4-(2-(4-fluorophenylacetyloxyl)ethoxy)-3-phenylfuran-2(5H)-one | 1450824-52-8

• 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: 4-(2-(4-fluorophenylacetyloxyl)ethoxy)-3-phenylfuran-2(5H)-one
• 英文别名: 2-[(5-oxo-4-phenyl-2H-furan-3-yl)oxy]ethyl 2-(4-fluorophenyl)acetate
• CAS: 1450824-52-8
• 化学式: C₂₀H₁₇FO₅
• 分子量: 356.35
• InChiKey: HOJIRSYLSJIVKE-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.1
• 重原子数：
  26
• 可旋转键数：
  8
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.2
• 拓扑面积：
  61.8
• 氢给体数：
  0
• 氢受体数：
  6

反应信息

• 作为产物：
  描述：

  苯乙酸 在 sodium hydride 、 三乙胺 、 sodium hydroxide 作用下， 以 四氢呋喃 、 水 、 二甲基亚砜 、 丙酮 为溶剂， 生成 4-(2-(4-fluorophenylacetyloxyl)ethoxy)-3-phenylfuran-2(5H)-one
  参考文献：
  名称：

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

  摘要：

  Thirty-eight 3-aryl-4-acyloxyethoxyfuran-2(5H)-ones were designed, prepared and tested for antibacterial activities. Some of them showed significant antibacterial activity against Gram-positive organism, Gram-negative organism and fungus. Out of these compounds, 4-(2-(3-chlorophenylformyloxy)ethoxy)-3-(4-chlorophenyl)furan-2(5H)-one (d40) showed the widest spectrum of activity with MIC50 of 2.0 mu g/mL against Staphylococcus aureus, 4.3 mu g/mL against Escherichia coli, 1.5 mu g/mL against Pseudomonas aeruginosa and 1.2 mu g/mL against Candida albicans. Our data disclosed that MIC50 values against whole cell bacteria are positive correlation with MIC50 values against tyrosyl-tRNA synthetase. Meanwhile, molecular docking of d40 into S. aureus tyrosyl-tRNA synthetase active site was also performed, and the inhibitor tightly fitting the active site might be an important reason why it has high antimicrobial activity. (C) 2013 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.bmc.2013.06.066

文献信息

• 3-Aryl-4-acyloxyethoxyfuran-2(5H)-ones as inhibitors of tyrosyl-tRNA synthetase: Synthesis, molecular docking and antibacterial evaluation
  作者：Xu-Dong Wang、Rui-Cheng Deng、Jing-Jun Dong、Zhi-Yun Peng、Xiao-Ming Gao、Shu-Ting Li、Wan-Qiang Lin、Chun-Lei Lu、Zhu-Ping Xiao、Hai-Liang Zhu

  DOI：10.1016/j.bmc.2013.06.066

  日期：2013.9

  Thirty-eight 3-aryl-4-acyloxyethoxyfuran-2(5H)-ones were designed, prepared and tested for antibacterial activities. Some of them showed significant antibacterial activity against Gram-positive organism, Gram-negative organism and fungus. Out of these compounds, 4-(2-(3-chlorophenylformyloxy)ethoxy)-3-(4-chlorophenyl)furan-2(5H)-one (d40) showed the widest spectrum of activity with MIC50 of 2.0 mu g/mL against Staphylococcus aureus, 4.3 mu g/mL against Escherichia coli, 1.5 mu g/mL against Pseudomonas aeruginosa and 1.2 mu g/mL against Candida albicans. Our data disclosed that MIC50 values against whole cell bacteria are positive correlation with MIC50 values against tyrosyl-tRNA synthetase. Meanwhile, molecular docking of d40 into S. aureus tyrosyl-tRNA synthetase active site was also performed, and the inhibitor tightly fitting the active site might be an important reason why it has high antimicrobial activity. (C) 2013 Elsevier Ltd. All rights reserved.