肼 作用下， 以 甲醇 为溶剂， 反应 72.0h， 以76%的产率得到3-[4-(methylsulfanyl)phenyl]imidazo[1,2-a]pyridine-6-carbohydrazide
  参考文献：
  名称：

  2-{3-[4-(Alkylsulfinyl)phenyl]-1-benzofuran-5-yl}-5-methyl-1,3,4-oxadiazole Derivatives as Novel Inhibitors of Glycogen Synthase Kinase-3β with Good Brain Permeability

  摘要：

  Glycogen synthase kinase 3beta (GSK-3beta) inhibition is expected to be a promising therapeutic approach for treating Alzheimer's disease. Previously we reported a series of 1,3,4-oxadiazole derivatives as potent and highly selective GSK-3beta inhibitors, however, the representative compounds 1a,b showed poor pharmacokinetic profiles. Efforts were made to address this issue by reducing molecular weight and lipophilicity, leading to the identification of oxadiazole derivatives containing a sulfinyl group, (S)-9b and (S)-9c. These compounds exhibited not only highly selective and potent inhibitory activity against GSK-3beta but also showed good pharmacokinetic profiles including favorable BBB penetration. In addition, (S)-9b and (S)-9c given orally to mice significantly inhibited cold water stress-induced tau hyperphosphorylation in mouse brain.

  DOI：

  10.1021/jm900647e
• 作为产物：
  描述：

  3-碘咪唑并[1,2-a]吡啶-6-羧酸甲酯 、 4-甲硫基苯硼酸 在 四(三苯基膦)钯 、 sodium carbonate 作用下， 以 乙二醇二甲醚 、 水 为溶剂， 以42%的产率得到methyl 3-[4-(methylsulfanyl)phenyl]imidazo[1,2-a]pyridine-6-carboxylate
  参考文献：
  名称：

  2-{3-[4-(Alkylsulfinyl)phenyl]-1-benzofuran-5-yl}-5-methyl-1,3,4-oxadiazole Derivatives as Novel Inhibitors of Glycogen Synthase Kinase-3β with Good Brain Permeability

  摘要：

  Glycogen synthase kinase 3beta (GSK-3beta) inhibition is expected to be a promising therapeutic approach for treating Alzheimer's disease. Previously we reported a series of 1,3,4-oxadiazole derivatives as potent and highly selective GSK-3beta inhibitors, however, the representative compounds 1a,b showed poor pharmacokinetic profiles. Efforts were made to address this issue by reducing molecular weight and lipophilicity, leading to the identification of oxadiazole derivatives containing a sulfinyl group, (S)-9b and (S)-9c. These compounds exhibited not only highly selective and potent inhibitory activity against GSK-3beta but also showed good pharmacokinetic profiles including favorable BBB penetration. In addition, (S)-9b and (S)-9c given orally to mice significantly inhibited cold water stress-induced tau hyperphosphorylation in mouse brain.

  DOI：

  10.1021/jm900647e