2-[(E)-3-(2,3-dihydro-1-benzofuran-6-yl)prop-2-enoyl]oxy-3-(3,4-dimethoxyphenyl)propanoic acid | 1430416-91-3

• 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: 2-[(E)-3-(2,3-dihydro-1-benzofuran-6-yl)prop-2-enoyl]oxy-3-(3,4-dimethoxyphenyl)propanoic acid
• CAS: 1430416-91-3
• 化学式: C₂₂H₂₂O₇
• 分子量: 398.412
• InChiKey: CFLSNCWXWVSDFJ-VMPITWQZSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.7
• 重原子数：
  29
• 可旋转键数：
  9
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.27
• 拓扑面积：
  91.3
• 氢给体数：
  1
• 氢受体数：
  7

反应信息

• 作为反应物：
  描述：

  2-[(E)-3-(2,3-dihydro-1-benzofuran-6-yl)prop-2-enoyl]oxy-3-(3,4-dimethoxyphenyl)propanoic acid 在 4-二甲氨基吡啶 、 N,N'-二环己基碳二亚胺 、 盐酸羟胺 作用下， 以 二氯甲烷 为溶剂， 反应 24.25h， 以69%的产率得到[3-(3,4-dimethoxyphenyl)-1-(hydroxyamino)-1-oxopropan-2-yl] (E)-3-(2,3-dihydro-1-benzofuran-6-yl)prop-2-enoate
  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 吗啉 、 4-二甲氨基吡啶 、 sodium tetrahydroborate 、 四(三苯基膦)钯 、 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 四氢呋喃 、 甲醇 、 二氯甲烷 、 甲苯 为溶剂， 反应 34.5h， 生成 2-[(E)-3-(2,3-dihydro-1-benzofuran-6-yl)prop-2-enoyl]oxy-3-(3,4-dimethoxyphenyl)propanoic 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

文献信息

• Synthesis of derivatives of methyl rosmarinate and their inhibitory activities against matrix metalloproteinase-1 (MMP-1)
  作者：Hu Yuan、Weiqiang Lu、Liyan Wang、Lei Shan、Honglin Li、Jin Huang、Qingyan Sun、Weidong Zhang

  DOI：10.1016/j.ejmech.2012.09.047

  日期：2013.4

  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.