2-[1-(4-chloro-2-methylphenyl)-3-methyl-5-(1H-pyrrol-1-yl)-1H-pyrazol-4-yl]acetonitrile | 1510825-98-5

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 唑类
• 英文名称: 2-[1-(4-chloro-2-methylphenyl)-3-methyl-5-(1H-pyrrol-1-yl)-1H-pyrazol-4-yl]acetonitrile
• CAS: 1510825-98-5
• 化学式: C₁₇H₁₅ClN₄
• 分子量: 310.786
• InChiKey: UGADLTZQOOQCBI-UHFFFAOYSA-N

物化性质

• 沸点：
  513.8±50.0 °C(predicted)
• 密度：
  1.23±0.1 g/cm3(Temp: 20 °C; Press: 760 Torr)(predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  4.0
• 重原子数：
  22.0
• 可旋转键数：
  3.0
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.18
• 拓扑面积：
  46.54
• 氢给体数：
  0.0
• 氢受体数：
  4.0

反应信息

• 作为反应物：
  描述：

  2-[1-(4-chloro-2-methylphenyl)-3-methyl-5-(1H-pyrrol-1-yl)-1H-pyrazol-4-yl]acetonitrile 在 potassium carbonate 作用下， 以 N,N-二甲基甲酰胺 、 甲苯 为溶剂， 反应 10.0h， 生成 ethyl 1-(4-chloro-2-methylphenyl)-4-cyano-3-methyl-1H-pyrazolo[3,4-e]indolizine-5-carboxylate
  参考文献：
  名称：

  Design, Synthesis, and Biological Evaluation of 1-Phenylpyrazolo[3,4-e]pyrrolo[3,4-g]indolizine-4,6(1H,5H)-diones as New Glycogen Synthase Kinase-3β Inhibitors

  摘要：

  Compound 5 was selected from our in-house library as a suitable starting point for the rational design of new GSK-3 beta inhibitors. MC/FEP calculations of 5 led to the identication of a structural class of new GSK-3 beta inhibitors. Compound 18 inhibited GSK-3 beta with an IC50 of 0.24 mu M and inhibited tau phosphorylation in a cell-based assay. It proved to be a selective inhibitor of GSK-3 against a panel of 17 kinases and showed >10-fold selectivity against CDK2. Calculated physicochemical properties and Volsurf predictions suggested that compound 18 has the potential to diffuse passively across the blood brain barrier.

  DOI：

  10.1021/jm401466v
• 作为产物：
  描述：

  sodium 3,4-dicyanobut-2-en-2-olate 在 溶剂黄146 作用下， 以 乙醇 为溶剂， 反应 2.5h， 生成 2-[1-(4-chloro-2-methylphenyl)-3-methyl-5-(1H-pyrrol-1-yl)-1H-pyrazol-4-yl]acetonitrile
  参考文献：
  名称：

  Design, Synthesis, and Biological Evaluation of 1-Phenylpyrazolo[3,4-e]pyrrolo[3,4-g]indolizine-4,6(1H,5H)-diones as New Glycogen Synthase Kinase-3β Inhibitors

  摘要：

  Compound 5 was selected from our in-house library as a suitable starting point for the rational design of new GSK-3 beta inhibitors. MC/FEP calculations of 5 led to the identication of a structural class of new GSK-3 beta inhibitors. Compound 18 inhibited GSK-3 beta with an IC50 of 0.24 mu M and inhibited tau phosphorylation in a cell-based assay. It proved to be a selective inhibitor of GSK-3 against a panel of 17 kinases and showed >10-fold selectivity against CDK2. Calculated physicochemical properties and Volsurf predictions suggested that compound 18 has the potential to diffuse passively across the blood brain barrier.

  DOI：

  10.1021/jm401466v