1-(3-(1H-imidazol-1-yl)propyl)-3-butylthiourea

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 唑类
• 英文名称: 1-(3-(1H-imidazol-1-yl)propyl)-3-butylthiourea
• 英文别名: 1-butyl-3-(3-imidazol-1-ylpropyl)thiourea
• 化学式: C₁₁H₂₀N₄S
• mdl: MFCD06349378
• 分子量: 240.373
• InChiKey: BFVKQJGXDBWMFD-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  1.3
• 重原子数：
  16
• 可旋转键数：
  7
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.636
• 拓扑面积：
  74
• 氢给体数：
  2
• 氢受体数：
  2

反应信息

• 作为产物：
  描述：

  1-(3-氨基丙基)咪唑 、 丁基异硫氰酸酯 以 乙醇 为溶剂， 反应 2.0h， 以28%的产率得到1-(3-(1H-imidazol-1-yl)propyl)-3-butylthiourea
  参考文献：
  名称：

  The First Potent Inhibitors for Human Glutaminyl Cyclase:  Synthesis and Structure−Activity Relationship

  摘要：

  The first effective inhibitors for human glutaminyl cyclase (QC) are described. The structures are developed by applying a ligand-based optimization approach starting from imidazole. Screening of derivatives of that heterocycle led to compounds of the imidazol-1-yl-alkyl thiourea type as a lead scaffold. A library of thiourea derivatives was synthesized, resulting in an inhibitory improvement by 2 orders of magnitude, leading to 1-(3-(1H-imidazol-1-yl)propyl)-3-(3,4-dimethoxyphenyl)thiourea as a potent inhibitor. Systematic exploitation of the scaffold revealed a strong impact on the inhibitory efficacy and resulted in the development of imidazole-propyl-thioamides as another new class of potent inhibitors. A flexible alignment of the most potent compounds of the thioamide and thiourea class and a QC substrate revealed a good match of characteristic features of the molecules, which suggests a similar binding mode of both inhibitors and the substrate to the active site of QC.

  DOI：

  10.1021/jm050756e

文献信息

• NOVEL INHIBITORS OF GLUTAMINYL CYCLASE
  申请人：Probiodrug AG

  公开号：EP1713780B1

  公开（公告）日：2012-01-18