(3E,5E)-3,5-bis(3,4-difluorobenzylidene)-1-ethylpiperidin-4-one | 1434133-44-4

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 哌啶类
• 英文名称: (3E,5E)-3,5-bis(3,4-difluorobenzylidene)-1-ethylpiperidin-4-one
• 英文别名: (3E,5E)-3,5-bis[(3,4-difluorophenyl)methylidene]-1-ethylpiperidin-4-one
• CAS: 1434133-44-4
• 化学式: C₂₁H₁₇F₄NO
• 分子量: 375.366
• InChiKey: CKAUHOZVOSLZEZ-BGPOSVGRSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  4.4
• 重原子数：
  27
• 可旋转键数：
  3
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.19
• 拓扑面积：
  20.3
• 氢给体数：
  0
• 氢受体数：
  6

反应信息

• 作为产物：
  描述：

  N-乙基-4-哌啶酮 、 3,4-二氟苯甲醛 在 sodium hydroxide 作用下， 以 乙醇 、 水 为溶剂， 以68.69%的产率得到(3E,5E)-3,5-bis(3,4-difluorobenzylidene)-1-ethylpiperidin-4-one
  参考文献：
  名称：

  Discovery and evaluation of piperid-4-one-containing mono-carbonyl analogs of curcumin as anti-inflammatory agents

  摘要：

  We previously reported the design and discovery of three series of 5-carbon linker-containing mono-carbonyl analogs of curcumin (MCACs) as excellent anti-inflammatory agents. In continuation of our ongoing research, we designed and synthesized the fourth series of MCACs, whose central linker is a piperid-4-one. Their inhibitory effects against IL-6 production were evaluated in lipopolysaccharide (LPS)-stimulated macrophages. Among them, compounds F8, F29, F33, F35, and F36 exhibited the IC50 values under 5 mu M. The structure-activity relationship was discussed. Mechanistically, F35 and F36 dose-dependently prevented LPS-induced NF-kappa B and ERK activation. Finally, pretreatment with F35 and F36 significantly protected the C57B/L6 mice from LPS-induced septic death. Together, these data present a series of new analogs of curcumin as promising anti-inflammatory agents. (C) 2013 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.bmc.2013.03.057

文献信息

• Discovery and evaluation of piperid-4-one-containing mono-carbonyl analogs of curcumin as anti-inflammatory agents
  作者：Jianzhang Wu、Yali Zhang、Yuepiao Cai、Jian Wang、Bixia Weng、Qinqin Tang、Xiangjian Chen、Zheer Pan、Guang Liang、Shulin Yang

  DOI：10.1016/j.bmc.2013.03.057

  日期：2013.6

  We previously reported the design and discovery of three series of 5-carbon linker-containing mono-carbonyl analogs of curcumin (MCACs) as excellent anti-inflammatory agents. In continuation of our ongoing research, we designed and synthesized the fourth series of MCACs, whose central linker is a piperid-4-one. Their inhibitory effects against IL-6 production were evaluated in lipopolysaccharide (LPS)-stimulated macrophages. Among them, compounds F8, F29, F33, F35, and F36 exhibited the IC50 values under 5 mu M. The structure-activity relationship was discussed. Mechanistically, F35 and F36 dose-dependently prevented LPS-induced NF-kappa B and ERK activation. Finally, pretreatment with F35 and F36 significantly protected the C57B/L6 mice from LPS-induced septic death. Together, these data present a series of new analogs of curcumin as promising anti-inflammatory agents. (C) 2013 Elsevier Ltd. All rights reserved.