methyl 4-ethyl-1,3-dioxo-2,3-dihydro-1H-benzo[e]isoindole-6-carboxylate | 1187745-40-9

• 分子结构分类: 有机化合物 - 苯类化合物 - 萘
• 英文名称: methyl 4-ethyl-1,3-dioxo-2,3-dihydro-1H-benzo[e]isoindole-6-carboxylate
• 英文别名: Methyl 4-ethyl-1,3-dioxobenzo[e]isoindole-6-carboxylate
• CAS: 1187745-40-9
• 化学式: C₁₆H₁₃NO₄
• 分子量: 283.284
• InChiKey: VFKLQAUIBCCMKQ-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.6
• 重原子数：
  21
• 可旋转键数：
  3
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.19
• 拓扑面积：
  72.5
• 氢给体数：
  1
• 氢受体数：
  4

反应信息

• 作为产物：
  描述：

  methyl 3-(1-methoxy-4-methyl-1-oxohexa-2,3-dien-2-yl)benzoate 、 1-异氰基-4-硝基苯 在 水 、 zinc trifluoromethanesulfonate 、 碘 、 氨 作用下， 以 四氢呋喃 、 二氯甲烷 、 甲醇 为溶剂， 以25 mg的产率得到methyl 4-ethyl-1,3-dioxo-2,3-dihydro-1H-benzo[e]isoindole-8-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