2,5-bis-(cyclopentylamino)-1,4-benzoquinone | 1521-05-7

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: 2,5-bis-(cyclopentylamino)-1,4-benzoquinone
• 英文别名: 2,5-(cyclopentyl amino)-1,4-benzoquinone；2,5-Biscyclopentylamino-[1,4]Benzoquinone；2,5-bis(cyclopentylamino)cyclohexa-2,5-diene-1,4-dione
• CAS: 1521-05-7
• 化学式: C₁₆H₂₂N₂O₂
• 分子量: 274.363
• InChiKey: VJPVWCSELFNAOR-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3
• 重原子数：
  20
• 可旋转键数：
  4
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.62
• 拓扑面积：
  58.2
• 氢给体数：
  2
• 氢受体数：
  4

反应信息

• 作为产物：
  描述：

  对苯二酚 、 环戊胺 以 甲醇 为溶剂， 反应 1.0h， 以92%的产率得到2,5-bis-(cyclopentylamino)-1,4-benzoquinone
  参考文献：
  名称：

  Synthesis, biological evaluation, and molecular docking studies of 2,5-substituted-1,4-benzoquinone as novel urease inhibitors

  摘要：

  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.

  DOI：

  10.1016/j.bmc.2012.07.002

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, electrochemical and anti-microbial study of 2,5-diamino benzoquinones
  作者：A. Asha、S. Suma

  DOI：10.1016/j.jics.2021.100316

  日期：2022.2
• 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.