2-phenyl-3-(phenylamino)naphthalene-1,4-dione | 18690-82-9

• 分子结构分类: 有机化合物 - 苯类化合物 - 萘
• 英文名称: 2-phenyl-3-(phenylamino)naphthalene-1,4-dione
• 英文别名: 2-Anilino-3-phenylnaphthalene-1,4-dione
• CAS: 18690-82-9
• 化学式: C₂₂H₁₅NO₂
• 分子量: 325.367
• InChiKey: ZFRMKMWVWYIEER-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  4
• 重原子数：
  25
• 可旋转键数：
  3
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.0
• 拓扑面积：
  46.2
• 氢给体数：
  1
• 氢受体数：
  3

反应信息

• 作为反应物：
  描述：

  2-phenyl-3-(phenylamino)naphthalene-1,4-dione 以22%的产率得到
  参考文献：
  名称：

  FORRESTER A. R.; INGRAM A. S.; JOHN I. L.; THOMSON R. H., J. CHEM. SOC. PERKIN TRANS. PART I, , 1975, NO 12, 1115-1120

  摘要：

  DOI：
• 作为产物：
  描述：

  2-溴-1,4-萘醌 在 palladium diacetate 作用下， 以 水 、 溶剂黄146 为溶剂， 生成 2-phenyl-3-(phenylamino)naphthalene-1,4-dione
  参考文献：
  名称：

  Synthesis, reactive oxygen species generation and copper-mediated nuclease activity profiles of 2-aryl-3-amino-1,4-naphthoquinones

  摘要：

  Here we report a series of 2-aryl-3-amino-1,4-naphthoquinones that generated reactive oxygen species (ROS) such as superoxide and hydrogen peroxide upon incubation in pH 7.4 under ambient aerobic conditions. ROS generation from these compounds was sensitive to structural modifications at the 3-amino position and a 2-aryl substituent promoted ROS generation. A number of these compounds were found to induce DNA damage in the presence of Cu(II) without any added reducing agent. Our data suggests that 2-aryl-3-amino-1,4-naphthoquinones' propensity to produce ROS correlated well with its DNA damage inducing ability. 2-Phenyl-3-pyrrolid-1-yl-1,4-naphthoquinone (22) was found to damage DNA at 1 mu M suggesting that these compounds may have therapeutic relevance in targeting cancers which over-express Cu(II) (C) 2012 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.bmcl.2012.04.009

文献信息

• 一种芳香胺吲哚萘醌衍生物及其制备方法
  申请人：成都师范学院

  公开号：CN112979529B

  公开（公告）日：2023-09-05

  本发明涉及有机合成技术领域，公开了一种芳香胺吲哚萘醌衍生物及其制备方法，化学结构式如下所示：其中，R1选自卤素基、C1～C6的烷基或烷氧基、苯基、氰基或氢，R2选自芳基或芳杂基；制备方法为，将芳香胺和吲哚萘醌衍生物加入反应容器中，并加入溶剂和碱，反应一段时间后，得到粗品，将粗品分离提纯得到产物。本申请通过吲哚萘醌类化合物与芳香胺一步合成目标产物，原料易得，操作简单，合成方便、快捷，可以应用于工业化生产。
• <i>t</i>-BuOK mediated oxidative coupling amination of 1,4-naphthoquinone and related 3-indolylnaphthoquinones with amines
  作者：Yu Dong、Ting Mei、Qi-Qi Luo、Qiang Feng、Bo Chang、Fan Yang、Hong-wei Zhou、Zhi-Chuan Shi、Ji-Yu Wang、Bing He

  DOI：10.1039/d1ra00193k

  日期：——

  3-indolylnaphthoquinones with amines, such as various (hetero)aromatic amine and aliphatic amine via t-BuOK-mediated oxidative coupling at room temperature has been developed. This reaction provides efficient access to the biologically important and synthetically useful 2-amino-1,4-naphthoquinones and 2-amino-3-indolylnaphthoquinones with good yields under mild conditions. The present protocol is simple

  1,4-萘醌和相关的 3-吲哚基萘醌与胺（例如各种（杂）芳香胺和脂肪胺）在室温下通过 t -BuOK 介导的氧化偶联进行无过渡金属胺化。该反应可以在温和条件下以良好的收率有效地获得具有重要生物学意义和合成用途的2-氨基-1,4-萘醌和2-氨基-3-吲哚基萘醌。本方案简单实用，具有良好的官能团耐受性。此外，将所得2-氨基-3-吲哚基萘醌进一步转化合成多环N-杂环。
• A SUCCESSFUL PREPARATION OF 2-ARYL-2,3-DIHYDRO-2,3-IMINO-1,4-NAPHTHOQUINONES
  作者：Kazuhiro Maruyama、Takuji Ogawa

  DOI：10.1246/cl.1981.1027

  日期：1981.7.5

  A new class of compounds, 2-aryl-2,3-dihydro-2,3-imino-1,4-naphthoquinones 3, was synthesized for the first time by heating 2-aryl-1,4-naphthoquinones with aryl azides. The yields were 30–50% when p-methoxyphenyl azide was used.

  通过加热 2-芳基-1,4-萘醌与芳基叠氮化物，首次合成了一类新化合物，即 2-芳基-2,3-二氢-2,3-亚氨基-1,4-萘醌 3。使用对甲氧基苯基叠氮化物时，产率为 30-50%。
• INHIBITORS OF THE MITF MOLECULAR PATHWAY
  申请人：THE GENERAL HOSPITAL CORPORATION

  公开号：US20160130222A1

  公开（公告）日：2016-05-12

  Provided herein are compounds of the formula (IV) as well as pharmaceutically acceptable salts thereof, wherein the substituents are as those disclosed in the specification. These compounds, and the pharmaceutical compositions containing them, are useful as MITF inhibitors, MITF pathway inhibitors and for the treatment of cancer.

  本文提供的是公式（IV）的化合物及其药学上可接受的盐，其中取代基如规范中所披露的那样。这些化合物及其含有的药物组合物可用作MITF抑制剂、MITF通路抑制剂以及治疗癌症的药物。
• BiCl₃ catalyzed synthesis of 2-amino-1,4-naphthoquinones and 1,4-naphthoquinon-2-sulfides and one-pot sequential amine-arylation of 1,4-naphthoquinone
  作者：Mayurakhi Bhuyan、Gakul Baishya

  DOI：10.1039/d2ob01792j

  日期：——

  Using the Lewis acid catalyst BiCl3, a new method for the synthesis of 2-amino-1,4-naphthoquinones and 1,4-naphthoquinon-2-sulfides from 1,4-naphthoquinone has been devised. This method has a broad substrate scope and product extraction is easy. It is low-cost, requires mild and sustainable reaction conditions and results in superior product yields. Additionally, this study presents the first technique

  使用路易斯酸催化剂BiCl 3，设计了一种从1,4-萘醌合成2-氨基-1,4-萘醌和1,4-萘醌-2-硫化物的新方法。该方法底物适用范围广，产物提取容易。它成本低廉，需要温和且可持续的反应条件，并可提高产品收率。此外，本研究提出了第一种用胺和芳基肼/K 2 S 2 O 8进行单锅顺序胺芳基化的技术直接从 1,4-萘醌生产芳基化 2-氨基-1,4-萘醌。这种从经历自由基偶联反应的芳基肼产生芳基自由基的操作上直接的通过自由基捕获控制实验得到了很好的证明。