(2E,5E)-2,5-bis(3-methoxy-4-((3-methylbut-2-en-1-yl)oxy)benzylidene)cyclopentanone | 1548331-46-9

• 分子结构分类: 有机化合物 - 苯类化合物 - 苯酚醚
• 英文名称: (2E,5E)-2,5-bis(3-methoxy-4-((3-methylbut-2-en-1-yl)oxy)benzylidene)cyclopentanone
• 英文别名: (2E,5E)-2,5-bis[[3-methoxy-4-(3-methylbut-2-enoxy)phenyl]methylidene]cyclopentan-1-one
• CAS: 1548331-46-9
• 化学式: C₃₁H₃₆O₅
• 分子量: 488.624
• InChiKey: GDJJSPBVCXPYHE-RPCRKUJJSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  7.4
• 重原子数：
  36
• 可旋转键数：
  10
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.32
• 拓扑面积：
  54
• 氢给体数：
  0
• 氢受体数：
  5

反应信息

• 作为产物：
  描述：

  3-甲氧基-4-[(四氢-2H-吡喃-2-基)氧基]苯甲醛 在 盐酸 、 potassium carbonate 、 sodium hydroxide 作用下， 以 乙醇 、 二氯甲烷 、 丙酮 为溶剂， 生成 (2E,5E)-2,5-bis(3-methoxy-4-((3-methylbut-2-en-1-yl)oxy)benzylidene)cyclopentanone
  参考文献：
  名称：

  姜黄素单羰基类似物作为潜在抗肿瘤剂的合成及细胞毒性评价。

  摘要：

  临床前研究

  DOI：

  10.1002/ddr.21291

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.