N,N'-bis[6-{[(2-methoxybenzyl)methyl]amino}hexyl]-1,8-octanediamine | 115962-56-6

• 分子结构分类: 有机化合物 - 苯类化合物 - 苯和取代衍生物
• 英文名称: N,N'-bis[6-{[(2-methoxybenzyl)methyl]amino}hexyl]-1,8-octanediamine
• 英文别名: N,N'-bis[6-[(2-methoxyphenyl)methyl-methylamino]hexyl]octane-1,8-diamine
• CAS: 115962-56-6
• 化学式: C₃₈H₆₆N₄O₂
• 分子量: 610.968
• InChiKey: COJNXXNQJHVLHN-UHFFFAOYSA-N

物化性质

• 沸点：
  674.7±55.0 °C(predicted)
• 密度：
  0.975±0.06 g/cm3(Temp: 20 °C; Press: 760 Torr)(predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  7.7
• 重原子数：
  44
• 可旋转键数：
  29
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.68
• 拓扑面积：
  49
• 氢给体数：
  2
• 氢受体数：
  6

反应信息

• 作为产物：
  描述：

  聚合甲醛 、 N,N'-bis<6-<(2-methoxybenzyl)methylamino>caproyl>-1,8-octanediamine 在 盐酸 、 dimethyl sulfide borane 作用下， 生成 N,N'-bis[6-{[(2-methoxybenzyl)methyl]amino}hexyl]-1,8-octanediamine
  参考文献：
  名称：

  Structure-activity relationships among methoctramine-related polymethylenetetramines. Chain length and substituent effects on M-2 muscarinic receptor blocking activity

  摘要：

  Several polymethylene tetraamines related to methoctramine (1) were prepared and evaluated for their blocking activity on M-2 muscarinic receptors in guinea pig atria and ileum. It turned out that antimuscarinic potency depends on the following parameters: (a) nature of the substituent on both inner and outer nitrogens and (b) carbon chain length separating the inner nitrogens as well as the inner and outer nitrogens. Optimum activity at cardiac M-2 muscarinic receptors was associated with the chain lengths present in 1, that is, eight methylenes between the inner nitrogens and six methylenes between the inner and outer nitrogens. With regard to the substituents, replacement of the benzylic moiety of 1 by a 2-furyl or a 5-methyl-2-furyl nucleus resulted in enhanced potency toward cardiac M-2 muscarinic receptors. In fact, furtramine (18) and mefurtramine (19) proved to be more potent and more selective than 1. Moreover, N-methylation of the four nitrogens of 1 gave different effects: methylation of the outer nitrogens, giving 22, caused a significant decrease in activity whereas methylation of the inner nitrogens, yielding 23, resulted in an increase in activity in both atria and ileum.

  DOI：

  10.1021/jm00121a017

文献信息

• Structure-activity relationships among methoctramine-related polymethylenetetramines. Chain length and substituent effects on M-2 muscarinic receptor blocking activity
  作者：Carlo Melchiorre、Wilma Quaglia、Maria T. Picchio、Dario Giardina、Livio Brasili、Piero Angeli

  DOI：10.1021/jm00121a017

  日期：1989.1

  Several polymethylene tetraamines related to methoctramine (1) were prepared and evaluated for their blocking activity on M-2 muscarinic receptors in guinea pig atria and ileum. It turned out that antimuscarinic potency depends on the following parameters: (a) nature of the substituent on both inner and outer nitrogens and (b) carbon chain length separating the inner nitrogens as well as the inner and outer nitrogens. Optimum activity at cardiac M-2 muscarinic receptors was associated with the chain lengths present in 1, that is, eight methylenes between the inner nitrogens and six methylenes between the inner and outer nitrogens. With regard to the substituents, replacement of the benzylic moiety of 1 by a 2-furyl or a 5-methyl-2-furyl nucleus resulted in enhanced potency toward cardiac M-2 muscarinic receptors. In fact, furtramine (18) and mefurtramine (19) proved to be more potent and more selective than 1. Moreover, N-methylation of the four nitrogens of 1 gave different effects: methylation of the outer nitrogens, giving 22, caused a significant decrease in activity whereas methylation of the inner nitrogens, yielding 23, resulted in an increase in activity in both atria and ileum.