3-(2-(benzyloxy)phenyl)-4-hydroxyfuran-2(5H)-one | 115883-13-1

• 分子结构分类: 有机化合物 - 苯类化合物 - 苯酚醚
• 英文名称: 3-(2-(benzyloxy)phenyl)-4-hydroxyfuran-2(5H)-one
• 英文别名: 3-hydroxy-4-(2-phenylmethoxyphenyl)-2H-furan-5-one
• CAS: 115883-13-1
• 化学式: C₁₇H₁₄O₄
• 分子量: 282.296
• InChiKey: PUMUXGFAMXTZEC-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.7
• 重原子数：
  21
• 可旋转键数：
  4
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.12
• 拓扑面积：
  55.8
• 氢给体数：
  1
• 氢受体数：
  4

反应信息

• 作为反应物：
  描述：

  3-(2-(benzyloxy)phenyl)-4-hydroxyfuran-2(5H)-one 在 三乙胺 作用下， 以 丙酮 为溶剂， 生成 7-(4-(2-(3-(2-(benzyloxy)phenyl)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：

  2-苄氧基苯乙酸 在 sodium hydride 、 sodium hydroxide 作用下， 以 四氢呋喃 、 水 为溶剂， 生成 3-(2-(benzyloxy)phenyl)-4-hydroxyfuran-2(5H)-one
  参考文献：
  名称：

  Synthesis, molecular docking and biological evaluation of 3-arylfuran-2(5H)-ones as anti-gastric ulcer agent

  摘要：

  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.

  DOI：

  10.1016/j.bmc.2015.05.026

文献信息

• 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.
• Novel 3-arylfuran-2(5H)-one-fluoroquinolone hybrid: Design, synthesis and evaluation as antibacterial agent
  作者：Xu-Dong Wang、Wei Wei、Peng-Fei Wang、Yun-Tao Tang、Rui-Cheng Deng、Biao Li、Sha-Sha Zhou、Jing-Wen Zhang、Lei Zhang、Zhu-Ping Xiao、Hui Ouyang、Hai-Liang Zhu

  DOI：10.1016/j.bmc.2014.05.018

  日期：2014.7

  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.