7-methoxy-2-[3-(trifluoromethyl)phenyl]-9H-indeno[1,2-c]pyridazin-9-one | 166760-67-4

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 二嗪类
• 英文名称: 7-methoxy-2-[3-(trifluoromethyl)phenyl]-9H-indeno[1,2-c]pyridazin-9-one
• 英文别名: 7-Methoxy-3-(3-trifluoromethyl-phenyl)-indeno[1,2-c]pyridazin-5-one；7-methoxy-3-[3-(trifluoromethyl)phenyl]indeno[1,2-c]pyridazin-5-one
• CAS: 166760-67-4
• 化学式: C₁₉H₁₁F₃N₂O₂
• 分子量: 356.304
• InChiKey: YWTWKPBBWASJFY-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.5
• 重原子数：
  26
• 可旋转键数：
  2
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.11
• 拓扑面积：
  52.1
• 氢给体数：
  0
• 氢受体数：
  7

反应信息

• 作为反应物：
  描述：

  7-methoxy-2-[3-(trifluoromethyl)phenyl]-9H-indeno[1,2-c]pyridazin-9-one 在 氢溴酸 、 溶剂黄146 作用下， 反应 2.0h， 以25%的产率得到7-Hydroxy-3-(3-trifluoromethyl-phenyl)-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：

  间三氟甲基苯乙酮 在 一水合肼 、 溶剂黄146 作用下， 生成 7-methoxy-2-[3-(trifluoromethyl)phenyl]-9H-indeno[1,2-c]pyridazin-9-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

文献信息

• Synthesis, Structural Reassignment, and Biological Activity of Type B MAO Inhibitors Based on the 5<i>H</i>-Indeno[1,2-<i>c</i>]pyridazin-5-one Core
  作者：Raphaël Frédérick、Willy Dumont、Frédéric Ooms、Lindsey Aschenbach、Cornelis J. Van der Schyf、Neal Castagnoli、Johan Wouters、Alain Krief

  DOI：10.1021/jm051091j

  日期：2006.6.1

  The synthesis and enzyme inhibitor properties of reversible type B monoamine oxidase inhibitors are described. These compounds belong to the 5H-indeno[ 1,2-c] pyridazine family and possess a hydrophobic benzyloxy or 4,4,4-trifluorobutoxy side chain which, in contrast to a previous assignment, has been unambiguously located at C( 8) of the heterocyclic moiety. Investigation of the regioisomeric structures establishes that substitution of the 5H-indeno[ 1,2-c] pyridazin-5-one core at C( 7) vs C( 8) dramatically influences the MAO-inhibiting properties of these compounds.