2-(3,4-二羟基苯甲酰)-2,4,6-三羟基-1-苯并呋喃-3-酮 | 102788-23-8

• 分子结构分类: 有机化合物 - 苯丙烷和聚酮 - 橙酮类黄酮
• 中文名称: 2-(3,4-二羟基苯甲酰)-2,4,6-三羟基-1-苯并呋喃-3-酮
• 英文名称: 2-(3,4-dihydroxybenzoyl)-2,4,6-trihydroxy-3(2H)-benzofuranone
• 英文别名: 2-(3,4-Dihydroxybenzoyl)-2,4,6-trihydroxy-1-benzofuran-3(2H)-one；2-(3,4-dihydroxybenzoyl)-2,4,6-trihydroxy-1-benzofuran-3-one
• CAS: 102788-23-8
• 化学式: C₁₅H₁₀O₈
• 分子量: 318.24
• InChiKey: UYFQPTAFLCOYSM-UHFFFAOYSA-N

物化性质

• 沸点：
  767.1±60.0 °C(Predicted)
• 密度：
  1.847±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  1.5
• 重原子数：
  23
• 可旋转键数：
  2
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.07
• 拓扑面积：
  145
• 氢给体数：
  5
• 氢受体数：
  8

反应信息

• 作为产物：
  描述：

  槲皮素 在 Selectfluor 作用下， 以 乙腈 为溶剂， 以20 %的产率得到2-(3,4-二羟基苯甲酰)-2,4,6-三羟基-1-苯并呋喃-3-酮
  参考文献：
  名称：

  选择性卤化黄酮木脂素的制备和抗菌活性。

  摘要：

  制备了以前未知的黄酮木脂素卤化衍生物（水飞蓟宾 A 和 B、2,3-脱氢水飞蓟宾、水飞蓟素 A 和 2,3-脱氢水飞蓟素 A）的文库。研究了卤化对黄酮木脂素生物活性的影响。卤化衍生物对细菌有显着影响。所有制备的衍生物在浓度低于 10 µM 时都会抑制 AI-2 类型的细菌通讯（群体感应）。所有制备的化合物还可以抑制细菌（金黄色葡萄球菌和铜绿假单胞菌）粘附到表面，防止生物膜形成。这两种作用表明卤代衍生物是很有前途的抗菌剂。此外，这些衍生物与抗生素协同作用，降低了抗生素耐药性金黄色葡萄球菌的生存能力。

  DOI：

  10.3390/ijms232315121

文献信息

• Flavonoid Oxidation by the Radical Generator AIBN:  A Unified Mechanism for Quercetin Radical Scavenging
  作者：Venkat Krishnamachari、Lanfang H. Levine、Paul W. Paré

  DOI：10.1021/jf020045e

  日期：2002.7.1

  nucleophiles revealed that two of the products, namely the substituted benzofuranone (2) and the depside (4), are generated from a common carbocation intermediate. Indirect evidence for the operation of a cyclic concerted mechanism in the formation of the dimeric product (3) is provided. The identification of these products supports the model that the principal site of scavenging reactive oxygen species (ROS)

  槲皮素（五羟基黄酮）与过氧自由基发生剂2,2'-偶氮二异丁腈（AIBN）反应生成的四种氧化的类黄酮衍生物通过色谱法分离，并通过NMR和MS分析鉴定。化合物包括2-（3,4-二羟基苯甲酰基）-2,4,6-三羟基-3（2H）-苯并呋喃酮（2）; 1,3,11a-三羟基-9-（3,5,7-三羟基-4H-1-苯并吡喃-4-基-2-基）-5a-（3,4-二羟基苯基）-5,6,11-六氢-5,6,11-三氧萘并蒽-12-一（3）; 2-（3,4-二羟基苯甲酰氧基）-4,6-二羟基苯甲酸（4）; 和3，4-二羟基苯基乙醛酸甲酯（5）。在不同氢离子浓度和外部亲核试剂下的产物比率表明，两种产物，即取代的苯并呋喃酮（2）和深度（4），是从一种常见的碳正离子中间体生成的。提供了在二聚产物（3）的形成中循环协同机制起作用的间接证据。这些产物的鉴定支持以下模型：槲皮素中清除活性氧（ROS）的主要位点是B环中的邻二羟基取代基以及C环烯烃键。
• Mechanistic study on the enzymatic oxidation of flavonols
  作者：Souhila Ghidouche、Nour-Eddine Es-Safi、Paul-Henri Ducrot

