1-(2-hydroxyethyl)-3-(N-1-naphthylbenzimidoyl)thiourea | 1281681-09-1

• 分子结构分类: 有机化合物 - 苯类化合物 - 萘
• 英文名称: 1-(2-hydroxyethyl)-3-(N-1-naphthylbenzimidoyl)thiourea
• 英文别名: (3E)-1-(2-hydroxyethyl)-3-[(naphthalen-1-ylamino)-phenylmethylidene]thiourea
• CAS: 1281681-09-1
• 化学式: C₂₀H₁₉N₃OS
• 分子量: 349.456
• InChiKey: CDORHJGAGVBJBX-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.8
• 重原子数：
  25
• 可旋转键数：
  5
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.1
• 拓扑面积：
  88.7
• 氢给体数：
  3
• 氢受体数：
  2

反应信息

• 作为反应物：
  描述：

  1-(2-hydroxyethyl)-3-(N-1-naphthylbenzimidoyl)thiourea 在 溴 作用下， 以 二氯甲烷 、 乙酸乙酯 为溶剂， 反应 24.0h， 生成 5-(2-hydroxyethylimino)-2-(1-naphthyl)-3-phenyl-2,5-dihydro-1,2,4-thiadiazole hydrobromide 、 5-(2-hydroxyethylimino)-2-(1-naphthyl)-3-phenyl-2,5-dihydro-1,2,4-thiadiazole hydrobromide
  参考文献：
  名称：

  5-Imino-1,2,4-Thiadiazoles: First Small Molecules As Substrate Competitive Inhibitors of Glycogen Synthase Kinase 3

  摘要：

  Cumulative evidence strongly supports that glycogen synthase kinase-3 (GSK-3) is a pathogenic molecule when it is up-dysregulated, emerging as an important therapeutic target in severe unmet human diseases. GSK-3 specific inhibitors might be promising effective drugs for the treatment of devastating pathologies such as neurodegenerative diseases, stroke, and mood disorders. As GSK-3 has the ability to phosphorylate primed substrates, small molecules able to bind to this site should be perfect drug candidates, able to partially block the activity of the enzyme over some specific substrates. Here, we report substituted 5-imino-1,2,4-thiadiazoles as the first small molecules able to inhibit GSK-3 in a substrate competitive manner. These compounds are cell permeable, able to decrease inflammatory activation and to selectively differentiate neural stem cells. Overall, 5-imino-1,2,4-thiadiazoles are presented here as new molecules able to decrease neuronal cell death and to increase endogenous neurogenesis blocking the GSK-3 substrate site

  DOI：

  10.1021/jm201463v
• 作为产物：
  描述：

  N-(1-naphthyl)benzimidoyl chloride 以 丙酮 为溶剂， 生成 1-(2-hydroxyethyl)-3-(N-1-naphthylbenzimidoyl)thiourea
  参考文献：
  名称：

  5-Imino-1,2,4-Thiadiazoles: First Small Molecules As Substrate Competitive Inhibitors of Glycogen Synthase Kinase 3

  摘要：

  Cumulative evidence strongly supports that glycogen synthase kinase-3 (GSK-3) is a pathogenic molecule when it is up-dysregulated, emerging as an important therapeutic target in severe unmet human diseases. GSK-3 specific inhibitors might be promising effective drugs for the treatment of devastating pathologies such as neurodegenerative diseases, stroke, and mood disorders. As GSK-3 has the ability to phosphorylate primed substrates, small molecules able to bind to this site should be perfect drug candidates, able to partially block the activity of the enzyme over some specific substrates. Here, we report substituted 5-imino-1,2,4-thiadiazoles as the first small molecules able to inhibit GSK-3 in a substrate competitive manner. These compounds are cell permeable, able to decrease inflammatory activation and to selectively differentiate neural stem cells. Overall, 5-imino-1,2,4-thiadiazoles are presented here as new molecules able to decrease neuronal cell death and to increase endogenous neurogenesis blocking the GSK-3 substrate site

  DOI：

  10.1021/jm201463v

文献信息

• SUBSTITUTED 5-IMINO-1,2,4-THIADIAZOLES THAT CAN BE USED TO TREAT NEURODEGENERATIVE DISEASES
  申请人：Consejo Superior De Investigaciones Científicas (CSIC)

  公开号：EP2484670B1

  公开（公告）日：2016-07-20
• US9604947B2
  申请人：——

  公开号：US9604947B2

  公开（公告）日：2017-03-28