N-[2-(3,4-二甲氧基苯基)乙基]-2-苯基-2-羟基乙胺 | 20011-97-6

• 分子结构分类: 有机化合物 - 苯类化合物 - 苯和取代衍生物
• 中文名称: N-[2-(3,4-二甲氧基苯基)乙基]-2-苯基-2-羟基乙胺
• 英文名称: N-[2-(3,4-dimethoxyphenyl)ethyl]-2-phenyl-2-hydroxyethylamine
• 英文别名: 2-amino>-1-phenylethanol；N-<(β-hydroxy-2-phenyl)ethyl>-2-(3,4-dimethoxyphenyl)ethylamine；1-phenyl-N-(3,4-dimethoxyphenethyl)ethanolamine；N-(2-hydroxy-2-phenylethyl)homoveratrylamine；N-(2-hydroxy-2-phenethyl)homoveratrylamine；N-[2-(3,4-dimethoxyphenyl)ethyl]2-phenyl-2-hydroxyethylamine；2-{[2-(3,4-Dimethoxyphenyl)ethyl]amino}-1-phenylethanol；2-[2-(3,4-dimethoxyphenyl)ethylamino]-1-phenylethanol
• CAS: 20011-97-6
• 化学式: C₁₈H₂₃NO₃
• 分子量: 301.386
• InChiKey: ZZTAKCGSXKWHAD-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.1
• 重原子数：
  22
• 可旋转键数：
  8
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.33
• 拓扑面积：
  50.7
• 氢给体数：
  2
• 氢受体数：
  4

反应信息

• 作为反应物：
  描述：

  N-[2-(3,4-二甲氧基苯基)乙基]-2-苯基-2-羟基乙胺 在 氢溴酸 作用下， 反应 3.0h， 以90%的产率得到(±)-1-苯基-2,3,4,5-四氢-(1H)-3-苯并ze庚因-7,8-二醇氢溴酸盐
  参考文献：
  名称：

  Dopamine agonists related to 3-allyl-6-chloro-2,3,4,5-tetrahydro-1-(4-hydroxyphenyl)-1H-3-benzazepine-7,8-diol, 6-position modifications

  摘要：

  The N-allyl derivative (SK&F 85174) of 6-chloro-2,3,4,5-tetrahydro-1-(4-hydroxyphenyl)-1H-3-benzazepine-7,8-diol (SK&F 82526) retains the DA-1 agonist potency of the latter compound but unlike the parent also shows substantial DA-2 agonist activity. In a previous study of N-substituted benzazepines these combined agonist effects were shown to be uniquely associated with the N-allyl group. A continuation of this research has examined dependency of combined DA-2/DA-1 agonist activities on 6-position modification with the specific objective of developing an agonist with maximum effectiveness and potency at the DA-2 receptor subtype. DA-2 agonist activity was measured in a rabbit ear artery assay, and DA-1 agonist activity was determined in an adenylate cyclase assay. Replacing chloro with bromo retains the activity pattern and the potency of the chloro compound; replacement with a hydrogen causes a decrease of both DA-1 and DA-2 receptor activating potency. Introduction of a 6-methyl group causes loss of DA-2 agonist activity and reduction in DA-1 agonist potency. Substitution with a 6-fluoro provides the best balance of DA-2 and DA-1 agonist activities; this compound was moderately potent in both assays.

  DOI：

  10.1021/jm00384a006
• 作为产物：
  描述：

  ethyl 2-(3,4-dimethoxyphenyl)acetoimidate hydrochloride 在 diborane(6) 作用下， 以 四氢呋喃 、 二氯甲烷 为溶剂， 反应 28.0h， 生成 N-[2-(3,4-二甲氧基苯基)乙基]-2-苯基-2-羟基乙胺
  参考文献：
  名称：

  Oxazolines. 2. 2-Substituted 2-oxazolines as synthons for N-(.beta.-hydroxyethyl)arylalkylamines, intermediates in a synthesis of 1,2,3,4-tetrahydroisoquinolines and 2,3,4,5-tetrahydro-1H-3-benzazepines

  摘要：

  DOI：

  10.1021/jo00132a001

文献信息

• (.+-.)-(Aminoalkyl)benzazepine Analogs: Novel Dopamine D1 Receptor Antagonists
  作者：Jamshed H. Shah、Sari Izenwasser、Beth Geter-Douglass、Jeffrey M. Witkin、Amy Hauck Newman

  DOI：10.1021/jm00021a018

  日期：1995.10

  (+/-)-(N-Alkylamino)benzazepine analogs were prepared as novel dopamine D1 receptor antagonists to further elucidate the role of these receptor subtypes in the pharmacology and toxicology of cocaine. In the first series of compounds, (+/-)-7-chloro-8-hydroxy-3- [6-(N,N-dimethylamino)-hexyl]-1-phenyl-2,3,4,5-tetrahydro-1H-3-benzazepi ne (15) showed the highest affinity (Ki = 49.3 nM) and subtype-selectivity

