((1E,6E)-3,5-dioxohepta-1,6-diene-1,7-diyl)bis(2-methoxy-4,1-phenylene) (2S,2'S)-bis(2-amino-3-methylbutanoate) | 1073666-63-3

• 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: ((1E,6E)-3,5-dioxohepta-1,6-diene-1,7-diyl)bis(2-methoxy-4,1-phenylene) (2S,2'S)-bis(2-amino-3-methylbutanoate)
• 英文别名: 1,7-bis-(4-O-valinoyl-3-methoxyphenyl)-1,6-heptadiene-3,5-dione；4,4'-di-O-(valinoyl)curcumin；[4-[(1E,6E)-7-[4-[(2S)-2-amino-3-methylbutanoyl]oxy-3-methoxyphenyl]-3,5-dioxohepta-1,6-dienyl]-2-methoxyphenyl] (2S)-2-amino-3-methylbutanoate
• CAS: 1073666-63-3
• 化学式: C₃₁H₃₈N₂O₈
• 分子量: 566.651
• InChiKey: RVFUPBDRJITFOE-ILTOYGKPSA-N

物化性质

• 熔点：
  166-168 °C
• 沸点：
  697.5±55.0 °C(Predicted)
• 密度：
  1.194±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  4.3
• 重原子数：
  41
• 可旋转键数：
  16
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.35
• 拓扑面积：
  157
• 氢给体数：
  2
• 氢受体数：
  10

反应信息

• 作为产物：
  描述：

  姜黄素 、 N-phthalimide l-valinyl chloride 在 吡啶 、 氨 作用下， 反应 8.0h， 以45%的产率得到((1E,6E)-3,5-dioxohepta-1,6-diene-1,7-diyl)bis(2-methoxy-4,1-phenylene) (2S,2'S)-bis(2-amino-3-methylbutanoate)
  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

• Curcumin Conjugates and Methods of Use Thereof
  申请人：Augusta University Research Institute, Inc.

  公开号：US20180110861A1

  公开（公告）日：2018-04-26

  Curcumin-based conjugates and methods of use thereof are provided. Pharmaceutical compositions including an effective amount of one or more curcumin conjugates are also provided. In particular embodiments, the compositions are formulated for oral delivery. The conjugates and pharmaceutical compositions thereof can be administered to a subject in need thereof to treat a host of diseases and disorders including but not limited to, cancer, inflammation, and microbial growth.

  提供基于姜黄素的共轭物及其使用方法。还提供包括一种或多种姜黄素共轭物的有效量的制药组合物。在特定实施例中，这些组合物是为口服递送而制剂的。这些共轭物和其制药组合物可以被用于治疗患有多种疾病和障碍的患者，包括但不限于癌症、炎症和微生物生长。
• Curcumin conjugates and methods of use thereof
  申请人：Augusta University Research Institute, Inc.

  公开号：US10660967B2

  公开（公告）日：2020-05-26

  Curcumin-based conjugates and methods of use thereof are provided. Pharmaceutical compositions including an effective amount of one or more curcumin conjugates are also provided. In particular embodiments, the compositions are formulated for oral delivery. The conjugates and pharmaceutical compositions thereof can be administered to a subject in need thereof to treat a host of diseases and disorders including but not limited to, cancer, inflammation, and microbial growth.

  提供了姜黄素类共轭物及其使用方法。还提供了包括有效量的一种或多种姜黄素共轭物的药物组合物。在特定的实施方案中，这些组合物配制成口服给药。其共轭物和药物组合物可给需要的受试者服用，以治疗一系列疾病和失调，包括但不限于癌症、炎症和微生物生长。
• 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.