(1E,4Z,6E)-1,7-bis(2,5-dimethoxyphenyl)-5-hydroxyhepta-1,4,6-trien-3-one | 1030861-09-6

• 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,4Z,6E)-1,7-bis(2,5-dimethoxyphenyl)-5-hydroxyhepta-1,4,6-trien-3-one
• 英文别名: (1E,6E)-1,7-bis(2,5-dimethoxyphenyl)-1,6-heptadiene-3,5-dione；1,7-bis((E)-2,5-dimethoxyphenyl)-1,6-heptadien-3,5-dione；2,5-dimethoxycurcuminoid；(1E,6E)-1,7-bis(2,5-dimethoxyphenyl)hepta-1,6-diene-3,5-dione
• CAS: 1030861-09-6
• 化学式: C₂₃H₂₄O₆
• 分子量: 396.44
• InChiKey: OVQMMMJUXPRROO-KQQUZDAGSA-N

物化性质

• 沸点：
  596.7±50.0 °C(Predicted)
• 密度：
  1.169±0.06 g/cm3(Temp: 20 °C; Press: 760 Torr)(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  3.9
• 重原子数：
  29
• 可旋转键数：
  10
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.22
• 拓扑面积：
  71.1
• 氢给体数：
  0
• 氢受体数：
  6

反应信息

• 作为反应物：
  描述：

  (1E,4Z,6E)-1,7-bis(2,5-dimethoxyphenyl)-5-hydroxyhepta-1,4,6-trien-3-one 、 diisopropyl (E)-azodicarboxylate 在 4-二甲氨基吡啶 作用下， 以 乙腈 为溶剂， 以65%的产率得到diisopropyl-1-((1E,6E)-1,7-bis(2,5-dimethoxyphenyl)-3,5-dioxohepta-1,6-dien-4-yl)hydrazine-1,2-dicarboxylate
  参考文献：
  名称：

  Conjugate addition of curcumins to chalcones and azodicarboxylates

  摘要：

  Cascade double Michael reaction of curcumins with chalcones in the presence of Cs2CO3 in CH3CN provided highly functionalized cyclohexanones in moderate to good yields (35-77%) and good to excellent diastereoselectivities (81:19 to 95:05). Similar reaction of curcumins with azodicarboxylates in the presence of DMAP in CH3CN stopped at the single Michael addition stage affording novel hydrazinodicarboxylates of curcumins in good to excellent yields (65-85%). (C) 2013 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.tet.2013.04.083
• 作为产物：
  描述：

  2,5-二甲氧基苯甲醛 、 乙酰丙酮 在 二碳酸二叔丁酯 、 硼酸三丁酯 作用下， 以 乙酸乙酯 为溶剂， 反应 18.25h， 生成 (1E,4Z,6E)-1,7-bis(2,5-dimethoxyphenyl)-5-hydroxyhepta-1,4,6-trien-3-one
  参考文献：
  名称：

  Activation of anti-oxidant Nrf2 signaling by enone analogues of curcumin

  摘要：

  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.

  DOI：

  10.1016/j.ejmech.2017.11.048

文献信息

• NOVEL CURCUMIN DERIVATIVE
  申请人：Takahashi Takashi

  公开号：US20100048901A1

  公开（公告）日：2010-02-25

  The present invention provides a novel compound that is structurally similar to curcumin and has a suppressive effect on Aβ aggregation, a degradative effect on Aβ aggregates, an inhibitory effect on β-secretase, and a protective effect on neurons. The novel compound is a compound represented by the following general formula (Ia) or a salt thereof: wherein R 1 represents a 4-hydroxy-3-methoxyphenyl group or the like, and R 2 represents a 1H-indol-6-yl group or the like.

  本发明提供了一种新型化合物，其结构类似于姜黄素，并具有抑制Aβ聚集、降解Aβ聚集体、抑制β-分泌酶以及保护神经元的作用。该新型化合物是由以下通式(Ia)或其盐所表示的化合物：其中，R1表示4-羟基-3-甲氧基苯基或类似基团，R2表示1H-吲哚-6-基基或类似基团。
• US8962674B2
  申请人：——

  公开号：US8962674B2

  公开（公告）日：2015-02-24
• 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.
• Conjugate addition of curcumins to chalcones and azodicarboxylates
  作者：Narasimham Ayyagari、Ankit Mehta、Elumalai Gopi、Indubhusan Deb、Shaikh M. Mobin、Irishi N.N. Namboothiri

  DOI：10.1016/j.tet.2013.04.083

  日期：2013.7

  Cascade double Michael reaction of curcumins with chalcones in the presence of Cs2CO3 in CH3CN provided highly functionalized cyclohexanones in moderate to good yields (35-77%) and good to excellent diastereoselectivities (81:19 to 95:05). Similar reaction of curcumins with azodicarboxylates in the presence of DMAP in CH3CN stopped at the single Michael addition stage affording novel hydrazinodicarboxylates of curcumins in good to excellent yields (65-85%). (C) 2013 Elsevier Ltd. All rights reserved.