1-(indol-4-yl)-2-propylaminopentane

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 吲哚及其衍生物
• 英文名称: 1-(indol-4-yl)-2-propylaminopentane
• 英文别名: 1-(1H-indol-4-yl)-N-propylpentan-2-amine
• 化学式: C₁₆H₂₄N₂
• 分子量: 244.38
• InChiKey: RJQCBJFDFFREPG-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  4.1
• 重原子数：
  18
• 可旋转键数：
  7
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.5
• 拓扑面积：
  27.8
• 氢给体数：
  2
• 氢受体数：
  1

反应信息

• 作为产物：
  描述：

  4-吲哚甲醛 在 aluminium hydride 、 乙酸铵 、 lithium aluminium tetrahydride 作用下， 以 乙醚 为溶剂， 生成 1-(indol-4-yl)-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

文献信息

• NOVEL ETHYLAMINE DERIVATIVES
  申请人：Fujimoto Brothers Co., Ltd.

  公开号：EP0957080A1

  公开（公告）日：1999-11-17

  General formula (I):    (wherein R1 is hydrogen, hydroxyl, lower alkoxy or halogen; R2 is alkyl having 2 to 5 carbon atoms; R3 is hydrogen, alkyl having 2 to 5 carbon atoms, alkylcarbonyl having 2 to 5 carbon atoms, aryl having 6 to 10 carbon atoms or arylalkyl having 7 to 11 carbon atoms; A ring is bicyclic compound which consists of at least one benzene ring and may contain a saturated or unsaturated five- or six-membered ring which may or my not have heteroatoms, providing that when A ring is indole or 1,3-benzodioxole, R2 and R3 do not constitute, at the same time, two carbon atoms members, and when R3 is hydrogen. A ring is other bicyclic compound than indole and benzo[b]thiophene and R2 is alkyl having 3 to 5 carbon atoms) and pharmceutically acceptable acid addition salts thereof. These compounds are promising as psychtropic drugs, antidepressants, drugs for Parkinson's disease and/or drugs for Alzheimer's disease.

  通式（I）： (其中 R1 是氢、羟基、低级烷氧基或卤素；R2 是具有 2 至 5 个碳原子的烷基；R3 是氢、具有 2 至 5 个碳原子的烷基、具有 2 至 5 个碳原子的烷羰基、具有 6 至 10 个碳原子的芳基或具有 7 至 11 个碳原子的芳烷基；环是双环化合物，由至少一个苯环组成，可包含饱和或不饱和的五元或六元环，可带或不带杂质原子，条件是当环是吲哚或 1,3-苯并二恶茂时，R2 和 R3 不同时构成两个碳原子成员，且当 R3 为氢时。环是吲哚和苯并[b]噻吩以外的其他双环化合物，R2 是具有 3 至 5 个碳原子的烷基）及其药学上可接受的酸加成盐。这些化合物有望成为精神药物、抗抑郁药物、帕金森病药物和/或阿尔茨海默病药物。
• US6214859B1
  申请人：——

  公开号：US6214859B1

  公开（公告）日：2001-04-10
• 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
  作者：F Yoneda

  DOI：10.1016/s0968-0896(01)00002-5

  日期：2001.5

  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.