methyl (2S,4S)-4-[2-[2-(3,4-dihydroxyphenyl)ethoxy]-2-oxoethyl]-3-formyl-2-methyl-3,4-dihydro-2H-pyran-5-carboxylate | 1372175-04-6

• 分子结构分类: 有机化合物 - 苯类化合物 - 酚类
• 英文名称: methyl (2S,4S)-4-[2-[2-(3,4-dihydroxyphenyl)ethoxy]-2-oxoethyl]-3-formyl-2-methyl-3,4-dihydro-2H-pyran-5-carboxylate
• CAS: 1372175-04-6
• 化学式: C₁₉H₂₂O₈
• 分子量: 378.379
• InChiKey: DEBZOPZQKONWTK-ULVQEXTCSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  1.1
• 重原子数：
  27
• 可旋转键数：
  9
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.42
• 拓扑面积：
  119
• 氢给体数：
  2
• 氢受体数：
  8

反应信息

• 作为产物：
  描述：

  甲醇 、 橄榄苦甙 在 erbium(III) triflate 作用下， 以 水 、 乙腈 、 二氯甲烷 为溶剂， 反应 8.0h， 生成 、 methyl (2S,4S)-4-[2-[2-(3,4-dihydroxyphenyl)ethoxy]-2-oxoethyl]-3-formyl-2-methyl-3,4-dihydro-2H-pyran-5-carboxylate 、 、 5-O-[2-(3,4-dihydroxyphenyl)ethyl] 1-O-methyl (3S)-2-(dihydroxymethyl)-3-[(E)-1-oxobut-2-en-2-yl]pentanedioate
  参考文献：
  名称：

  Synthesis, Biological Evaluation, and Molecular Modeling of Oleuropein and Its Semisynthetic Derivatives as Cyclooxygenase Inhibitors

  摘要：

  Oleuropein, the main phenolic compound in virgin olive oil, and several of its derivatives such as oleuropein aglycone, hydroxytyrosol, and their respective acetylated lipophilic forms were obtained by simple and environmentally friendly semisynthetic protocols. The same molecules were then tested in vitro and in vivo, comparing their intriguing anti-COX-1 and anti-COX-2 properties to those of well-known anti-inflammatory drugs such as ibuprofen and celecoxib. Finally, molecular modeling experiments displaying the most probable binding modes within the classical binding clefts of the enzymes suggest the heme moiety as a potential alternative target.

  DOI：

  10.1021/jf9033305

文献信息

• Synthesis, Biological Evaluation, and Molecular Modeling of Oleuropein and Its Semisynthetic Derivatives as Cyclooxygenase Inhibitors
  作者：Antonio Procopio、Stefano Alcaro、Monica Nardi、Manuela Oliverio、Francesco Ortuso、Paolo Sacchetta、Damiana Pieragostino、Giovanni Sindona

  DOI：10.1021/jf9033305

  日期：2009.12.9

  Oleuropein, the main phenolic compound in virgin olive oil, and several of its derivatives such as oleuropein aglycone, hydroxytyrosol, and their respective acetylated lipophilic forms were obtained by simple and environmentally friendly semisynthetic protocols. The same molecules were then tested in vitro and in vivo, comparing their intriguing anti-COX-1 and anti-COX-2 properties to those of well-known anti-inflammatory drugs such as ibuprofen and celecoxib. Finally, molecular modeling experiments displaying the most probable binding modes within the classical binding clefts of the enzymes suggest the heme moiety as a potential alternative target.