methyl 4-(2-hydroxyethyl)-1,3-dioxo-2,3-dihydro-1H-benzo[e]isoindole-7-carboxylate | 1187745-53-4

• 分子结构分类: 有机化合物 - 苯类化合物 - 萘
• 英文名称: methyl 4-(2-hydroxyethyl)-1,3-dioxo-2,3-dihydro-1H-benzo[e]isoindole-7-carboxylate
• 英文别名: Methyl 4-(2-hydroxyethyl)-1,3-dioxobenzo[e]isoindole-7-carboxylate
• CAS: 1187745-53-4
• 化学式: C₁₆H₁₃NO₅
• 分子量: 299.283
• InChiKey: JGROFDQABJLMDE-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  1.4
• 重原子数：
  22
• 可旋转键数：
  4
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.19
• 拓扑面积：
  92.7
• 氢给体数：
  2
• 氢受体数：
  5

反应信息

• 作为产物：
  描述：

  methyl 4-(2-(benzyloxy)ethyl)-1,3-dioxo-2,3-dihydro-1H-benzo[e]isoindole-7-carboxylate 在 palladium 10% on activated carbon 、 氢气 作用下， 以 四氢呋喃 、 甲醇 为溶剂， 反应 16.0h， 以85%的产率得到methyl 4-(2-hydroxyethyl)-1,3-dioxo-2,3-dihydro-1H-benzo[e]isoindole-7-carboxylate
  参考文献：
  名称：

  Benzo[e]isoindole-1,3-diones as Potential Inhibitors of Glycogen Synthase Kinase-3 (GSK-3). Synthesis, Kinase Inhibitory Activity, Zebrafish Phenotype, and Modeling of Binding Mode

  摘要：

  Benzo[e]isoindole-1,3-dione derivatives were synthesized, and the effects on GSK-3 beta activity and zebrafish embryo growth were evaluated. A series of derivatives show obvious inhibitory activity against GSK-3 beta. The most potent inhibitor, 7,8-dimethoxy-5-methylbenzo[e]isoindole-1,3-dione (8a), shows nanomolar IC50 and obvious phenotype on zebrafish embryo growth associated with the inhibition of GSK-3 beta at low micromolar concentration. The interaction mode between 8a and GSK-3 beta was characterized by computational modeling.

  DOI：

  10.1021/jm9013373