1,7-bis-(4-O-glutamoyl-3-methoxyphenyl)-1,6-heptadiene-3,5-dione | 1073666-62-2

• 分子结构分类: 有机化合物 - 苯丙烷和聚酮 - 二芳基庚烷
• 英文名称: 1,7-bis-(4-O-glutamoyl-3-methoxyphenyl)-1,6-heptadiene-3,5-dione
• 英文别名: 4,4'-di-O-(glutamoyl)curcumin；(4S)-4-amino-5-[4-[(1E,6E)-7-[4-[(2S)-2-amino-4-carboxybutanoyl]oxy-3-methoxyphenyl]-3,5-dioxohepta-1,6-dienyl]-2-methoxyphenoxy]-5-oxopentanoic acid
• CAS: 1073666-62-2
• 化学式: C₃₁H₃₄N₂O₁₂
• 分子量: 626.617
• InChiKey: KIWSNQUBEPTHQS-LHVYAWJFSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  -3.2
• 重原子数：
  45
• 可旋转键数：
  20
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.29
• 拓扑面积：
  232
• 氢给体数：
  4
• 氢受体数：
  14

反应信息

• 作为产物：
  描述：

  N-phthaloylglutamoyl chloride 、 姜黄素 在 吡啶 、 氨 作用下， 反应 8.0h， 以40%的产率得到1,7-bis-(4-O-glutamoyl-3-methoxyphenyl)-1,6-heptadiene-3,5-dione
  参考文献：
  名称：

  Design, synthesis and characterization of some bioactive conjugates of curcumin with glycine, glutamic acid, valine and demethylenated piperic acid and study of their antimicrobial and antiproliferative properties

  摘要：

  The monoesters of curcumin, a symmetric diphenol with valine and glycine have been prepared by a novel solid phase synthesis and its diesters with valine, glutamic acid and demethylenated piperic acid have been prepared by solution phase method. The assessment of their antimicrobial and anticancer (anti proliferative) activities suggested that diesters of curcumin are relatively more active than curcumin itself due to their increased solubility, slow metabolism and better cellular uptake. Furthermore, significant observation was that monoesters of curcumin have even better antimicrobial activity than their corresponding diesters, emphasizing the role of free phenolic group. The conjugate of curcumin with demethylenated piperic acid in which methylenedioxy ring was open also shows enhanced activity than the corresponding piperic acid conjugate, emphasizing the role of free phenolics in the transport or in the binding processes. (C) 2007 Elsevier Masson SAS. All rights reserved.

  DOI：

  10.1016/j.ejmech.2007.11.027

文献信息

• Design, synthesis and characterization of some bioactive conjugates of curcumin with glycine, glutamic acid, valine and demethylenated piperic acid and study of their antimicrobial and antiproliferative properties
  作者：Shiv K. Dubey、Anuj K. Sharma、Upma Narain、Krishna Misra、Uttam Pati

  DOI：10.1016/j.ejmech.2007.11.027

  日期：2008.9

  The monoesters of curcumin, a symmetric diphenol with valine and glycine have been prepared by a novel solid phase synthesis and its diesters with valine, glutamic acid and demethylenated piperic acid have been prepared by solution phase method. The assessment of their antimicrobial and anticancer (anti proliferative) activities suggested that diesters of curcumin are relatively more active than curcumin itself due to their increased solubility, slow metabolism and better cellular uptake. Furthermore, significant observation was that monoesters of curcumin have even better antimicrobial activity than their corresponding diesters, emphasizing the role of free phenolic group. The conjugate of curcumin with demethylenated piperic acid in which methylenedioxy ring was open also shows enhanced activity than the corresponding piperic acid conjugate, emphasizing the role of free phenolics in the transport or in the binding processes. (C) 2007 Elsevier Masson SAS. All rights reserved.