N-trans-feruloyl-4′-O-methyldopamine

• 分子结构分类: 有机化合物 - 苯类化合物 - 酚类
• 英文名称: N-trans-feruloyl-4′-O-methyldopamine
• 英文别名: N-trans-feruloyldopamine；(E)-N-[2-(3,4-dihydroxyphenyl)ethyl]-3-(3,4-dimethoxyphenyl)prop-2-enamide
• 化学式: C₁₉H₂₁NO₅
• 分子量: 343.379
• InChiKey: OAGITLBXMBRXEW-VMPITWQZSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.1
• 重原子数：
  25
• 可旋转键数：
  7
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.21
• 拓扑面积：
  88
• 氢给体数：
  3
• 氢受体数：
  5

反应信息

• 作为产物：
  描述：

  多巴胺 、 3,4-二甲氧基肉酸酸 在 (benzotriazo-1-yloxy)tris(dimethylamino)phosphonium hexafluorophosphate 、 三乙胺 作用下， 以 N,N-二甲基甲酰胺 为溶剂， 反应 20.0h， 生成 N-trans-feruloyl-4′-O-methyldopamine
  参考文献：
  名称：

  N-Caffeoylphenalkylamide derivatives as bacterial efflux pump inhibitors

  摘要：

  As part of an ongoing project to identify plant natural products as efflux pump inhibitors (EPIs), bioassay-guided fractionation of the methanolic extract of Mirabilis jalapa Linn. (Nyetaginaceae) led to the isolation of an active polyphenolic amide: N-trans-feruloyl 4'-O-methyldopamine. This compound showed moderate activity as an EPI against multidrug-resistant (MDR) Staphylococcus aureus overexpressing the multidrug efflux transporter NorA, causing an 8-fold reduction of norfloxacin MIC at 292 mu M (100 mu g/mL). This prompted us to synthesize derivatives in order to provide structure-activity relationships and to access more potent inhibitors. Among the synthetic compounds, some were more active than the natural compound and N-trans-3,4-O-dimethylcaffeoyl tryptamine showed potentiation of norfloxacin in MDR S. aureus comparable to that of the standard reserpine. (c) 2007 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.bmcl.2006.12.059