3-(3-chlorophenyl)-4-(2-morpholinoethylamino)furan-2(5H)-one | 1275608-96-2

• 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-chlorophenyl)-4-(2-morpholinoethylamino)furan-2(5H)-one
• 英文别名: 4-(3-chlorophenyl)-3-(2-morpholin-4-ylethylamino)-2H-furan-5-one
• CAS: 1275608-96-2
• 化学式: C₁₆H₁₉ClN₂O₃
• 分子量: 322.791
• InChiKey: ICLAXGFWKBWCDR-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  1.8
• 重原子数：
  22
• 可旋转键数：
  5
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.44
• 拓扑面积：
  50.8
• 氢给体数：
  1
• 氢受体数：
  5

反应信息

• 作为产物：
  描述：

  3-氯苯乙酸 在 sodium ethanolate 、 sodium hydride 、 三氯化磷 作用下， 以 四氢呋喃 、 乙醚 、 乙醇 、 N,N-二甲基甲酰胺 为溶剂， 反应 0.17h， 生成 3-(3-chlorophenyl)-4-(2-morpholinoethylamino)furan-2(5H)-one
  参考文献：
  名称：

  Synthesis, structure, molecular docking, and structure–activity relationship analysis of enamines: 3-Aryl-4-alkylaminofuran-2(5H)-ones as potential antibacterials

  摘要：

  Thirty-one 3-aryl-4-alkylaminofuran-2(5H)-ones were designed, prepared and tested for their antibacterial activity. Some of them showed significant antibacterial activity against Gram-positive organisms, especially against Staphylococcus aureus ATCC 25923, but all were inactive against Gram-negative organisms. Out of these compounds, 3-(4-bromophenyl)-4-(2-(4-nitrophenyl)hydrazinyl)furan-2(5H)-one (4a11) showed the most potent antibacterial activity against S. aureus ATCC 25923 with MIC50 of 0.42 mu g/mL. The enzyme assay revealed that the possible antibacterial mechanism of the synthetic compounds might be due to their inhibitory activity against tyrosyl-tRNA synthetase. Molecular dockings of 4a11 into S. aureus tyrosyl-tRNA synthetase active site were also performed. This inhibitor snugly fitting the active site might well explain its excellent inhibitory activity. Meanwhile, this modeling disclosed that a more suitable optimization strategy might be to modify the benzene ring at 3-position of furanone with hydrophilic groups. (C) 2011 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.bmc.2011.01.051

文献信息

• Synthesis, structure, molecular docking, and structure–activity relationship analysis of enamines: 3-Aryl-4-alkylaminofuran-2(5H)-ones as potential antibacterials
  作者：Zhu-Ping Xiao、Xing-Bing He、Zhi-Yun Peng、Tao-Ju Xiong、Juan Peng、Li-Hua Chen、Hai-Liang Zhu

  DOI：10.1016/j.bmc.2011.01.051

  日期：2011.3

  Thirty-one 3-aryl-4-alkylaminofuran-2(5H)-ones were designed, prepared and tested for their antibacterial activity. Some of them showed significant antibacterial activity against Gram-positive organisms, especially against Staphylococcus aureus ATCC 25923, but all were inactive against Gram-negative organisms. Out of these compounds, 3-(4-bromophenyl)-4-(2-(4-nitrophenyl)hydrazinyl)furan-2(5H)-one (4a11) showed the most potent antibacterial activity against S. aureus ATCC 25923 with MIC50 of 0.42 mu g/mL. The enzyme assay revealed that the possible antibacterial mechanism of the synthetic compounds might be due to their inhibitory activity against tyrosyl-tRNA synthetase. Molecular dockings of 4a11 into S. aureus tyrosyl-tRNA synthetase active site were also performed. This inhibitor snugly fitting the active site might well explain its excellent inhibitory activity. Meanwhile, this modeling disclosed that a more suitable optimization strategy might be to modify the benzene ring at 3-position of furanone with hydrophilic groups. (C) 2011 Elsevier Ltd. All rights reserved.