5,7-dimethoxy-4'-nitroflavone | 836608-01-6

• 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: 5,7-dimethoxy-4'-nitroflavone
• 英文别名: 5,7-Dimethoxy-2-(4-nitrophenyl)-4H-1-benzopyran-4-one；5,7-dimethoxy-2-(4-nitrophenyl)chromen-4-one
• CAS: 836608-01-6
• 化学式: C₁₇H₁₃NO₆
• 分子量: 327.293
• InChiKey: SRROBMUGHNPBTN-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2
• 重原子数：
  24
• 可旋转键数：
  3
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.12
• 拓扑面积：
  90.6
• 氢给体数：
  0
• 氢受体数：
  6

反应信息

• 作为反应物：
  描述：

  5,7-dimethoxy-4'-nitroflavone 在 盐酸 、 三氯化铝 、 铁粉 、 溶剂黄146 、 硝基苯 、 sodium nitrite 作用下， 生成 4',5-二羟基-7-甲氧基黄酮
  参考文献：
  名称：

  Anand; Venkataraman, Proceedings - Indian Academy of Sciences, Section A, 1947, # 26, p. 279,282

  摘要：

  DOI：
• 作为产物：
  描述：

  2'-hydroxy-4',6'-dimethoxy-4-nitrochalcone 在 indium(III) bromide 、 silica gel 作用下， 反应 0.75h， 以80%的产率得到5,7-dimethoxy-4'-nitroflavone
  参考文献：
  名称：

  硅胶负载的InBr 3和InCl 3：在无溶剂条件下将2'-羟基查耳酮和黄烷酮轻松快速氧化为相应的黄酮的新型催化剂

  摘要：

  硅胶负载的InBr 3或InCl 3（15–20 mol％）被研究为一种新型的固体载体催化剂，可在无溶剂条件下方便，有效地氧化2'-羟基查耳酮和黄烷酮，以产生>的相应黄酮。 80％的产率。在温和的反应条件下，该催化剂易于制备，稳定且有效。

  DOI：

  10.1016/j.tetlet.2004.11.062

文献信息

• Synthesis and Preliminary Biological Evaluation of Chrysin Derivatives as Potential Anticancer Drugs
  作者：Xing Zheng、Fei Fei Zhao、Yun Mei Liu、Xu Yao、Zi Tong Zheng、Xing Luo、Duan Fang Liao

  DOI：10.2174/157340610791208763

  日期：2010.1.1

  A series of chrysin derivatives were prepared from 2-hydroxyacetophenone, 2,4-dihydroxyacetophenone, 2,4,6- trihydroxy- acetophenone, using modified Baker-Venkataraman transformation. Their anticancer activities in vitro were evaluated by the standard MTT method. The results of biological test showed that some of chrysin derivatives showed stronger anticancer activity than 5-fluorouracil.

  一系列白杨素衍生物从2-羟基乙酰苯、2,4-二羟基乙酰苯和2,4,6-三羟基乙酰苯通过改进的Baker-Venkataraman变换法制备而成。它们在体外的抗癌活性通过标准的MTT方法进行评估。生物测试结果显示，一些白杨素衍生物显示出比5-氟尿嘧啶更强的抗癌活性。
• Silica-gel-supported Ce(SO₄)₂·4H₂O-mediated cyclization of 2′-amino and 2′-hydroxychalcones under solvent-free conditions
  作者：Ruihuan Liu、Yan Zhang、Kangping Xu、Guishan Tan

  DOI：10.1080/00397911.2016.1230217

  日期：2017.1.2

  efficient, and environmentally friendly approach for the synthesis of flavones, aza-flavones, and aza-flavanones from corresponding 2′-hydroxy or 2′-aminochalcones has been developed. The reactions are successfully conducted in presence of silica-gel-supported Ce(SO4)2·4H2O under solvent-free conditions. GRAPHICAL ABSTRACT

