2,5-bis(cyclohexylamino)-1,4-benzoquinone | 1653-85-6

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: 2,5-bis(cyclohexylamino)-1,4-benzoquinone
• 英文别名: 2,5-biscyclohexylamino-[1,4]benzoquinone；2,5-bis-cyclohexylamino-[1,4]benzoquinone；2,5-Bis-cyclohexylamino-[1,4]benzochinon；2,5-Cyclohexadiene-1,4-dione, 2,5-bis(cyclohexylamino)-；2,5-bis(cyclohexylamino)cyclohexa-2,5-diene-1,4-dione
• CAS: 1653-85-6
• 化学式: C₁₈H₂₆N₂O₂
• 分子量: 302.417
• InChiKey: XLIUAPHHAGSADZ-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  4
• 重原子数：
  22
• 可旋转键数：
  4
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.67
• 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：

  alkaline earth salt of/the/ methylsulfuric acid 在 mineral acid 作用下， 生成 2,5-bis(cyclohexylamino)-1,4-benzoquinone
  参考文献：
  名称：

  Garreau, Annales de Chimie (Cachan, France), 1938, vol. <11> 10, p. 485,546

  摘要：

  DOI：

文献信息

• Synthesis of 2,5-Diaminoquinones by One-Pot Copper-Catalyzed Aerobic Oxidation of Hydroquinones and Addition Reaction of Amines
  作者：Sungjin Kim、Daehwan Kim、Jaiwook Park

  DOI：10.1002/adsc.200900347

  日期：2009.11

  oxidation of various hydroquinones was achieved by using copper nanoparticles entrapped in aluminum oxyhydroxide [Cu/AlO(OH)] at room temperature. Furthermore, 2,5-diamino-1,4-benzoquinones were synthesized directly from hydroquinone and amines by a one-pot procedure consisting of the copper-catalyzed aerobic oxidation of hydroquinones and the double addition of amines to the resulting quinones.

  在室温下，通过使用羟基氧化铝[Cu / AlO（OH）]截留的铜纳米颗粒，可实现各种对苯二酚的好氧氧化。此外，通过一锅法直接由对苯二酚和胺合成2，5-二氨基-1,4-苯醌，该一锅法由铜催化的对苯二酚好氧氧化和向所得醌双加胺。
• Study on self-assembling molecular complexes through hydrogen bonding
  作者：Ruifeng Zhang、Haipeng Zheng、Jiacong Shen

  DOI：10.1016/s0022-2860(97)00436-5

  日期：1998.4

  Abstract A self-complementary hydrogen-bonding recognition unit—2,5-bis(alkylamino)-1,4-benzoquinone has been synthesized and studied. The formation of hydrogen bond in both solid and solution state has been further investigated by means of FTIR, 1 H NMR and UV-visible spectra, as well as X-ray diffraction. It can be concluded from the obtained results that the molecular complexes of this kind of compounds

  摘要 合成并研究了一种自互补氢键识别单元——2,5-双(烷基氨基)-1,4-苯醌。通过 FTIR、 1 H NMR 和紫外-可见光谱以及 X 射线衍射进一步研究了固体和溶液状态下氢键的形成。由所得结果可知，该类化合物的分子配合物具有带状主链，对保持层状超分子结构起重要作用。
• Structure-Activity Studies on Therapeutic Potential of Thymoquinone Analogs in Pancreatic Cancer
  作者：Sanjeev Banerjee、Asfar S. Azmi、Subhash Padhye、Marjit W. Singh、Jubaraj B. Baruah、Philip A. Philip、Fazlul H. Sarkar、Ramzi M. Mohammad

  DOI：10.1007/s11095-010-0145-3

  日期：2010.6

  Pancreatic cancer (PC) is one of the deadliest of all tumors. Previously, we were the first to show that Thymoquinone (TQ) derived from black seed (Nigella sativa) oil has anti-tumor activity against PC. However, the concentration of TQ required was considered to be high to show this efficacy. Therefore, novel analogs of TQ with lower IC50 are highly desirable. We have synthesized a series of 27 new analogs of TQ by modifications at the carbonyl sites or the benzenoid sites using single pot synthesis and tested their biological activity in PC cells. Among these compounds, TQ-2G, TQ-4A1 and TQ-5A1 (patent pending) were found to be more potent than TQ in terms of inhibition of cell growth, induction of apoptosis and modulation of transcription factor-NF-κB. We also found that our novel analogs were able to sensitize gemcitabine and oxaliplatin-induced apoptosis in MiaPaCa-2 (gemcitabine resistant) PC cells, which was associated with down-regulation of Bcl-2, Bcl-xL, survivin, XIAP, COX-2 and the associated Prostaglandin E2. From our results, we conclude that three of our novel TQ analogs warrant further investigation against PC, especially in combination with conventional chemotherapeutic agents.

  胰腺癌（PC）是所有肿瘤中最致命的一种。此前，我们首次证明了一种源自黑种草（Nigella sativa）油的成分——胸腺酮（TQ）对胰腺癌具有抗肿瘤活性。然而，所需的TQ浓度被认为过高，难以显示其疗效。因此，具有更低IC50的新型TQ类似物是非常渴望的。我们通过对羰基位点或苯环位点进行改造，采用单锅合成方法合成了一系列27种新型TQ类似物，并测试了它们在胰腺癌细胞中的生物活性。在这些化合物中，TQ-2G、TQ-4A1和TQ-5A1（专利申请中）在抑制细胞生长、诱导凋亡和调节转录因子NF-κB方面显示出比TQ更强的活性。我们还发现，我们的新型类似物能够增强MiaPaCa-2（耐吉西他滨）胰腺癌细胞中吉西他滨和奥沙利铂诱导的凋亡，这与Bcl-2、Bcl-xL、survivin、XIAP、COX-2及相关前列腺素E2的下调有关。综上所述，我们得出结论，三种新型TQ类似物值得进一步对胰腺癌的研究，特别是与传统化疗药物结合使用。
• 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
• Facile synthesis and spectral characterization of 2, 5-bis (cyclohexylamino)-1, 4-benzoquinone polymorphs from methyl and ethyl protocatechuic aldehydes
  作者：A. Asha、A. Sheena Mohan、S. Suma、M.R. Sudarsanakumar、M.R. Prathapachandra Kurup

  DOI：10.1016/j.molstruc.2017.03.106

  日期：2017.8

  Two polymorphs of 2,5-bis(cyclohexylamino)-1,4-benzoquinone (BCBQI&BCBQII) are synthesized by an efficient alternate method which includes the oxidation of an aromatic aldehyde to benzoquinone moiety followed by its nucleophilic substitution in a single pot. The synthesized polymorphs have been characterized and distinguished by spectral and single crystal X-ray diffraction methods. A possible mechanism for the conversion is also suggested. (C) 2017 Elsevier B.V. All rights reserved.