8-trifluoromethoxy-2-(4-hydroxy-3-nitrophenyl)pyrazolo[4,3-c]quinolin-3(5H)-one | 340811-91-8

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 唑类
• 英文名称: 8-trifluoromethoxy-2-(4-hydroxy-3-nitrophenyl)pyrazolo[4,3-c]quinolin-3(5H)-one
• CAS: 340811-91-8
• 化学式: C₁₇H₉F₃N₄O₅
• 分子量: 406.277
• InChiKey: YVONGPFJWPZPDU-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.33
• 重原子数：
  29.0
• 可旋转键数：
  3.0
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.06
• 拓扑面积：
  123.28
• 氢给体数：
  2.0
• 氢受体数：
  7.0

反应信息

• 作为反应物：
  描述：

  8-trifluoromethoxy-2-(4-hydroxy-3-nitrophenyl)pyrazolo[4,3-c]quinolin-3(5H)-one 在 palladium on activated charcoal 氢气 作用下， 以 乙醇 为溶剂， 20.0 ℃ 、275.79 kPa 条件下， 反应 4.0h， 生成
  参考文献：
  名称：

  High affinity central benzodiazepine receptor ligands. Part 2: quantitative structure–activity relationships and comparative molecular field analysis of pyrazolo[4,3- c ]quinolin-3-ones

  摘要：

  A large series of 2-aryl(heteroaryl)-2,5-dihydropyrazolo[4,3-c]quinolin-3(3H)-ones (PQ, 106 compounds), carrying appropriate substituents at the quinoline and N-2-phenyl rings, were designed, prepared and tested as central benzodiazepine receptor ligands. Compounds with an affinity significantly higher than the parent compound CGS-8216 were obtained, the most active ligand showing a pIC(50) = 10.35. Hansch and comparative molecular field analyses gave coherent results suggesting the main structural requirements of high receptor binding affinity. The possible formation of a three-centred hydrogen bond (HB) at the HB donor site H-2, as a key interaction for high receptor binding affinity, was assessed by the calculation and comparison of the molecular electrostatic potentials of a series of selected ligands. (C) 2001 Elsevier Science Ltd. All rights reserved.

  DOI：

  10.1016/s0968-0896(00)00262-5
• 作为产物：
  描述：

  4-hydroxyphenylhydrazine 在 硫酸 、 potassium nitrate 、 sodium nitrite 作用下， 以 乙醇 为溶剂， 生成 8-trifluoromethoxy-2-(4-hydroxy-3-nitrophenyl)pyrazolo[4,3-c]quinolin-3(5H)-one
  参考文献：
  名称：

  High affinity central benzodiazepine receptor ligands. Part 2: quantitative structure–activity relationships and comparative molecular field analysis of pyrazolo[4,3- c ]quinolin-3-ones

  摘要：

  A large series of 2-aryl(heteroaryl)-2,5-dihydropyrazolo[4,3-c]quinolin-3(3H)-ones (PQ, 106 compounds), carrying appropriate substituents at the quinoline and N-2-phenyl rings, were designed, prepared and tested as central benzodiazepine receptor ligands. Compounds with an affinity significantly higher than the parent compound CGS-8216 were obtained, the most active ligand showing a pIC(50) = 10.35. Hansch and comparative molecular field analyses gave coherent results suggesting the main structural requirements of high receptor binding affinity. The possible formation of a three-centred hydrogen bond (HB) at the HB donor site H-2, as a key interaction for high receptor binding affinity, was assessed by the calculation and comparison of the molecular electrostatic potentials of a series of selected ligands. (C) 2001 Elsevier Science Ltd. All rights reserved.

  DOI：

  10.1016/s0968-0896(00)00262-5