3-(4-methylphenyl)-4-hydroxyfuran-2(5H)-one | 100074-53-1

• 分子结构分类: 有机化合物 - 苯类化合物 - 苯和取代衍生物
• 英文名称: 3-(4-methylphenyl)-4-hydroxyfuran-2(5H)-one
• 英文别名: 4-hydroxy-3-p-tolylfuran-2(5H)-one；4-hydroxy-3-(4'-methylphenyl)furan-2(5H)-one；3-hydroxy-4-(4-methylphenyl)-2H-furan-5-one
• CAS: 100074-53-1
• 化学式: C₁₁H₁₀O₃
• 分子量: 190.199
• InChiKey: AABKQBNCAREVSD-UHFFFAOYSA-N

物化性质

• 沸点：
  402.0±45.0 °C(Predicted)
• 密度：
  1.330±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  1.6
• 重原子数：
  14
• 可旋转键数：
  1
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.18
• 拓扑面积：
  46.5
• 氢给体数：
  1
• 氢受体数：
  3

反应信息

• 作为反应物：
  描述：

  3-(4-methylphenyl)-4-hydroxyfuran-2(5H)-one 在 三乙胺 作用下， 以 丙酮 为溶剂， 生成 7-(4-(2-(3-(4-methylphenyl)furan-2(5H)-one-4-yloxy)ethyl)piperazin-1-yl)-1-(4-fluorophenyl)-6-fluoro-4-oxo-1,4-dihydroquinoline-3-carboxylic acid
  参考文献：
  名称：

  Novel 3-arylfuran-2(5H)-one-fluoroquinolone hybrid: Design, synthesis and evaluation as antibacterial agent

  摘要：

  3-Arylfuran-2(5H)-one, a novel antibacterial pharmacophore targeting tyrosyl-tRNA synthetase (TyrRS), was hybridized with the clinically used fluoroquinolones to give a series of novel multi-target antimicrobial agents. Thus, twenty seven 3-arylfuran-2(5H)-one-fluoroquinolone hybrids were synthesized and evaluated for their antimicrobial activities. Some of the hybrids exhibited merits from both parents, displaying a broad spectrum of activity against resistant strains including both Gram-negative and Gram-positive bacteria. The most potent compound (11) in antibacterial assay shows MIC50 of 0.11μg/mL against Multiple drug resistant Escherichia coli, being about 51-fold more potent than ciprofloxacin. The enzyme assays reveal that 11 is a potent multi-target inhibitor with IC50 of 1.15±0.07μM against DNA gyrase and 0.12±0.04μM against TyrRS, respectively. Its excellent inhibitory activities against isolated enzymes and intact cells strongly suggest that 11 deserves to further research as a novel antibiotic.

  DOI：

  10.1016/j.bmc.2014.05.018
• 作为产物：
  描述：

  对甲基苯乙酸 在 potassium tert-butylate 、 sodium ethanolate 作用下， 以 乙醇 、 叔丁醇 为溶剂， 反应 5.0h， 生成 3-(4-methylphenyl)-4-hydroxyfuran-2(5H)-one
  参考文献：
  名称：

  （E）-和（Z）-pulvinones的合成

  摘要：

  已经开发出两种新的途径获得pulvinones，其中一种涉及新颖的Wittig反应。首次报道了E系列的成员，包括母体（E）-普尔维酮，并描述了几何异构体的结构。提出了一种将（E）-普尔维酮定量转化为（Z）-普尔维酮的方法，以及区分异构体的技术。

  DOI：

  10.1039/p19850001567

文献信息

• A facile synthesis, antibacterial activity of pulvinone and its derivatives
  作者：Hai-Wei Xu、Chao Xu、Zi-qi Fan、Ling-Jie Zhao、Hong-Min Liu

  DOI：10.1016/j.bmcl.2012.11.090

  日期：2013.2

  Pulvinone and several 3-fluoro-4-morpholino substituted pulvinone derivatives were synthesized in five steps from a common precursor, phenyl acetic acid. Most of synthetic morpholine substituted pulvinones showed inhibitory activity against Esherichia coli. For the first time, the inhibition of pulvinone and its derivatives against Gram-negative bacteria was reported.

