(2E,6E)-2,6-bis(3,5-dimethoxybenzylidene)cyclohexanone | 1417561-59-1

• 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: (2E,6E)-2,6-bis(3,5-dimethoxybenzylidene)cyclohexanone
• 英文别名: 2,6-bis((E)-3,5-dimethoxybenzylidene)cyclohexanone；(2E,6E)-2,6-bis[(3,5-dimethoxyphenyl)methylidene]cyclohexan-1-one
• CAS: 1417561-59-1
• 化学式: C₂₄H₂₆O₅
• 分子量: 394.467
• InChiKey: LCTMHSXNDBNPAF-GCBPPVMSSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  4.9
• 重原子数：
  29
• 可旋转键数：
  6
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.29
• 拓扑面积：
  54
• 氢给体数：
  0
• 氢受体数：
  5

反应信息

• 作为反应物：
  描述：

  肌氨酸 、 水合茚三酮 、 (2E,6E)-2,6-bis(3,5-dimethoxybenzylidene)cyclohexanone 、 邻苯二胺 以 乙醇 为溶剂， 以48%的产率得到3-(3,5-dimethoxybenzylidene)-4′-(3,5-dimethoxyphenyl)-1′-methyldispiro [cyclohexane-1,3′-pyrrolidine-2′,11′′-indeno[1,2-b]quinoxalin]-2-one
  参考文献：
  名称：

  One-Pot Two-Step Four-Component Synthesis of 1′-N-Methylspiro[2′,11′′]indeno[1,2-b]quinoxalinespiro[3′,2]-6-arylmethylene-cyclohexanone-4′-arylpyrrolidines via [3+2] Cycloaddition Reaction

  摘要：

  DOI：

  10.1134/s1070363223040278
• 作为产物：
  描述：

  3,5-二甲氧基苯甲醛 、 (E)-2-(3,5-dimethoxybenzylidene)cyclohexanone 在 sodium hydroxide 作用下， 以 乙醇 为溶剂， 反应 0.5h， 以78%的产率得到(2E,6E)-2,6-bis(3,5-dimethoxybenzylidene)cyclohexanone
  参考文献：
  名称：

  Design, synthesis and molecular docking of α,β-unsaturated cyclohexanone analogous of curcumin as potent EGFR inhibitors with antiproliferative activity

  摘要：

  A type of novel alpha,beta-unsaturated cyclohexanone analogous, which designed based on the curcumin core structure, have been discovered as potential EGFR inhibitors. These compounds exhibit potent antiproliferative activity in two human tumor cell lines (Hep G2 and B16-F10). Among them, compounds I-3 and I-12 displayed the most potent EGFR inhibitory activity (IC50 = 0.43 mu M and 1.54 mu M, respectively). Molecular docking of I-12 into EGFR TK active site was also performed. This inhibitor nicely fitting the active site might well explain its excellent inhibitory activity. (C) 2012 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.bmc.2012.11.031

文献信息

• Activation of anti-oxidant Nrf2 signaling by enone analogues of curcumin
  作者：Lorraine M. Deck、Lucy A. Hunsaker、Thomas A. Vander Jagt、Lisa J. Whalen、Robert E. Royer、David L. Vander Jagt

  DOI：10.1016/j.ejmech.2017.11.048

  日期：2018.1

  Inflammation and oxidative stress are common in many chronic diseases. Targeting signaling pathways that contribute to these conditions may have therapeutic potential. The transcription factor Nrf2 is a major regulator of phase II detoxification and anti-oxidant genes as well as anti-inflammatory and neuroprotective genes. Nrf2 is widespread in the CNS and is recognized as an important regulator of brain inflammation. The natural product curcumin exhibits numerous biological activities including ability, to induce the expression of Nrf2-dependent phase II and anti-oxidant enzymes. Curcumin has been examined in a number of clinical studies with limited success, mainly owing to limited bioavailability and rapid metabolism. Enone analogues of curcumin were examined with an Nrf2 reporter assay to identify Nrf2 activators. Analogues were separated into groups with a 7-carbon dienone spacer, as found in curcumin; a 5-carbon enone spacer with and without a ring; and a 3-carbon enone spacer. Activators of Nrf2 were found in all three groups, many of which were more active than curcumin. Dose response studies demonstrated that a range of substituents on the aromatic rings of these enones influenced not only the sensitivity to activation, reflected in EC50 values, but also the extent of activation, which suggests that multiple mechanisms are involved in the activation of Nrf2 by these analogues. (C) 2017 Published by Elsevier Masson SAS.
• Substituted Stilbenes as Inhibitors of NF-kappaB and Activators of Nrf2
  申请人：STC.UNM

  公开号：US20190160021A1

  公开（公告）日：2019-05-30

  The present invention relates to substituted stilbenes and dienones which exhibit unexpected dual activity, as inhibitors of NFκB and as agonists (activators) of Nrf2. In particular, these compounds show dual activity and makes them particularly useful in the treatment of inflammation, including chronic inflammation and a number of related chronic disease states and conditions, including neurological diseases, including Alzheimer's, Alzheimer's prodrome and mild cognitive impairment, and other diseases and conditions, such as Parkinson's disease, depression, bipolar disorders and autism spectrum disorders. Compounds, pharmaceutical compositions and methods of treatment are described.
• COSMETIC COMPOSITIONS AND METHODS OF USE
  申请人：K&K BIOTECH

  公开号：US20200397676A1

  公开（公告）日：2020-12-24

  The present invention relates to substituted stilbenes and dienones which exhibit unexpected dual activity, as inhibitors of NFκB and as agonists (activators) of Nrf2. In particular, these compounds show dual activity and it has been discovered that these compounds are particularly useful in the treatment of certain cosmetic applications and in rejuvenating and beautifying skin and other keratinous tissue of a subject in need. Cosmetic compositions and methods of using said compositions in combination with other components are disclosed herein.
• Design, synthesis and molecular docking of α,β-unsaturated cyclohexanone analogous of curcumin as potent EGFR inhibitors with antiproliferative activity
  作者：Yun-Yun Xu、Yi Cao、Hailkuo Ma、Huan-Qiu Li、Gui-Zhen Ao

  DOI：10.1016/j.bmc.2012.11.031

  日期：2013.1

  A type of novel alpha,beta-unsaturated cyclohexanone analogous, which designed based on the curcumin core structure, have been discovered as potential EGFR inhibitors. These compounds exhibit potent antiproliferative activity in two human tumor cell lines (Hep G2 and B16-F10). Among them, compounds I-3 and I-12 displayed the most potent EGFR inhibitory activity (IC50 = 0.43 mu M and 1.54 mu M, respectively). Molecular docking of I-12 into EGFR TK active site was also performed. This inhibitor nicely fitting the active site might well explain its excellent inhibitory activity. (C) 2012 Elsevier Ltd. All rights reserved.
• One-Pot Two-Step Four-Component Synthesis of 1′-N-Methylspiro[2′,11′′]indeno[1,2-b]quinoxalinespiro[3′,2]-6-arylmethylene-cyclohexanone-4′-arylpyrrolidines via [3+2] Cycloaddition Reaction
  作者：H. Tao

  DOI：10.1134/s1070363223040278

  日期：2023.4