(E)-1-(allyloxy)-3-(3,4-dimethoxyphenyl)-1-oxopropan-2-yl 3-(3,4-dimethoxyphenyl)acrylate | 1322088-12-9

• 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)-1-(allyloxy)-3-(3,4-dimethoxyphenyl)-1-oxopropan-2-yl 3-(3,4-dimethoxyphenyl)acrylate
• 英文别名: prop-2-enyl 3-(3,4-dimethoxyphenyl)-2-[(E)-3-(3,4-dimethoxyphenyl)prop-2-enoyl]oxypropanoate
• CAS: 1322088-12-9
• 化学式: C₂₅H₂₈O₈
• 分子量: 456.493
• InChiKey: GFRISCYQUDIWKE-FMIVXFBMSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  4.6
• 重原子数：
  33
• 可旋转键数：
  14
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.28
• 拓扑面积：
  89.5
• 氢给体数：
  0
• 氢受体数：
  8

反应信息

• 作为反应物：
  描述：

  (E)-1-(allyloxy)-3-(3,4-dimethoxyphenyl)-1-oxopropan-2-yl 3-(3,4-dimethoxyphenyl)acrylate 在 吗啉 、 四(三苯基膦)钯 、 碘代三甲硅烷 作用下， 以 四氢呋喃 、 喹啉 为溶剂， 反应 4.5h， 生成 rosmarinic acid
  参考文献：
  名称：

  Synthesis of derivatives of methyl rosmarinate and their inhibitory activities against matrix metalloproteinase-1 (MMP-1)

  摘要：

  A series of MMP-1 inhibitors have been identified based upon a methyl rosmarinate scaffold using structure-based drug design methods. The best compound in the series showed an IC50 value of 0.4 mu M. A docking study was conducted for compound (S)-10n in order to investigate its binding interactions with MMP-1. The structure activity relationships (SAR) were also briefly discussed. Useful SAR was established which provides important guidelines for the design of future generations of potent inhibitors against MMP-1. (C) 2012 Elsevier Masson SAS. All rights reserved.

  DOI：

  10.1016/j.ejmech.2012.09.047
• 作为产物：
  描述：

  (Z)-3-(3,4-dimethoxyphenyl)-2-hydroxyacrylic acid 在 4-二甲氨基吡啶 、 sodium tetrahydroborate 、 对甲苯磺酸 、 盐酸-N-乙基-Nˊ-(3-二甲氨基丙基)碳二亚胺 、 sodium hydroxide 作用下， 以 甲醇 、 二氯甲烷 、 甲苯 为溶剂， 反应 34.0h， 生成 (E)-1-(allyloxy)-3-(3,4-dimethoxyphenyl)-1-oxopropan-2-yl 3-(3,4-dimethoxyphenyl)acrylate
  参考文献：
  名称：

  Synthesis of derivatives of methyl rosmarinate and their inhibitory activities against matrix metalloproteinase-1 (MMP-1)

  摘要：

  A series of MMP-1 inhibitors have been identified based upon a methyl rosmarinate scaffold using structure-based drug design methods. The best compound in the series showed an IC50 value of 0.4 mu M. A docking study was conducted for compound (S)-10n in order to investigate its binding interactions with MMP-1. The structure activity relationships (SAR) were also briefly discussed. Useful SAR was established which provides important guidelines for the design of future generations of potent inhibitors against MMP-1. (C) 2012 Elsevier Masson SAS. All rights reserved.

  DOI：

  10.1016/j.ejmech.2012.09.047