1-methyl-2-(2-naphthyl)-ethylamine hydrochloride | 18085-04-6

• 分子结构分类: 有机化合物 - 苯类化合物 - 萘
• 英文名称: 1-methyl-2-(2-naphthyl)-ethylamine hydrochloride
• 英文别名: PAL-287；1-naphthyl-2-propylamine hydrochloride；1-(2-Naphthyl)-2-aminopropan-hydrochlorid；1-(Naphthalen-2-yl)propan-2-amine hydrochloride；1-naphthalen-2-ylpropan-2-amine;hydrochloride
• CAS: 18085-04-6
• 化学式: C₁₃H₁₅N*ClH
• 分子量: 221.73
• InChiKey: VXUUXPYFLWRNFU-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.15
• 重原子数：
  15
• 可旋转键数：
  2
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.23
• 拓扑面积：
  26
• 氢给体数：
  2
• 氢受体数：
  1

反应信息

• 作为产物：
  描述：

  1-(β-naphthyl)-2-nitro-1-propene 在 lithium aluminium tetrahydride 、 sodium hydroxide 、 水 、 盐酸 作用下， 以 四氢呋喃 、 水 、 异丙醇 为溶剂， 以40%的产率得到1-methyl-2-(2-naphthyl)-ethylamine hydrochloride
  参考文献：
  名称：

  Naphthylisopropylamine and N-benzylamphetamine derivatives as monoamine oxidase inhibitors

  摘要：

  A series of naphthylisopropylamine and N-benzyl-4-methylthioamphetamine derivatives were evaluated as monoamine oxidase inhibitors. Their potencies were compared with those of a series of amphetamine derivatives, to test if the increase of electron richness of the aromatic ring and overall size of the molecule might improve their potency as enzyme inhibitors. Molecular dockings were performed to gain insight regarding the binding mode of these inhibitors and rationalize their different potencies. In the case of naphthylisopropylamine derivatives, the increased electron-donating capacity and size of the aromatic moiety resulting from replacement of the phenyl ring of amphetamine derivatives by a naphthalene system resulted in more potent compounds. In the other case, extension of the arylisopropylamine molecule by N-benzylation of the amino group led to a decrease in potency as monoamine oxidase inhibitors. (C) 2009 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.bmc.2009.01.074

文献信息

• Synthesis of Primary sec-alkylamines via nucleophilic ring-opening of N-phosphorylated aziridines
  作者：Tadeusz Gajda、Anna Napieraj、Krystyna Osowska-Pacewicka、Stefan Zawadzki、Andrzej Zwierzak

  DOI：10.1016/s0040-4020(97)00188-9

  日期：1997.3

  3-Disubstituted N-phosphorylated aziridines except N-phosphorylated cyclohexenimine (4) do not react under the described conditions. Copper-mediated reaction of 2-phenyl-N-(diethoxyphosphoryl)aziridine (7) with Grignard reagents affords a mixture of regioisomers (8) and (9) but still with the preference of ring-opening at the carbon of lesser substitution.

  各种2-烷基和2，2-二甲基-N-（二乙氧基磷酰基）氮丙啶（1）和（10）与铜修饰的格氏试剂的新颖开环反应在受阻较少的碳上进行区域特异性的反应。通过与20％盐酸回流，可以将由此获得的N-仲-烷基膦酰胺酸二乙酯（2）有效地转化为仲仲烷基胺盐酸盐（3）。除了N-磷酸化的环己胺（4）以外，2，3-二取代的N-磷酸化的氮丙啶在所述条件下不反应。铜介导的2-苯基-N-（二乙氧基磷酰基）氮丙啶反应（7）与格氏试剂一起提供区域异构体（8）和（9）的混合物，但仍然优选在较少取代的碳上开环。
• Novel arylaminopropane analogues and their use for the treatment of glaucoma
  申请人：——

  公开号：US20040110791A1

  公开（公告）日：2004-06-10

  Arylaminopropane analogues are disclosed. Also disclosed are methods for the lowering and controlling of normal or elevated intraocular pressure as well as a method for the treatment of glaucoma using compositions containing one or more of the compounds of the present invention.

  本发明公开了芳基氨基丙烷类似物。还公开了用含有本发明化合物中的一种或多种的组合物降低和控制正常或升高的眼压的方法，以及治疗青光眼的方法。
• US7071225B2
  申请人：——

  公开号：US7071225B2

  公开（公告）日：2006-07-04
• Naphthylisopropylamine and N-benzylamphetamine derivatives as monoamine oxidase inhibitors
  作者：Marcelo Vilches-Herrera、Juan Miranda-Sepúlveda、Marco Rebolledo-Fuentes、Angélica Fierro、Susan Lühr、Patricio Iturriaga-Vasquez、Bruce K. Cassels、Miguel Reyes-Parada

  DOI：10.1016/j.bmc.2009.01.074

  日期：2009.3

  A series of naphthylisopropylamine and N-benzyl-4-methylthioamphetamine derivatives were evaluated as monoamine oxidase inhibitors. Their potencies were compared with those of a series of amphetamine derivatives, to test if the increase of electron richness of the aromatic ring and overall size of the molecule might improve their potency as enzyme inhibitors. Molecular dockings were performed to gain insight regarding the binding mode of these inhibitors and rationalize their different potencies. In the case of naphthylisopropylamine derivatives, the increased electron-donating capacity and size of the aromatic moiety resulting from replacement of the phenyl ring of amphetamine derivatives by a naphthalene system resulted in more potent compounds. In the other case, extension of the arylisopropylamine molecule by N-benzylation of the amino group led to a decrease in potency as monoamine oxidase inhibitors. (C) 2009 Elsevier Ltd. All rights reserved.