3-benzyl-5H-indeno<1,2-c>pyridazin-5-one | 153615-43-1

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: 3-benzyl-5H-indeno<1,2-c>pyridazin-5-one
• 英文别名: 3-benzyl-5H-indeno[1,2-c]pyridazin-5-one；3-benzylindeno[1,2-c]pyridazin-5-one
• CAS: 153615-43-1
• 化学式: C₁₈H₁₂N₂O
• 分子量: 272.306
• InChiKey: RJTWQOKLTDFVPE-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3
• 重原子数：
  21
• 可旋转键数：
  2
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.06
• 拓扑面积：
  42.8
• 氢给体数：
  0
• 氢受体数：
  3

反应信息

• 作为反应物：
  描述：

  3-benzyl-5H-indeno<1,2-c>pyridazin-5-one 在 chromium(VI) oxide 、 溶剂黄146 作用下， 反应 2.0h， 以94%的产率得到3-Benzoyl-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：

  2-hydroxy-2-(2-oxo-3-phenylpropyl)indane-1,3-dione 在 一水合肼 、 三氟乙酸 作用下， 以 乙醇 为溶剂， 反应 1.0h， 以90%的产率得到3-benzyl-5H-indeno<1,2-c>pyridazin-5-one
  参考文献：
  名称：

  3取代的5 H-茚并[1,2- c ]哒嗪的合成及单胺氧化酶抑制活性

  摘要：

  描述了九种5 H-茚并[1,2- c ]哒嗪的一锅合成。这些化合物显示为单胺氧化酶B（MAO-B）的有效可逆抑制剂，对单胺氧化酶A（MAO-A）几乎没有影响。定性的结构-活性关系表明，MAO-B抑制活性受取代基的电子和本体性质的强烈影响。

  DOI：

  10.1002/hlca.19930760514

文献信息

• Synthesis and Monoamine Oxidase Inhibitory Activity of 3-Substituted 5<i>H</i>-Indeno[1,2-<i>c</i>]pyridazines
  作者：Silvia Kneubühler、Bernard Testa、Vincenzo Carta、Cosimo Altomare、Angelo Carotti

  DOI：10.1002/hlca.19930760514

  日期：1993.8.11

  The one-pot synthesis of nine 5H-indeno[1,2-c]pyridazines is described. These compounds are shown to be potent, reversible inhibitors of monoamine oxidase B (MAO-B) with little or no effect on monoamine oxidase A (MAO-A). Qualitative structure-activity relations indicate that the MAO-B inhibitory activity is strongly influenced by electronic and bulk properties of substitutents.

  描述了九种5 H-茚并[1,2- c ]哒嗪的一锅合成。这些化合物显示为单胺氧化酶B（MAO-B）的有效可逆抑制剂，对单胺氧化酶A（MAO-A）几乎没有影响。定性的结构-活性关系表明，MAO-B抑制活性受取代基的电子和本体性质的强烈影响。
• 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).
• Altomare; Campagna; Carta, Il Farmaco, 1994, vol. 49, # 5, p. 313 - 323
  作者：Altomare、Campagna、Carta、Cellamare、Carotti、Genchi、De Sarro

  DOI：——

  日期：——