N-(6-hydroxy-2-hexyl)-N-methylpropargylamine | 143347-12-0

• 分子结构分类: 有机化合物 - 有机氮化合物
• 英文名称: N-(6-hydroxy-2-hexyl)-N-methylpropargylamine
• 英文别名: 5-(Methyl-prop-2-ynyl-amino)-hexan-1-ol; hydrochloride；5-[methyl(prop-2-ynyl)amino]hexan-1-ol
• CAS: 143347-12-0
• 化学式: C₁₀H₁₉NO
• 分子量: 169.267
• InChiKey: HBDDRJJEDYDFCF-UHFFFAOYSA-N

物化性质

• 沸点：
  253.4±20.0 °C(Predicted)
• 密度：
  0.927±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  1.2
• 重原子数：
  12
• 可旋转键数：
  6
• 环数：
  0.0
• sp3杂化的碳原子比例：
  0.8
• 拓扑面积：
  23.5
• 氢给体数：
  1
• 氢受体数：
  2

反应信息

• 作为产物：
  描述：

  5-羟基己酸乙酯 在 lithium aluminium tetrahydride 、 三氯化铝 、 三甲基溴硅烷 、 sodium carbonate 作用下， 以 乙醚 、 乙醇 、 氯仿 为溶剂， 反应 387.0h， 生成 N-(6-hydroxy-2-hexyl)-N-methylpropargylamine
  参考文献：
  名称：

  Aliphatic propargylamines: potent, selective, irreversible monoamine oxidase B inhibitors

  摘要：

  A series of aliphatic propargylamine derivatives has been synthesized. Some of them possess highly potent, irreversible, selective, inhibitory activity toward monoamine oxidase B (MAO-B). The potency of the inhibitors is related to chain length and substitution of a hydrogen on the terminal carbon of the aliphatic chain. MAO inhibitory activity as assessed in vitro increased as the aliphatic carbon chain length increased. Substitution of a hydrogen by hydroxyl, carboxyl, or carbethoxyl groups at the aliphatic chain terminal or replacement of the methyl group on the nitrogen atom by an ethyl group considerably reduced the inhibitory activity. Stereospecific effects were observed with the R-(-)-enantiomer being 20-fold more active than the S-(+)-enantiomer. Inhibitors with relatively short carbon chain lengths (i.e. four to six carbons) were found to be more potent than those with longer chains in inhibiting brain MAO-B activity in vivo especially after oral administration. Chronic administration of low doses of the aliphatic propargylamines caused a slight cumulative inhibition of MAO-A activity in the mouse brain. These MAO-B inhibitors appear to be nontoxic, and they do not possess an amphetamine-like moiety in their structure as is the case for deprenyl. We expect that these aliphatic propargylamines may be useful in the treatment in certain neuropsychiatric disorders.

  DOI：

  10.1021/jm00098a017

文献信息

• Aliphatic propargylamines: potent, selective, irreversible monoamine oxidase B inhibitors
  作者：Peter H. Yu、Bruce A. Davis、Alan A. Boulton

  DOI：10.1021/jm00098a017

  日期：1992.10

  A series of aliphatic propargylamine derivatives has been synthesized. Some of them possess highly potent, irreversible, selective, inhibitory activity toward monoamine oxidase B (MAO-B). The potency of the inhibitors is related to chain length and substitution of a hydrogen on the terminal carbon of the aliphatic chain. MAO inhibitory activity as assessed in vitro increased as the aliphatic carbon chain length increased. Substitution of a hydrogen by hydroxyl, carboxyl, or carbethoxyl groups at the aliphatic chain terminal or replacement of the methyl group on the nitrogen atom by an ethyl group considerably reduced the inhibitory activity. Stereospecific effects were observed with the R-(-)-enantiomer being 20-fold more active than the S-(+)-enantiomer. Inhibitors with relatively short carbon chain lengths (i.e. four to six carbons) were found to be more potent than those with longer chains in inhibiting brain MAO-B activity in vivo especially after oral administration. Chronic administration of low doses of the aliphatic propargylamines caused a slight cumulative inhibition of MAO-A activity in the mouse brain. These MAO-B inhibitors appear to be nontoxic, and they do not possess an amphetamine-like moiety in their structure as is the case for deprenyl. We expect that these aliphatic propargylamines may be useful in the treatment in certain neuropsychiatric disorders.