2,5-bis(phenethylamino)-1,4-benzoquinone | 90785-72-1

• 分子结构分类: 有机化合物 - 苯类化合物 - 苯和取代衍生物
• 英文名称: 2,5-bis(phenethylamino)-1,4-benzoquinone
• 英文别名: 2,5-Bis(2-phenylethylamino)cyclohexa-2,5-diene-1,4-dione；2,5-bis(2-phenylethylamino)cyclohexa-2,5-diene-1,4-dione
• CAS: 90785-72-1
• 化学式: C₂₂H₂₂N₂O₂
• 分子量: 346.429
• InChiKey: ILMSIPQZRMTNBI-UHFFFAOYSA-N

物化性质

• 熔点：
  218-220 °C
• 沸点：
  553.6±50.0 °C(Predicted)
• 密度：
  1.19±0.1 g/cm3(Temp: 20 °C; Press: 760 Torr)(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  4.3
• 重原子数：
  26
• 可旋转键数：
  8
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.18
• 拓扑面积：
  58.2
• 氢给体数：
  2
• 氢受体数：
  4

反应信息

• 作为反应物：
  描述：

  十羰基二铼 、 2,5-bis(phenethylamino)-1,4-benzoquinone 、 1,2-二(4-吡啶基)乙烯 以 均三甲苯 为溶剂， 反应 10.0h， 以66%的产率得到{(CO)₃Re(μ-η⁴-2,5-bis(phenethylamino)-1,4-benzoquinonato)Re(CO)₃}₂(μ-trans-1,2-bis(4-pyridyl)ethylene)₂
  参考文献：
  名称：

  Synthesis, Structural Characterization, and Host–Guest Studies of Aminoquinonato-Bridged Re(I) Supramolecular Rectangles

  摘要：

  Aminoquinonato bridged Re(I)-based metallarectangles have been constructed via an orthogonal bonding approach. Self-assembly of Re-2(CO)(10) and aminoquinone ligands in the presence of ditopic linear pyridyl ligands has resulted in the formation of metallarectangles of the general formula [{(CO)(3)Re(mu-eta(4)-L)Re(CO)(3)}(2)(mu-N-L'-N)(2)] (1-4), wherein 1, L = 2,5-bis(n-butylamino)-1,4-benzoquinonato (bbbq) and N-L'-N = 4,4'-bipyridine (bpy); 2, L = 2,5-bis(phenethylamino)-1,4-benzoquinonato (bpbq) and N-L'-N = 4,4'-bipyridine; 3, L = 2,5-bis(n-butylamino)-1,4-benzoquinonato (bbbq) and N-L'-N = trans-1,2-bis(4-pyridyl)ethylene (bpe) and 4, L = 2,5-bis(phenethylamino)-1,4-benzoquinonato (bpbq) and N-L'-N = trans-1,2-bis(4-pyridyl)ethylene (bpe). Metallarectangles 1-4 have been characterized by elemental analysis, IR, NMR, and UV-vis absorption spectroscopic techniques. The molecular structures of 1 and 4 were determined by single-crystal X-ray diffraction methods. The molecular recognition capability of 1 and 3 with pyrene and triphenylene has been investigated using UV-vis absorption and emission spectroscopic techniques. The formation of host guest complex has been further corroborated by the single-crystal X-ray structural evidence of carceplex system (3Dpyrene).(DMF).

  DOI：

  10.1021/acs.inorgchem.5b01543
• 作为产物：
  描述：

  2-苯乙胺 、 对苯醌 以 乙醇 为溶剂， 反应 18.0h， 以61%的产率得到2,5-bis(phenethylamino)-1,4-benzoquinone
  参考文献：
  名称：

  醌类似物作为动力蛋白GTPase抑制剂的开发

  摘要：

  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。

  DOI：

  10.1016/j.ejmech.2014.06.070

文献信息

• Multicomponent Self-Assembly of Diaminobenzoquinonato-Bridged Manganese(I) Metallosupramolecular Rectangles: Host–Guest Interactions, Anticancer Activity, and Visible-Light-Induced CO Releasing Studies
  作者：Dhanaraj Divya、Ramadoss Govindarajan、Ramamurthy Nagarajaprakash、Robert R. Fayzullin、Pitchavel Vidhyapriya、Natarajan Sakthivel、Bala. Manimaran

