4-nitro-2'-hydroxy-4',6'-dimethoxychalcone | 182618-23-1

• 分子结构分类: 有机化合物 - 苯丙烷和聚酮 - 直链 1,3-二芳基丙烷
• 英文名称: 4-nitro-2'-hydroxy-4',6'-dimethoxychalcone
• 英文别名: 1-(2-Hydroxy-4,6-dimethoxyphenyl)-3-(4-nitrophenyl)prop-2-en-1-one
• CAS: 182618-23-1
• 化学式: C₁₇H₁₅NO₆
• 分子量: 329.309
• InChiKey: ZEDWAUANRLMMQK-UHFFFAOYSA-N

物化性质

• 沸点：
  560.1±50.0 °C(Predicted)
• 密度：
  1.327±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  3.21
• 重原子数：
  24.0
• 可旋转键数：
  6.0
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.12
• 拓扑面积：
  98.9
• 氢给体数：
  1.0
• 氢受体数：
  6.0

反应信息

• 作为反应物：
  描述：

  4-nitro-2'-hydroxy-4',6'-dimethoxychalcone 在 cerium (IV) sulfate tetrahydrate 、 silica gel 作用下， 以 neat (no solvent) 为溶剂， 反应 2.0h， 以93%的产率得到5,7-dimethoxy-4'-nitroflavone
  参考文献：
  名称：

  在无溶剂条件下硅胶负载的 Ce(SO4)2·4H2O 介导的 2'-氨基和 2'-羟基查尔酮环化

  摘要：

  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

  DOI：

  10.1080/00397911.2016.1230217
• 作为产物：
  描述：

  2,4,6-三甲氧基苯乙酮 在 盐酸 、 氢氧化钾 、 aluminum tri-bromide 作用下， 以 乙醇 为溶剂， 反应 3.0h， 生成 4-nitro-2'-hydroxy-4',6'-dimethoxychalcone
  参考文献：
  名称：

  甲醇中的硝酸al（III）将3'-和5'-位无取代基的2'-羟基查耳酮氧化重排

  摘要：

  al在3'和5'位置没有取代基的2'-羟基查耳酮的氧化（III）已经详细研究了甲醇中的硝酸盐（TTN），并获得了以下结果。（1）由于6'-甲氧基氧原子的参与，2'-羟基-4,6'-二甲氧基查耳酮（1b和2b）相对于它们的甲基醚具有增加的反应性；但是2'-羟基-4,4'-二甲氧基查耳酮3b的反应性降低。（2）反应受到A和B环上取代基的极大影响，并形成相应的1,2-二芳基-3,3-二甲氧基丙烷-1-酮（乙缩醛）和/或2-（α-甲氧基苄基）香豆烷酮（香豆酮）：通过在4-和/或2-位上的甲氧基极大地促进了氧化重排，从而得到了作为主要产物的乙缩醛。（3）仅当2′-羟基查耳酮在6′-位具有甲氧基且具有较弱的供电子性的B环时，才观察到香豆素的形成。（4）在2'在4'-位没有取代基的反应中形成的香豆烷酮的比率低于在2'-羟基和相邻的羰基之间迅速形成环状TTN配合物的1的比率。仅2'-羟基-6'-甲氧基查耳

  DOI：

  10.1039/p19960001987

文献信息

• Synthesis of chalcone analogues with increased antileishmanial activity
  作者：Paula Boeck、Camila Alves Bandeira Falcão、Paulo César Leal、Rosendo Augusto Yunes、Valdir Cechinel Filho、Eduardo Caio Torres-Santos、Bartira Rossi-Bergmann

  DOI：10.1016/j.bmc.2005.10.005

  日期：2006.3

  Eighteen analogues of an active natural chalcone were synthesized using xanhoxyline and some derivatives, and these analogues were tested for selective activity against both promastigotes and intracellular amastigotes of Leishmania amazonensis in vitro. Three analogues (10, 12, and 19) containing nitro, fluorine or bromine groups, respectively, displayed increased selective activity against the parasites as compared with the natural chalcone. The nitrosylated chalcone 10 was also tested intralesionally in infected mice and was found to be as effective as Pentostan reference drug at a dose 100 times higher than that of the chalcone in controlling both the lesion growth and the parasite burden. (c) 2005 Elsevier Ltd. All rights reserved.
• 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.