4,6-二羟基-3-苯并呋喃酮 | 3260-49-9

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 苯并呋喃
• 中文名称: 4,6-二羟基-3-苯并呋喃酮
• 英文名称: 4,6-dihydroxybenzofuran-3(2H)-one
• 英文别名: 4,6-dihydroxy-1-benzofuran-3-one
• CAS: 3260-49-9
• 化学式: C₈H₆O₄
• mdl: MFCD00597844
• 分子量: 166.133
• InChiKey: OPSLRXQDYBYKHC-UHFFFAOYSA-N

物化性质

• 熔点：
  260℃
• 沸点：
  429.4±40.0 °C(Predicted)
• 密度：
  1.614±0.06 g/cm3 (20 ºC 760 Torr)
• 溶解度：
  溶于氯仿

计算性质

• 辛醇/水分配系数(LogP)：
  1.3
• 重原子数：
  12
• 可旋转键数：
  0
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.125
• 拓扑面积：
  66.8
• 氢给体数：
  2
• 氢受体数：
  4

安全信息

• 海关编码：
  2932999099
• 储存条件：
  | 2-8°C |

反应信息

• 作为反应物：
  描述：

  4,6-二羟基-3-苯并呋喃酮 在 potassium carbonate 、 potassium hydroxide 作用下， 以 甲醇 、 乙二醇二甲醚 、 水 为溶剂， 反应 3.0h， 生成 (Z)-2-(2,4-dimethoxybenzylidene)-4,6-dimethoxybenzofuran-3(2H)-one
  参考文献：
  名称：

  Discovery of Naturally Occurring Aurones That Are Potent Allosteric Inhibitors of Hepatitis C Virus RNA-Dependent RNA Polymerase

  摘要：

  We have identified naturally occurring 2-benzylidenebenzofuran-3-ones (aurones) as new templates for non-nucleoside hepatitis C virus (HCV) RNA-dependent RNA polymerase (RdRp) inhibitors. The aurone target site, identified by site-directed mutagenesis, is located in thumb pocket I of HCV RdRp. The RdRp inhibitory activity of 42 aurones was rationally explored in an enzyme assay. Molecular docking studies were used to determine how aurones bind to HCV RdRp and to predict their range of inhibitory activity. Seven aurone derivatives were found to have potent inhibitory effects on HCV RdRp, with IC(50) below 5 mu M and excellent selectivity index (inhibition activity versus cellular cytotoxicity). The most active aurone analogue was (Z)-2-((1-butyl-1H-indo1-3-yl)methylene)-4,6-dihydroxybenzofuran-3(2H)-one (compound 51), with an IC(50) of 2.2 mu M. Their potent RdRp inhibitory activity and their low toxicity make these molecules attractive candidates as direct-acting anti-HCV agents.

  DOI：

  10.1021/jm200242p
• 作为产物：
  描述：

  2-(3,5-dihydroxyphenyl)acetonitrile 在 水 作用下， 反应 5.0h， 生成 4,6-二羟基-3-苯并呋喃酮
  参考文献：
  名称：

  2-Indolylmethylenebenzofuranones as first effective inhibitors of ABCC2

  摘要：

  ABC-transporters play a vital role in drugs bioavailability. They prevent intracellular accumulation of toxic compounds, rendering them a major defense mechanism against harmful substances. In this large family, ABCC2 is an apical efflux pump representing about 10% of all membrane proteins in liver and small intestine, and up to 25% in colon. In these tissues, ABCC2 plays a major role in the pharmacokinetics and pharmacodynamics of endo-and xenobiotics. To gain insight in the function of this crucial protein, we have investigated and developed the first effective inhibitors of this pump. Firstly, we set up a cellular flow cytometry assay for monitoring the drug efflux carried out by ABCC2, and used it for the screening of chemical libraries derived from several chemical classes. We found that 2-indolylmethylenebenzofuranone derivatives as promising candidates. Optimization of the hits provided new compounds that inhibit ABCC2 in the micromolar range, maldng them the first potent ABCC2 inhibitors reported so far. Such compounds would constitute valuable tools to further investigate the role of ABCC2 in the pharmacokinetics and pharmacodynamics of drugs. (C) 2016 Elsevier Masson SAS. All rights reserved.

  DOI：

  10.1016/j.ejmech.2016.06.039

文献信息

• Design, synthesis, and biological activity studies of a new class of sulfonated aurones: First synthesis of acidoaurone isolated from<scp><i>Phyllanthus acidus</i></scp>
  作者：Somepalli Venkateswarlu、Gandrotu Narasimha Murty、Meka Satyanarayana、Vidavalur Siddaiah

  DOI：10.1002/jhet.4358

  日期：2021.12

  comparison with their corresponding natural aurones. Ring-B sulfonated aurones exhibited potent 5-LOX inhibitory activity and significant antioxidant activity. Acidoaurone, a first sulfonated aurone isolated from Phyllanthus acidus was synthesized for the first time and was well characterized using NMR, LC–MS, and further confirmed by HMBC.

