(2-氨基苯基)(3-乙基苯基)甲酮 | 497875-66-8

• 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: (2-氨基苯基)(3-乙基苯基)甲酮
• 英文名称: (2-Amino-phenyl)-(3-ethyl-phenyl)-methanone
• 英文别名: (2-Aminophenyl)(3-ethylphenyl)methanone；(2-aminophenyl)-(3-ethylphenyl)methanone
• CAS: 497875-66-8
• 化学式: C₁₅H₁₅NO
• 分子量: 225.29
• InChiKey: AJQKCZXOPAOQJC-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.9
• 重原子数：
  17
• 可旋转键数：
  3
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.13
• 拓扑面积：
  43.1
• 氢给体数：
  1
• 氢受体数：
  2

反应信息

• 作为反应物：
  描述：

  (2-氨基苯基)(3-乙基苯基)甲酮 在 氨 、 水 、 potassium carbonate 作用下， 以 甲醇 、 二氯甲烷 、 N,N-二甲基甲酰胺 为溶剂， 反应 16.0h， 生成 5-(3-Ethyl-phenyl)-1-(4-methoxy-benzyl)-1,3-dihydro-benzo[e][1,4]diazepin-2-one
  参考文献：
  名称：

  Novel Benzo[1,4]diazepin-2-one Derivatives as Endothelin Receptor Antagonists

  摘要：

  Since its discovery in 1988 by Yanagisawa et al., endothelin (ET), a potent vasoconstrictor, has been widely implicated in the pathophysiology of cardiovascular, cerebrovascular, and renal diseases. Many research groups have embarked on the discovery and development of ET receptor antagonists for the treatment of such diseases. While several compounds, e.g., ambrisentan 2, are in late clinical trials for various indications, one compound (bosentan, Tracleer) is being marketed to treat pulmonary arterial hypertension. Inspired by the structure of ambrisentan 2, we designed a novel class of ET receptor antagonists based on a 1,3,4,5-tetrahydro-1H-benzo[e] [1,4]diazepin-2-one scaffold. Here, we report on the preparation as well as the in vitro and in vivo structure-activity relationships of these derivatives. Potent dual ETA/ETB receptor antagonists with affinities in the low nanomolar range have been identified. In addition, several compounds efficiently reduced arterial blood pressure after oral administration to Dahl salt sensitive rats. In this animal model, the efficacy of the benzo [e] [1,4] diazepin-2-one derivative rac-39au was superior to that of racemic ambrisentan, rac-2.

  DOI：

  10.1021/jm031115r
• 作为产物：
  描述：

  1-溴-3-乙基苯 、 2-氨基苯甲腈 在 magnesium 、 盐酸 作用下， 以 乙醚 为溶剂， 以53%的产率得到(2-氨基苯基)(3-乙基苯基)甲酮
  参考文献：
  名称：

  Novel Benzo[1,4]diazepin-2-one Derivatives as Endothelin Receptor Antagonists

  摘要：

  Since its discovery in 1988 by Yanagisawa et al., endothelin (ET), a potent vasoconstrictor, has been widely implicated in the pathophysiology of cardiovascular, cerebrovascular, and renal diseases. Many research groups have embarked on the discovery and development of ET receptor antagonists for the treatment of such diseases. While several compounds, e.g., ambrisentan 2, are in late clinical trials for various indications, one compound (bosentan, Tracleer) is being marketed to treat pulmonary arterial hypertension. Inspired by the structure of ambrisentan 2, we designed a novel class of ET receptor antagonists based on a 1,3,4,5-tetrahydro-1H-benzo[e] [1,4]diazepin-2-one scaffold. Here, we report on the preparation as well as the in vitro and in vivo structure-activity relationships of these derivatives. Potent dual ETA/ETB receptor antagonists with affinities in the low nanomolar range have been identified. In addition, several compounds efficiently reduced arterial blood pressure after oral administration to Dahl salt sensitive rats. In this animal model, the efficacy of the benzo [e] [1,4] diazepin-2-one derivative rac-39au was superior to that of racemic ambrisentan, rac-2.