  摘要 我们开发了一种简单、高效且环保的方法，用于从相应的 2'-羟基或 2'-氨基查耳酮合成黄酮、氮杂黄酮和氮杂黄烷酮。该反应在硅胶负载的Ce(SO4)2·4H2O存在下，在无溶剂条件下成功进行。图形概要
• Synthesis and structure elucidation of five series of aminoflavones using 1D and 2D NMR spectroscopy
  作者：Ana I. R. N. A. Barros、Artur M. S. Silva

  DOI：10.1002/mrc.1895

  日期：2006.12

  Twenty‐six new aminoflavones have been synthesised by two different methods and the structure elucidation was accomplished using extensive 1D (1H, 13C) and 2D NMR spectroscopic studies (COSY, HSQC and HMBC experiments). Copyright © 2006 John Wiley & Sons, Ltd.

  通过两种不同的方法合成了 26 种新的氨基黄酮，并使用广泛的 1D（1H、13C）和 2D NMR 光谱研究（COSY、HSQC 和 HMBC 实验）完成了结构解析。版权所有 © 2006 John Wiley & Sons, Ltd.
• Efficient Synthesis of Nitroflavones by Cyclodehydrogenation of 2′-Hydroxychalcones and by the Baker-Venkataraman Method
  作者：Ana I. R. N. A. Barros、Artur M. S. Silva

  DOI：10.1007/s00706-006-0550-9

  日期：2006.12

  Several nitroflavone derivatives were synthesized by cyclodehydrogenation of 2'-hydroxychalcones and by the Baker-Venkataraman approach, starting from 2'-hydroxyacetophenones and benzoic acid derivatives. Nitroflavones synthesised by the first synthetic approach were obtained in better global yields than those obtained by the later method. The structures of all new compounds were elucidated by microanalyses, 1D and 2D NMR, IR, and mass spectroscopic measurements.
• Collateral sensitivity of resistant MRP1-overexpressing cells to flavonoids and derivatives through GSH efflux
  作者：Doriane Lorendeau、Lauriane Dury、Estelle Genoux-Bastide、Florine Lecerf-Schmidt、Claudia Simões-Pires、Pierre-Alain Carrupt、Raphaël Terreux、Sandrine Magnard、Attilio Di Pietro、Ahcène Boumendjel、Hélène Baubichon-Cortay

  DOI：10.1016/j.bcp.2014.05.017

  日期：2014.8

  The multidrug resistance protein 1 (MRP1) is involved in multidrug resistance of cancer cells by mediating drug efflux out of cells, often in co-transport with glutathione (GSH). GSH efflux mediated by MRP1 can be stimulated by verapamil. In cells overexpressing MRP1, we have previously shown that verapamil induced a huge intracellular GSH depletion which triggered apoptosis of the cells. That phenomenon takes place in the more global anticancer strategy called "collateral sensitivity" and could be exploited to eradicate some chemoresistant cancer cells. Seeking alternative compounds to verapamil, we screened a library of natural flavonoids and synthetic derivatives. A large number of these compounds stimulate MRP1-mediated GSH efflux and the most active ones have been evaluated for their cytotoxic effect on MRP1-overexpressing cells versus parental cells. Interestingly, some are highly and selectively cytotoxic for MRP1-cells, leading them to apoptosis. However, some others do not exhibit any cytotoxicity while promoting a strong GSH efflux, indicating that GSH efflux is necessary but not sufficient for MRP1-cells apoptosis. In support to this hypothesis, structure activity relationships show that the absence of a hydroxyl group at position 3 of the flavonoid C ring is an absolute requirement for induction of MRP1-cells death, but is not for GSH efflux stimulation. Chrysin (compound 8) and its derivatives, compounds 11 and 22, exhibit a high selectivity toward MRP1-cells with a IC50 value of 4.1 mu M for compound 11 and 4.9 mu M for chrysin and compound 22, making them among the best described selective killer compounds of multidrug ABC transporter-overexpressing cells. (C) 2014 Elsevier Inc. All rights reserved.