2-(3-dimethylamino-2-methylpropyl)isoindoline-1,3-dione | 837407-31-5

• 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: 2-(3-dimethylamino-2-methylpropyl)isoindoline-1,3-dione
• 英文别名: 2-[3-(Dimethylamino)-2-methylpropyl]isoindole-1,3-dione
• CAS: 837407-31-5
• 化学式: C₁₄H₁₈N₂O₂
• 分子量: 246.309
• InChiKey: FGKHUIAFXPTQAZ-UHFFFAOYSA-N

物化性质

• 熔点：
  62 °C
• 沸点：
  352.9±25.0 °C(Predicted)
• 密度：
  1.151±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  2.3
• 重原子数：
  18
• 可旋转键数：
  4
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.43
• 拓扑面积：
  40.6
• 氢给体数：
  0
• 氢受体数：
  3

反应信息

• 作为反应物：
  描述：

  2-(3-dimethylamino-2-methylpropyl)isoindoline-1,3-dione 、 1,6-二溴己烷 在 potassium carbonate 、 potassium iodide 作用下， 以 乙腈 为溶剂， 反应 96.0h， 以65%的产率得到2-{3-[1-(6-{1,1-dimethyl-1-[3-(1,3-dioxo-1,3-dihydroisoindol-2-yl)-2-methylpropyl]ammonio}hexyl)-1,1-dimethylammonio]-2-methylpropyl}isoindoline-1,3-dione dibromide
  参考文献：
  名称：

  Muscarinic Allosteric Enhancers of Ligand Binding:  Pivotal Pharmacophoric Elements in Hexamethonio-Type Agents

  摘要：

  Bisphthalimidopropyl-substituted hexamethonio compounds have been established as allosteric modulators of ligand binding to muscarinic acetylcholine receptors. Enhancers of ligand binding are of special interest. This study aimed to unravel the structural elements inducing positive cooperativity with the binding of an antagonist. [H-3]-N-methylscopolamine binding to muscarinic M-2 receptors was measured in porcine heart homogenates. Dimethylation, but not monomethylation, of the lateral propyl chain in combination with an affinity increasing aromatic imide moiety, such as a 5-methylphthalimide and naphthalimide, on the same side of the molecule shifts the cooperativity toward positive values, resulting in enhancers of antagonist binding. Thus, lateral side chain dimethylation is a pivotal pharmacophoric element for positive cooperativity in hexamethonio-type muscarinic allosteric agents.

  DOI：

  10.1021/jm049616f
• 作为产物：
  描述：

  苯酐 、 (3-氨基-2-甲基丙基)二甲基胺 在 对甲苯磺酸 作用下， 以 甲苯 为溶剂， 反应 4.0h， 以64%的产率得到2-(3-dimethylamino-2-methylpropyl)isoindoline-1,3-dione
  参考文献：
  名称：

  Muscarinic Allosteric Enhancers of Ligand Binding:  Pivotal Pharmacophoric Elements in Hexamethonio-Type Agents

  摘要：

  Bisphthalimidopropyl-substituted hexamethonio compounds have been established as allosteric modulators of ligand binding to muscarinic acetylcholine receptors. Enhancers of ligand binding are of special interest. This study aimed to unravel the structural elements inducing positive cooperativity with the binding of an antagonist. [H-3]-N-methylscopolamine binding to muscarinic M-2 receptors was measured in porcine heart homogenates. Dimethylation, but not monomethylation, of the lateral propyl chain in combination with an affinity increasing aromatic imide moiety, such as a 5-methylphthalimide and naphthalimide, on the same side of the molecule shifts the cooperativity toward positive values, resulting in enhancers of antagonist binding. Thus, lateral side chain dimethylation is a pivotal pharmacophoric element for positive cooperativity in hexamethonio-type muscarinic allosteric agents.

  DOI：

  10.1021/jm049616f