3-(3,4-dichlorophenyl)-4-hydroxyfuran-2(5H)-one | 100074-50-8

• 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-(3,4-dichlorophenyl)-4-hydroxyfuran-2(5H)-one
• 英文别名: 4-(3,4-dichlorophenyl)-3-hydroxy-2H-furan-5-one
• CAS: 100074-50-8
• 化学式: C₁₀H₆Cl₂O₃
• 分子量: 245.062
• InChiKey: ZMKCVJDQEMPYNS-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.5
• 重原子数：
  15
• 可旋转键数：
  1
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.1
• 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-(3,4-dichlorophenyl)-4-hydroxyfuran-2(5H)-one 在 potassium carbonate 、 O-(benzotriazol-1-yl)-N,N,N',N'-tetramethyluronium tetrafluoroborate 、 三乙胺 、 sodium hydroxide 作用下， 以 四氢呋喃 、 二氯甲烷 、 丙酮 为溶剂， 生成 N-(((3aR,4R,6R,6aR)-6-(6-amino-9H-purin-9-yl)-2,2-dimethyltetrahydrofuro[3,4-d][1,3]dioxol-4-yl)methyl)-2-(4-(3,4-dichlorophenyl)-5-oxo-2,5-dihydrofuran-3-yloxy)acetamide
  参考文献：
  名称：

  含3-芳基呋喃-2（5H）-酮作为酪氨酰-tRNA合成酶抑制剂的腺苷的合成和评估。

  摘要：

  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。

  DOI：

  10.1016/j.ejmech.2017.03.074
• 作为产物：
  描述：

  3,4-二氯苯乙酸 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-(3,4-dichlorophenyl)-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

• 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。
• 4-Alkoxy-3-arylfuran-2(5H)-ones as inhibitors of tyrosyl-tRNA synthetase: Synthesis, molecular docking and antibacterial evaluation
  作者：Zhu-Ping Xiao、Hui Ouyang、Xu-Dong Wang、Peng-Cheng Lv、Ze-Jun Huang、She-Rong Yu、Tian-Fang Yi、Ye-Ling Yang、Hai-Liang Zhu

  DOI：10.1016/j.bmc.2011.05.042

  日期：2011.7

  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.
• Synthesis, molecular docking and biological evaluation of 3-arylfuran-2(5H)-ones as anti-gastric ulcer agent
  作者：Xu-Dong Wang、Wei Wei、Peng-Fei Wang、Li-Cheng Yi、Wei-Kang Shi、Yong-Xiang Xie、Lang-Zhou Wu、Nian Tang、Liang-Song Zhu、Jia Peng、Chan Liu、Xian-Hui Li、Shi Tang、Zhu-Ping Xiao、Hai-Liang Zhu

  DOI：10.1016/j.bmc.2015.05.026

  日期：2015.8

  3-Arylfuran-2(5H)-one derivatives show good antibacterial activity and were determined as tyrosyl-tRNA synthetase (TyrRS) inhibitors. In a systematic medicinal chemistry exploration, we demonstrated chemical opportunities to treat infections caused by Helicobacter pylori. Twenty 3-arylfuran-2(5H)-ones were synthesized and evaluated for anti-H. pylori, antioxidant and anti-urease activities which are closely interconnected with H. pylori infection. The results displayed that some of the compounds show excellent antioxidant activity, and good anti-H. pylori and urease inhibitory activities. Out of these compounds, 3( 3-methylphenyl) furan-2(5H)-one (b9) showed the most potent antioxidant activity (IC50 = 8.2 mu M) and good anti-H. pylori activity (MIC50 = 2.6 mu g/mL), and it can be used as a good candidate for discovering novel anti-gastric ulcer agent. (C) 2015 Elsevier Ltd. All rights reserved.
• 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。