3-(3,4-dimethoxyphenyl)-4-(2-(4-methylpiperazin-1-yl)ethoxy)furan-2(5H)-one | 1320275-56-6

• 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-(3,4-dimethoxyphenyl)-4-(2-(4-methylpiperazin-1-yl)ethoxy)furan-2(5H)-one
• 英文别名: 4-(3,4-dimethoxyphenyl)-3-[2-(4-methylpiperazin-1-yl)ethoxy]-2H-furan-5-one
• CAS: 1320275-56-6
• 化学式: C₁₉H₂₆N₂O₅
• 分子量: 362.426
• InChiKey: PJHASRNIASJLQT-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  1.3
• 重原子数：
  26
• 可旋转键数：
  7
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.53
• 拓扑面积：
  60.5
• 氢给体数：
  0
• 氢受体数：
  7

反应信息

• 作为产物：
  描述：

  3-(3,4-二甲氧基苯基)-4-羟基-5H-呋喃-2-酮 在 三乙胺 作用下， 以 N,N-二甲基甲酰胺 、 丙酮 为溶剂， 生成 3-(3,4-dimethoxyphenyl)-4-(2-(4-methylpiperazin-1-yl)ethoxy)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

• Structure and Antibacterial Activity of 3-(3,4-Dimethoxyphenyl)furan-2(5H)-ones
  作者：Zhu-Ping Xiao、Li-Cheng Yi、Tian-Fang Yi、Kai-Shuang Xiang、Ze-Jun Huang、Hai-Liang Zhu

  DOI：10.1007/s10870-011-0246-9

  日期：2012.4

  Crystalline hydrate of the title compound (5), C19H26N2O5·2(H2O), was structurally characterized by single crystal X-ray diffraction. It crystallizes in monoclinic system space group P 21/c with a = 7.3987(7) Å, b = 17.8691(16) Å, c = 17.0022(13) Å, β = 112.944(3)°, V = 2070.0(3) Å3, Z = 4, R 1 = 0.0592, wR 2 = 0.1016, and T = 298(2) K. The X-ray structure determination revealed that the center furanone ring is nearly coplanar with 3,4-dimethoxybenzene ring, making a dihedral angle of 0.860(69)°. Two kinds of centrosymmetric tetramers characterized by graph-set motifs of R 7 8 (36) and R 4 6 (32) are formed through O–H···O, O–H···N and C–H···O hydrogen bonding interactions, which generate a sheet of edge-fused rings parallel to the (011) plane. These sheets are further linked into a three dimensional network by C–H···π interactions. Nine 3-(3,4-dimethoxyphenyl)furan-2(5H)-ones were synthesized and fully characterized by elemental analysis, MS and 1H NMR. All of them were evaluated for antimicrobial activities against three Gram-positive organisms and a Gram-negative organism, and compound 5 was the most active against Staphylococcus aureus ATCC 25923. Two kinds of centrosymmetric tetramers characterized by graph-set motifs of R 7 8 (36) and R 4 6 (32) are formed through O–H···O, O–H···N and C–H···O hydrogen bonding interactions, which generate a sheet of edge-fused rings parallel to the (011) plane.

  标题化合物的结晶水合物（5），C19H26N2O5·2（H2O），通过单晶X射线衍射进行了结构表征。它以单斜晶系空间群P 21/c结晶，其中a = 7.3987（7）Å，b = 17.8691（16）Å，c = 17.0022（13）Å，β = 112.944（3）°，V = 2070.0（3）ų，Z = 4，R 1 = 0.0592，wR 2 = 0.1016，T = 298（2）K。X射线结构测定揭示了中心呋喃酮环与3,4-二甲氧基苯环几乎共面，形成0.860（69）°的二面角。通过O-H···O、O-H···N和C-H···O氢键相互作用，形成了两种由图集基序R 7 8（36）和R 4 6（32）表征的对称四聚体，这些氢键相互作用生成了一张边缘融合的环片，平行于（011）平面。这些片层通过C-H···π相互作用进一步连接成三维网络。合成了九种3-（3,4-二甲氧苯基）呋喃-2（5H）-酮，并通过元素分析、MS和¹H NMR进行了全面表征。所有这些化合物都对三种革兰氏阳性菌和一种革兰氏阴性菌进行了抗菌活性评估，其中化合物5对金黄色葡萄球菌ATCC 25923最为活性。通过O-H···O、O-H···N和C-H···O氢键相互作用，形成了两种由图集基序R 7 8（36）和R 4 6（32）表征的对称四聚体，这些氢键相互作用生成了一张边缘融合的环片，平行于（011）平面。
• 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.