N-<2-ethyl>-3-phenylpropylamine | 140890-64-8

• 分子结构分类: 有机化合物 - 苯类化合物 - 苯和取代衍生物
• 英文名称: N-<2-ethyl>-3-phenylpropylamine
• 英文别名: N-(2-((bis(4-fluorophenyl)methyl)thio)ethyl)-3-phenylpropan-1-amine；JJC8-016；VUF8968；N-[2-[bis(4-fluorophenyl)methylsulfanyl]ethyl]-3-phenylpropan-1-amine
• CAS: 140890-64-8
• 化学式: C₂₄H₂₅F₂NS
• 分子量: 397.532
• InChiKey: IWZNOFWARONDLD-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  6.1
• 重原子数：
  28
• 可旋转键数：
  10
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.25
• 拓扑面积：
  37.3
• 氢给体数：
  1
• 氢受体数：
  4

反应信息

• 作为反应物：
  描述：

  N-<2-ethyl>-3-phenylpropylamine 在 双氧水 作用下， 以 甲醇 、 溶剂黄146 、 异丙醇 、 丙酮 为溶剂， 生成 N-(2-((bis(4-fluorophenyl)methyl)sulfinyl)ethyl)-3-phenylpropan-1-amine oxalate
  参考文献：
  名称：

  Elucidation of Structural Elements for Selectivity across Monoamine Transporters: Novel 2-[(Diphenylmethyl)sulfinyl]acetamide (Modafinil) Analogues

  摘要：

  2-[(Diphenylmethyl)sulfinyl]acetamide (modafinil, (+/-)-1) is a unique dopamine uptake inhibitor that binds the dopamine transporter (DAT) differently than cocaine and may have potential for the treatment of psychostimulant abuse. To further investigate structural requirements for this divergent binding mode, novel thio- and sulfinylacetamide and ethanamine analogues of (+/-)-1 were synthesized wherein (1) the diphenyl rings were substituted with methyl, trifluoromethyl, and halogen substituents and (2) substituents were added to the terminal amide/amine nitrogen. Halogen substitution of the diphenyl rings of (+/-)-1 gave several amide analogues with improved binding affinity for DAT and robust selectivity over the serotonin transporter (SERT), whereas affinity improved at SERT over DAT for the p-halo-substituted amine analogues. Molecular docking studies, using a subset of analogues with DAT and SEAT homology models, and functional data obtained with DAT (A480T) and SERT (T497A) mutants defined a role for TM10 in the substrate/inhibitor S1 binding sites of DAT and SERT.

  DOI：

  10.1021/jm401754x
• 作为产物：
  描述：

  4,4'-二氟二苯甲醇 在 三氟化硼 、 sodium cyanoborohydride 作用下， 以 四氢呋喃 、 乙醚 、 溶剂黄146 为溶剂， 反应 0.25h， 生成 N-<2-ethyl>-3-phenylpropylamine
  参考文献：
  名称：

  New prenylamine analogues: synthesis and Ca2+-entry blocking activity

  摘要：

  The synthesis of a series of diphenylalkylamine derivatives related to prenylamine is reported. The amphetamine group in the prenylamine structure was replaced by other moieties. In addition to substitutions in the aromatic rings, heteroatoms such as sulphur and oxygen were introduced in the chain. The calcium-entry blocking activity was assayed in binding experiments on a guinea-pig brain membrane preparation by displacing [H-3]-nitrendipine.

  DOI：

  10.1016/0223-5234(92)90136-o
• 作为试剂：
  描述：

  N-<2-(diphenylmethylthiol)ethyl>-3-phenylpropylamine 、 2-((bis(4-fluorophenyl)methyl)thio)-N-(3-phenylpropyl)acetamide 在 N-<2-ethyl>-3-phenylpropylamine 、 水 、 sodium hydroxide 、 crude product 、 Chloroform methanol ammonium hydroxide 作用下， 反应 18.0h， 以to give the pure product, 4g (820 mg, 86.6%)的产率得到N-<2-ethyl>-3-phenylpropylamine
  参考文献：
  名称：

  POTENT AND SELECTIVE INHIBITORS OF MONOAMINE TRANSPORTERS; METHOD OF MAKING; AND USE THEREOF

  摘要：

  本文揭示了双芳基甲硫基乙酰胺和双芳基甲硫基乙胺作为单胺转运体抑制剂的用途。这些化合物是通过它们各自的转运体DAT、SERT和NET对多巴胺（DA）、5-羟色胺（5-HT）和/或去甲肾上腺素（NE）的再摄取具有强效和/或选择性抑制作用。还揭示了利用这些化合物引发促醒、认知或注意力增强效应以及治疗物质使用障碍、注意缺陷（多动）障碍、抑郁障碍、双相障碍或其他神经精神障碍、睡眠障碍或认知障碍的方法。

  公开号：

  US20160009644A1

文献信息

• Benzhydryl derivatives having calmodulin inhibitor properties
  申请人：Akzo Nobel N.V.

