(2Z)-2-(4-chlorobenzylidene)-4,6-dimethoxy-1-benzofuran-3(2H)-one | 350982-88-6

• 分子结构分类: 有机化合物 - 苯丙烷和聚酮 - 橙酮类黄酮
• 英文名称: (2Z)-2-(4-chlorobenzylidene)-4,6-dimethoxy-1-benzofuran-3(2H)-one
• 英文别名: (Z)-(4'-chlorobenzylidene)-4,6-dimethoxybenzofuran-3(2H)-one；2-(4'-chlorobenzylidene)-4,6-dimethoxybenzofuran-3(2H)-one；4'-chloro-4,6-dimethoxyaurone；(2Z)-2-[(4-chlorophenyl)methylidene]-4,6-dimethoxy-1-benzofuran-3-one
• CAS: 350982-88-6
• 化学式: C₁₇H₁₃ClO₄
• 分子量: 316.741
• InChiKey: AUBBPUJONLUVIZ-CHHVJCJISA-N

计算性质

• 辛醇/水分配系数(LogP)：
  4.2
• 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：
  44.8
• 氢给体数：
  0
• 氢受体数：
  4

反应信息

• 作为反应物：
  描述：

  (2Z)-2-(4-chlorobenzylidene)-4,6-dimethoxy-1-benzofuran-3(2H)-one 在 三溴化硼 作用下， 以 二氯甲烷 为溶剂， 反应 24.0h， 生成 (Z)-(4'-chlorobenzylidene)-4-hydroxy-6-methoxybenzofuran-3(2H)-one
  参考文献：
  名称：

  4-Hydroxy-6-methoxyaurones with High-Affinity Binding to Cytosolic Domain of P-Glycoprotein.

  摘要：

  一系列的4-羟基-6-甲氧基黄烷酮和4,6-二甲氧基黄烷酮已经被合成并测试了其对P-糖蛋白核苷酸结合域的结合亲和力，P-糖蛋白是一种介导癌细胞耐药性对化疗的ABC（ATP结合盒）转运蛋白。这些化合物在黄烷酮B环上的取代基性质上有差异。结合亲和力似乎与取代基的性质以及4位上羟基的有无相关。活性最强的化合物是4′-溴-4-羟基-6-甲氧基黄烷酮和4-羟基-4′-碘-6-甲氧基黄烷酮。

  DOI：

  10.1248/cpb.50.854
• 作为产物：
  描述：

  (E)-3-(4-chlorophenyl)-1-(2-hydroxy-4,6-dimethoxyphenyl)prop-2-en-1-one 在 吡啶 、 mercury(II) diacetate 作用下， 以65%的产率得到(2Z)-2-(4-chlorobenzylidene)-4,6-dimethoxy-1-benzofuran-3(2H)-one
  参考文献：
  名称：

  Natural and synthetic 2′-hydroxy-chalcones and aurones: Synthesis, characterization and evaluation of the antioxidant and soybean lipoxygenase inhibitory activity

  摘要：

  A series of 2'-hydroxy-chalcones and their oxidative cyclization products, aurones, have been synthesized and tested for their antioxidant and lipoxygenase inhibitory activity. The natural product aureusidin (31) was synthesized in high yield by a new approach. An extensive structure-relationship study was performed and revealed that several chalcones and aurones possess an appealing pharmacological profile combining high antioxidant and lipid peroxidation activity with potent soybean LOX inhibition. (C) 2009 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.bmc.2009.10.002

文献信息

• Dimethoxyaurones: Potent inhibitors of ABCG2 (breast cancer resistance protein)
  作者：Hong-May Sim、Chong-Yew Lee、Pui Lai Rachel Ee、Mei-Lin Go

  DOI：10.1016/j.ejps.2008.07.008

  日期：2008.11

  their ability to modulate ABCG2 (breast cancer resistance protein)-mediated multidrug resistance in vitro. Several members (0.5 microM) increased the accumulation of mitoxantrone (MX) in human breast cancer cells (MDA-MB-231) transfected with ABCG2 and re-sensitized these cells to the cytotoxic effects of MX. In the re-sensitization assay, aurones at 0.5 microM reduced the resistance of the transfected

