1-[2-(1H-imidazol-4-yl)-ethyl]-3-methyl-thiourea | 717098-36-7

• 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-[2-(1H-imidazol-4-yl)-ethyl]-3-methyl-thiourea
• 英文别名: 1-[2-(1h-Imidazol-4-yl)ethyl]-3-methylthiourea；1-[2-(1H-imidazol-5-yl)ethyl]-3-methylthiourea
• CAS: 717098-36-7
• 化学式: C₇H₁₂N₄S
• 分子量: 184.265
• InChiKey: MRRGISSXOKOWTB-UHFFFAOYSA-N

物化性质

• 沸点：
  400.5±47.0 °C(Predicted)
• 密度：
  1.233±0.06 g/cm3(Temp: 20 °C; Press: 760 Torr)(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  -0.3
• 重原子数：
  12
• 可旋转键数：
  3
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.43
• 拓扑面积：
  84.8
• 氢给体数：
  3
• 氢受体数：
  2

反应信息

• 作为产物：
  描述：

  histamine dichloride 、 异硫氰酸甲酯 在 sodium ethanolate 作用下， 生成 1-[2-(1H-imidazol-4-yl)-ethyl]-3-methyl-thiourea
  参考文献：
  名称：

  New Analogs of Burimamide as Potent and Selective Histamine H3 Receptor Antagonists: The Effect of Chain Length Variation of the Alkyl Spacer and Modifications of the N-Thiourea Substituent

  摘要：

  Burimamide was one of the first compounds reported to antagonize the activation of the histamine H-3 receptor by histamine. We have prepared a large series of burimamide analogs by variation of the alkyl spacer length of burimamide from two methylene groups to six methylene groups and also by replacement of the N-methyl group with other alkyl and aryl groups. All analogs are reversible, competitive H-3 antagonists as determined on the guinea pig intestine. Elongation of the alkyl chain from an ethylene chain to a hexylene chain results in an increase of the H-3 antagonistic activity. The H-3 selective pentylene and hexylene analogs of burimamide are about 10 times more potent than burimamide. The N-thiourea substituents, however, have no beneficial influence on the affinity.

  DOI：

  10.1021/jm00012a025

文献信息

• New Analogs of Burimamide as Potent and Selective Histamine H3 Receptor Antagonists: The Effect of Chain Length Variation of the Alkyl Spacer and Modifications of the N-Thiourea Substituent
  作者：Roeland C. Vollinga、Wiro M. P. B. Menge、Rob Leurs、Hendrik Timmerman

  DOI：10.1021/jm00012a025

  日期：1995.6

  Burimamide was one of the first compounds reported to antagonize the activation of the histamine H-3 receptor by histamine. We have prepared a large series of burimamide analogs by variation of the alkyl spacer length of burimamide from two methylene groups to six methylene groups and also by replacement of the N-methyl group with other alkyl and aryl groups. All analogs are reversible, competitive H-3 antagonists as determined on the guinea pig intestine. Elongation of the alkyl chain from an ethylene chain to a hexylene chain results in an increase of the H-3 antagonistic activity. The H-3 selective pentylene and hexylene analogs of burimamide are about 10 times more potent than burimamide. The N-thiourea substituents, however, have no beneficial influence on the affinity.