  DOI：

  10.1021/jm031115r

文献信息

• Enantioselective Copper-Catalyzed Borylative Cyclization with Cyclic Imides
  作者：Andrew Whyte、Alexa Torelli、Bijan Mirabi、Mark Lautens

  DOI：10.1021/acs.orglett.9b03144

  日期：2019.10.18

  enantioselective borylative cyclization cascade utilizing cyclic imides has been developed. We employ a highly enantioselective borylcupration process that includes a 1,2-addition to a cyclic imide. The products contain a valuable hemiaminal and boronate handle for further elaborations within a congested framework. This work demonstrates the utility of cyclic imides as simple precursors to unlock access to sought-after

  已经开发了利用环状酰亚胺的对映选择性硼化环化级联反应。我们采用高度对映体选择性的硼基缩合工艺，该工艺包括向环状酰亚胺中添加1,2。该产品包含有价值的Hemiaminal和硼酸盐处理，可在拥挤的框架内进行进一步的处理。这项工作证明了环酰亚胺作为简单的前体的用途，可以用来解锁对广受欢迎的多环二氢吲哚的获取。此外，该报告强调了利用反应性催化中间体开发原本不反应的官能团的能力。
• Nickel-Catalyzed Synthesis of Benzo[<i>b</i>]naphtho[1,2-<i>d</i>]azepine via Intramolecular Radical Tandem Cyclization of Alkyl Bromide-Tethered Alkylidenecyclopropanes
  作者：Bo Jiang、Jia-Xin Liu、Yin Wei、Min Shi

  DOI：10.1021/acs.orglett.8b02699

  日期：2018.10.5

  A Ni(II)-catalyzed tandem cyclopropane ring opening and radical alkylation of the aromatic ring using unactivated alkyl bromide-tethered alkylidenecyclopropanes (ACPs) have been described in this paper. This ring-forming process exhibits a broad substrate scope with a variety of primary alkyl bromides and aromatic rings, affording diversified benzo[b]naphtho[1,2-d]azepine derivatives in moderate-to-excellent

  本文描述了Ni（II）催化的串联环丙烷丙烷开环和使用未活化的烷基溴-束缚的亚烷基环丙烷（ACP）对芳环进行自由基烷基化。这种成环过程显示出具有多种伯烷基溴和芳族环的广泛底物范围，在温和条件下以中等至优异的产率提供了多种苯并[ b ]萘[1,2- d ] a庚因衍生物。在包括氘标记检查在内的几个对照实验的基础上，提出了合理的反应机理。还对获得的多环产物进行了进一步的衍生化。
• Novel benzo-fused heterocycles as endothelin antagonisits
  申请人：Bolli Martin

  公开号：US20050124605A1

  公开（公告）日：2005-06-09

  The invention relates to novel benzo-fused heterocycles and their use as active ingredients in the preparation of pharmaceutical compositions. The invention also concerns related aspects including processes for the preparation of the compounds, pharmaceutical compositions containing one or more of those compounds and especially their use as endothelin receptor antagonists.

  本发明涉及新型苯并杂环化合物及其用作制备药物组成物的活性成分。本发明还涉及相关方面，包括制备化合物的过程，含有其中一种或多种化合物的药物组成物，特别是它们作为内皮素受体拮抗剂的用途。
• Phenyl substituted pyrido(1,4)benzodiazepines and intermediates therefor
  申请人：A.H. ROBINS COMPANY, INCORPORATED

  公开号：EP0076017A2

  公开（公告）日：1983-04-06

  [2-[(Aminopyridinyl)amino]Phenyl]aryl-methanones which also have antidepressant activity are used to prepare pyrido[1,4]benzodiazepines having antidepressant activity of the formula wherein Ar is 2, 3 and 4-pyridinyl, 2 or 3-thienyl, phenyl or a substituted phenyl; R is hydrogen, loweralkyl or an amine on the end of a hydrocarbon chain; Z is hydrogen, halogen, trifluoromethyl, loweralkyl, loweralkoxy, hydroxy or nitro; and Y is hydrogen, loweralkyl, loweralkoxy or hydroxy; and the pharmaceutical salts thereof.

  具有抗抑郁活性的[2-[(氨基吡啶基)氨基]苯基]芳基甲酮可用于制备具有抗抑郁活性的吡啶并[1,4]苯并二氮杂卓，其式为 其中 Ar 是 2、3 和 4-吡啶基、2 或 3-噻吩基、苯基或取代苯基；R 是氢、低级烷基或烃链末端的胺；Z 是氢、卤素、三氟甲基、低级烷基、低级烷氧基、羟基或硝基；Y 是氢、低级烷基、低级烷氧基或羟基；以及它们的药用盐。
• US4447361A
  申请人：——

  公开号：US4447361A

  公开（公告）日：1984-05-08