2-(4-bromophenyl)-5,7-dihydroxy-4H-chromen-4-one | 152969-70-5

• 分子结构分类: 有机化合物 - 苯丙烷和聚酮 - 黄酮类化合物
• 英文名称: 2-(4-bromophenyl)-5,7-dihydroxy-4H-chromen-4-one
• 英文别名: 5,7-dimethoxy-4'-bromoflavone；2-(4-bromophenyl)-5’,7’-dihydroxy-chromen-4-one；2-(4-bromophenyl)-5,7-dihydroxychromen-4-one
• CAS: 152969-70-5
• 化学式: C₁₅H₉BrO₄
• 分子量: 333.138
• InChiKey: WZIDCTPTSYWUCA-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.8
• 重原子数：
  20
• 可旋转键数：
  1
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.0
• 拓扑面积：
  66.8
• 氢给体数：
  2
• 氢受体数：
  4

反应信息

• 作为产物：
  描述：

  1-[2-羟基-4,6-双(甲氧基甲氧基)苯基]乙酮,2',4'-双(甲氧基甲氧基)-6'-羟基苯乙酮 在 Amberlyst 、 sodium hydride 作用下， 以 四氢呋喃 、 异丙醇 为溶剂， 生成 2-(4-bromophenyl)-5,7-dihydroxy-4H-chromen-4-one
  参考文献：
  名称：

  Mavel, S.; Dikic, B.; Emond, P., Journal of labelled compounds and radiopharmaceuticals, 2003, vol. 46, p. S134 - S134

  摘要：

  DOI：

文献信息

• Novel synthesised flavone derivatives provide significant insight into the structural features required for enhanced anti-proliferative activity
  作者：Divyashree Ravishankar、Kimberly A. Watson、Francesca Greco、Helen M. I. Osborn

  DOI：10.1039/c6ra11041j

  日期：——

  = 1.81 μM)). Overall, 15f and 16f exhibited 7–46 fold greater anti-proliferative potency than the natural flavone chrysin (2d). A systematic structure–activity relationship study against the breast cancer cell lines highlighted that free hydroxyl groups and the B-ring phenyl groups were essential for enhanced anti-proliferative activities. Substitution of the 4-CO functionality with a 4-CS functionality

  随着许多癌症显示出对当前化学疗法的抗性，寻找新型抗癌药引起了极大的关注。天然类黄酮已被确认为此类计划的有用线索。然而，由于通常缺乏对最佳活性的结构要求的深入了解，因此在实现类黄酮作为抗增殖剂的全部潜力之前，需要进行进一步的研究。本文构建了一个包含76个甲氧基和羟基黄酮及其4-硫代类似物的宽泛文库，并建立了它们与乳腺癌细胞系MCF-7（ER + ve），MCF-7 /的抗增殖活性的结构-活性关系。探测了DX（ER + ve，抗蒽环类）和MDA-MB-231（ER -ve）。在该库中，有42种化合物是新颖的，所有化合物的收率都很高，纯度95％。最有前途的先导化合物，特别是新型羟基4-硫代黄酮美国国家癌症研究所（NCI）进一步评估了15f和16f对多种癌细胞系的抗增殖活性，并显示出显着的生长抑制特征（例如化合物15f：MCF-7（GI 50 = 0.18μM），T-47D（GI 50 = 0.03μM）和MDA-MB-468（GI
• Synthetic flavonoid derivatives targeting the glycogen phosphorylase inhibitor site: QM/MM-PBSA motivated synthesis of substituted 5,7-dihydroxyflavones, crystallography, in vitro kinetics and ex-vivo cellular experiments reveal novel potent inhibitors
  作者：Ben A. Chetter、Efthimios Kyriakis、Daniel Barr、Aikaterini G. Karra、Elisabeth Katsidou、Symeon M. Koulas、Vassiliki T. Skamnaki、Timothy J. Snape、Anna-Maria G. Psarra、Demetres D. Leonidas、Joseph M. Hayes

