(1E,6E)-1,7-bis(4-nitrophenyl)hepta-1,6-diene-3,5-dione

• 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)-1,7-bis(4-nitrophenyl)hepta-1,6-diene-3,5-dione
• 化学式: C₁₉H₁₄N₂O₆
• 分子量: 366.33
• InChiKey: PUSMMINTTLUFQM-YDWXAUTNSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.76
• 重原子数：
  27.0
• 可旋转键数：
  8.0
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.05
• 拓扑面积：
  120.42
• 氢给体数：
  0.0
• 氢受体数：
  6.0

反应信息

• 作为反应物：
  描述：

  (1E,6E)-1,7-bis(4-nitrophenyl)hepta-1,6-diene-3,5-dione 、 diisopropyl (E)-azodicarboxylate 在 4-二甲氨基吡啶 作用下， 以 乙腈 为溶剂， 以85%的产率得到
  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：

  对硝基苯甲醛 、 乙酰丙酮 在 sodium hydroxide 作用下， 以 乙醇 为溶剂， 反应 2.0h， 以31%的产率得到(1E,6E)-1,7-bis(4-nitrophenyl)hepta-1,6-diene-3,5-dione
  参考文献：
  名称：

  Attenuation of Scopolamine-Induced Amnesia via Cholinergic Modulation in Mice by Synthetic Curcumin Analogs

  摘要：

  阿尔茨海默病是一种与认知能力下降和记忆丧失相关的新兴健康障碍。本研究合成了六种姜黄素类似物（1a-1f），并进行了体外胆碱酯酶抑制潜力筛选。在有前途的结果基础上，使用升高十字迷宫（EPM）、Y迷宫和新物体识别（NOR）行为模型进行了进一步的体内分析。确定了合成化合物与胆碱酯酶活性部位的结合模式以及脑海马胆碱能系统的参与。合成的姜黄素类似物1d（p＜0.001，n=6）和1c（p＜0.01，n=6）通过减少EPM中的保持时间、显著增加Y迷宫中的%SAP，以及显著（p＜0.001）增强NORT小鼠行为模型中的%鉴别指数（DI）和探索新物体的时间，显示出有前途的结果。使用MOE软件进行分子对接研究以验证胆碱酯酶抑制作用。从当前研究工作中可以看出，合成的姜黄素类似物增强了小鼠模型的记忆功能，并可作为治疗神经退行性疾病的有价值的治疗分子。为了确定它们的确切作用机制，建议进行进一步的研究。

  DOI：

  10.3390/molecules27082468

文献信息

• 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.
• Attenuation of Scopolamine-Induced Amnesia via Cholinergic Modulation in Mice by Synthetic Curcumin Analogs
  作者：Haya Hussain、Shujaat Ahmad、Syed Wadood Ali Shah、Abid Ullah、Niaz Ali、Mazen Almehmadi、Manzoor Ahmad、Atif Ali Khan Khalil、Syed Babar Jamal、Hanif Ahmad、Mustafa Halawi

  DOI：10.3390/molecules27082468

  日期：——

  Alzheimer’s disease is an emerging health disorder associated with cognitive decline and memory loss. In this study, six curcumin analogs (1a–1f) were synthesized and screened for in vitro cholinesterase inhibitory potential. On the basis of promising results, they were further investigated for in vivo analysis using elevated plus maze (EPM), Y-maze, and novel object recognition (NOR) behavioral models. The binding mode of the synthesized compounds with the active sites of cholinesterases, and the involvement of the cholinergic system in brain hippocampus was determined. The synthesized curcumin analog 1d (p < 0.001, n = 6), and 1c (p < 0.01, n = 6) showed promising results by decreasing retention time in EPM, significantly increasing % SAP in Y-maze, while significantly (p < 0.001) enhancing the % discrimination index (DI) and the time exploring the novel objects in NORT mice behavioral models. A molecular docking study using MOE software was used for validation of the inhibition of cholinesterase(s). It has been indicated from the current research work that the synthesized curcumin analogs enhanced memory functions in mice models and could be used as valuable therapeutic molecules against neurodegenerative disorders. To determine their exact mechanism of action, further studies are suggested.

  阿尔茨海默病是一种与认知能力下降和记忆丧失相关的新兴健康障碍。本研究合成了六种姜黄素类似物（1a-1f），并进行了体外胆碱酯酶抑制潜力筛选。在有前途的结果基础上，使用升高十字迷宫（EPM）、Y迷宫和新物体识别（NOR）行为模型进行了进一步的体内分析。确定了合成化合物与胆碱酯酶活性部位的结合模式以及脑海马胆碱能系统的参与。合成的姜黄素类似物1d（p＜0.001，n=6）和1c（p＜0.01，n=6）通过减少EPM中的保持时间、显著增加Y迷宫中的%SAP，以及显著（p＜0.001）增强NORT小鼠行为模型中的%鉴别指数（DI）和探索新物体的时间，显示出有前途的结果。使用MOE软件进行分子对接研究以验证胆碱酯酶抑制作用。从当前研究工作中可以看出，合成的姜黄素类似物增强了小鼠模型的记忆功能，并可作为治疗神经退行性疾病的有价值的治疗分子。为了确定它们的确切作用机制，建议进行进一步的研究。