  通过在已知的天然aurones，如hispidol、suretin、seastin和aureusidin的环-A和环-B上引入磺酸基团，设计了一系列新的aurones。这些磺化的金黄酮是通过一种独特的方法合成的。环-A 或环-B 上的磺化作用将不溶于水的金黄酮转化为高度溶于水的金黄酮。测试了磺化的 aurone 及其天然 aurone 的抗氧化、抗炎和 AChE 抑制活性。与相应的天然金酮相比，环 A 磺化的金酮显示出更高的抗氧化活性、5-LOX 和 AChE 抑制。环 B 磺化的 aurone 表现出有效的 5-LOX 抑制活性和显着的抗氧化活性。Acidoaurone，第一个从Phyllanthus acidus 中分离出来的磺化的 aurone 首次合成并使用 NMR、LC-MS 进行了充分表征，并通过 HMBC 进一步确认。
• Aurone derivatives as promising antibacterial agents against resistant Gram-positive pathogens
  作者：Hamza Olleik、Samir Yahiaoui、Brayan Roulier、Elise Courvoisier-Dezord、Josette Perrier、Basile Pérès、Akram Hijazi、Elias Baydoun、Josette Raymond、Ahcène Boumendjel、Marc Maresca、Romain Haudecoeur

  DOI：10.1016/j.ejmech.2019.01.022

  日期：2019.3

  variously substituted aurones was synthesized and evaluated against Methicillin-Resistant S. aureus (MRSA) and P. aeruginosa. Several analogues were found active against MRSA, but no effect was recorded against P. aeruginosa. Compounds 27, 30 and 33 showed low cytotoxicity, and were tested against a full range of bacterial (Gram-positive and Gram-negative) and fungal species, including resistant strains

  合成了一组各种取代的金酮，并针对耐甲氧西林的金黄色葡萄球菌（MRSA）和铜绿假单胞菌进行了评估。发现几种类似物对MRSA具有活性，但未记录到对铜绿假单胞菌的作用。化合物27，30和33显示出低细胞毒性，并针对全方位细菌（革兰氏阳性和革兰氏阴性）和真菌种类，包括耐药菌株的测试。这些金星显示出对革兰氏阳性细菌的选择性抑制，具有极好的治疗指数值，而对几种革兰氏阴性菌株幽门螺杆菌和溶藻弧菌则没有明显作用。是测试的革兰氏阴性细菌中唯一易感的菌株。透化测定表明，至少一些金黄色素的抗菌活性可能与细菌膜的改变有关。总的来说，这项研究支持将金刚烷支架用于新的有效和选择性抗菌剂的开发。
• Synthesis of structurally diverse biflavonoids
  作者：Tze Jing Sum、Tze Han Sum、Warren R.J.D. Galloway、David G. Twigg、Joe J. Ciardiello、David R. Spring

  DOI：10.1016/j.tet.2018.05.003

  日期：2018.9

  a growing interest in synthetic approaches that can provide access to structurally novel biflavonoids so that the biological usefulness of this compound class can be more fully investigated. Herein, we report upon the exploration of strategies based around Suzuki-Miyaura cross-coupling and alcohol methylenation for the synthesis of two classes of biflavonoids: (i) rare ‘hybrid’ derivatives containing

  合成的双黄酮类化合物与有趣的生物学活性有关，但在药物发现中仍缺乏很好的探索。近年来，目睹了对合成方法的日益增长的兴趣，这些方法可以提供结构新颖的双黄酮类化合物，因此可以更充分地研究此类化合物的生物学用途。在本文中，我们报告了基于铃木-宫浦交叉偶联和醇甲基化的策略，用于合成两类双黄酮类化合物：（i）含有属于不同亚类的类黄酮单体的稀有“杂化”衍生物，以及（ii）同二聚体化合物，其中两个类黄酮单体通过亚甲二氧基连接。
• New pseudodimeric aurones as palm pocket inhibitors of Hepatitis C virus RNA-dependent RNA polymerase
  作者：Amel Meguellati、Abdelhakim Ahmed-Belkacem、Alessandra Nurisso、Wei Yi、Rozenn Brillet、Nawel Berqouch、Laura Chavoutier、Antoine Fortuné、Jean-Michel Pawlotsky、Ahcène Boumendjel、Marine Peuchmaur

  DOI：10.1016/j.ejmech.2016.03.005

  日期：2016.6

  polymerase (RdRp) is a key enzyme for Hepatitis C Virus (HCV) replication. In addition to the catalytic site, this enzyme is characterized by the presence of at least four allosteric pockets making it an interesting target for development of inhibitors as potential anti-HCV drugs. Based on a previous study showing the potential of the naturally occurring aurones as inhibitors of NS5B, we pursued our efforts

  NS5B RNA依赖性RNA聚合酶（RdRp）是丙型肝炎病毒（HCV）复制的关键酶。除催化位点外，该酶的特征还在于存在至少四个变构口袋，使其成为开发作为潜在抗HCV药物的抑制剂的有趣靶标。根据先前的研究表明天然存在的金黄色素作为NS5B抑制剂的潜力，我们继续致力于目前尚未研究的假二聚体金黄色素。因此，合成了以苯并呋喃酮部分之间存在间隔基为特征的14种原始化合物，并通过体外试验研究了它们作为HCV RdRp抑制剂。活性最高的抑制剂假二聚体金酮4诱导了高抑制活性（IC50  = 1.3μM）。诱变和分子建模研究表明，活性最高的衍生物的结合位点可能是手掌口袋I，而不是单体衍生物的拇指口袋I。
• 具有肝病疗效的化合物
  申请人：江苏新元素医药科技有限公司

  公开号：CN112250689B

  公开（公告）日：2022-01-18

  本发明公开了一类具有肝病疗效的化合物，它为具有通式(I)所示的化合物、光学异构体或其药学上可接受的盐，本发明的化合物可应用于肝病的治疗或预防，特别是在治疗或预防脂肪肝、肝纤维化或肝硬化的药物方面，具有良好的应用前景。