  通过将4，6-二甲氧基苯并呋喃-3（2H）-1与各种苯甲醛在碱催化的醛醇缩合反应中反应，合成了一系列4,6-二甲氧基金错误。根据光谱和晶体学数据将AZ构型分配给了光环。测试了金黄色素在体外调节ABCG2（乳腺癌抗性蛋白）介导的多药抗性的能力。几个成员（0.5 microM）增加了用ABCG2转染的人乳腺癌细胞（MDA-MB-231）中米托蒽醌（MX）的积累，并使这些细胞对MX的细胞毒性作用重新敏感。在再敏化试验中，0.5 microM的金黄色素使转染细胞对MX的抗性降至亲代细胞的两倍，超过在相同浓度下测试的泛黄霉素C（FTC）。金黄色素（10 microM）还增加了钙黄绿素-AM在用ABCB1（P-糖蛋白）转染的MDCKII / MDR1细胞中的蓄积，其水平与在相同浓度下测试的维拉帕米相当。结构活性分析表明，对于ABCG2抑制作用，金质模板中亚苄基环B的取代作用不那么重要，对于具有未取代环
• A One-Pot Synthesis of Aurones from Substituted Acetophenones and Benz­aldehydes: A Concise Synthesis of Aureusidin
  作者：Zhixiang Xie、Ying Li、Xiaolong Zhao、Jie Liu

  DOI：10.1055/s-0031-1291153

  日期：2012.7

  A one-pot synthesis of aurones from substituted acetophenone and benzaldehyde has been developed on the basis of an improved Algar-Flynn-Oyamada reaction. By using this method, several aurones were prepared in three steps from commercial starting materials. The usefulness of this one-pot strategy was confirmed by a synthesis of aureusidin, an inhibitor of iodothyronine deiodinase, in 41% overall yield. In comparison with a two-step synthesis of this product from the same substrates, the one-pot strategy was more effective, giving a higher yield and requiring fewer and simpler operations.
• Functionalized aurones as inducers of NAD(P)H:quinone oxidoreductase 1 that activate AhR/XRE and Nrf2/ARE signaling pathways: Synthesis, evaluation and SAR
  作者：Chong-Yew Lee、Eng-Hui Chew、Mei-Lin Go

  DOI：10.1016/j.ejmech.2010.03.023

  日期：2010.7

  The chemopreventive potential of functionalized aurones and related compounds as inducers of NAD(P) H:quinone oxidoreductase 1 (NQO1, EC 1.6.99.2) are described. Several 4,6-dimethoxy and 5-hydroxyaurones induced NQO1 activity of Hepa1c1c7 cells by 2-fold at submicromolar concentrations, making these the most potent inducers to be identified from this class. Mechanistically, induction of NQO1 was mediated by the activation of AhR/XRE and Nrf2/ARE pathways, indicating that aurones may be mixed activators of NQO1 induction or agents capable of exploiting the proposed cross-talk between the AhR and Nrf2 gene batteries. QSAR analysis by partial least squares projection to latent structures (PLS) identified size parameters, in particular those associated with non-polar surface areas, as an important determinant of induction activity. These were largely determined by the substitution on rings A and B. A stereoelectronic role for the exocyclic double bond as reflected in the E-LUMO term was also identified. The electrophilicity of the double bond or its effect on the conformation of the target compound are possible key features for induction activity. (c) 2010 Elsevier Masson SAS. All rights reserved.
• An Efficient Synthesis of 4,6-Dimethoxyaurones
  作者：Ahcène Boumendjel、Chantal Beney、Anne-Marie Mariotte

  DOI：10.3987/com-01-9182

  日期：——
• Natural and synthetic 2′-hydroxy-chalcones and aurones: Synthesis, characterization and evaluation of the antioxidant and soybean lipoxygenase inhibitory activity
  作者：Anastasia Detsi、Maya Majdalani、Christos A. Kontogiorgis、Dimitra Hadjipavlou-Litina、Panagiotis Kefalas

  DOI：10.1016/j.bmc.2009.10.002

  日期：2009.12

  A series of 2'-hydroxy-chalcones and their oxidative cyclization products, aurones, have been synthesized and tested for their antioxidant and lipoxygenase inhibitory activity. The natural product aureusidin (31) was synthesized in high yield by a new approach. An extensive structure-relationship study was performed and revealed that several chalcones and aurones possess an appealing pharmacological profile combining high antioxidant and lipid peroxidation activity with potent soybean LOX inhibition. (C) 2009 Elsevier Ltd. All rights reserved.