3-(3-bromophenyl)-4-(2-morpholinoethoxy)furan-2(5H)-one | 1320275-61-3

• 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-bromophenyl)-4-(2-morpholinoethoxy)furan-2(5H)-one
• 英文别名: 4-(3-bromophenyl)-3-(2-morpholin-4-ylethoxy)-2H-furan-5-one
• CAS: 1320275-61-3
• 化学式: C₁₆H₁₈BrNO₄
• 分子量: 368.227
• InChiKey: SJQRXLWXOFJHHI-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  1.9
• 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：
  48
• 氢给体数：
  0
• 氢受体数：
  5

反应信息

• 作为产物：
  描述：

  2-ethoxy-2-oxoethyl 2-(3-bromophenyl)acetate 在 sodium hydride 、 三乙胺 作用下， 以 四氢呋喃 、 N,N-二甲基甲酰胺 、 丙酮 为溶剂， 生成 3-(3-bromophenyl)-4-(2-morpholinoethoxy)furan-2(5H)-one
  参考文献：
  名称：

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

  摘要：

  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.

  DOI：

  10.1016/j.bmc.2011.05.042

文献信息

• 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.