N,N'-Bis-(6-amino-hexyl)-nonane-1,9-diamine | 104807-25-2

• 分子结构分类: 有机化合物 - 有机氮化合物
• 英文名称: N,N'-Bis-(6-amino-hexyl)-nonane-1,9-diamine
• CAS: 104807-25-2
• 化学式: C₂₁H₄₈N₄
• 分子量: 356.639
• InChiKey: PMZOLWGGASEKBE-UHFFFAOYSA-N

物化性质

• 沸点：
  453.3±13.0 °C(Predicted)
• 密度：
  0.891±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  3.93
• 重原子数：
  25.0
• 可旋转键数：
  22.0
• 环数：
  0.0
• sp3杂化的碳原子比例：
  1.0
• 拓扑面积：
  76.1
• 氢给体数：
  4.0
• 氢受体数：
  4.0

反应信息

• 作为产物：
  描述：

  N-苄氧羰基--6-氨基己酸 在 palladium on activated charcoal dimethyl sulfide borane 、 氢气 、 氯甲酸乙酯 、 三乙胺 作用下， 反应 75.5h， 生成 N,N'-Bis-(6-amino-hexyl)-nonane-1,9-diamine
  参考文献：
  名称：

  Differential blockade of muscarinic receptor subtypes by polymethylene tetraamines. Novel class of selective antagonists of cardiac M-2 muscarinic receptors

  摘要：

  Several N,N'-bis[6-[(2-methoxybenzyl)amino]hexyl]-1, omega-alkanediamine tetrahydrochlorides were synthesized and evaluated for their blocking activity on muscarinic receptors in guinea pig atria and rat ileum and bladder. The results were compared with those obtained for the classical nonselective muscarinic antagonist atropine. It was discovered that optimum activity is associated with an eight-carbon chain (compound 4) in guinea pig atria whereas, in both rat ileum and bladder, the 12-carbon analogue 7 had the highest activity. In addition, polymethylene tetraamines 1-6 displayed high selectivity toward guinea pig atria muscarinic receptors. The discriminatory power of 1-6 was not shared by 7. All the tetraamines were shown to be competitive antagonists of muscarinic receptors. N,N'-Bis[6-[(2-methoxybenzyl)amino]hexyl]-1,8-octanediamine was the most potent and selective toward muscarinic receptors in atria, with a pA2 value of 8.13 and a selectivity ratio (atria vs. ileum or bladder) of ca. 270. At a concentration of 10 microM, tetraamine 4 did not affect histamine and 5-hydroxytryptamine receptors of guinea pig ileum or alpha-adrenoreceptors of guinea pig atria whereas it inhibited postsynaptic alpha-adrenoreceptors of rat vas deferens with a -log K value of 5.23 and nicotinic receptors of frog rectus abdominis with an IC50 value of 0.23 microM. It is concluded that 4 is a novel, powerful, and selective tool in the characterization of muscarinic receptor subtypes.

  DOI：

  10.1021/jm00384a034