4-benzyl-1,7-bis(4-hydroxy-3-methoxyphenyl)-1,6-heptadiene-3,5-dione | 98886-30-7

• 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: 4-benzyl-1,7-bis(4-hydroxy-3-methoxyphenyl)-1,6-heptadiene-3,5-dione
• 英文别名: (1E,6E)-4-benzyl-1,7-bis(4-hydroxy-3-methoxyphenyl)hepta-1,6-diene-3,5-dione
• CAS: 98886-30-7
• 化学式: C₂₈H₂₆O₆
• 分子量: 458.511
• InChiKey: GTGLMUJJAAXYGJ-QHKWOANTSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  5.2
• 重原子数：
  34
• 可旋转键数：
  10
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.14
• 拓扑面积：
  93.1
• 氢给体数：
  2
• 氢受体数：
  6

反应信息

• 作为反应物：
  描述：

  4-benzyl-1,7-bis(4-hydroxy-3-methoxyphenyl)-1,6-heptadiene-3,5-dione 在 palladium on activated charcoal 氢气 作用下， 以48%的产率得到4-benzyl-1,7-bis(4-hydroxy-3-methoxyphenyl)heptane-3,5-dione
  参考文献：
  名称：

  TPA-induced up-regulation of activator protein-1 can be inhibited or enhanced by analogs of the natural product curcumin

  摘要：

  The activator protein-1 (AP-1) family of transcription factors, including the most common member c-Jun-c-Fos, participates in regulation of expression of numerous genes involved in proliferation, apoptosis, and tumorigenesis in response to a wide array of stimuli including pro-inflammatory cytokines, growth factors, stress, and tumor promoters. A number of plant polyphenols including curcumin, a yellow compound in the spice turmeric, have been shown to inhibit the activation of AP-1. Curcumin is a polyphenolic dienone that is potentially reactive as a Michael acceptor and also is a strong anti-oxidant. Multiple activities reported for curcumin, including inhibition of the stress-induced activation of AP-1, have been suggested to involve the anti-oxidant properties of curcumin. In the present study, a library of analogs of curcumin was screened for activity against the TPA-induced activation of AP-1 using the Panomics AP-1 Reporter 293 stable cell line which is designed for screening potential inhibitors. Numerous analogs were identified that were more active than curcumin, including analogs that were not anti-oxidants and analogs that were not Michael acceptors. Clearly, anti-oxidant activity or reactivity as a Michael acceptor is not an essential feature of active compounds. In addition, a number of analogs were identified that enhanced the TPA-induced activation of AP-1. The results from screening were confirmed using BV-2 microglial cells where curcumin and analogs were shown to inhibit LPS-induced COX-2 expression; analogs identified as more potent than curcumin in the screening assay were also more potent than curcumin in preventing COX-2 expression. (c) 2006 Elsevier Inc. All rights reserved.

  DOI：

  10.1016/j.bcp.2006.07.007
• 作为产物：
  描述：

  3-苄基-2,4-戊二酮 、 香草醛 在 硼酸三丁酯 、 正丁胺 作用下， 生成 4-benzyl-1,7-bis(4-hydroxy-3-methoxyphenyl)-1,6-heptadiene-3,5-dione
  参考文献：
  名称：

  Electron ionization mass spectrometry of curcumin analogues: an olefin metathesis reaction in the fragmentation of radical cations

  摘要：

  The natural compound curcumin, used in cosmetics, traditional medicines and as a spice in food, is known as a multi-factorial anti-inflammatory agent. To study the anti-inflammatory activity of curcumin derivatives, 24 analogues were synthesized and their structures were confirmed by H-1 MMR and electron ionization (EI) mass spectrometry. Most signals in the EI mass spectra can be attributed to commonly known fragmentations, but the formation of ring-substituted 1,2-diphenylethene (stilbene)-type radical cations, observed in the spectra of all compounds investigated and resulting in the base peak for some compounds, requires a peculiar rearrangement. Metastable ion spectra and C-13 labelling studies show that the stilbene-type ions are formed directly from the molecular ions and contain the two original aryl groups and the 1 and 7 carbon atoms of the olefinic system. It is proposed that the formation of stilbene-type ions results from an intramolecular olefin metathesis reaction; this suggestion is supported by semi-empirical (MNDO/PM3) calculations. (C) 1998 John Wiley & Sons, Ltd.

  DOI：

  10.1002/(sici)1096-9888(199804)33:4<319::aid-jms636>3.0.co;2-u

文献信息

• Cancer treatment using curcumin derivatives
  申请人：Vander Jagt L. David

  公开号：US20060276536A1

  公开（公告）日：2006-12-07

  Cancer or a precancerous condition is treated by administering a curcumin derivative to a subject.

  癌症或癌前病变可以通过向受试者施用姜黄素衍生物来治疗。
• Therapeutic curcumin derivatives
  申请人：Vander Jagt L. David

  公开号：US20070060644A1

  公开（公告）日：2007-03-15

  Curcumin analogues and methods are provided for treatment of disease.

  提供了类姜黄素和治疗疾病的方法。
• THERAPEUTIC CURCUMIN DERIVATIVES
  申请人：STC.UNM

  公开号：US20150011494A1

  公开（公告）日：2015-01-08

  Curcumin analogues and methods are provided for treatment of disease.

  提供了类姜黄素及其方法，用于治疗疾病。
• Pedersen, Uffe; Rasmussen, Preben B.; Lawesson, Sven-Olov, Liebigs Annalen der Chemie, 1985, # 8, p. 1557 - 1569
  作者：Pedersen, Uffe、Rasmussen, Preben B.、Lawesson, Sven-Olov

  DOI：——

  日期：——
• US8841326B2
  申请人：——

  公开号：US8841326B2

  公开（公告）日：2014-09-23