  公开号：EP0467435A2

  公开（公告）日：1992-01-22

  The invention relates to a benzhydryl derivative having the formula wherein each of the groups Ri, R2, and R3 represents one to four substituents independently selected from the group consisting of hydrogen, lower alkyl, halogen, and CF3, and at least one of the groups Ri, R2, and R3 is halogen or CF3; R4 represents hydrogen or methyl; n is 2, 3, or 4; m is 1, 2, or 3; and X represents O or S; or its pharmaceutically acceptable salts. The benzhydryl derivative of the invention can be used to treat patients who are suffering from diseases which are influenced by calmodulin.

  本发明涉及一种具有以下式子的苯甲酰衍生物 其中每个基团 Ri、R2 和 R3 代表一至四个取代基，这些取代基独立地选自氢、低级烷基、卤素和 CF3 组成的组，且至少一个基团 Ri、R2 和 R3 是卤素或 CF3； R4 代表氢或甲基； n 是 2、3 或 4； m 是 1、2 或 3；以及 X 代表 O 或 S； 或其药学上可接受的盐类。 本发明的苄基衍生物可用于治疗受钙调素影响的疾病患者。
• Potent and selective inhibitors of monoamine transporters; method of making; and use thereof
  申请人：THE UNITED STATES OF AMERICA, as represented by the Secretary, Department of Health and Human Services, Office of Technology Transfer, National Institutes of Health

  公开号：US10590074B2

  公开（公告）日：2020-03-17

  Disclosed herein are bisarylmethylthioacetamides and bisarylmethylthioethylamines useful as inhibitors of monoamine transporters. The compounds are potent and/or selective inhibitors of dopamine (DA), serotonin (5-HT), and/or norepinephrine (NE) reuptake via their respective transporters, DAT, SERT and NET. Also disclosed are methods for eliciting a wake-promoting or cognitive or attention enhancing effect and for treating substance use disorders, attention deficit (hyperactivity) disorder, depressive disorders, bipolar disorder or other neuropsychiatric disorders sleep disorders or cognitive impairment using the compounds.

  本文公开了可用作单胺转运体抑制剂的双芳基甲硫基乙酰胺和双芳基甲硫基乙胺。这些化合物是多巴胺（DA）、5-羟色胺（5-HT）和/或去甲肾上腺素（NE）通过各自的转运体 DAT、SERT 和 NET 再摄取的强效和/或选择性抑制剂。此外，还公开了利用这些化合物激发促进觉醒或认知或注意力增强效应以及治疗药物使用障碍、注意力缺陷（多动）症、抑郁症、双相情感障碍或其他神经精神疾病睡眠障碍或认知障碍的方法。
• New prenylamine analogues: synthesis and Ca2+-entry blocking activity
  作者：PM Caldirola、H van der Goot、H Timmerman

  DOI：10.1016/0223-5234(92)90136-o

  日期：1992.9

  The synthesis of a series of diphenylalkylamine derivatives related to prenylamine is reported. The amphetamine group in the prenylamine structure was replaced by other moieties. In addition to substitutions in the aromatic rings, heteroatoms such as sulphur and oxygen were introduced in the chain. The calcium-entry blocking activity was assayed in binding experiments on a guinea-pig brain membrane preparation by displacing [H-3]-nitrendipine.
• [EN] POTENT AND SELECTIVE INHIBITORS OF MONOAMINE TRANSPORTERS; METHOD OF MAKING; AND USE THEREOF<br/>[FR] INHIBITEURS PUISSANTS ET SÉLECTIFS DE TRANSPORTEURS DE MONOAMINE; PROCÉDÉ DE FABRICATION; ET LEUR UTILISATION
  申请人：US HEALTH

  公开号：WO2014138518A3

  公开（公告）日：2014-11-06
• US5171752A
  申请人：——

  公开号：US5171752A

  公开（公告）日：1992-12-15