(E)-1-(3,4-dihydroxyphenyl)-5-(3,4-dimethoxyphenyl)-pent-1-en-3-one | 1443545-71-8

• 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)-1-(3,4-dihydroxyphenyl)-5-(3,4-dimethoxyphenyl)-pent-1-en-3-one
• 英文别名: (E)-1-(3,4-dihydroxyphenyl)-5-(3,4-dimethoxyphenyl)pent-1-en-3-one
• CAS: 1443545-71-8
• 化学式: C₁₉H₂₀O₅
• 分子量: 328.365
• InChiKey: PUTZMDYOTOIIAG-XVNBXDOJSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.4
• 重原子数：
  24
• 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：
  76
• 氢给体数：
  2
• 氢受体数：
  5

反应信息

• 作为反应物：
  描述：

  (E)-1-(3,4-dihydroxyphenyl)-5-(3,4-dimethoxyphenyl)-pent-1-en-3-one 、 乙酸酐 在 吡啶 作用下， 以93%的产率得到acetic acid (E)-2-acetoxy-4-[5-(3,4-dimethoxyphenyl)-3-oxo-pent-1-enyl]phenyl ester
  参考文献：
  名称：

  Synthesis and neuroprotective effect of E-3,4-dihydroxy styryl aralkyl ketones derivatives against oxidative stress and inflammation

  摘要：

  E-3,4-Dihydroxy styryl aralkyl ketones as well as their 3,4-diacetylated derivatives as the analogues of neuroprotective agent CAPE were designed and synthesized for improving stability and lipid solubility. The neuroprotective activities of target compounds 10a-g and 11a-g were tested by three models in vitro, including 1,1-diphenyl-2-picrylhydrazyl radical scavenging capacity, neuronal protecting effect against damage induced by H2O2 in PC12 cells and nitric oxide suppression effect in BV2 microglial cells. The results demonstrated that compounds 10f and 11f exhibited the most potent neuroprotective effect against oxidative stress and inflammation, which is higher than that of the lead compound CAPE. (C) 2013 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.bmcl.2013.05.016
• 作为产物：
  描述：

  3,4-二甲氧基苯甲醛 在 四氢吡咯 、 palladium 10% on activated carbon 、 氢气 、 溶剂黄146 作用下， 以 四氢呋喃 、 二氯甲烷 、 水 为溶剂， 生成 (E)-1-(3,4-dihydroxyphenyl)-5-(3,4-dimethoxyphenyl)-pent-1-en-3-one
  参考文献：
  名称：

  Synthesis and neuroprotective effect of E-3,4-dihydroxy styryl aralkyl ketones derivatives against oxidative stress and inflammation

  摘要：

  E-3,4-Dihydroxy styryl aralkyl ketones as well as their 3,4-diacetylated derivatives as the analogues of neuroprotective agent CAPE were designed and synthesized for improving stability and lipid solubility. The neuroprotective activities of target compounds 10a-g and 11a-g were tested by three models in vitro, including 1,1-diphenyl-2-picrylhydrazyl radical scavenging capacity, neuronal protecting effect against damage induced by H2O2 in PC12 cells and nitric oxide suppression effect in BV2 microglial cells. The results demonstrated that compounds 10f and 11f exhibited the most potent neuroprotective effect against oxidative stress and inflammation, which is higher than that of the lead compound CAPE. (C) 2013 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.bmcl.2013.05.016