2-(3,4-dimethoxyphenethyl)aniline | 110997-95-0

• 分子结构分类: 有机化合物 - 苯丙烷和聚酮 - 二苯乙烯类
• 英文名称: 2-(3,4-dimethoxyphenethyl)aniline
• 英文别名: 2-[2-(3,4-dimethoxyphenyl)ethyl]aniline；2-[2-(3,4-Dimethoxyphenyl)ethyl]benzenamine
• CAS: 110997-95-0
• 化学式: C₁₆H₁₉NO₂
• 分子量: 257.332
• InChiKey: WJNQJPLVDJDAGO-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.4
• 重原子数：
  19
• 可旋转键数：
  5
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.25
• 拓扑面积：
  44.5
• 氢给体数：
  1
• 氢受体数：
  3

反应信息

• 作为反应物：
  描述：

  2-(3,4-dimethoxyphenethyl)aniline 、 四氯苯二甲酸酐 生成 4,5,6,7-tetrachloro-2-(2-(3,4-dimethoxyphenethyl)phenyl)isoindoline-1,3-dione
  参考文献：
  名称：

  沙利度胺衍生的苯乙基苯基邻苯二甲酰亚胺类似物的抗流感活性

  摘要：

  源自猪的甲型流感病毒已在​​全世界引起大流行，甲型流感被认为是严重的全球健康问题。因此，非常需要靶向这些病毒的新型药物。甲型流感病毒表达对其转录和复制必不可少的RNA聚合酶，该酶包含PA，PB1和PB2亚基。我们从34种合成的来自沙利度胺的苯乙基苯基邻苯二甲酰亚胺类似物（PPT类似物）的筛选中鉴定出潜在的新型抗流感药。对于此筛选，我们使用了PA核酸内切酶抑制测定，PB2致病性决定域结合测定和抗A型流感病毒测定。发现三种PPT类似物PPT-65，PPT-66和PPT-67均能抑制PA核酸内切酶活性并延缓甲型流感的生长，表明它们的活性之间存在相关性。还发现PPT-28抑制甲型流感的生长。这四个类似物共有3,4-二羟基苯乙基。我们还讨论了3,4-二羟基苯乙基柔韧性可能在PA核酸内切酶抑制中起重要功能作用的可能性。另一个带有二甲氧基苯乙基的类似物PPT-62具有PB2致病性决定域结合活性，但没有抑

  DOI：

  10.1016/j.bmc.2010.05.035
• 作为产物：
  描述：

  3,4-二甲氧基苄醇 在 18-冠醚-6 、 palladium 10% on activated carbon 、 氢气 、 三溴化磷 、 potassium carbonate 作用下， 以 二氯甲烷 、 乙酸乙酯 、 甲苯 为溶剂， 反应 7.5h， 生成 2-(3,4-dimethoxyphenethyl)aniline
  参考文献：
  名称：

  四氯邻苯二甲酰亚胺作为肝脏X受体β（LXRβ）选择性激动剂的开发

  摘要：

  肝X受体（LXR）激动剂是通过诱导ABCA1（ATP结合盒A1）基因表达来治疗动脉粥样硬化的候选药物，该基因表达有助于逆转胆固醇转运（RCT）并促进肝脏和肠道中胆固醇的排出。但是，LXR激动剂也会诱导参与脂肪形成的基因，例如SREBP-1c（固醇调节结合元件蛋白1c）和FAS（脂肪酸合酶），从而引起血浆和肝甘油三酯（TG）水平的不良增加。最近的研究表明，LXRα有助于肝脏中的脂肪生成，选择性LXRβ活化可改善小鼠的RCT。因此，LXRβ选择性激动剂有望在不增加血浆或肝TG水平的情况下改善动脉粥样硬化。但是，两个LXR同工型α/β中的配体结合结构域具有较高的序列同一性，几乎没有LXR配体显示出亚型选择性。在这项研究中，我们确定了四氯邻苯二甲酰亚胺类似物作为LXRβ选择性激动剂。结构发展导致（E）-4,5,6,7-四氯-2-（2-苯乙烯基苯基）异吲哚啉-1,3-二酮（24 a），这在报告基因测

  DOI：

  10.1002/cmdc.201600305

文献信息

• Iodine(III)‐Mediated Oxidation of Anilines to Construct Dibenzazepines**
  作者：Carmen Margaret White、Naranchimeg Zorigt、Tianning Deng、Tom G. Driver

  DOI：10.1002/chem.202301141

  日期：2023.7.3

  Cyclization: A mild, room temperature oxidative cyclization of 2-substituted anilines that accesses a broad range of medium-ring N-heterocycles via radical intermediates is reported.

