N-(2-(1-(2-naphthyl))pentyl)propionamide | 220491-43-0

• 分子结构分类: 有机化合物 - 苯类化合物 - 萘
• 英文名称: N-(2-(1-(2-naphthyl))pentyl)propionamide
• 英文别名: N-(1-naphthalen-2-ylpentan-2-yl)propanamide
• CAS: 220491-43-0
• 化学式: C₁₈H₂₃NO
• 分子量: 269.387
• InChiKey: WPKDVGQUWYTHAE-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  4.5
• 重原子数：
  20
• 可旋转键数：
  6
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.39
• 拓扑面积：
  29.1
• 氢给体数：
  1
• 氢受体数：
  1

反应信息

• 作为反应物：
  描述：

  N-(2-(1-(2-naphthyl))pentyl)propionamide 在 aluminium hydride 作用下， 以 乙醚 为溶剂， 以52.8%的产率得到1-(2-naphthyl)-2-propylaminopentane
  参考文献：
  名称：

  Structure–activity studies leading to (−)1-(Benzofuran-2-yl)-2-propylaminopentane, ((−)BPAP), a highly potent, selective enhancer of the impulse propagation mediated release of Catecholamines and Serotonin in the brain

  摘要：

  The catecholaminergic and serotoninergic neurons in the brain change their performance according to the physiological need via a catecholaminergic/serotoninergic activity enhancer (CAE/SAE) mechanism. Phenylethylamine (PEA), tyramine and tryptamine are the presently known endogenous CAE/SAE substances which enhance the impulse propagation mediated release of catecholamines and serotonin in the brain. A PEA derivative, (-)deprenyl (selegiline), known as a selective inhibitor of MAO-B, is for the time being the only CAE/SAE substance in clinical use. Aiming to develop a selective CAE/SAE substance much more potent than (-)deprenyl, a series of new 1-aryl-2-alkylaminoalkanes, structurally unrelated to PEA and the amphetamines, was designed and prepared. Among them, (-)1-(benzofuran-2-yl)-2-propylaminopentane ((-)BPAP) was selected as a promising candidate substance for further studies. (-)BPAP significantly enhanced in rats the impulse propagation mediated release of catecholamines and serotonin in the brain 30 min after acute injection of 0.36 nmol/kg sc. In the shuttle box, (-)BPAP was in rats about 130 times more potent than (-)deprenyl in antagonizing tetrabenazine induced inhibition of performance. (-)BPAP protected cultured hippocampal neurons from the neurotoxic effect of P-amyloid in 10(-14)-10(-15) concentration. (C) 2001 Elsevier Science Ltd. All rights reserved.

  DOI：

  10.1016/s0968-0896(01)00002-5
• 作为产物：
  描述：

  1-(2-naphthyl)-2-nitro-1-pentene 在 lithium aluminium tetrahydride 、 三乙胺 作用下， 以 四氢呋喃 为溶剂， 反应 5.0h， 生成 N-(2-(1-(2-naphthyl))pentyl)propionamide
  参考文献：
  名称：

  Structure–activity studies leading to (−)1-(Benzofuran-2-yl)-2-propylaminopentane, ((−)BPAP), a highly potent, selective enhancer of the impulse propagation mediated release of Catecholamines and Serotonin in the brain

  摘要：

  The catecholaminergic and serotoninergic neurons in the brain change their performance according to the physiological need via a catecholaminergic/serotoninergic activity enhancer (CAE/SAE) mechanism. Phenylethylamine (PEA), tyramine and tryptamine are the presently known endogenous CAE/SAE substances which enhance the impulse propagation mediated release of catecholamines and serotonin in the brain. A PEA derivative, (-)deprenyl (selegiline), known as a selective inhibitor of MAO-B, is for the time being the only CAE/SAE substance in clinical use. Aiming to develop a selective CAE/SAE substance much more potent than (-)deprenyl, a series of new 1-aryl-2-alkylaminoalkanes, structurally unrelated to PEA and the amphetamines, was designed and prepared. Among them, (-)1-(benzofuran-2-yl)-2-propylaminopentane ((-)BPAP) was selected as a promising candidate substance for further studies. (-)BPAP significantly enhanced in rats the impulse propagation mediated release of catecholamines and serotonin in the brain 30 min after acute injection of 0.36 nmol/kg sc. In the shuttle box, (-)BPAP was in rats about 130 times more potent than (-)deprenyl in antagonizing tetrabenazine induced inhibition of performance. (-)BPAP protected cultured hippocampal neurons from the neurotoxic effect of P-amyloid in 10(-14)-10(-15) concentration. (C) 2001 Elsevier Science Ltd. All rights reserved.

  DOI：

  10.1016/s0968-0896(01)00002-5