(E)-3-(3,4-bis(ethoxymethoxy)phenyl)acrylic acid | 1426125-92-9

• 分子结构分类: 有机化合物 - 苯丙烷和聚酮 - 肉桂酸及其衍生物
• 英文名称: (E)-3-(3,4-bis(ethoxymethoxy)phenyl)acrylic acid
• 英文别名: (E)-3-[3,4-bis(ethoxymethoxy)phenyl]prop-2-enoic acid
• CAS: 1426125-92-9
• 化学式: C₁₅H₂₀O₆
• 分子量: 296.32
• InChiKey: IEKCZRDEDSOFGM-SOFGYWHQSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.4
• 重原子数：
  21
• 可旋转键数：
  10
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.4
• 拓扑面积：
  74.2
• 氢给体数：
  1
• 氢受体数：
  6

反应信息

• 作为反应物：
  描述：

  [(S)-3-((R)-1-Hydroxy-ethyl)-4-oxo-azetidin-(2Z)-ylidene]-acetic acid benzyl ester 、 (E)-3-(3,4-bis(ethoxymethoxy)phenyl)acrylic acid 在 4-二甲氨基吡啶 、 N,N'-二环己基碳二亚胺 作用下， 以 二氯甲烷 为溶剂， 反应 16.0h， 以38%的产率得到(E)-(R)-1-((S,Z)-2-(2-(benzyloxy)-2-oxoethylidene)-4-oxoazetidin-3-yl)ethyl 3-(3,4-bis(ethoxymethoxy)phenyl)acrylate
  参考文献：
  名称：

  4-Alkyliden-azetidinones modified with plant derived polyphenols: Antibacterial and antioxidant properties

  摘要：

  Antimicrobial resistance is one of the major and growing concerns in hospital-and community acquired infections, and new antimicrobial agents are therefore urgently required. It was reported that oxidative stress could contribute to the selection of resistant bacterial strains, since reactive oxygen species (ROS) revealed to be an essential driving force. In the present work 4-allcylidene-azetidinones, a new class of antibacterial agents, were functionalized with phytochemical polyphenolic acids such as protocatechuic, piperonyl, caffeic, ferulic, or sinapic acids and investigated as dual target antibacterial-antioxidant compounds. The best candidates showed good activities against multidrug resistant clinical isolates of MRSA (MICs 2-8 mu g/mL). Among the new compounds, two revealed the best antioxidant capacity with TEAC-DPPH and TEAC-ABTS being significantly more active than Troloxe. (C) 2017 Elsevier Masson SAS. All rights reserved.

  DOI：

  10.1016/j.ejmech.2017.09.048
• 作为产物：
  描述：

  (E)-methyl 3-(3,4-bis(ethoxymethoxy)phenyl)acrylate 在 sodium hydroxide 作用下， 以 四氢呋喃 、 甲醇 为溶剂， 反应 4.0h， 以96%的产率得到(E)-3-(3,4-bis(ethoxymethoxy)phenyl)acrylic acid
  参考文献：
  名称：

  单环β-内酰胺类作为抗菌剂：面对N-甲硫基氮杂环丁烷酮的抗氧化活性

  摘要：

  一系列具有抗菌活性的N-甲硫基-β-内酰胺类被彻底评估为抗氧化剂。我们发现仅锚定至β-内酰胺环的多酚部分的存在确保了足够的抗氧化剂效力。在一种结构中有效结合抗氧化剂和抗菌活性的新化合物可能为开发可用于不良临床状况的新线索提供有希望的基础，例如在囊性纤维化患者中，MRSA会引起定植，慢性肺氧化应激会导致上皮损伤地方。

  DOI：

  10.1016/j.ejmech.2012.12.024

文献信息

• 4-Alkyliden-azetidinones modified with plant derived polyphenols: Antibacterial and antioxidant properties
  作者：Daria Giacomini、Rosario Musumeci、Paola Galletti、Giulia Martelli、Lorenzo Assennato、Gianni Sacchetti、Alessandra Guerrini、Enrico Calaresu、Marianna Martinelli、Clementina Cocuzza

  DOI：10.1016/j.ejmech.2017.09.048

  日期：2017.11

  Antimicrobial resistance is one of the major and growing concerns in hospital-and community acquired infections, and new antimicrobial agents are therefore urgently required. It was reported that oxidative stress could contribute to the selection of resistant bacterial strains, since reactive oxygen species (ROS) revealed to be an essential driving force. In the present work 4-allcylidene-azetidinones, a new class of antibacterial agents, were functionalized with phytochemical polyphenolic acids such as protocatechuic, piperonyl, caffeic, ferulic, or sinapic acids and investigated as dual target antibacterial-antioxidant compounds. The best candidates showed good activities against multidrug resistant clinical isolates of MRSA (MICs 2-8 mu g/mL). Among the new compounds, two revealed the best antioxidant capacity with TEAC-DPPH and TEAC-ABTS being significantly more active than Troloxe. (C) 2017 Elsevier Masson SAS. All rights reserved.
• Monocyclic β-lactams as antibacterial agents: Facing antioxidant activity of N-methylthio-azetidinones
  作者：Rinaldo Cervellati、Paola Galletti、Emanuela Greco、Clementina E.A. Cocuzza、Rosario Musumeci、Luca Bardini、Francesco Paolucci、Matteo Pori、Roberto Soldati、Daria Giacomini

  DOI：10.1016/j.ejmech.2012.12.024

  日期：2013.2

  anchored to the β-lactam ring ensured an adequate antioxidant potency. New compounds, efficiently combining in one structure antioxidant and antibacterial activity, may provide a promising basis for the development of new leads useful in adverse clinical conditions such as in cystic fibrosis patients, in whom colonization by MRSA and epithelial damage by chronic pulmonary oxidative stress take place

  一系列具有抗菌活性的N-甲硫基-β-内酰胺类被彻底评估为抗氧化剂。我们发现仅锚定至β-内酰胺环的多酚部分的存在确保了足够的抗氧化剂效力。在一种结构中有效结合抗氧化剂和抗菌活性的新化合物可能为开发可用于不良临床状况的新线索提供有希望的基础，例如在囊性纤维化患者中，MRSA会引起定植，慢性肺氧化应激会导致上皮损伤地方。