3-(3,4-二甲氧基苯基)-4-羟基-5H-呋喃-2-酮 | 263764-91-6

• 分子结构分类: 有机化合物 - 苯类化合物 - 苯和取代衍生物
• 中文名称: 3-(3,4-二甲氧基苯基)-4-羟基-5H-呋喃-2-酮
• 英文名称: 3-(3,4-dimethoxyphenyl)-4-hydroxyfuran-2(5H)-one
• 英文别名: 4-(3,4-dimethoxyphenyl)-3-hydroxy-2H-furan-5-one
• CAS: 263764-91-6
• 化学式: C₁₂H₁₂O₅
• 分子量: 236.224
• InChiKey: OLTOJSITAUVGKL-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  1.2
• 重原子数：
  17
• 可旋转键数：
  3
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.25
• 拓扑面积：
  65
• 氢给体数：
  1
• 氢受体数：
  5

反应信息

• 作为反应物：
  描述：

  3-(3,4-二甲氧基苯基)-4-羟基-5H-呋喃-2-酮 在 三乙胺 作用下， 以 N,N-二甲基甲酰胺 、 丙酮 为溶剂， 生成 3-(3,4-dimethoxyphenyl)-4-(2-(piperidin-1-yl)ethoxy)furan-2(5H)-one
  参考文献：
  名称：

  4-Alkoxy-3-arylfuran-2(5H)-ones as inhibitors of tyrosyl-tRNA synthetase: Synthesis, molecular docking and antibacterial evaluation

  摘要：

  A series of novel 4-alkoxy-3-arylfuran-2(5H)-ones as tyrosyl-tRNA synthetase inhibitors were synthesized. Of these compounds, 3-(4-hydroxyphenyl)-4-(2-morpholinoethoxy)furan-2(5H)-one (27) was the most potent. The binding model and structure-activity relationship indicate that replacement of morpholine-ring in the side chain of 27 with a substituent containing more hydrophilic groups would be more suitable for further modification. Antibacterial assay revealed that the synthetic compounds are effective against growth of Gram-positive organisms, and 27 is the most potent agent against Staphylococcus ;aureus ATCC 25923 with MIC50 value of 0.23 mu g/mL. (C) 2011 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.bmc.2011.05.042
• 作为产物：
  描述：

  3,4-二甲氧基苯乙酸 在 sodium ethanolate 、 sodium hydride 作用下， 生成 3-(3,4-二甲氧基苯基)-4-羟基-5H-呋喃-2-酮
  参考文献：
  名称：

  Structure and Antibacterial Activity of 3-(3,4-Dimethoxyphenyl)furan-2(5H)-ones

  摘要：

  标题化合物的结晶水合物（5），C19H26N2O5·2（H2O），通过单晶X射线衍射进行了结构表征。它以单斜晶系空间群P 21/c结晶，其中a = 7.3987（7）Å，b = 17.8691（16）Å，c = 17.0022（13）Å，β = 112.944（3）°，V = 2070.0（3）ų，Z = 4，R 1 = 0.0592，wR 2 = 0.1016，T = 298（2）K。X射线结构测定揭示了中心呋喃酮环与3,4-二甲氧基苯环几乎共面，形成0.860（69）°的二面角。通过O-H···O、O-H···N和C-H···O氢键相互作用，形成了两种由图集基序R 7 8（36）和R 4 6（32）表征的对称四聚体，这些氢键相互作用生成了一张边缘融合的环片，平行于（011）平面。这些片层通过C-H···π相互作用进一步连接成三维网络。合成了九种3-（3,4-二甲氧苯基）呋喃-2（5H）-酮，并通过元素分析、MS和¹H NMR进行了全面表征。所有这些化合物都对三种革兰氏阳性菌和一种革兰氏阴性菌进行了抗菌活性评估，其中化合物5对金黄色葡萄球菌ATCC 25923最为活性。通过O-H···O、O-H···N和C-H···O氢键相互作用，形成了两种由图集基序R 7 8（36）和R 4 6（32）表征的对称四聚体，这些氢键相互作用生成了一张边缘融合的环片，平行于（011）平面。

  DOI：

  10.1007/s10870-011-0246-9

文献信息

• 3-Aryltetronic Acids: Efficient Preparation and Use as Precursors for Vulpinic Acids
  作者：Aurélie Mallinger、Thierry Le Gall、Charles Mioskowski

  DOI：10.1021/jo802038z

  日期：2009.2.6

  3-Aryltetronic acids were prepared in one step by treatment of a mixture of methyl arylacetates and methyl hydroxyacetates with potassium tert-butoxide, via tandem transesterification/Dieckmann condensation. Several mushroom or lichen pigments, vulpinic acids, were synthesized from 3-(4-methoxyphenyl)tetronic acid in three steps involving the reaction of the corresponding dianion with an α-ketoester

