3-(N-phenylbenzimidoyl)-1-(3-pyridylmethyl)thiourea | 1281680-93-0

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 吡啶及其衍生物
• 英文名称: 3-(N-phenylbenzimidoyl)-1-(3-pyridylmethyl)thiourea
• 英文别名: (1E)-1-[anilino(phenyl)methylidene]-3-(pyridin-3-ylmethyl)thiourea
• CAS: 1281680-93-0
• 化学式: C₂₀H₁₈N₄S
• 分子量: 346.456
• InChiKey: OSKZJXIOCDLNBC-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.7
• 重原子数：
  25
• 可旋转键数：
  5
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.05
• 拓扑面积：
  81.4
• 氢给体数：
  2
• 氢受体数：
  2

反应信息

• 作为反应物：
  描述：

  3-(N-phenylbenzimidoyl)-1-(3-pyridylmethyl)thiourea 在 溴 作用下， 以 二氯甲烷 、 乙酸乙酯 为溶剂， 以64%的产率得到2,3-diphenyl-5-(3-pyridinylmethylimino)-2,5-dihydro-1,2,4-thiadiazole dihydrobromide
  参考文献：
  名称：

  SUBSTITUTED 5-IMINO-1,2,4-THIADIAZOLES THAT CAN BE USED TO TREAT NEURODEGENERATIVE DISEASES

  摘要：

  本发明基于使用广泛的5-亚氨基-1,2,4-噻二唑家族作为治疗PDE7抑制对其重要的疾病的潜在新药物，特别是炎症性疾病、自身免疫和神经退行性疾病。另一方面，描述了5-亚氨基-1,2,4-噻二唑家族的化合物，以及它们的合成方法，它们可能具有作为药物或药物候选物的广泛应用。因此，本发明的第一个方面涉及式(I)的化合物：

  公开号：

  US20120225879A1
• 作为产物：
  描述：

  N-苯基亚胺苄基氯 以 丙酮 为溶剂， 生成 3-(N-phenylbenzimidoyl)-1-(3-pyridylmethyl)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

• US9604947B2
  申请人：——

  公开号：US9604947B2

  公开（公告）日：2017-03-28
• 5-Imino-1,2,4-Thiadiazoles: First Small Molecules As Substrate Competitive Inhibitors of Glycogen Synthase Kinase 3
  作者：Valle Palomo、Daniel I. Perez、Concepcion Perez、Jose A. Morales-Garcia、Ignacio Soteras、Sandra Alonso-Gil、Arantxa Encinas、Ana Castro、Nuria E. Campillo、Ana Perez-Castillo、Carmen Gil、Ana Martinez

  DOI：10.1021/jm201463v

  日期：2012.2.23

  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
• 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