  环化：据报道，2-取代苯胺在室温下进行温和的氧化环化，通过自由基中间体形成多种中环N-杂环。
• Novel enolamides, process for their manufacture and pharmaceutical compositions thereof with an activity as modulators of the arachidonic acid cascade
  申请人：WARNER-LAMBERT COMPANY

  公开号：EP0221345A1

  公开（公告）日：1987-05-13

  The present invention relates to novel enolamide type compounds, pharmaceutical compositions, and methods of use thereof, useful in the treatment of diseases in which products of lipoxygenase enzyme activity or the action of leukotrienes contribute to the pathological condition.

  本发明涉及新型烯酰胺类化合物、药物组合物及其使用方法，可用于治疗脂氧合酶酶活性产物或白三烯作用导致病理状态的疾病。
• Styrylphenylphthalimides as Novel Transrepression-Selective Liver X Receptor (LXR) Modulators
  作者：Sayaka Nomura、Kaori Endo-Umeda、Atsushi Aoyama、Makoto Makishima、Yuichi Hashimoto、Minoru Ishikawa

  DOI：10.1021/acsmedchemlett.5b00170

  日期：2015.8.13

  Anti-inflammatory effects of liver X receptor (LXR) ligands are thought to be largely due to LXR-mediated transrepression, whereas side effects are caused by activation of LXR-responsive gene expression (transactivation). Therefore, selective LXR modulators that preferentially exhibit transrepression activity should exhibit anti-inflammatory properties with fewer side effects. Here, we synthesized a series of styrylphenylphthalirnide analogues and evaluated their structure activity relationships focusing on LXRs-transactivating-agonistic/antagonistic activities and transrepressional activity. Among the compounds examined, 171 showed potent LXR-transrepressional activity with high selectivity over transactivating activity and did not show characteristic side effects of LXR-transactivating agonists in cells. This representative compound, 171, was confirmed to have LXR-dependent transrepressional activity and to bind directly to LXR beta. Compound 171 should be useful not only as a chemical tool for studying the biological functions of LXRs transrepression but also as a candidate for a safer agent to treat inflammatory diseases.
• Separation of α-glucosidase-inhibitory and liver X receptor-antagonistic activities of phenethylphenyl phthalimide analogs and generation of LXRα-selective antagonists
  作者：Kazunori Motoshima、Tomomi Noguchi-Yachide、Kazuyuki Sugita、Yuichi Hashimoto、Minoru Ishikawa

  DOI：10.1016/j.bmc.2009.05.066

  日期：2009.7

  Liver X receptor (LXR) alpha/beta dual agonists are candidate medicaments for the treatment of metabolic syndrome, because their biological actions include increasing cholesterol efflux mediated by LXR beta. However, their clinical application is currently limited by their enhancing effect on triglyceride (TG) synthesis mediated by LXR alpha. Combination of an LXR alpha-selective antagonist with an LXR alpha/beta dual agonist may overcome this disadvantage. In the present work, structural development studies of phenethylphenyl phthalimide 9, which possesses LXR alpha/beta dual-antagonistic activity and alpha-glucosidase-inhibitory activity, led to the LXR alpha-selective antagonist 23f. Specific alpha-glucosidase inhibitors were also obtained. (C) 2009 Elsevier Ltd. All rights reserved.
• (N-substituted-2-hydroxy) benzamides and N-substituted-2-hydroxy-alpha-oxo-benzeneacetamides and pharmaceutical compositions thereof having activity as modulators of the arachidonic acid cascade
  申请人：WARNER-LAMBERT COMPANY

  公开号：EP0221346B1

  公开（公告）日：1991-01-30