  通过串联酯交换反应/ Dieckmann缩合反应，用叔丁醇钾处理芳基乙酸甲酯和羟基乙酸甲酯的混合物，一步制得3-芳基酸。在三个步骤中，由3-（4-甲氧基苯基）tetronic酸合成了几种蘑菇或地衣颜料的硫化松香酸，这三个步骤涉及相应的二价阴离子与α-酮酸酯的反应以及所获得的叔醇的脱水成（E）的混合物-和（Z）-烯烃，它们在254nm的紫外线辐射下转化为天然（E）-异构体。樟脑酸，4,4'-二甲氧基硫代乙酸的合成，以及最近分离出的甲基3'，5'-dichloro-4,4'-di- O的首次合成因此，以有效的方式获得了苹果酸-草酸甲酯。
• Catalytic Undirected Intermolecular C–H Functionalization of Arenes with 3-Diazofuran-2,4-dione: Synthesis of 3-Aryl Tetronic Acids, Vulpinic Acid, Pinastric Acid, and Methyl Isoxerocomate
  作者：Amarender Manchoju、Sunil V. Pansare

  DOI：10.1021/acs.orglett.6b03087

  日期：2016.11.18

  A variety of 3-aryl tetronic acids have been synthesized by an undirected, intermolecular C–H functionalization of arenes with 3-diazofuran-2,4-dione. This methodology featured as a key step in the synthesis of a series of naturally occurring 3-aryl-5-arylidene tetronic acids (pulvinates) from commercially available tetronic acid. Salient features of the pulvinic acid synthesis include a one-step,

  通过使用3-重氮呋喃-2,4-二酮对芳烃进行无方向的CH-H分子间官能化反应，已经合成了多种3-芳基tetronic酸。该方法学是从可商购的tetronic酸合成一系列天然存在的3-芳基-5-芳基亚芳基tetronic酸（pulvinates）的关键步骤。戊酸合成的显着特征包括C5芳基的一步一步立体选择性合成和C3芳基取代基的一步导入。
• Synthesis and evaluation of adenosine containing 3-arylfuran-2(5 H )-ones as tyrosyl-tRNA synthetase inhibitors
  作者：Wei Wei、Qi Liu、Zhen-Zhen Li、Wei-Kang Shi、Xing Fu、Jia Liu、Xuan Zhu、Xiao-Cong Wang、Ning Xu、Teng-Fei Li、Fu-Rui Jiang、Zhu-Ping Xiao、Hai-Liang Zhu

  DOI：10.1016/j.ejmech.2017.03.074

  日期：2017.6

  Tyrosyl-tRNA synthetase (TyrRS) is an aminoacyl-tRNA synthetase family protein that possesses an essential role in bacterial protein synthesis. The synthesis, structure-activity relationship, and evolution of a novel series of adenosine-containing 3-arylfuran-2(5H)-ones as TyrRS inhibitors are described. Advanced compound d3 from this series exhibited excellent affinity for TyrRS with IC50 of 0.61

  酪氨酰-tRNA合成酶（TyrRS）是一种氨酰基-tRNA合成酶家族蛋白，在细菌蛋白合成中具有重要作用。描述了一系列新型的含腺苷的3-芳基呋喃-2（5H）-酮作为TyrRS抑制剂的合成，结构-活性关系和演变。该系列的先进化合物d3对TyrRS表现出优异的亲和力，IC50为0.61±0.04μM。细菌生长抑制试验表明，d3对大肠杆菌和铜绿假单胞菌显示出亚微摩尔抗菌力，并且与市售的环丙沙星抗生素相比。
• 4-Azidotetronic Acids: A New Class of Azido Derivatives
  作者：E. M. Beccalli、E. Erba、P. Trimarco

  DOI：10.1080/00397910008087364

  日期：2000.2

  4-Azidotetronic derivatives bearing different substituent groups on the carbon atom in position 3 were easily obtained by reaction of the corresponding 4-bromotetronic compounds with sodium azide in methanol at room temperature.
• Synthesis, structure, molecular docking, and structure–activity relationship analysis of enamines: 3-Aryl-4-alkylaminofuran-2(5H)-ones as potential antibacterials
  作者：Zhu-Ping Xiao、Xing-Bing He、Zhi-Yun Peng、Tao-Ju Xiong、Juan Peng、Li-Hua Chen、Hai-Liang Zhu

  DOI：10.1016/j.bmc.2011.01.051

  日期：2011.3

  Thirty-one 3-aryl-4-alkylaminofuran-2(5H)-ones were designed, prepared and tested for their antibacterial activity. Some of them showed significant antibacterial activity against Gram-positive organisms, especially against Staphylococcus aureus ATCC 25923, but all were inactive against Gram-negative organisms. Out of these compounds, 3-(4-bromophenyl)-4-(2-(4-nitrophenyl)hydrazinyl)furan-2(5H)-one (4a11) showed the most potent antibacterial activity against S. aureus ATCC 25923 with MIC50 of 0.42 mu g/mL. The enzyme assay revealed that the possible antibacterial mechanism of the synthetic compounds might be due to their inhibitory activity against tyrosyl-tRNA synthetase. Molecular dockings of 4a11 into S. aureus tyrosyl-tRNA synthetase active site were also performed. This inhibitor snugly fitting the active site might well explain its excellent inhibitory activity. Meanwhile, this modeling disclosed that a more suitable optimization strategy might be to modify the benzene ring at 3-position of furanone with hydrophilic groups. (C) 2011 Elsevier Ltd. All rights reserved.