2-(4-hydroxyphenyl)-N-phenethylacetamide | 911123-05-2

• 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-(4-hydroxyphenyl)-N-phenethylacetamide
• 英文别名: p-hydroxyphenylacetylphenylethylamine；2-(4-hydroxyphenyl)-N-(2-phenylethyl)acetamide
• CAS: 911123-05-2
• 化学式: C₁₆H₁₇NO₂
• 分子量: 255.316
• InChiKey: BFXBKUXOHGIALT-UHFFFAOYSA-N

物化性质

• 沸点：
  521.0±43.0 °C(Predicted)
• 密度：
  1.158±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  2.7
• 重原子数：
  19
• 可旋转键数：
  5
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.19
• 拓扑面积：
  49.3
• 氢给体数：
  2
• 氢受体数：
  2

反应信息

• 作为反应物：
  描述：

  2-(4-hydroxyphenyl)-N-phenethylacetamide 在 硼烷四氢呋喃络合物 、 碳酸氢钠 、 potassium iodide 作用下， 以 四氢呋喃 为溶剂， 生成 4-[2-[(cyclopentylmethyl)(phenethyl)amino]ethyl]phenol
  参考文献：
  名称：

  Diphenethylamine Derivatives Which Are Inter Alia Useful As Analgesics And Method For Their Production

  摘要：

  二苯乙胺衍生物可用作高活性镇痛剂、利尿剂、抗焦虑药，用于治疗神经退行性、精神疾病和神经精神疾病，以及作为抗瘙痒、抗成瘾、抗炎、抗肥胖、抗癫痫、抗抽搐、抗癫痫发作、抗压力、抗精神病和抗抑郁药物及其药学上可接受的盐和易于获取的衍生物（例如酯、醚、酰胺），以及它们的制备过程和在药品制造中的应用。

  公开号：

  US20180072654A1
• 作为产物：
  描述：

  2-(4-methoxyphenyl)-N-(2-phenylethyl)acetamide 在 三溴化硼 作用下， 以 二氯甲烷 为溶剂， 以49%的产率得到2-(4-hydroxyphenyl)-N-phenethylacetamide
  参考文献：
  名称：

  Antileukotrienic N-arylethyl-2-arylacetamides in the treatment of ulcerative colitis

  摘要：

  A series of arylacetic acid derivatives bearing methyl(aryiethyl)amino groups were prepared and their antileukotrienic activities involving LTB4 were evaluated. Regression analysis has shown a strong dependence of these activities on lipophilicity for both LTB4 receptor binding and inhibition of LTB4 biosynthesis; parabolic relationships were derived. The values of slopes of the ascending linear parts of these dependences indicate various types of hydrophobic binding at the site of ligand interaction with relevant biomacromolecules. The anti-inflammatory effect of the compounds under study was also evaluated in three animal models of inflammation and their possible utilization in the treatment of ulcerative colitis (UC) was followed. The importance of antileukotrienic activities for the anti-inflammatory effect, especially in the model of UC was discussed, but further experiments are necessary to confirm the respective relations. (c) 2007 Elsevier Masson SAS. All rights reserved.

  DOI：

  10.1016/j.ejmech.2007.01.014

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
• Diphenethylamine derivatives which are inter alia useful as analgesics and method for their production
  申请人：UNIVERSITY OF INNSBRUCK

  公开号：US10377698B2

  公开（公告）日：2019-08-13

  Diphenethylamine derivatives for use as highly active analgesics, diuretics, anxiolytics, for the treatment of neurodegenerative, psychiatric and neuropsychiatric disorders, and also as anti-itch, anti-addiction, anti-inflammatory, anti-obesity, anti-epileptic, anti-convulsant, anti-seizure, anti-stress, anti-psychotic and anti-depressant medications and their pharmaceutically acceptable salts and easily accessible derivatives thereof (e.g. esters, ethers, amides), processes for their preparation and their application in the manufacture of pharmaceutical products.

  用作高活性镇痛剂、利尿剂、抗焦虑剂、治疗神经退行性疾病、精神疾病和神经 精神疾病的苯乙胺衍生物，以及用作止痒、抗成瘾、抗炎、抗肥胖、抗癫痫、抗惊厥、 抗癫痫、抗应激、抗精神病和抗抑郁药物的苯乙胺衍生物及其药学上可接受的盐类和 易于获得的衍生物（如酯类、醚类、酰胺类），以及它们的制备工艺和在药品生产中的应 用。如酯、醚、酰胺）、其制备工艺以及在药品生产中的应用。
• PHENYL-CONTAINING N-ACYL AMINE AND AMINOACID DERIVATIVES, METHODS FOR THE PRODUCTION THEREOF, A PHARMACEUTICAL COMPOSITION AND THE USE THEREOF
  申请人：Obschestvo S Ogranichennoi Otvetstennostiyu "Pharmenterprises"

  公开号：EP1876169B1

  公开（公告）日：2015-12-30
• Phenyl-containing n-acyl amine and aminoacid derivatives, methods for the production thereof, a pharmaceutical composition and the use thereof
  申请人：Nebolsin Vladimir Evgenievich

  公开号：US20090111874A1

  公开（公告）日：2009-04-30

  The present invention relates to novel phenyl-N-acyl derivatives of biogenic amines and amino acids of general formula (I) as cyclooxynease inhibitors, possessing analgetic and anti-inflammatory properties and devoid of side effects in particular ulcerogeneity and pro-spasmodic actions, as well as capability to potentiate effect of other analgetics, and possessing in addition antihypoxic, antidepressant and anti-Parkinsonistic action; as well as to the processes for the preparation novel and known phenyl-N-acyl derivatives of biogenic amines, to a pharmaceutical composition and to an agent comprising compounds of general formula (I) as well as to use thereof and a method of treating.
• PHENYL-N-ACYL DERIVATIVES OF AMINES AND AMINO ACIDS, A PROCESS FOR THE PREPARATION THEREOF, A PHARMACEUTICAL COMPOSITION AND USE THEREOF
  申请人：Obschestvo S Ogranichennoi Otvetstvennostiyu

  公开号：US20130109880A1

  公开（公告）日：2013-05-02

  The present invention relates to novel phenyl-N-acyl derivatives of biogenic amines and amino acids of general formula (I) as cyclooxynease inhibitors, possessing analgetic and anti-inflammatory properties and devoid of side effects in particular ulcerogeneity and pro-spasmodic actions, as well as capability to potentiate effect of other analgetics, and possessing in addition antihypoxic, antidepressant and anti-Parkinsonistic action; as well as to the processes for the preparation novel and known phenyl-N-acyl derivatives of biogenic amines, to a pharmaceutical composition and to an agent comprising compounds of general formula (I) as well as to use thereof and a method of treating.