N-[4-(1H-imidazol-1-yl)butyl]-2-thiophenecarboxamide | 95082-35-2

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 噻吩类
• 英文名称: N-[4-(1H-imidazol-1-yl)butyl]-2-thiophenecarboxamide
• 英文别名: N-[4-(1H-imidazol-1-yl)butyl]thiophene-2-carboxamide；N-(4-imidazol-1-ylbutyl)thiophene-2-carboxamide
• CAS: 95082-35-2
• 化学式: C₁₂H₁₅N₃OS
• mdl: MFCD16973828
• 分子量: 249.337
• InChiKey: JADYERCEZASDCW-UHFFFAOYSA-N

物化性质

• 沸点：
  543.2±30.0 °C(Predicted)
• 密度：
  1.24±0.1 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  1.6
• 重原子数：
  17
• 可旋转键数：
  6
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.333
• 拓扑面积：
  75.2
• 氢给体数：
  1
• 氢受体数：
  3

反应信息

• 作为产物：
  描述：

  2-噻吩甲酸 、 1H-咪唑-1-丁胺 在 水 、 N,N'-羰基二咪唑 作用下， 生成 N-[4-(1H-imidazol-1-yl)butyl]-2-thiophenecarboxamide
  参考文献：
  名称：

  Thromboxane synthetase inhibitors and antihypertensive agents. 3. N-[(1H-imidazol-1-yl)alkyl]heteroaryl amides as potent enzyme inhibitors

  摘要：

  The title compounds were prepared as the heterocyclic analogues of thromboxane (TX) synthetase inhibitors and antihypertensive agents previously reported from our laboratories. These compounds were at least as active TX synthetase inhibitors as their benzene isosteres with the indole derivatives 50-55 having the most potent enzyme inhibiting activity measured to date in our laboratories. The best compound, 54, is more than 200-fold more potent than the standard, dazoxiben. In contrast, the antihypertensive activity of these series of compounds was no better than their benzene counterparts and is far lower than the isoindoledione derivatives prepared in a related series. The structure-activity relationship results from this study were similar to our previous observations and include the fact that the amide moiety effectively replaces a carboxylic acid for potent TX synthetase inhibition and that a four to six methylene unit separation (approximately 8.5 A) between amide and imidazole moieties achieves maximal activity.

  DOI：

  10.1021/jm00389a013

文献信息

• US4489089A
  申请人：——

  公开号：US4489089A

  公开（公告）日：1984-12-18
• Thromboxane synthetase inhibitors and antihypertensive agents. 3. N-[(1H-imidazol-1-yl)alkyl]heteroaryl amides as potent enzyme inhibitors
  作者：Jeffery B. Press、William B. Wright、Peter S. Chan、Margie F. Haug、Joseph W. Marsico、Andrew S. Tomcufcik

  DOI：10.1021/jm00389a013

  日期：1987.6

  The title compounds were prepared as the heterocyclic analogues of thromboxane (TX) synthetase inhibitors and antihypertensive agents previously reported from our laboratories. These compounds were at least as active TX synthetase inhibitors as their benzene isosteres with the indole derivatives 50-55 having the most potent enzyme inhibiting activity measured to date in our laboratories. The best compound, 54, is more than 200-fold more potent than the standard, dazoxiben. In contrast, the antihypertensive activity of these series of compounds was no better than their benzene counterparts and is far lower than the isoindoledione derivatives prepared in a related series. The structure-activity relationship results from this study were similar to our previous observations and include the fact that the amide moiety effectively replaces a carboxylic acid for potent TX synthetase inhibition and that a four to six methylene unit separation (approximately 8.5 A) between amide and imidazole moieties achieves maximal activity.