N-phthaloylglutamoyl chloride | 1073666-68-8

• 分子结构分类: 有机化合物 - 有机酸及其衍生物 - 羧酸及其衍生物
• 英文名称: N-phthaloylglutamoyl chloride
• 英文别名: (4S)-5-chloro-4-(1,3-dioxoisoindol-2-yl)-5-oxopentanoic acid
• CAS: 1073666-68-8
• 化学式: C₁₃H₁₀ClNO₅
• 分子量: 295.679
• InChiKey: ZUUOFAQVTZWVFN-VIFPVBQESA-N

物化性质

• 沸点：
  500.0±40.0 °C(Predicted)
• 密度：
  1.549±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  1.4
• 重原子数：
  20
• 可旋转键数：
  5
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.23
• 拓扑面积：
  91.8
• 氢给体数：
  1
• 氢受体数：
  5

反应信息

• 作为反应物：
  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

• Derivatives of octahydro-6,10-dioxo-6H-pyridazino [1,2-a] [1,2] diazepine-1-carboxylic acid, their preparation process and their use in the preparation of therapeutically active compounds
  申请人：Aventis Pharma S.A.

  公开号：US20020128473A1

  公开（公告）日：2002-09-12

  Novel intermediates of the formulae 1 where the substituents are defined as in the specification.

  新颖的中间体，其化学式中的取代基如规范中所定义。
• Derivatives of octahydro-6, 10-dioxo-6H-pyridazino [1,2-a] [1,2] diazepine-1-carboxylic acid, their preparation process and their use in the preparation of therapeutically active compounds
  申请人：Aventis Pharma S.A.

  公开号：US20030130269A1

  公开（公告）日：2003-07-10

  A compound of the formula 1 of SR configuration or a SR+SS wherein R is selected from the group consisting of hydrogen, alkyl of up to 18 carbon atoms and aryl and aralkyl of up to 18 carbon atoms and the —NH 2 is free or protected useful as intermediates.

  化合物的公式为1，其中R被选自以下群组：氢、碳数为18或以下的烷基、芳基和芳烷基，而—NH2是自由的或保护的，可用作中间体。其中SR的构型为单一硫原子，SS是二硫原子。
• DERIVES DE L'ACIDE OCTAHYDRO-6, 10-DIOXO-6H-PYRIDAZINO/1,2-A/ /1,2/ DIAZEPINE-1-CARBOXYLIQUE, LEUR PROCEDE DE PREPARATION ET LEUR APPLICATION A LA PREPARATION DE COMPOSES THERAPEUTIQUEMENT ACTIFS
  申请人：Aventis Pharma S.A.

  公开号：EP1073673B1

  公开（公告）日：2007-01-10
• US6548664B1
  申请人：——

  公开号：US6548664B1

  公开（公告）日：2003-04-15
• 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.