  DOI：10.1016/j.bioorg.2020.104003

  日期：2020.9

  agents. Flavonoids are novel inhibitors of GP, but their mode of action is unspecific in terms of the GP binding sites involved. Towards design of synthetic flavonoid analogues acting specifically at the inhibitor site and to exploit the site’s hydrophobic pocket, chrysin has been employed as a lead compound for the in silico screening of 1169 new analogues with different B ring substitutions. QM/MM-PBSA

  糖原磷酸化酶（GP）是开发新型抗高血糖药的重要目标。黄酮类化合物是GP的新型抑制剂，但是它们的作用方式在涉及的GP结合位点方面没有特异性。为了设计专门作用于抑制剂位点的合成类黄酮类似物，并利用该位点的疏水口袋，采用了菊花蛋白作为先导化合物，用于计算机筛选1169种具有不同B环取代的新类似物。QM / MM-PBSA结合自由能的计算指导了8种化合物的最终选择，随后使用Baker-Venkataraman重排-环化方法进行合成。针对兔肌肉GPa和GPb以及人肝脏GPa的动力学实验揭示了其中的三种化合物（11，20和43）中的最有效的，其结合在现场（ķ我小号<4μM对于所有三种同种型），和比以前更有效报道的天然类黄酮抑制剂。多次抑制研究表明，仅在抑制剂位点结合。该结合与葡萄糖是协同的，表明抑制作用可以通过血糖水平来调节，并且随着达到正常血糖而降低。化合物43是肝细胞糖原分解的有效抑制剂（IC 50
• Copper-mediated trimethylsilyl azide in amination of bromoflavonoids to synthesize unique aminoflavonoids
  作者：Tzenge-Lien Shih、Chi-En Chou、Wen-Yu Liao、Chih-Ang Hsiao

  DOI：10.1016/j.tet.2014.04.022

  日期：2014.6

  Aminoflavonoids are unique antioxidants comparing to other abundant flavonoids in nature. Their syntheses and biological activities were scarcely reported. An effectively copper-mediated amination of the corresponding bromoflavonoids to synthesize a series of new aminoflavonoids is described.

  与自然界中其他丰富的类黄酮相比，氨基类黄酮是独特的抗氧化剂。几乎没有报道它们的合成和生物学活性。描述了一种有效的铜介导的相应溴代类黄酮的胺化反应，以合成一系列新的氨基类黄酮。
• Synthesis and biological evaluation of a series of flavone derivatives as potential radioligands for imaging the multidrug resistance-associated protein 1 (ABCC1/MRP1)
  作者：Sylvie Mavel、Branko Dikic、Somchit Palakas、Patrick Emond、Ivan Greguric、Adrienne Gomez de Gracia、Filomena Mattner、Manuel Garrigos、Denis Guilloteau、Andrew Katsifis

  DOI：10.1016/j.bmc.2005.10.009

  日期：2006.3

  Multidrug resistance (MDR) is one of the major problems affecting the treatment of cancer. In vivo visualization and quantification of MDR proteins would be of great value to better select the therapeutic strategy. Six flavone-based compounds were synthesized and evaluated for their cytotoxic activity and MDR-reversing capacity using hMRP1 or hMDR1 overexpressing cell lines for in vitro assays. All the flavone derivatives were highly selective for hMRP1-expressing cell lines. These derivatives each used at 4 mu M (a non-cytotoxic concentration) enhance significantly the sensitivity of hMRP1-mediated MDR cell line toward doxorubicin toxicity. Their MDR-reversing capacity suggests that, in particular, the 4'-fluoroalkyloxy and 4'-iodo apigenin derivatives are potential new radiopharmaceuticals to visualize in vivo MRP1-mediated MDR phenomenon by PET or SPECT. (c) 2005 Elsevier Ltd. All rights reserved.
• Mavel, S.; Dikic, B.; Emond, P., Journal of labelled compounds and radiopharmaceuticals, 2003, vol. 46, p. S134 - S134
  作者：Mavel, S.、Dikic, B.、Emond, P.、Greguric, I.、Palakas, S.、Katsifis, A.、Gracia, A. Gomez de、Mattner, F.、Garrigos, M.、Besnard, J. C.、Guilloteau, D.

  DOI：——

  日期：——