2,5-bis(2-(morpholin-4-yl)ethylamino)-[1,4]benzoquinone | 101873-27-2

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: 2,5-bis(2-(morpholin-4-yl)ethylamino)-[1,4]benzoquinone
• 英文别名: 2,5-bis-(4-(2-aminoethyl)morfoline)-1,4-benzoquinone；2,5-bis((2-morpholinoethyl)amino)-1,4-benzoquinone；2,5-bis-(2-morpholino-ethylamino)-[1,4]benzoquinone；2,5-Bis-(2-morpholino-aethylamino)-[1,4]benzochinon；2,5-Bis(2-morpholin-4-ylethylamino)cyclohexa-2,5-diene-1,4-dione
• CAS: 101873-27-2
• 化学式: C₁₈H₂₈N₄O₄
• 分子量: 364.445
• InChiKey: ZRNYJVSWAZNWRB-UHFFFAOYSA-N

物化性质

• 熔点：
  189-190 °C
• 沸点：
  560.6±50.0 °C(Predicted)
• 密度：
  1.26±0.1 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  -0.3
• 重原子数：
  26
• 可旋转键数：
  8
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.67
• 拓扑面积：
  83.1
• 氢给体数：
  2
• 氢受体数：
  8

反应信息

• 作为产物：
  描述：

  (3-piperidino-propylamino)-[1,4]benzoquinone 在 1,4-二氧六环 、 氧气 作用下， 生成 2,5-bis(2-(morpholin-4-yl)ethylamino)-[1,4]benzoquinone
  参考文献：
  名称：

  Amino- and Ammonium-alkylaminobenzoquinones as Curarimimetic Agents

  摘要：

  DOI：

  10.1021/ja01162a088

文献信息

• 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。
• Synthesis and Biological Evaluation of 2,5-Bis(alkylamino)-1,4-benzoquinones
  作者：Luiz Cláudio Almeida Barbosa、Ulisses Alves Pereira、Célia Regina Alvares Maltha、Róbson Ricardo Teixeira、Vânia Maria Moreira Valente、José Roberto Oliveira Ferreira、Letícia Veras Costa-Lotufo、Manoel Odorico Moraes、Cláudia Pessoa

  DOI：10.3390/molecules15085629

  日期：——

  A series of twelve 2,5-bis(alkylamino)-1,4-benzoquinones were prepared in yields ranging from 9-58% via the reaction between p-benzoquinone and various amines. The structures of the synthesized compounds were confirmed by IR, 1H- and 13C-NMR and MS analyses. The phytotoxicity of the 2,5-bis(alkylamino)-1,4-benzoquinones was evaluated against two crop species, Cucumis sativus and Sorgum bicolor, at

  通过对苯醌与各种胺之间的反应，以 9-58% 的产率制备了一系列 12 种 2,5-双（烷基氨基）-1,4-苯醌。合成化合物的结构通过IR、1H-和13C-NMR和MS分析证实。2,5-双(烷基氨基)-1,4-苯醌对两种作物物种、Cucumis sativus 和双色高粱的植物毒性进行了评估，浓度为 1.0 x 10(-3) mol/L。一般来说，醌类对双子叶植物 C. sativus (7-74%) 显示出抑制作用。另一方面，在双色链球菌（单子叶植物）上观察到刺激作用。在对杂草物种 Ipomoea grandifolia（双子叶）和 Brachiaria decumbens（单子叶）进行的生物测定中观察到类似的结果。此外，2,5-双(烷基氨基)-1的细胞毒性，4-苯醌针对 HL-60（白血病）、MDA-MB-435（黑色素瘤）、SF-295（脑）和 HCT-8（结肠）人癌细胞系和人外周血单核细胞
• Makarowa; Berlin, Zhurnal Obshchei Khimii, 1959, vol. 29, p. 666,667,668,670
  作者：Makarowa、Berlin

  DOI：——

  日期：——
• Synthesis, biological evaluation, and molecular docking studies of 2,5-substituted-1,4-benzoquinone as novel urease inhibitors
  作者：Zhong-Lu You、Dong-Mei Xian、Mei Zhang、Xiao-Shan Cheng、Xiao-Fang Li

  DOI：10.1016/j.bmc.2012.07.002

  日期：2012.8

  A series of 2,5-substituted-1,4-benzoquinone (1-6) were prepared and structurally characterized by elemental analysis, IR spectra, H-1 and C-13 NMR spectra, and single crystal X-ray determination. The urease inhibitory activities of the compounds against H. pylori urease were studied. Among the compounds, 2,5-bis(2-morpholin-4-ylethylamino)-[1,4]benzoquinone (2) shows the most effective activity with IC50 value of 27.30 +/- 2.17 mu M. Docking simulation was performed to insert compound 2 into the crystal structure of H. pylori urease at the active site to determine the probable binding mode. As a result, compound 2 may be used as a potential urease inhibitor. (C) 2012 Elsevier Ltd. All rights reserved.