  DOI：10.1021/acs.inorgchem.2c01829

  日期：2022.10.3

  were determined by the single-crystal X-ray diffraction method. Host–guest binding abilities of 1, 3, and 7 with coronene, pyrene, and 4,4′-dihydroxybiphenyl were investigated using UV–vis absorption and emission spectroscopic techniques. Formation of host–guest complexes was further confirmed by the single-crystal X-ray structural analysis. Absorption of spectra of these metallorectangles showed high-intensity

  Mn 2 (CO) 10、双螯合二氨基苯并醌 (ON∩ON) 桥 (L) 和线性双位接头 (N∩N) (L')的一锅自组装导致形成M 4 L 2 L 2 '型锰(I)基四核金属矩形通式[(CO) 3 Mn(μ-η 4 -L)Mn(CO) 3 } 2 (μ-(NN) 2 )] ( 1 – 8 )，其中 L 为 2,5-双(正丁胺)-1,4-苯醌 ( bbbq )和/或 2,5-双(苯乙氨基)-1,4-苯醌 ( bpbq ) NN 是 4,4'-联吡啶 (bpy )、反式-1,2-双(4-吡啶基)乙烯( bpe )、苯基-1,4-双(异烟酸酯)( pbin )和N , N'-双(4-吡啶基甲酰胺)-1,4 -苯（bpfb）。金属矩形1-8的特征在于红外、紫外-可见 (UV-vis )吸收和1 H 核磁共振光谱、元素分析和电喷雾电离质谱。1 • n (CHCl 3 ) 和coronene⊂ 3的分子和晶体结构•
• Kanao; Inagawa, Yakugaku Zasshi/Journal of the Pharmaceutical Society of Japan, 1938, vol. 58, p. 347,351; dtsch. Ref. S. 71, 74
  作者：Kanao、Inagawa

  DOI：——

  日期：——
• 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
• 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。
• Synthesis, Structural Characterization, and Host–Guest Studies of Aminoquinonato-Bridged Re(I) Supramolecular Rectangles
  作者：R. Govindarajan、R. Nagarajaprakash、Bala. Manimaran

  DOI：10.1021/acs.inorgchem.5b01543

  日期：2015.11.16

  Aminoquinonato bridged Re(I)-based metallarectangles have been constructed via an orthogonal bonding approach. Self-assembly of Re-2(CO)(10) and aminoquinone ligands in the presence of ditopic linear pyridyl ligands has resulted in the formation of metallarectangles of the general formula [(CO)(3)Re(mu-eta(4)-L)Re(CO)(3)}(2)(mu-N-L'-N)(2)] (1-4), wherein 1, L = 2,5-bis(n-butylamino)-1,4-benzoquinonato (bbbq) and N-L'-N = 4,4'-bipyridine (bpy); 2, L = 2,5-bis(phenethylamino)-1,4-benzoquinonato (bpbq) and N-L'-N = 4,4'-bipyridine; 3, L = 2,5-bis(n-butylamino)-1,4-benzoquinonato (bbbq) and N-L'-N = trans-1,2-bis(4-pyridyl)ethylene (bpe) and 4, L = 2,5-bis(phenethylamino)-1,4-benzoquinonato (bpbq) and N-L'-N = trans-1,2-bis(4-pyridyl)ethylene (bpe). Metallarectangles 1-4 have been characterized by elemental analysis, IR, NMR, and UV-vis absorption spectroscopic techniques. The molecular structures of 1 and 4 were determined by single-crystal X-ray diffraction methods. The molecular recognition capability of 1 and 3 with pyrene and triphenylene has been investigated using UV-vis absorption and emission spectroscopic techniques. The formation of host guest complex has been further corroborated by the single-crystal X-ray structural evidence of carceplex system (3Dpyrene).(DMF).