2-Hydroxy-2-[2-oxo-2-(4-trifluoromethyl-phenyl)-ethyl]-indan-1,3-dione

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: 2-Hydroxy-2-[2-oxo-2-(4-trifluoromethyl-phenyl)-ethyl]-indan-1,3-dione
• 英文别名: 2-Hydroxy-2-[2-oxo-2-[4-(trifluoromethyl)phenyl]ethyl]indene-1,3-dione
• 化学式: C₁₈H₁₁F₃O₄
• 分子量: 348.278
• InChiKey: XPCPETPZJPACAP-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.4
• 重原子数：
  25
• 可旋转键数：
  3
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.17
• 拓扑面积：
  71.4
• 氢给体数：
  1
• 氢受体数：
  7

反应信息

• 作为反应物：
  描述：

  2-Hydroxy-2-[2-oxo-2-(4-trifluoromethyl-phenyl)-ethyl]-indan-1,3-dione 在 一水合肼 作用下， 生成 3-(4-(trifluoromethyl)phenyl)-5H-indeno[1,2-c]pyridazin-5-one
  参考文献：
  名称：

  Inhibition of Monoamine Oxidase-B by 5H-Indeno[1,2-c]pyridazines: Biological Activities, Quantitative Structure-Activity Relationships (QSARs) and 3D-QSARs

  摘要：

  A large series (66 compounds) of indeno[1,2-c]pyridazin-5-ones (IPs) were synthesized and tested on their monoamine oxidase-A (MAO-A) and MAO-B inhibitory activity. All of the tested compounds acted preferentially on MAO-B displaying weak (nonmeasurable IC50 values) to high (submicromolar IC50 values) activities. The most active compound was p-CF3-3-phenyl-IP (IC50 = 90 nM). Multiple linear regression analysis of the substituted 3-phenyl-IPs yielded good statistical results (q(2) = 0.74; r(2) = 0.86) and showed the importance of lipophilic, electronic, and steric properties of the substituents in determining inhibitory potency. Various comparative molecular field analysis studies were performed with different alignments and including the molecular lipophilicity potential. This led to a model including the steric, electrostatic and lipophilicity fields and having a good predictive value (q(2) = 0.75; r(2) = 0.93).

  DOI：

  10.1021/jm00019a018
• 作为产物：
  描述：

  4'-三氟甲基苯乙酮 、 水合茚三酮 在 溶剂黄146 作用下， 生成 2-Hydroxy-2-[2-oxo-2-(4-trifluoromethyl-phenyl)-ethyl]-indan-1,3-dione
  参考文献：
  名称：

  Inhibition of Monoamine Oxidase-B by 5H-Indeno[1,2-c]pyridazines: Biological Activities, Quantitative Structure-Activity Relationships (QSARs) and 3D-QSARs

  摘要：

  A large series (66 compounds) of indeno[1,2-c]pyridazin-5-ones (IPs) were synthesized and tested on their monoamine oxidase-A (MAO-A) and MAO-B inhibitory activity. All of the tested compounds acted preferentially on MAO-B displaying weak (nonmeasurable IC50 values) to high (submicromolar IC50 values) activities. The most active compound was p-CF3-3-phenyl-IP (IC50 = 90 nM). Multiple linear regression analysis of the substituted 3-phenyl-IPs yielded good statistical results (q(2) = 0.74; r(2) = 0.86) and showed the importance of lipophilic, electronic, and steric properties of the substituents in determining inhibitory potency. Various comparative molecular field analysis studies were performed with different alignments and including the molecular lipophilicity potential. This led to a model including the steric, electrostatic and lipophilicity fields and having a good predictive value (q(2) = 0.75; r(2) = 0.93).

  DOI：

  10.1021/jm00019a018

文献信息

• Inhibition of Monoamine Oxidase-B by 5H-Indeno[1,2-c]pyridazines: Biological Activities, Quantitative Structure-Activity Relationships (QSARs) and 3D-QSARs
  作者：Silvia Kneubuehler、Ulrike Thull、Cosimo Altomare、Vincenco Carta、Patrick Gaillard、Pierre-Alain Carrupt、Angelo Carotti、Bernard Testa

  DOI：10.1021/jm00019a018

  日期：1995.9

  A large series (66 compounds) of indeno[1,2-c]pyridazin-5-ones (IPs) were synthesized and tested on their monoamine oxidase-A (MAO-A) and MAO-B inhibitory activity. All of the tested compounds acted preferentially on MAO-B displaying weak (nonmeasurable IC50 values) to high (submicromolar IC50 values) activities. The most active compound was p-CF3-3-phenyl-IP (IC50 = 90 nM). Multiple linear regression analysis of the substituted 3-phenyl-IPs yielded good statistical results (q(2) = 0.74; r(2) = 0.86) and showed the importance of lipophilic, electronic, and steric properties of the substituents in determining inhibitory potency. Various comparative molecular field analysis studies were performed with different alignments and including the molecular lipophilicity potential. This led to a model including the steric, electrostatic and lipophilicity fields and having a good predictive value (q(2) = 0.75; r(2) = 0.93).