3,4-dihydroxyphenylethyl 4-O-((trans)-p-chlorocinnamoyl)-β-D-glucopyranoside

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: 3,4-dihydroxyphenylethyl 4-O-((trans)-p-chlorocinnamoyl)-β-D-glucopyranoside
• 英文别名: [(2R,3S,4R,5R,6R)-6-[2-(3,4-dihydroxyphenyl)ethoxy]-4,5-dihydroxy-2-(hydroxymethyl)oxan-3-yl] (E)-3-(4-chlorophenyl)prop-2-enoate
• 化学式: C₂₃H₂₅ClO₉
• 分子量: 480.899
• InChiKey: CTGDQJCLVLSVSO-WDIXTDMMSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  1.9
• 重原子数：
  33
• 可旋转键数：
  9
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.35
• 拓扑面积：
  146
• 氢给体数：
  5
• 氢受体数：
  9

反应信息

• 作为产物：
  描述：

  羟基酪醇 在 4-二甲氨基吡啶 、 三氟甲磺酸三甲基硅酯 、 palladium 10% on activated carbon 、 4-甲基苯磺酸吡啶 、 potassium carbonate 、 三乙胺 、 乙酰氯 、 N,N'-二环己基碳二亚胺 作用下， 以 甲醇 、 二氯甲烷 、 水 、 丙酮 、 乙腈 为溶剂， 反应 46.0h， 生成 3,4-dihydroxyphenylethyl 4-O-((trans)-p-chlorocinnamoyl)-β-D-glucopyranoside
  参考文献：
  名称：

  Synthetic phenylethanoid glycoside derivatives as potent neuroprotective agents

  摘要：

  Several phenylethanoid glycoside derivatives were designed and synthesized. Most of the synthetic compounds showed significant neuroprotective effects, including antioxidative and anti-apoptotic properties. Specifically, target compounds displayed potent effects against various toxicities such as H2O2 and 6-hydroxydopamine (6-OHDA) in PCl2 cells. Among the synthetic derivatives, three compounds (5, 6, 8) exhibited much superior activities to the marketed drug Edaravone. The compounds were able to prevent the 6-OHDA-induced damage in PCl2 cells in a dose-dependent manner. The antiapoptotic effects could be observed via cell morphological changes. Moreover, the compounds significantly reduced the intracellular ROS increase resulting from 6-OHDA treatment. The preliminary structure activity relationships were also explored. Compounds 5, 6, 8 may hold the potential as promising neuroprotective agents and new lead compounds for the treatment of neurodegenerative diseases or cerebral ischemia. (C) 2015 Elsevier Masson SAS. All rights reserved.

  DOI：

  10.1016/j.ejmech.2015.03.038

文献信息

• Synthetic phenylethanoid glycoside derivatives as potent neuroprotective agents
  作者：Ying-Guo Liu、Xiaxi Li、De-Cai Xiong、Binhan Yu、Xiaoping Pu、Xin-Shan Ye

  DOI：10.1016/j.ejmech.2015.03.038

  日期：2015.5

  Several phenylethanoid glycoside derivatives were designed and synthesized. Most of the synthetic compounds showed significant neuroprotective effects, including antioxidative and anti-apoptotic properties. Specifically, target compounds displayed potent effects against various toxicities such as H2O2 and 6-hydroxydopamine (6-OHDA) in PCl2 cells. Among the synthetic derivatives, three compounds (5, 6, 8) exhibited much superior activities to the marketed drug Edaravone. The compounds were able to prevent the 6-OHDA-induced damage in PCl2 cells in a dose-dependent manner. The antiapoptotic effects could be observed via cell morphological changes. Moreover, the compounds significantly reduced the intracellular ROS increase resulting from 6-OHDA treatment. The preliminary structure activity relationships were also explored. Compounds 5, 6, 8 may hold the potential as promising neuroprotective agents and new lead compounds for the treatment of neurodegenerative diseases or cerebral ischemia. (C) 2015 Elsevier Masson SAS. All rights reserved.