(1E,4E)-1,5-bis(4-((3-methylbut-2-en-1-yl)oxy)phenyl)penta-1,4-dien-3-one | 1548331-34-5

• 分子结构分类: 有机化合物 - 苯丙烷和聚酮 - 肉桂酸及其衍生物
• 英文名称: (1E,4E)-1,5-bis(4-((3-methylbut-2-en-1-yl)oxy)phenyl)penta-1,4-dien-3-one
• 英文别名: (1E,4E)-1,5-bis[4-(3-methylbut-2-enoxy)phenyl]penta-1,4-dien-3-one
• CAS: 1548331-34-5
• 化学式: C₂₇H₃₀O₃
• 分子量: 402.533
• InChiKey: BINYENXZFSWDFX-YDWXAUTNSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  7.1
• 重原子数：
  30
• 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：
  35.5
• 氢给体数：
  0
• 氢受体数：
  3

反应信息

• 作为产物：
  描述：

  对羟基苯甲醛 在 potassium carbonate 、 sodium hydroxide 作用下， 以 乙醇 、 水 、 丙酮 为溶剂， 生成 (1E,4E)-1,5-bis(4-((3-methylbut-2-en-1-yl)oxy)phenyl)penta-1,4-dien-3-one
  参考文献：
  名称：

  Synthesis and biological evaluation of allylated and prenylated mono-carbonyl analogs of curcumin as anti-inflammatory agents

  摘要：

  Curcumin has been shown to possess anti-inflammatory activities but has been limited for its low stability and poor bioavailability. We have previously reported four series of 5-carbon linker-containing mono-carbonyl analogs of curcumin (MACs). In continuation of our ongoing research, we designed and synthesized 33 novel allylated or prenylated MACs here, and evaluated their anti-inflammatory effects in RAW 264.7 macrophages. A majority of them effectively inhibited the LPS-induced expression of TNF-alpha and IL-6, especially IL-6. The preliminary SAR and quantitative SAR analysis were conducted. Compound 14q is the most potent analog among them, and exhibits significant protection against LPS-induced death in septic mice. Together, these data present a series of new analogs of curcumin as promising anti-inflammatory agents. (C) 2013 Elsevier Masson SAS. All rights reserved.

  DOI：

  10.1016/j.ejmech.2013.10.061

文献信息

• Prenylated Curcumin Analogues as Multipotent Tools To Tackle Alzheimer’s Disease
  作者：Federica Bisceglia、Francesca Seghetti、Massimo Serra、Morena Zusso、Silvia Gervasoni、Laura Verga、Giulio Vistoli、Cristina Lanni、Michele Catanzaro、Ersilia De Lorenzi、Federica Belluti

  DOI：10.1021/acschemneuro.8b00463

  日期：2019.3.20

  caused by copathogenic factors including aggregation of Aβ peptides into oligomers and fibrils, neuroinflammation, and oxidative stress. To date, no effective treatments are available, and because of the multifactorial nature of the disease, it emerges the need to act on different and simultaneous fronts. Despite the multiple biological activities ascribed to curcumin as neuroprotector, its poor bioavailability

  阿尔茨海默氏病可能是由致病性因素引起的，包括Aβ肽聚集成低聚物和原纤维，神经炎症和氧化应激。迄今为止，尚无有效的治疗方法，并且由于该疾病的多因素性质，因此有必要在不同和同时的领域采取行动。尽管姜黄素作为神经保护剂具有多种生物学活性，但其生物利用度和毒性差限制了临床结果的成功。为了在这些方面解决阿尔茨海默氏病，对姜黄素模板进行了适当的修饰，并获得了一小组类似物。特别地，证明衍生物1的毒性小于姜黄素。毛细管电泳和透射电镜研究表明1证明通过将平衡转移到较小的无毒组件上来抑制大型有毒Aβ低聚物的形成，并限制了不溶性原纤维的形成。这些发现得到分子对接和分子动力学模拟的支持，证实了1结合不同复杂性的Aβ结构的优越能力。值得注意的是，1还显示出体外的抗炎和抗氧化特性。总之，基于姜黄素的类似物1作为多能化合物出现，值得在阿尔茨海默氏病多靶点背景下进一步研究和开发。
• Synthesis and biological evaluation of allylated and prenylated mono-carbonyl analogs of curcumin as anti-inflammatory agents
  作者：Zhiguo Liu、Longguang Tang、Peng Zou、Yali Zhang、Zhe Wang、Qilu Fang、Lili Jiang、Gaozhi Chen、Zheng Xu、Huajie Zhang、Guang Liang

  DOI：10.1016/j.ejmech.2013.10.061

  日期：2014.3

  Curcumin has been shown to possess anti-inflammatory activities but has been limited for its low stability and poor bioavailability. We have previously reported four series of 5-carbon linker-containing mono-carbonyl analogs of curcumin (MACs). In continuation of our ongoing research, we designed and synthesized 33 novel allylated or prenylated MACs here, and evaluated their anti-inflammatory effects in RAW 264.7 macrophages. A majority of them effectively inhibited the LPS-induced expression of TNF-alpha and IL-6, especially IL-6. The preliminary SAR and quantitative SAR analysis were conducted. Compound 14q is the most potent analog among them, and exhibits significant protection against LPS-induced death in septic mice. Together, these data present a series of new analogs of curcumin as promising anti-inflammatory agents. (C) 2013 Elsevier Masson SAS. All rights reserved.