3-benzyl-2-[3-(N,N-dimethylamino)propyl]-1-isoindolinone | 111977-23-2

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 异吲哚及其衍生物
• 英文名称: 3-benzyl-2-[3-(N,N-dimethylamino)propyl]-1-isoindolinone
• 英文别名: 3-Benzyl-2-<3-dimethylamino-propyl>-phthalimidin；3-benzyl-2-[3-(dimethylamino)propyl]-3H-isoindol-1-one
• CAS: 111977-23-2
• 化学式: C₂₀H₂₄N₂O
• 分子量: 308.423
• InChiKey: OXQOGDISVRIPMC-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.3
• 重原子数：
  23
• 可旋转键数：
  6
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.35
• 拓扑面积：
  23.6
• 氢给体数：
  0
• 氢受体数：
  2

反应信息

• 作为反应物：
  描述：

  1,6-二溴己烷 、 3-benzyl-2-[3-(N,N-dimethylamino)propyl]-1-isoindolinone 以 乙腈 为溶剂， 反应 5.0h， 以54%的产率得到
  参考文献：
  名称：

  Structure−Activity Relationships in a Series of Bisquaternary Bisphthalimidine Derivatives Modulating the Muscarinic M₂-Receptor Allosterically

  摘要：

  Hexane-bisammonium-type compounds containing lateral phthalimide moieties are well-established ligands of the common allosteric binding site of muscarinic M-2 receptors. Previous structure-activity relationships (SAR) revealed two positively charged centers and two lateral phthalimide moieties in a defined arrangement to be essential of a high allosteric potency. The purpose of this study was to replace one carbonyl group of the phthalimides with hydrogens, hydroxy, alkoxy, phenyl, benzyl, and benzylidene groups in order to check the influence of these substituents on the allosteric activity in antagonist-linked receptors. The analysis of the quantitative SAR indicated that a high allosteric potency is related to a certain amount of rigidity as well as polarizibility and the ability to form hydrophobic interactions.

  DOI：

  10.1021/jm991136e
• 作为产物：
  描述：

  3-(E,Z)-benzylidene-N-[3-(N,N-dimethylamino)propyl]-1-isoindolinone 在 palladium on activated charcoal 氢气 作用下， 以 乙醇 为溶剂， 20.0 ℃ 、440.0 kPa 条件下， 反应 16.0h， 以82%的产率得到3-benzyl-2-[3-(N,N-dimethylamino)propyl]-1-isoindolinone
  参考文献：
  名称：

  Structure−Activity Relationships in a Series of Bisquaternary Bisphthalimidine Derivatives Modulating the Muscarinic M₂-Receptor Allosterically

  摘要：

  Hexane-bisammonium-type compounds containing lateral phthalimide moieties are well-established ligands of the common allosteric binding site of muscarinic M-2 receptors. Previous structure-activity relationships (SAR) revealed two positively charged centers and two lateral phthalimide moieties in a defined arrangement to be essential of a high allosteric potency. The purpose of this study was to replace one carbonyl group of the phthalimides with hydrogens, hydroxy, alkoxy, phenyl, benzyl, and benzylidene groups in order to check the influence of these substituents on the allosteric activity in antagonist-linked receptors. The analysis of the quantitative SAR indicated that a high allosteric potency is related to a certain amount of rigidity as well as polarizibility and the ability to form hydrophobic interactions.

  DOI：

  10.1021/jm991136e

文献信息

• Structure−Activity Relationships in a Series of Bisquaternary Bisphthalimidine Derivatives Modulating the Muscarinic M₂-Receptor Allosterically
  作者：Hector M. Botero Cid、Christian Tränkle、Knut Baumann、Rainer Pick、Elisabeth Mies-Klomfass、Evi Kostenis、Klaus Mohr、Ulrike Holzgrabe

  DOI：10.1021/jm991136e

  日期：2000.6.1

  Hexane-bisammonium-type compounds containing lateral phthalimide moieties are well-established ligands of the common allosteric binding site of muscarinic M-2 receptors. Previous structure-activity relationships (SAR) revealed two positively charged centers and two lateral phthalimide moieties in a defined arrangement to be essential of a high allosteric potency. The purpose of this study was to replace one carbonyl group of the phthalimides with hydrogens, hydroxy, alkoxy, phenyl, benzyl, and benzylidene groups in order to check the influence of these substituents on the allosteric activity in antagonist-linked receptors. The analysis of the quantitative SAR indicated that a high allosteric potency is related to a certain amount of rigidity as well as polarizibility and the ability to form hydrophobic interactions.