2-(2,3-dihydrobenzo[b][1,4]dioxin-6-yl)-5-hydroxy-7-(2-(piperidin-1-yl)ethoxy)-4H-chromen-4-one | 1144510-01-9

• 分子结构分类: 有机化合物 - 木脂素、新木脂素和相关化合物 - 黄酮木脂素
• 英文名称: 2-(2,3-dihydrobenzo[b][1,4]dioxin-6-yl)-5-hydroxy-7-(2-(piperidin-1-yl)ethoxy)-4H-chromen-4-one
• 英文别名: 2-(2,3-Dihydro-1,4-benzodioxin-6-yl)-5-hydroxy-7-(2-piperidin-1-ylethoxy)chromen-4-one
• CAS: 1144510-01-9
• 化学式: C₂₄H₂₅NO₆
• 分子量: 423.466
• InChiKey: AURSPSAEXNSNJN-UHFFFAOYSA-N

物化性质

• 熔点：
  145-146 °C
• 沸点：
  642.1±55.0 °C(predicted)
• 密度：
  1.320±0.06 g/cm3(Temp: 20 °C; Press: 760 Torr)(predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  3.9
• 重原子数：
  31
• 可旋转键数：
  5
• 环数：
  5.0
• sp3杂化的碳原子比例：
  0.38
• 拓扑面积：
  77.5
• 氢给体数：
  1
• 氢受体数：
  7

反应信息

• 作为产物：
  描述：

  哌啶 、 O7-bromethyl-O3',O4'-ethylidene luteolin 以 N,N-二甲基甲酰胺 为溶剂， 反应 1.0h， 以82%的产率得到2-(2,3-dihydrobenzo[b][1,4]dioxin-6-yl)-5-hydroxy-7-(2-(piperidin-1-yl)ethoxy)-4H-chromen-4-one
  参考文献：
  名称：

  Synthesis and biological evaluation of novel luteolin derivatives as antibacterial agents

  摘要：

  A series of luteolin derivatives 2-20 were prepared, 3-20 of which were first reported. The chemical structures of these compounds were confirmed by means of H-1 NMR, ESI-MS and elemental analyses. The compounds were assayed for antibacterial (Bacillus subtilis, Staphylococcus aureus, Pseudomonas fluorescens and Escherichia coli) activities by MTT (3-(4,5-dimethylthiazol-2-yl)-2,5-diphenyl trtrazolium bromide) method. Among the compounds tested, most of them displayed significant activity against the tested strains, and 2-(2,3-dihydrobenzo[b][1,4]dioxin-6-yl)-5-hydroxy-7-(2-(3-morpholinopropylamino)ethoxy)-4H-chromen-4-one (17) showed the most favorable antibacterial activity in vitro with MICs of 1.562, 3.125, 3.125, and 6.25 mu g/mL against B. subtilis, S. aureus, P. fluorescens and E. coli, respectively. Structure-activity relationships (SAR) were also discussed based on the obtained experimental data. (C) 2008 Elsevier Masson SAS. All rights reserved.

  DOI：

  10.1016/j.ejmech.2008.01.013

文献信息

• Synthesis and biological evaluation of novel luteolin derivatives as antibacterial agents
  作者：Peng-Cheng Lv、Huan-Qiu Li、Jia-Yu Xue、Lei Shi、Hai-Liang Zhu

  DOI：10.1016/j.ejmech.2008.01.013

  日期：2009.2

  A series of luteolin derivatives 2-20 were prepared, 3-20 of which were first reported. The chemical structures of these compounds were confirmed by means of H-1 NMR, ESI-MS and elemental analyses. The compounds were assayed for antibacterial (Bacillus subtilis, Staphylococcus aureus, Pseudomonas fluorescens and Escherichia coli) activities by MTT (3-(4,5-dimethylthiazol-2-yl)-2,5-diphenyl trtrazolium bromide) method. Among the compounds tested, most of them displayed significant activity against the tested strains, and 2-(2,3-dihydrobenzo[b][1,4]dioxin-6-yl)-5-hydroxy-7-(2-(3-morpholinopropylamino)ethoxy)-4H-chromen-4-one (17) showed the most favorable antibacterial activity in vitro with MICs of 1.562, 3.125, 3.125, and 6.25 mu g/mL against B. subtilis, S. aureus, P. fluorescens and E. coli, respectively. Structure-activity relationships (SAR) were also discussed based on the obtained experimental data. (C) 2008 Elsevier Masson SAS. All rights reserved.