2-(4-aminophenyl)-5,7-dimethoxy-4H-chromen-4-one | 921942-45-2

• 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-aminophenyl)-5,7-dimethoxy-4H-chromen-4-one
• 英文别名: 5,7-dimethoxy-4'-aminoflavone；2-(4-amino-phenyl)-5,7-dimethoxy-chromen-4-one；2-(4-Amino-phenyl)-5,7-dimethoxy-chromen-4-on；2-(4-Aminophenyl)-5,7-dimethoxy-4H-1-benzopyran-4-one；2-(4-aminophenyl)-5,7-dimethoxychromen-4-one
• CAS: 921942-45-2
• 化学式: C₁₇H₁₅NO₄
• 分子量: 297.31
• InChiKey: HPXNXNNSUFBIAX-UHFFFAOYSA-N

物化性质

• 沸点：
  536.1±50.0 °C(Predicted)
• 密度：
  1.295±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  1.5
• 重原子数：
  22
• 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：
  70.8
• 氢给体数：
  1
• 氢受体数：
  5

反应信息

• 作为反应物：
  描述：

  2-(4-aminophenyl)-5,7-dimethoxy-4H-chromen-4-one 在 盐酸 、 三氯化铝 、 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-羟基-4,6-二甲氧基苯乙酮 在 吡啶 、 叠氮基三甲基硅烷 、 硫酸 、 铜 、 C.I.酸性橙108 、 溶剂黄146 、 盐酸-N-乙基-Nˊ-(3-二甲氨基丙基)碳二亚胺 、 potassium hydroxide 作用下， 以 二氯甲烷 、 N,N-二甲基乙酰胺 为溶剂， 反应 19.0h， 生成 2-(4-aminophenyl)-5,7-dimethoxy-4H-chromen-4-one
  参考文献：
  名称：

  铜介导的三甲基甲硅烷基叠氮化物用于溴代类黄酮的胺化反应以合成独特的氨基类黄酮

  摘要：

  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。

  DOI：

  10.1016/j.tet.2014.04.022

文献信息

• 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.
• 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.