  从五个共同的前体苯乙酸中分五步合成了普尔维酮和几种3-氟-4-吗啉代取代的普尔维酮衍生物。大多数合成吗啉取代的聚乙烯醇对大肠杆菌均具有抑制作用。首次报道了普尔维酮及其衍生物对革兰氏阴性菌的抑制作用。
• Synthesis of (E)- and (Z)-pulvinones
  作者：Alexander C. Campbell、Maurice S. Maidment、John H. Pick、Donald F. M. Stevenson

  DOI：10.1039/p19850001567

  日期：——

  one of which involves a novel Wittig reaction. For the first time, members of the E-series, including the parent (E)-pulvinone, are reported and the structural elucidation of the geometric isomers is described. A method for quantitatively converting (E)-pulvinones into (Z)-pulvinones is presented, together with a technique for differentiating between the isomers.

  已经开发出两种新的途径获得pulvinones，其中一种涉及新颖的Wittig反应。首次报道了E系列的成员，包括母体（E）-普尔维酮，并描述了几何异构体的结构。提出了一种将（E）-普尔维酮定量转化为（Z）-普尔维酮的方法，以及区分异构体的技术。
• Synthesis and Bio-Evaluation of Natural Butenolides-Acrylate Conjugates
  作者：Longzhu Bao、Shuangshuang Wang、Di Song、Jingjing Wang、Xiufang Cao、Shaoyong Ke

  DOI：10.3390/molecules24071304

  日期：——

  A series of novel 3-aryl-4-hydroxy-2(5H) furanone-acrylate hybrids were designed and synthesized based on the natural butenolides and acrylates scaffolds. The structures of the prepared compounds were characterized by 1H-NMR, 13C-NMR and electrospray ionization mass spectrometry (ESI-MS), and the bioactivity of the target compounds against twelve phytopathogenic fungi was investigated. The preliminary in vitro antifungal activity screening showed that most of the target compounds had moderate inhibition on various pathogenic fungi at the concentration of 100 mg·L−1, and presented broad-spectrum antifungal activities. Further studies also indicated that compounds 7e and 7k still showed some inhibitory activity against Pestallozzia theae, Sclerotinia sclerotiorum and Gibberella zeae on rape plants at lower concentrations, which could be optimized as a secondary lead for further research.

  一系列新颖的3-芳基-4-羟基-2(5H) 呋喃酮-丙烯酸酯混合物是基于天然丁内酯和丙烯酸酯骨架设计和合成的。所制备化合物的结构经过1H-NMR、13C-NMR和电喷雾电离质谱（ESI-MS）表征，对目标化合物对十二种植物病原真菌的生物活性进行了研究。初步的体外抗真菌活性筛选显示，大多数目标化合物在浓度为100 mg·L−1时对各种病原真菌有中等抑制作用，并表现出广谱抗真菌活性。进一步研究还表明，化合物7e和7k在较低浓度下仍对油菜植物上的茶树萎凋病、软腐病和赤霉病菌有一定的抑制活性，可作为进一步研究的次级引物进行优化。
• 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。
• 一种化合物以及制备方法和应用
  申请人：郑州大学

  公开号：CN110872263B

  公开（公告）日：2021-09-28

  本申请公开了一种化合物，其结构式如下式所示：其中，R1选自F、Cl、Br、C1～C5的烷基、具有式(1)所示结构式的基团中的任意一种；n＝0、1、2、3、4或5；R2选自具有式(1)所示结构式的基团、具有式(2)所示结构式的基团、具有式(3)所示结构式的基团中的任意一种。所述化合物制备方法简单，可作为神经氨酸酶抑制剂，具有良好的抗病毒活性。