2-[3-(trifluoromethyl)phenyl]-5H-pyrazolo[3,4-c]quinolin-4-one | 1120368-33-3

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 唑类
• 英文名称: 2-[3-(trifluoromethyl)phenyl]-5H-pyrazolo[3,4-c]quinolin-4-one
• CAS: 1120368-33-3
• 化学式: C₁₇H₁₀F₃N₃O
• 分子量: 329.281
• InChiKey: FMEJYOMHDJCIAR-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.6
• 重原子数：
  24
• 可旋转键数：
  1
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.06
• 拓扑面积：
  46.9
• 氢给体数：
  1
• 氢受体数：
  5

反应信息

• 作为反应物：
  描述：

  2-[3-(trifluoromethyl)phenyl]-5H-pyrazolo[3,4-c]quinolin-4-one 在 五氯化磷 、 三氯氧磷 作用下， 以85%的产率得到4-chloro-2-(3-(trifluoromethyl)phenyl)-2H-pyrazolo[3,4-c]quinoline
  参考文献：
  名称：

  Novel potent and highly selective human A3 adenosine receptor antagonists belonging to the 4-amido-2-arylpyrazolo[3,4-c]quinoline series: Molecular docking analysis and pharmacological studies

  摘要：

  The study of novel 2-arylpyrazolo[3,4-c]quinolin-4-(hetero)arylamides, designed as human (h) A(3) adenosine receptor antagonists, is reported. The new derivatives are endowed with nanomolar hA(3) receptor affinity and high selectivity versus hA(1), hA(2A) and hA(2B) receptors. Among the (hetero) aroyl residues introduced on the 4-amino group, the 2-furyl and 4-pyridyl rings turned out to be the most beneficial for hA(3) affinity (K-i = 3.4 and 5.0 nM, respectively). An intensive molecular docking study to a rhodopsin-based homology model of the hA(3) receptor was carried out to obtain a 'structure-based pharmacophore model' that proved to be helpful for the interpretation of the observed affinities of the new hA(3) pyrazoloquino-line antagonists. (C) 2008 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.bmc.2008.10.018
• 作为产物：
  描述：

  2-氧代-3-吲哚羧酸乙酯 、 3-(三氟甲基)苯肼盐酸盐 在 溶剂黄146 作用下， 以 乙醇 为溶剂， 反应 0.17h， 以34%的产率得到2-[3-(trifluoromethyl)phenyl]-5H-pyrazolo[3,4-c]quinolin-4-one
  参考文献：
  名称：

  Novel potent and highly selective human A3 adenosine receptor antagonists belonging to the 4-amido-2-arylpyrazolo[3,4-c]quinoline series: Molecular docking analysis and pharmacological studies

  摘要：

  The study of novel 2-arylpyrazolo[3,4-c]quinolin-4-(hetero)arylamides, designed as human (h) A(3) adenosine receptor antagonists, is reported. The new derivatives are endowed with nanomolar hA(3) receptor affinity and high selectivity versus hA(1), hA(2A) and hA(2B) receptors. Among the (hetero) aroyl residues introduced on the 4-amino group, the 2-furyl and 4-pyridyl rings turned out to be the most beneficial for hA(3) affinity (K-i = 3.4 and 5.0 nM, respectively). An intensive molecular docking study to a rhodopsin-based homology model of the hA(3) receptor was carried out to obtain a 'structure-based pharmacophore model' that proved to be helpful for the interpretation of the observed affinities of the new hA(3) pyrazoloquino-line antagonists. (C) 2008 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.bmc.2008.10.018