(E)-3-(4-ethoxy-3-methoxyphenyl)-1-(p-tolyl)prop-2-en-1-one

• 分子结构分类: 有机化合物 - 苯丙烷和聚酮 - 直链 1,3-二芳基丙烷
• 英文名称: (E)-3-(4-ethoxy-3-methoxyphenyl)-1-(p-tolyl)prop-2-en-1-one
• 英文别名: (E)-3-(4-ethoxy-3-methoxyphenyl)-1-(4-methylphenyl)prop-2-en-1-one
• 化学式: C₁₉H₂₀O₃
• 分子量: 296.366
• InChiKey: UACMGELGJYFQBN-YRNVUSSQSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  4.4
• 重原子数：
  22
• 可旋转键数：
  6
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.21
• 拓扑面积：
  35.5
• 氢给体数：
  0
• 氢受体数：
  3

反应信息

• 作为产物：
  描述：

  4-乙氧基-3-甲氧基苯甲醛 、 对甲基苯乙酮 在 sodium hydroxide 作用下， 以 乙醇 为溶剂， 生成 (E)-3-(4-ethoxy-3-methoxyphenyl)-1-(p-tolyl)prop-2-en-1-one
  参考文献：
  名称：

  Chalcones and Bis-Chalcones Analogs as DPPH and ABTS Radical Scavengers

  摘要：

  背景：许多合成支架物以及天然产物被确定为有效的抗氧化剂。本研究涉及对不同取代、具有药用特性的化合物类别“查尔酮和双查尔酮”进行抗氧化潜力评估。 方法：对一系列合成查尔酮1-13和双查尔酮14-18进行体外自由基清除活性测试。 结果：所有分子1-18在IC50范围内显示出明显的2,2-二苯基-1-苯基-亚硝基肼（DPPH）和2,2'-联苯二(3-乙基苯并噻唑啉-6-磺酸)（ABTS）自由基清除潜力，分别为0.58 ± 0.14 - 1.72 ± 0.03和0.49 ± 0.3 - 1.48 ± 0.06 μM。抗坏血酸（DPPH和ABTS的IC50分别为0.5 ± 0.1和0.46 ± 0.17 μM）被用作标准自由基清除剂。 结论：结构活性关系（SAR）显示了各种基团，包括-SMe和-OMe在清除活性中的积极参与。

  DOI：

  10.2174/1570180817999201001155032

文献信息

• Chalcones and bis-chalcones: As potential α-amylase inhibitors; synthesis, in vitro screening, and molecular modelling studies
  作者：Adebayo Tajudeen Bale、Khalid Mohammed Khan、Uzma Salar、Sridevi Chigurupati、Tolulope Fasina、Farman Ali、Kanwal、Abdul Wadood、Muhammad Taha、Sitansu Sekhar Nanda、Mehreen Ghufran、Shahnaz Perveen

  DOI：10.1016/j.bioorg.2018.05.003

  日期：2018.9

  Despite of a diverse range of biological activities associated with chalcones and bis-chalcones, they are still neglected by the medicinal chemist for their possible alpha-amylase inhibitory activity. So, the current study is based on the evaluation of this class for the identification of new leads as alpha-amylase inhibitors. For that purpose, a library of substituted chalcones 1-13 and bis-chalcones 14-18 were synthesized and characterized by spectroscopic techniques EI-MS and H-1 NMR. CHN analysis was carried out and found in agreement with the calculated values. All compounds were evaluated for in vitro alpha-amylase inhibitory activity and demonstrated good activities in the range of IC50 = 1.25 +/- 1.05-2.40 +/- 0.09 mu M as compared to the standard acarbose (IC50 = 1.04 +/- 0.3 mu M). Limited structure-activity relationship (SAR) was established by considering the effect of different groups attached to aryl rings on varying inhibitory activity. SMe group in chalcones and OMe group in bis-chalcones were found more influential on the activity than other groups. However, in order to predict the involvement of different groups in the binding interactions with the active site of alpha-amylase enzyme, in silico studies were also conducted.