3-(4-bromophenyl)-4-(2-methoxyphenylamino)furan-2(5H)-one | 1339962-21-8

• 分子结构分类: 有机化合物 - 苯类化合物 - 苯酚醚
• 英文名称: 3-(4-bromophenyl)-4-(2-methoxyphenylamino)furan-2(5H)-one
• 英文别名: 4-(4-bromophenyl)-3-(2-methoxyanilino)-2H-furan-5-one
• CAS: 1339962-21-8
• 化学式: C₁₇H₁₄BrNO₃
• 分子量: 360.207
• InChiKey: PDRRBPIVMILZPT-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.8
• 重原子数：
  22
• 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：
  47.6
• 氢给体数：
  1
• 氢受体数：
  4

反应信息

• 作为产物：
  描述：

  phenylacetic acid 在 sodium hydride 、 对甲苯磺酸 作用下， 以 四氢呋喃 、 甲苯 、 mineral oil 为溶剂， 生成 3-(4-bromophenyl)-4-(2-methoxyphenylamino)furan-2(5H)-one
  参考文献：
  名称：

  Tyrosyl-tRNA synthetase inhibitors as antibacterial agents: Synthesis, molecular docking and structure–activity relationship analysis of 3-aryl-4-arylaminofuran-2(5H)-ones

  摘要：

  Thirty-five 3-aryl-4-arylaminofuran-2(5H)-one derivatives were designed, prepared and tested for their inhibitory activity against tyrosyl-tRNA synthetase. Out of these compounds, 3-(3-bromophenyl)-4-(3,5-dichlorophenylamino)furan-2(5H)-one (35) was the most active with IC50 of 0.09 +/- 0.02 mu M. The structure activity relationship revealed that introduction of chlorine atoms at both meta positions of aniline moiety significantly increased the enzyme inhibitory activity. The results of antibacterial assay revealed that the tested compounds showed good activity against Gram-positive bacteria, with 35 being the most potent with MIC50 of 0.06 mu g/mL against Staphylococcus aureus ATCC 25923. Molecular docking of 35 into S. aureus tyrosyl-tRNA synthetase active site was also performed. The inhibitor snugly fitting the active site may well explain its excellent inhibitory activity. (C) 2011 Elsevier Masson SAS. All rights reserved.

  DOI：

  10.1016/j.ejmech.2011.07.047

文献信息

• Tyrosyl-tRNA synthetase inhibitors as antibacterial agents: Synthesis, molecular docking and structure–activity relationship analysis of 3-aryl-4-arylaminofuran-2(5H)-ones
  作者：Zhu-Ping Xiao、Tao-Wu Ma、Mei-Lin Liao、Yu-Ting Feng、Xiao-Chun Peng、Jia-Liang Li、Zhi-Ping Li、Ying Wu、Qun Luo、Yang Deng、Xiao Liang、Hai-Liang Zhu

  DOI：10.1016/j.ejmech.2011.07.047

  日期：2011.10

  Thirty-five 3-aryl-4-arylaminofuran-2(5H)-one derivatives were designed, prepared and tested for their inhibitory activity against tyrosyl-tRNA synthetase. Out of these compounds, 3-(3-bromophenyl)-4-(3,5-dichlorophenylamino)furan-2(5H)-one (35) was the most active with IC50 of 0.09 +/- 0.02 mu M. The structure activity relationship revealed that introduction of chlorine atoms at both meta positions of aniline moiety significantly increased the enzyme inhibitory activity. The results of antibacterial assay revealed that the tested compounds showed good activity against Gram-positive bacteria, with 35 being the most potent with MIC50 of 0.06 mu g/mL against Staphylococcus aureus ATCC 25923. Molecular docking of 35 into S. aureus tyrosyl-tRNA synthetase active site was also performed. The inhibitor snugly fitting the active site may well explain its excellent inhibitory activity. (C) 2011 Elsevier Masson SAS. All rights reserved.