2,5-bis(butylamino)-1,4-benzoquinone | 1520-99-6

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: 2,5-bis(butylamino)-1,4-benzoquinone
• 英文别名: 2,5-bis(n-butylamino)-1,4-benzoquinone；2,5-bis(butylamino)cyclohexa-2,5-diene-1,4-dione；2,5-Bis-butylamino-p-benzochinon；2,5-Di(butylamino)-p-benzochinon；2,5-Bis-(n-butylamino)-p-benzochinon
• CAS: 1520-99-6
• 化学式: C₁₄H₂₂N₂O₂
• 分子量: 250.341
• InChiKey: DUZAFCNACLLQPK-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.8
• 重原子数：
  18
• 可旋转键数：
  8
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.57
• 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：

  4,4'-联吡啶 、 十羰基二铼 、 2,5-bis(butylamino)-1,4-benzoquinone 以 均三甲苯 为溶剂， 反应 10.0h， 以68%的产率得到{(CO)₃Re(μ-η⁴-2,5-bis(phenethylamino)-1,4-benzoquinonato)Re(CO)₃}₂(μ-4,4′-bipyridine)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：

  N-(1,1,3,3-tetramethylbutyl)-p-benzoquinone imine N-oxide 以 苯 为溶剂， 反应 14.0h， 生成 2,5-bis(butylamino)-1,4-benzoquinone
  参考文献：
  名称：

  Baldry, Peter J.; Forrester, Alexander R.; Ogilvy, Munro M., Journal of the Chemical Society. Perkin transactions I, 1982, # 9, p. 2027 - 2034

  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。
• A Catalytic Oxidative Quinone Heterofunctionalization Method: Synthesis of Strongylophorine-26
  作者：Wanwan Yu、Per Hjerrild、Kristian M. Jacobsen、Henriette N. Tobiesen、Line Clemmensen、Thomas B. Poulsen

  DOI：10.1002/anie.201805580

  日期：2018.7.26

  functionalization with a collection of O, N, and S nucleophiles, using oxygen as the terminal oxidant. Preliminary mechanistic observations and the first synthesis of the cytotoxic natural product strongylophorine‐26 is presented.

  理想情况下，杂原子取代的对苯醌的制备是通过直接添加亲核试剂，然后进行原位再氧化来完成的。尽管是一种引人注目的策略，但对p-醌部分的反应性不容易驯服，也没有广泛适用的杂原子官能化方法。这里示出的是，钴（OAC）2和Mn（OAc）3 ⋅2ħ 2 ö充当强大催化剂氧化p为O，N的集合-quinone官能化，和S的亲核试剂，使用氧作为氧化剂终端。介绍了初步的机械观察结果和细胞毒性天然产物Strongylophorine-26的首次合成。
• 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。
• 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