  DOI：10.1016/j.tetlet.2007.11.147

  日期：2008.1

  Several flavonols have been transformed upon treatment by Trametes versicolor laccase. Most of the major oxidation products have been isolated by HPLC as pure compounds and their structures have been, when possible, investigated through spectral methods (HPLC–MS and NMR). The results are coherent with the predominance of a dismutation process, leading to cation formation, over direct radical–radical

  Trametes versicolor laccase经处理后已转化了几种黄酮醇。大部分主要氧化产物已通过HPLC分离为纯净化合物，并且在可能的情况下，通过光谱方法（HPLC-MS和NMR）对其结构进行了研究。结果与直接自由基-自由基偶合过程中导致阳离子形成的歧化过程的优势相一致。
• Effect of pH on the chemical modification of quercetin and structurally related flavonoids characterized by optical (UV-visible and Raman) spectroscopy
  作者：Z. Jurasekova、C. Domingo、J. V. Garcia-Ramos、S. Sanchez-Cortes

  DOI：10.1039/c4cp00864b

  日期：——

  The chemical modifications undergone by flavonoids under alkaline conditions in aqueous solution and on Ag nanoparticles studied by optical spectroscopy are presented and discussed.

  在光谱学的研究中，介绍并讨论了黄酮类化合物在水性溶液中和银纳米粒子上在碱性条件下发生的化学修饰。
• Copper(II)-catalysed oxidation of quercetin and 3-hydroxyflavone
  作者：Masanori Utaka、Akira Takeda

  DOI：10.1039/c39850001824

  日期：——

  Quercetin and 3-hydroxyflavone are oxidized to the corresponding 2-alkoxyflavan-3,4-diones by CuCl2 catalysis in MeOH or EtOH under oxygen or nitrogen, the mechanism of which is proposed.

  槲皮素和3-羟基黄酮通过在氧气或氮气中的MeOH或EtOH中的CuCl 2催化氧化为相应的2-烷氧基黄烷-3,4-二酮。
• Unraveling the anti-influenza effect of flavonoids: Experimental validation of luteolin and its congeners as potent influenza endonuclease inhibitors
  作者：Václav Zima、Kateřina Radilová、Milan Kožíšek、Carlos Berenguer Albiñana、Elena Karlukova、Jiří Brynda、Jindřich Fanfrlík、Miroslav Flieger、Jan Hodek、Jan Weber、Pavel Majer、Jan Konvalinka、Aleš Machara

  DOI：10.1016/j.ejmech.2020.112754

  日期：2020.12

  The biological effects of flavonoids on mammal cells are diverse, ranging from scavenging free radicals and anti-cancer activity to anti-influenza activity. Despite appreciable effort to understand the anti-influenza activity of flavonoids, there is no clear consensus about their precise mode-of-action at a cellular level. Here, we report the development and validation of a screening assay based on AlphaScreen technology and illustrate its application for determination of the inhibitory potency of a large set of polyols against PA N-terminal domain (PA-Nter) of influenza RNA-dependent RNA polymerase featuring endonuclease activity. The most potent inhibitors we identified were luteolin with an IC₅₀ of 72 ± 2 nM and its 8-C-glucoside orientin with an IC₅₀ of 43 ± 2 nM. Submicromolar inhibitors were also evaluated by an in vitro endonuclease activity assay using single-stranded DNA, and the results were in full agreement with data from the competitive AlphaScreen assay. Using X-ray crystallography, we analyzed structures of the PA-Nter in complex with luteolin at 2.0 Å resolution and quambalarine B at 2.5 Å resolution, which clearly revealed the binding pose of these polyols coordinated to two manganese ions in the endonuclease active site. Using two distinct assays along with the structural work, we have presumably identified and characterized the molecular mode-of-action of flavonoids in influenza-infected cells.