3-hydroxy-5-ethyl-7,8-dimethoxy-2-(2-phenylpropyn-2-yl)-2,3-dihydro-1H-benzo[e]isoindol-1-one | 1187745-66-9

• 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-hydroxy-5-ethyl-7,8-dimethoxy-2-(2-phenylpropyn-2-yl)-2,3-dihydro-1H-benzo[e]isoindol-1-one
• 英文别名: 5-ethyl-3-hydroxy-7,8-dimethoxy-2-(2-phenylpropan-2-yl)-3H-benzo[g]isoindol-1-one
• CAS: 1187745-66-9
• 化学式: C₂₅H₂₇NO₄
• 分子量: 405.494
• InChiKey: JGGRTRZWYQEFEP-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  4.5
• 重原子数：
  30
• 可旋转键数：
  5
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.32
• 拓扑面积：
  59
• 氢给体数：
  1
• 氢受体数：
  4

反应信息

• 作为反应物：
  描述：

  3-hydroxy-5-ethyl-7,8-dimethoxy-2-(2-phenylpropyn-2-yl)-2,3-dihydro-1H-benzo[e]isoindol-1-one 在 重铬酸吡啶 作用下， 以 N,N-二甲基甲酰胺 为溶剂， 反应 6.0h， 以88%的产率得到5-ethyl-7,8-dimethoxy-2-(2-phenylpropyn-2-yl)-1H-benzo[e]isoindole-1,3(2H)-dione
  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
• 作为产物：
  描述：

  4-ethyl-6,7-dimethoxy-N-(2-phenylpropan-2-yl)-1-naphthamide 、 N,N-二甲基甲酰胺 在 四甲基乙二胺 、 叔丁基锂 作用下， 以 四氢呋喃 为溶剂， 反应 4.0h， 以91%的产率得到3-hydroxy-5-ethyl-7,8-dimethoxy-2-(2-phenylpropyn-2-yl)-2,3-dihydro-1H-benzo[e]isoindol-1-one
  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

文献信息

• Benzo[<i>e</i>]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
  作者：Haixia Zou、Liyan Zhou、Yuanzhen Li、Yi Cui、Hanbing Zhong、Zhengying Pan、Zhen Yang、Junmin Quan

  DOI：10.1021/jm9013373

  日期：2010.2.11

  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.