1-(2-naphthyl)-2-nitro-1-pentene | 220491-84-9

• 分子结构分类: 有机化合物 - 苯类化合物 - 萘
• 英文名称: 1-(2-naphthyl)-2-nitro-1-pentene
• 英文别名: 2-(2-nitropent-1-enyl)naphthalene
• CAS: 220491-84-9
• 化学式: C₁₅H₁₅NO₂
• 分子量: 241.29
• InChiKey: KGPAZHWKLUUSBB-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  4.6
• 重原子数：
  18
• 可旋转键数：
  3
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.2
• 拓扑面积：
  45.8
• 氢给体数：
  0
• 氢受体数：
  2

反应信息

• 作为反应物：
  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
• 作为产物：
  描述：

  1-硝基丁烷 、 2-萘甲醛 在 乙酸铵 、 溶剂黄146 作用下， 反应 10.0h， 以55.4%的产率得到1-(2-naphthyl)-2-nitro-1-pentene
  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

• Ethylamine derivatives
  申请人：Fujimoto Brothers Co., Ltd.

  公开号：US06214859B1

  公开（公告）日：2001-04-10

  Ethylamine derivatives of the 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; the ring is a bicyclic compound which consists of at least one benzene ring and may comprise a saturated or unsaturated five- or six-membered ring which may or may not have heteroatoms, providing that when the 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, the ring is a bicyclic compound which is not indole, benzothiophene or benzodioxole and R2 is alkyl having 3 to 5 carbon atoms and pharmaceutically acceptable acid addition salts thereof. These compounds are promising as psychotropic drugs, antidepressants, drugs for Parkinson's disease and/or drugs for Alzeimer's disease.

  公式（I）的乙基胺衍生物：（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个碳原子的烷基羰基，具有6至10个碳原子的芳基或具有7至11个碳原子的芳基烷基；环是由至少一个苯环组成的二环化合物，可以包括一个饱和或不饱和的五元或六元环，该环可能具有或不具有杂原子，但当环为吲哚或1,3-苯并二氧杂环时，R2和R3不同时构成两个碳原子成员，并且当R3为氢时，该环是一个不是吲哚，苯并噻吩或苯并二氧杂环的二环化合物，R2是具有3至5个碳原子的烷基和药学上可接受的酸盐。这些化合物有望作为精神药物，抗抑郁药，帕金森病药物和/或阿尔茨海默病药物。