2,5-bis(4-methoxyphenylamino)-p-benzoquinone | 24605-58-1

• 分子结构分类: 有机化合物 - 苯类化合物 - 苯酚醚
• 英文名称: 2,5-bis(4-methoxyphenylamino)-p-benzoquinone
• 英文别名: 2,5-bis(4-methoxyanilino)-1,4-benzoquinone；2,5-bis-(4-methoxylanilino)-1,4-benzoquinone；2,5-(4-methoxy anilino)-1,4-benzoquinone；2.5-Di(p-methoxy-anilino)-1.4-p-benzochinon；2,5-di-p-anisidino-[1,4]benzoquinone；2,5-Di-p-anisidino-[1,4]benzochinon；2,5-Bis[(4-methoxyphenyl)amino]cyclohexa-2,5-diene-1,4-dione；2,5-bis(4-methoxyanilino)cyclohexa-2,5-diene-1,4-dione
• CAS: 24605-58-1
• 化学式: C₂₀H₁₈N₂O₄
• 分子量: 350.374
• InChiKey: IPVQVWWHIYQFKZ-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.5
• 重原子数：
  26
• 可旋转键数：
  6
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.1
• 拓扑面积：
  76.7
• 氢给体数：
  2
• 氢受体数：
  6

反应信息

• 作为产物：
  描述：

  对苯醌 生成 2,5-bis(4-methoxyphenylamino)-p-benzoquinone
  参考文献：
  名称：

  OSMAN A. M.; HAMMAM A. S.; SALAH A. T., INDIAN J. CHEM., 1977, B15, NO 12, 1118-1120

  摘要：

  DOI：

文献信息

• Development of quinone analogues as dynamin GTPase inhibitors
  作者：Kylie A. MacGregor、Mohammed K. Abdel-Hamid、Luke R. Odell、Ngoc Chau、Ainslie Whiting、Phillip J. Robinson、Adam McCluskey

  DOI：10.1016/j.ejmech.2014.06.070

  日期：2014.10

  Virtual screening of the ChemDiversity and ChemBridge compound databases against dynamin I (dynI) GTPase activity identified 2,5-bis-(benzylamino)-1,4-benzoquinone 1 as a 273 ± 106 μM inhibitor. In silico lead optimization and focused library-led synthesis resulted in the development of four discrete benzoquinone/naphthoquinone based compound libraries comprising 54 compounds in total. Sixteen analogues

  针对dynamin I（dynI）GTPase活性对ChemDiversity和ChemBridge化合物数据库进行的虚拟筛选确定了2,5-双-（苄氨基）-1,4-苯醌1为273±106μM抑制剂。在计算机上进行了铅优化和以库为主导的合成，开发了四个基于苯醌/萘醌的化合物库，总共包含54种化合物。16种类似物比铅1更有效，其中2,5-双-（4-羟基苯胺基）-1,4-苯醌（45）和2,5-双（4-羧基苯胺基）-1,4-苯醌（49） IC 50最活跃值分别为11.1±3.6和10.6±1.6μM。分子建模表明，dynI GTP结合位点内49个分子的稳定化涉及许多氢键和疏水相互作用。评价了六个活性最高的抑制剂对网格蛋白介导的内吞作用（CME）的潜在抑制作用。醌45是最有效的CME抑制剂，IC 50（CME）为36±16μM。
• Benzoquinone Derivatives For Treatment Of Cancer And Methods Of Making The Benzoquinone Derivatives
  申请人：United Arab Emirates University

  公开号：US20170283366A1

  公开（公告）日：2017-10-05

  The present invention benzoquinone derivatives of the formula (I): and to pharmaceutically acceptable salts or solvates thereof. In formula (I) one of X or Y is hydrogen and the other one of X or Y is 3-Trifluoro-methylaniline; 3,4,5-trifluoroaniline; 4-methoxylaniline; 4-fluoroaniline; 3,3′-Dimethyl-1,1′-Biphenyl-4,4′-diamine; 2-(pyrrolidin-l-yl)ethyl)amine; 4-trifluoromethyl-benzylamine ; 4-fluorobenzyl-amine; 3,4-dimethoxybenzylamine; or 3,5-ditrifluoromethyl-benzylamine. Compounds of formula (I) have been identified as being useful in the treatment of cancer, in particular lung, breast and pancreatic cancer. The invention relates also to a method of making the benzoquinone derivatives and to methods of treatment.

  本发明涉及公式(I)的苯醌衍生物，以及其药学上可接受的盐或溶剂化合物。在公式(I)中，X或Y中的一个是氢，另一个是3-三氟甲基苯胺；3,4,5-三氟苯胺；4-甲氧基苯胺；4-氟苯胺；3,3′-二甲基-1,1′-联苯-4,4′-二胺；2-(吡咯啉-1-基)乙基)胺；4-三氟甲基苄胺；4-氟苄胺；3,4-二甲氧基苄胺；或3,5-二三氟甲基苄胺。已确定公式(I)的化合物在治疗癌症，特别是肺癌、乳腺癌和胰腺癌方面具有用途。本发明还涉及制备苯醌衍生物的方法以及治疗方法。
• Aryl nitrenes from N,N′-diarylbenzoquinone di-imine N,N′-dioxides and N-arylbenzoquinone imine N-oxides
  作者：Alexander R. Forrester、Munro M. Ogilvy、Ronald H. Thomson

  DOI：10.1039/p19820002023

  日期：——

  Photolyses of the title quinone imine N-oxides give mainly azoarenes formed by dimerisation of triplet aryl nitrenes.

  标题醌亚胺N-氧化物的光解主要产生由三重芳基腈的二聚作用形成的偶氮芳烃。
• Synthesis of 3-[(N-carboalkoxy)ethylamino]-indazole-dione derivatives and their biological activities on human liver carbonyl reductase
  作者：Solomon Berhe、Andrew Slupe、Choice Luster、Henry A. Charlier、Don L. Warner、Leon H. Zalkow、Edward M. Burgess、Nkechi M. Enwerem、Oladapo Bakare

  DOI：10.1016/j.bmc.2009.11.011

  日期：2010.1

  A series of indazole-dione derivatives were synthesized by the 1,3-dipolar cycloaddition reaction of appropriate substituted benzoquinones or naphthoquinones and N-carboalkoxyamino diazopropane derivatives. These compounds were evaluated for their effects on human carbonyl reductase. Several of the analogs were found to serve as substrates for carbonyl reductase with a wide range of catalytic efficiencies, while four analogs display inhibitory activities with IC50 values ranging from 3-5 mu M. Two of the inhibitors were studied in greater detail and were found to be noncompetitive inhibitors against both NADPH and menadione with K-I values ranging between 2 and 11 mu M. Computational studies suggest that conformation of the compounds may determine whether the indazole-diones bind productively to yield product or nonproductively to inhibit the enzyme. (C) 2009 Elsevier Ltd. All rights reserved.
• 2,5-Diamino-1,4-benzoquinones¹
  作者：John H. Billman、Donald G. Thomas、David K. Barnes

  DOI：10.1021/ja01214a503

  日期：1946.10