N-[2-(3,4-dihydroxyphenyl)ethyl]-3-(3,4,5-trimethoxyphenyl)-2-propenamide

• 分子结构分类: 有机化合物 - 苯类化合物 - 酚类
• 英文名称: N-[2-(3,4-dihydroxyphenyl)ethyl]-3-(3,4,5-trimethoxyphenyl)-2-propenamide
• 英文别名: (E)-N-(3,4-dihydroxyphenethyl)-3-(3,4,5-trimethoxyphenyl)acrylamide；(E)-N-[2-(3,4-dihydroxyphenyl)ethyl]-3-(3,4,5-trimethoxyphenyl)prop-2-enamide
• 化学式: C₂₀H₂₃NO₆
• 分子量: 373.406
• InChiKey: QSCCUBSGQZSNLV-FNORWQNLSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2
• 重原子数：
  27
• 可旋转键数：
  8
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.25
• 拓扑面积：
  97.2
• 氢给体数：
  3
• 氢受体数：
  6

反应信息

• 作为产物：
  描述：

  (E)-3-(3,4,5-trimethoxyphenyl)acryloyl chloride 在 三乙胺 作用下， 以 乙醇 、 甲苯 为溶剂， 反应 18.0h， 生成 N-[2-(3,4-dihydroxyphenyl)ethyl]-3-(3,4,5-trimethoxyphenyl)-2-propenamide
  参考文献：
  名称：

  N-酰基-2-哌啶酮的轻度，无金属和无保护的氨基转移为氨基酸，氨基醇和脂肪胺以及N-酰基-2-哌啶酮的酯化

  摘要：

  一种高选择性，温和且无金属的方案，可在短反应时间（30–45分钟）内将N-酰基哌啶酮转氨成未保护的氨基酸，氨基醇和其他脂肪族胺，且无其他碱且在纯净条件下进行。N酰基哌啶酮在85°C下用脂肪族醇酯化。酰胺键捻，τ= -20.39°和pyramidalization，χ Ñ = -11.73°。

  DOI：

  10.1002/ejoc.201900517

文献信息

• N-Caffeoylphenalkylamide derivatives as bacterial efflux pump inhibitors
  作者：Serge Michalet、Gilbert Cartier、Bruno David、Anne-Marie Mariotte、Marie-Geneviève Dijoux-franca、Glenn W. Kaatz、Michael Stavri、Simon Gibbons

  DOI：10.1016/j.bmcl.2006.12.059

  日期：2007.3

  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.