4-(5-(pyridin-4-yl)-1H-pyrazol-3-yl)benzene-1,3-diol | 60122-28-3

• 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-(5-(pyridin-4-yl)-1H-pyrazol-3-yl)benzene-1,3-diol
• 英文别名: 4-(5-pyridin-4-yl-1(2)H-pyrazol-3-yl)-benzene-1,3-diol
• CAS: 60122-28-3
• 化学式: C₁₄H₁₁N₃O₂
• 分子量: 253.26
• InChiKey: YOLISBKFYWLZCG-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.55
• 重原子数：
  19.0
• 可旋转键数：
  2.0
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.0
• 拓扑面积：
  82.03
• 氢给体数：
  3.0
• 氢受体数：
  4.0

反应信息

• 作为反应物：
  描述：

  聚合甲醛 、 N-甲基苄胺 、 4-(5-(pyridin-4-yl)-1H-pyrazol-3-yl)benzene-1,3-diol 以 1,4-二氧六环 为溶剂， 以39%的产率得到2,4-bis((benzyl(methyl)amino)methyl)-6-(5-(pyridin-4-yl)-1H-pyrazol-3-yl)benzene-1,3-diol
  参考文献：
  名称：

  Design, Synthesis, Biological Evaluation, and Molecular Docking of Novel Benzopyran and Phenylpyrazole Derivatives as Akt Inhibitors

  摘要：

  By inspiration of good Akt1 inhibitory and cytotoxic activity of our previously screened hits 1 and 2, a series of novel benzopyrans 3a–c, 4 and phenylpyrazoles 5a–c, 6a–b, and 7 were designed, synthesized, and biologically evaluated for their in vitro Akt1 inhibitory and cytotoxic activity. The results revealed that all of these compounds showed moderate‐to‐excellent antiproliferative effects against the tested cancer cell lines (i.e. HL‐60, OVCAR, PC‐3, and HepG2). Among them, compounds 3a and 3c exhibited preferable Akt1 inhibitory activities (IC50 of 3a and 3c are 6.18 and 5.28 μm, respectively), while compounds 4, 5a–c, 6a–b, and 7 only showed weak Akt1 inhibitory activities. Consequently, we used molecular docking and dynamic simulation to propose a mode of binding between Akt1 and the 3c compound.

  DOI：

  10.1111/cbdd.12489
• 作为产物：
  描述：

  在 硫酸 、 5%-palladium/activated carbon 、 氢气 、 一水合肼 、 potassium hydroxide 作用下， 以 甲醇 、 乙醇 、 溶剂黄146 、 N,N-二甲基甲酰胺 为溶剂， 反应 14.0h， 生成 4-(5-(pyridin-4-yl)-1H-pyrazol-3-yl)benzene-1,3-diol
  参考文献：
  名称：

  Design, Synthesis, Biological Evaluation, and Molecular Docking of Novel Benzopyran and Phenylpyrazole Derivatives as Akt Inhibitors

  摘要：

  By inspiration of good Akt1 inhibitory and cytotoxic activity of our previously screened hits 1 and 2, a series of novel benzopyrans 3a–c, 4 and phenylpyrazoles 5a–c, 6a–b, and 7 were designed, synthesized, and biologically evaluated for their in vitro Akt1 inhibitory and cytotoxic activity. The results revealed that all of these compounds showed moderate‐to‐excellent antiproliferative effects against the tested cancer cell lines (i.e. HL‐60, OVCAR, PC‐3, and HepG2). Among them, compounds 3a and 3c exhibited preferable Akt1 inhibitory activities (IC50 of 3a and 3c are 6.18 and 5.28 μm, respectively), while compounds 4, 5a–c, 6a–b, and 7 only showed weak Akt1 inhibitory activities. Consequently, we used molecular docking and dynamic simulation to propose a mode of binding between Akt1 and the 3c compound.

  DOI：

  10.1111/cbdd.12489

文献信息

• JURKOWSKA-KOWALCZYK E., ROCZ. CHEM. <ROCH-AC>, 1976, 50, NO 3, 489-497
  作者：JURKOWSKA-KOWALCZYK E.

  DOI：——

  日期：——