  制备（+/-）-（N-烷基氨基）苯并ze庚因类似物作为新型多巴胺D1受体拮抗剂，以进一步阐明这些受体亚型在可卡因药理和毒理学中的作用。在第一批化合物中，（+/-）-7-氯-8-羟基-3- [6-（N，N-二甲基氨基）-己基] -1-苯基-2,3,4,5-四氢-1H-3-苯并ze庚因（15）与多巴胺D2、5-HT2a和5-HT2c受体相比，对多巴胺D1具有最高的亲和力（Ki = 49.3 nM）和亚型选择性。化合物7a [（+/-）-7-氯8-羟基-3- [4-（N，N-二甲基氨基）丁基] -1-苯基-2,3,4,5-四氢-1H-3-苯并ze庚因]，11 [（+/-）-7-氯-8-羟基-3- [6-[（N，N-二甲基氨基）己基] -1-苯基-2,3,4,5-四氢-1H -3-苯并ze庚因-氰基硼烷]，15和15是中等强度的多巴胺D1受体拮抗剂，这是由于它们具有阻断多巴胺刺激的大鼠尾状腺腺苷酸
• Glycerine and CeCl3˙7H2O: An Efficient and Recyclable Reaction Medium for Ring Opening of Epoxides with Thioamides and Amines
  作者：A. Narsaiah、Sachin Wadavrao、A. Reddy、J. Yadav

  DOI：10.1055/s-0030-1258366

  日期：2011.2

  Oxiranes undergo rapid ring-opening reaction with a range of thioamides and amines to afford the corresponding β-amino alcohol derivatives. The reactions were carried out using glycerine and cerium(III) chloride as a recyclable reaction medium. All the reactions were carried out at room temperature and the products were obtained in excellent yields.

  环氧乙烷与一系列硫酰胺和胺迅速发生开环反应，生成相应的β-氨基醇衍生物。反应采用甘油和氯化铈(III)作为可回收反应介质进行。所有反应均在室温下进行，产物收率极佳。
• Pharmaceutical compositions and methods involving benzazepine derivatives
  申请人：SmithKline Corporation

  公开号：US04011319A1

  公开（公告）日：1977-03-08

  Pharmaceutical compositions and a method of stimulating peripheral dopamine receptors by administering internally a nontoxic effective quantity of a benzazepine derivative to an animal. Renal vasodilator and diuretic methods are also disclosed.

  药用组合物及通过向动物体内施用非毒性有效量的苯并氮杂卓衍生物来刺激外周多巴胺受体的方法。还公开了肾血管扩张剂和利尿剂的方法。
• (.+-.)-3-Allyl-6-bromo-7,8-dihydroxy-1-phenyl-2,3,4,5-tetrahydro-1H-3-benzazepine, a new high affinity D1 dopamine receptor ligand: synthesis and structure-activity relationship
  作者：John L. Neumeyer、Nandkishore Baindur、Hyman B. Niznik、H. C. Guan、Philip Seeman

  DOI：10.1021/jm00116a004

  日期：1991.12

  The 7,8-dihydroxy-1-phenyl-2,3,4,5-tetrahydro-1H-3-benzazepines form a series of compounds having a high affinity at the D1 dopamine receptor. The 6-chloro derivative has been previously shown to have enhanced affinity, selectivity, and agonist activity. In an attempt to study the effect of substitution of a 6-bromo group in place of the 6-chloro, we have synthesized a series of compounds and evaluated

  7,8-二羟基-1-苯基-2,3,4,5-四氢-1H-3-苯并ze庚因形成一系列对D1多巴胺受体具有高亲和力的化合物。先前已证明6-氯衍生物具有增强的亲和力，选择性和激动剂活性。为了研究取代6-氯取代6-溴的效果，我们合成了一系列化合物并评估了它们对D1受体的亲和力。结果表明6-溴衍生物与6-氯衍生物具有几乎相同的亲和力，这一发现与D1拮抗剂7-卤代-8-羟基-1-苯基-2,3,4,5-相似。四氢-1H-3-苯并ze庚因系列。从目前的工作来看，3-allyl-6-bromo-7,8-dihydroxy-1-phenyl-2,3,4，
• Pharmaceutical compositions and method of producing anti-Parkinsonism
  申请人：SmithKline Corporation

  公开号：US04052506A1

  公开（公告）日：1977-10-04

  Pharmaceutical compositions and method of producing anti-Parkinsonism activity by administering internally a nontoxic effective quantity of a benzazepine derivative to an animal.

  药物组合物和通过内服对动物施加一种苯并二氮杂环衍生物的无毒有效量来产生抗帕金森症活性的制备方法。