2-(3-methoxyphenyl)ethyl-N-phenethylamine | 65934-55-6

• 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: 2-(3-methoxyphenyl)ethyl-N-phenethylamine
• 英文别名: [2-(3-methoxyphenyl)ethyl]phenethylamine；(3-methoxyphenyl)-N-phenethaneamine；N-phenethyl-3-methoxyphenethylamine；(2-Phenyl-aethyl)-<2-(3-methoxy-phenyl)-aethyl>-amin；(2-Phenyl-aethyl)-[2-(3-methoxy-phenyl)-aethyl]-amin；N-[2-(3-methoxyphenyl)ethyl]-2-phenylethanamine
• CAS: 65934-55-6
• 化学式: C₁₇H₂₁NO
• 分子量: 255.36
• InChiKey: YOXDHVFZOSHAFM-UHFFFAOYSA-N

物化性质

• 沸点：
  391.4±22.0 °C(Predicted)
• 密度：
  1.026±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  3.7
• 重原子数：
  19
• 可旋转键数：
  7
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.29
• 拓扑面积：
  21.3
• 氢给体数：
  1
• 氢受体数：
  2

反应信息

• 作为反应物：
  描述：

  2-(3-methoxyphenyl)ethyl-N-phenethylamine 在 potassium carbonate 、 乙硫醇钠 作用下， 以 N,N-二甲基甲酰胺 为溶剂， 反应 22.0h， 生成 HS666
  参考文献：
  名称：

  Discovery and Pharmacological Evaluation of a Diphenethylamine Derivative (HS665), a Highly Potent and Selective κ Opioid Receptor Agonist

  摘要：

  Here we report on the design, synthesis, and biological characterization of novel kappa opioid (KOP) receptor ligands of diphenethylamines. In opioid receptor binding and functional assays, the N-cyclobutylmethyl substituted derivative 4 (HS665) showed the highest affinity and selectivity for the KOP receptor and KOP-agonist potency. Compound 4 inhibited acetic acid induced writhing after subcutaneous administration in mice via KOP receptor mediated mechanisms, being equipotent as an analgesic to the KOP agonist U50,488.

  DOI：

  10.1021/jm301258w
• 作为产物：
  描述：

  3-甲氧基苯乙酸 在 lithium aluminium tetrahydride 作用下， 以 5,5-dimethyl-1,3-cyclohexadiene 、 甲基叔丁基醚 为溶剂， 反应 16.0h， 生成 2-(3-methoxyphenyl)ethyl-N-phenethylamine
  参考文献：
  名称：

  A New Class of Selective and Potent 7-Dehydrocholesterol Reductase Inhibitors

  摘要：

  We prepared a number of N-phenethyltetrahydroisoquinolines structurally related to protoberberines. They were tested for activity against bacteria, fungi, and human leukemia HL-60 cells and also for inhibition of biosynthesis: ergosterol in yeasts and cholesterol in human cells. In the latter assay panel, several of the compounds were distinguished by a strong and selective inhibition of 7-dehydrocholesterol reductase (7-DHCR, EC 1.3.1.21), an enzyme responsible for the conversion of 7-dehydrocholesterol to cholesterol in the last step of cholesterol biosynthesis. In a whole-cell assay, the most active compound 5f showed a much stronger inhibition of overall cholesterol biosynthesis (IC50 2.3 nM) than BM 15.766 (IC50 500 nM), presently the most selective known inhibitor of 7-DHCR Since a defect of 7-dehydrocholesterol reductase is associated with Smith-Lemli-Opitz syndrome (SLOS), the potent and selective inhibitors reported here will enable more detailed investigation of the pathogenesis of SLOS.

  DOI：

  10.1021/jm3006096

文献信息

• Structural determinants of diphenethylamines for interaction with the κ opioid receptor: Synthesis, pharmacology and molecular modeling studies
  作者：Elena Guerrieri、Marcel Bermudez、Gerhard Wolber、Ilona P. Berzetei-Gurske、Helmut Schmidhammer、Mariana Spetea

  DOI：10.1016/j.bmcl.2016.08.031

  日期：2016.10

  into receptor function. We describe the synthesis, pharmacological evaluation and docking calculations of KOP receptor ligands from the class of diphenethylamines using an active-like structure of the KOP receptor attained by molecular dynamics simulations. The structure-activity relationships derived from computational studies was in accordance with pharmacological activities of targeted diphenethylamines

  处于非活动状态的κ阿片样物质（KOP）受体晶体结构为当今研究受体功能提供了宝贵的平台。我们描述了使用分子动力学模拟获得的KOP受体的活性样结构，从苯二乙胺类中合成了KOP受体配体的合成，药理学评价和对接计算。从计算研究中得出的构效关系与目标二苯乙胺在KOP受体上的药理活性一致，该KOP受体是通过体外竞争结合和G蛋白活化而建立的。我们的分析确定，激动剂结合会导致Arg156-Thr273氢键断裂，从而稳定非活性受体构象，并与His291形成关键的氢键。具有酚4-羟基的化合物不会与His291形成氢键，而His291是KOP亲和力和激动剂活性的重要残基。由Val108，Ile316和Tyr320形成的疏水性口袋占据的N-取代基的大小极大地影响了结合和选择性，n-烷基的大小限制为5个碳原子，而庞大的取代基则成为拮抗剂中的KOP激动剂。因此，实验和分子建模策略的组合为理解苯乙胺的结构特征提供了一个
• Novel phenethylamines
  申请人：Roussel Uclaf

  公开号：US04130658A1

  公开（公告）日：1978-12-19

  Novel phenethylamines of the formula ##STR1## wherein X is selected from the group consisting of hydrogen, acyl of an aliphatic carboxylic acid of 2 to 6 carbon atoms and benzoyl and Y is selected from the group consisting of hydrogen and --OX and their non-toxic, pharmaceutically acceptable acid addition salts having dopaminergic stimulating activity and their preparation and novel intermediates.

  本发明涉及一种新的苯乙胺类衍生物，其化学式为##STR1##其中X选自氢、2-6个碳原子的脂肪族羧酸酰基和苯甲酰基，Y选自氢和—OX，以及它们的非毒性、药学上可接受的酸盐，具有多巴胺能兴奋活性，以及它们的制备方法和新中间体。
• NEDELEC L.; DUMONT C.; OBERLANDER C.; FRECHET D.; LAURENT J.; BOISSIER J.+, FUR. J. MED. CHEM.-CHIM. THER., 1978, 13, NO 6, 553-563
  作者：NEDELEC L.、 DUMONT C.、 OBERLANDER C.、 FRECHET D.、 LAURENT J.、 BOISSIER J.+

  DOI：——

  日期：——
• Nouveau dérivé d'hydroxyphénéthylamine et ses sels, procédé de préparation, application à titre de médicaments et utilisation comme outil pharmacologique spécifique
  申请人：ROUSSEL-UCLAF

  公开号：EP0395529B1

  公开（公告）日：1993-11-03
• US4130658A
  申请人：——

  公开号：US4130658A

  公开（公告）日：1978-12-19