4-Oxo-1-phenyl-1,4-dihydro-indeno[1,2-c]pyrazole-3-carboxylic acid ethyl ester | 847069-23-2

• 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-Oxo-1-phenyl-1,4-dihydro-indeno[1,2-c]pyrazole-3-carboxylic acid ethyl ester
• CAS: 847069-23-2
• 化学式: C₁₉H₁₄N₂O₃
• 分子量: 318.332
• InChiKey: HDRRIEFKBJQLPI-UHFFFAOYSA-N

物化性质

• 熔点：
  207-209 °C(Solv: chloroform (67-66-3); hexane (110-54-3))
• 沸点：
  523.7±38.0 °C(Predicted)
• 密度：
  1.32±0.1 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  3.26
• 重原子数：
  24.0
• 可旋转键数：
  3.0
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.11
• 拓扑面积：
  61.19
• 氢给体数：
  0.0
• 氢受体数：
  5.0

反应信息

• 作为反应物：
  描述：

  4-Oxo-1-phenyl-1,4-dihydro-indeno[1,2-c]pyrazole-3-carboxylic acid ethyl ester 在 sodium hydroxide 作用下， 以 乙醇 为溶剂， 反应 2.0h， 以70%的产率得到4-Oxo-1-phenyl-1,4-dihydro-indeno[1,2-c]pyrazole-3-carboxylic acid
  参考文献：
  名称：

  Synthesis, central and peripheral benzodiazepine receptor affinity of pyrazole and pyrazole-containing polycyclic derivatives

  摘要：

  A series of new pyrazole-condensed 6,5,5 tricyclic compounds were synthesized and tested to evaluate their binding affinities at both central (CBR) and peripheral (PBR) benzodiazepine receptors. Some 1-aryl-5-phenylpyrazole derivatives were also prepared and tested for comparison with their corresponding rigid tricyclic analogs. Among the newly synthesized 1-aryl-1,4-dihydro-indeno[1,2-c]pyrazoles bearing both an ethoxycarbonyl group at position 3 and a carbonyl function at the position 4, compound 4b emerged as a new potent (IC(50) = 26.4 nM) and selective CBR ligand. The 4-oxo-1-aryl-1,4-dihydro-indeno[1,2-c]pyrazole diethylamide derivative 14a was instead identified as a relatively potent (IC(50) = 124 nM) but highly selective PBR ligand.

  DOI：

  10.1016/j.farmac.2004.05.008
• 作为产物：
  描述：

  1,4-Dihydro-1-phenyl-indeno[1,2-c]pyrazole-3-carboxylic acid,ethyl ester 在 chromium(VI) oxide 、 溶剂黄146 作用下， 反应 48.0h， 以21%的产率得到4-Oxo-1-phenyl-1,4-dihydro-indeno[1,2-c]pyrazole-3-carboxylic acid ethyl ester
  参考文献：
  名称：

  Synthesis, central and peripheral benzodiazepine receptor affinity of pyrazole and pyrazole-containing polycyclic derivatives

  摘要：

  A series of new pyrazole-condensed 6,5,5 tricyclic compounds were synthesized and tested to evaluate their binding affinities at both central (CBR) and peripheral (PBR) benzodiazepine receptors. Some 1-aryl-5-phenylpyrazole derivatives were also prepared and tested for comparison with their corresponding rigid tricyclic analogs. Among the newly synthesized 1-aryl-1,4-dihydro-indeno[1,2-c]pyrazoles bearing both an ethoxycarbonyl group at position 3 and a carbonyl function at the position 4, compound 4b emerged as a new potent (IC(50) = 26.4 nM) and selective CBR ligand. The 4-oxo-1-aryl-1,4-dihydro-indeno[1,2-c]pyrazole diethylamide derivative 14a was instead identified as a relatively potent (IC(50) = 124 nM) but highly selective PBR ligand.

  DOI：

  10.1016/j.farmac.2004.05.008