3-methyl-N-(2-phenyl-2H-pyrazolo[3,4-c]quinolin-4-yl)benzamide | 1120368-27-5

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 唑类
• 英文名称: 3-methyl-N-(2-phenyl-2H-pyrazolo[3,4-c]quinolin-4-yl)benzamide
• 英文别名: 3-methyl-N-(2-phenylpyrazolo[3,4-c]quinolin-4-yl)benzamide
• CAS: 1120368-27-5
• 化学式: C₂₄H₁₈N₄O
• 分子量: 378.433
• InChiKey: MKXZGGLSDMDQBU-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  5
• 重原子数：
  29
• 可旋转键数：
  3
• 环数：
  5.0
• sp3杂化的碳原子比例：
  0.04
• 拓扑面积：
  59.8
• 氢给体数：
  1
• 氢受体数：
  3

反应信息

• 作为产物：
  描述：

  2-Phenyl-2H-pyrazolo[3,4-c]quinolin-4-ylamine 、 间甲基苯甲酸 在 4-二甲氨基吡啶 、 1-羟基苯并三唑 、 盐酸-N-乙基-Nˊ-(3-二甲氨基丙基)碳二亚胺 、 三乙胺 作用下， 以 N,N-二甲基甲酰胺 为溶剂， 以40%的产率得到3-methyl-N-(2-phenyl-2H-pyrazolo[3,4-c]quinolin-4-yl)benzamide
  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

文献信息

• 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
  作者：Vittoria Colotta、Francesca Capelli、Ombretta Lenzi、Daniela Catarzi、Flavia Varano、Daniela Poli、Fabrizio Vincenzi、Katia Varani、Pier Andrea Borea、Diego Dal Ben、Rosaria Volpini、Gloria Cristalli、Guido Filacchioni

  DOI：10.1016/j.bmc.2008.10.018

  日期：2009.1

  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.