4-methyl-3-((1-phenyl-1H-pyrazolo[3,4-d]pyrimidin-4-yl)amino)benzoic acid | 1030274-25-9

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 唑类
• 英文名称: 4-methyl-3-((1-phenyl-1H-pyrazolo[3,4-d]pyrimidin-4-yl)amino)benzoic acid
• CAS: 1030274-25-9
• 化学式: C₁₉H₁₅N₅O₂
• 分子量: 345.36
• InChiKey: RSTRMIBEIVBEAT-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.57
• 重原子数：
  26.0
• 可旋转键数：
  4.0
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.05
• 拓扑面积：
  92.93
• 氢给体数：
  2.0
• 氢受体数：
  6.0

反应信息

• 作为反应物：
  描述：

  4-methyl-3-((1-phenyl-1H-pyrazolo[3,4-d]pyrimidin-4-yl)amino)benzoic acid 在 N,N-二异丙基乙胺 氨 、 1-羟基苯并三唑 、 1-(3-二甲基氨基丙基)-3-乙基碳二亚胺 作用下， 以 四氢呋喃 、 乙醇 、 N,N-二甲基甲酰胺 为溶剂， 反应 7.0h， 生成 4-Methyl-3-[(1-phenylpyrazolo[3,4-d]pyrimidin-4-yl)amino]benzamide
  参考文献：
  名称：

  Pyrazolo-pyrimidines: A novel heterocyclic scaffold for potent and selective p38α inhibitors

  摘要：

  The synthesis and structure-activity relationships ( SAR) of p38 alpha MAP kinase inhibitors based on a pyrazolo-pyrimidine scaffold are described. These studies led to the identification of compound 2x as a potent and selective inhibitor of p38 alpha MAP kinase with excellent cellular potency toward the inhibition of TNF alpha production. Compound 2x was highly efficacious in vivo in inhibiting TNF alpha production in an acute murine model of TNF alpha production. X-ray co-crystallography of a pyrazolo-pyrimidine analog 2b bound to unphosphorylated p38 alpha is also disclosed. (C) 2008 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.bmcl.2008.03.019
• 作为产物：
  描述：

  ethyl 4-methyl-3-((1-phenyl-1H-pyrazolo[3,4-d]pyrimidin-4-yl)amino)benzoate 在 sodium hydroxide 作用下， 以 四氢呋喃 、 甲醇 为溶剂， 反应 16.0h， 以85%的产率得到4-methyl-3-((1-phenyl-1H-pyrazolo[3,4-d]pyrimidin-4-yl)amino)benzoic acid
  参考文献：
  名称：

  Pyrazolo-pyrimidines: A novel heterocyclic scaffold for potent and selective p38α inhibitors

  摘要：

  The synthesis and structure-activity relationships ( SAR) of p38 alpha MAP kinase inhibitors based on a pyrazolo-pyrimidine scaffold are described. These studies led to the identification of compound 2x as a potent and selective inhibitor of p38 alpha MAP kinase with excellent cellular potency toward the inhibition of TNF alpha production. Compound 2x was highly efficacious in vivo in inhibiting TNF alpha production in an acute murine model of TNF alpha production. X-ray co-crystallography of a pyrazolo-pyrimidine analog 2b bound to unphosphorylated p38 alpha is also disclosed. (C) 2008 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.bmcl.2008.03.019