N-丁基-6-[2-(1H-咪唑-5-基)乙胺基]庚酰胺 | 103827-18-5

• 分子结构分类: 有机化合物 - 有机氮化合物
• 中文名称: N-丁基-6-[2-(1H-咪唑-5-基)乙胺基]庚酰胺
• 英文名称: 6-[2-(1H-Imidazol-4-yl)-ethylamino]-heptanoic acid butylamide
• 英文别名: N-Butyl-6-{[2-(1H-imidazol-5-yl)ethyl]amino}heptanamide；N-butyl-6-[2-(1H-imidazol-5-yl)ethylamino]heptanamide
• CAS: 103827-18-5
• 化学式: C₁₆H₃₀N₄O
• 分子量: 294.44
• InChiKey: ZNEWKFPYDSIEPE-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  1.9
• 重原子数：
  21
• 可旋转键数：
  12
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.75
• 拓扑面积：
  69.8
• 氢给体数：
  3
• 氢受体数：
  3

反应信息

• 作为产物：
  描述：

  histamine dichloride 、 N-butyl-6-oxoheptanamide 在 sodium cyanoborohydride 作用下， 以 甲醇 为溶剂， 生成 N-丁基-6-[2-(1H-咪唑-5-基)乙胺基]庚酰胺
  参考文献：
  名称：

  Congener derivatives and conjugates of histamine: synthesis and tissue and receptor selectivity of the derivatives

  摘要：

  A series of 19 congener derivatives and conjugates of histamine was synthesized and tested to determine whether the ligands would alter the conventional histamine activity in various tissues. The derivatives, which contained either branched or unbranched aliphatic groups, aromatic amide groups, or dipeptides, exhibited affinities for histamine type 1 and/or type 2 receptors that were widely different from the progenitor. The p-trifluoromethyl derivative of histamine with an intermediate chain length of four methylenes (compound 13) was the most potent lymphocytes H2 receptor agonist but was inactive on guinea pig myocardium H2 receptors. The deletion of a single methylene chain (compound 12) from this compound resulted in total loss of its H2 activity on lymphocytes and its H1 activity on aorta. Compound 12 became an exclusive H1 agonist on lymphocytes H1 receptors. The dipeptide conjugate (compound 17) and the aliphatic congener derivative (compound 18), both with four methylenes, retained some of the activity on guinea pig myocardium H2 receptors, but lost their activity on lymphocytes H2 receptors. Therefore, histamine can be modified at sites that are at a distance from the imidazole moiety, resulting in tissue selective histamine receptor agonists.

  DOI：

  10.1021/jm00394a031

文献信息

• Congener derivatives and conjugates of histamine: synthesis and tissue and receptor selectivity of the derivatives
  作者：M. M. Khan、K. L. Melmon、D. Marr-Leisy、M. S. Verlander、M. Egli、S. Lok、M. Goodman

  DOI：10.1021/jm00394a031

  日期：1987.11

  A series of 19 congener derivatives and conjugates of histamine was synthesized and tested to determine whether the ligands would alter the conventional histamine activity in various tissues. The derivatives, which contained either branched or unbranched aliphatic groups, aromatic amide groups, or dipeptides, exhibited affinities for histamine type 1 and/or type 2 receptors that were widely different from the progenitor. The p-trifluoromethyl derivative of histamine with an intermediate chain length of four methylenes (compound 13) was the most potent lymphocytes H2 receptor agonist but was inactive on guinea pig myocardium H2 receptors. The deletion of a single methylene chain (compound 12) from this compound resulted in total loss of its H2 activity on lymphocytes and its H1 activity on aorta. Compound 12 became an exclusive H1 agonist on lymphocytes H1 receptors. The dipeptide conjugate (compound 17) and the aliphatic congener derivative (compound 18), both with four methylenes, retained some of the activity on guinea pig myocardium H2 receptors, but lost their activity on lymphocytes H2 receptors. Therefore, histamine can be modified at sites that are at a distance from the imidazole moiety, resulting in tissue selective histamine receptor agonists.