(1E,4Ε)-1-(3-allyl-4-methoxyphenyl)-5-(2,5-dibromophenyl)penta-1,4-dien-3-one | 1548332-41-7

• 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,4Ε)-1-(3-allyl-4-methoxyphenyl)-5-(2,5-dibromophenyl)penta-1,4-dien-3-one
• 英文别名: (1E,4E)-1-(3-allyl-4-methoxyphenyl)-5-(2,5-dibromophenyl)penta-1,4-dien-3-one；(1E,4E)-1-(2,5-dibromophenyl)-5-(4-methoxy-3-prop-2-enylphenyl)penta-1,4-dien-3-one
• CAS: 1548332-41-7
• 化学式: C₂₁H₁₈Br₂O₂
• 分子量: 462.181
• InChiKey: PRBFWIUFSFJKJH-FWMCCXIMSA-N

物化性质

• 熔点：
  83.4-85.2 °C
• 沸点：
  549.1±50.0 °C(predicted)
• 密度：
  1.473±0.06 g/cm3(Temp: 20 °C; Press: 760 Torr)(predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  6.5
• 重原子数：
  25
• 可旋转键数：
  7
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.1
• 拓扑面积：
  26.3
• 氢给体数：
  0
• 氢受体数：
  2

反应信息

• 作为产物：
  描述：

  3-烯丙基-4-甲氧基-苯甲醛 在 sodium hydroxide 作用下， 以 乙醇 、 水 为溶剂， 反应 4.0h， 生成 (1E,4Ε)-1-(3-allyl-4-methoxyphenyl)-5-(2,5-dibromophenyl)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

• 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.