(Z)-5-(3-ethoxy-4-((3,5,6-trimethylpyrazin-2-yl)methoxy)benzylidene) thiazolidine-2,4-dione

• 分子结构分类: 有机化合物 - 苯类化合物 - 苯酚醚
• 英文名称: (Z)-5-(3-ethoxy-4-((3,5,6-trimethylpyrazin-2-yl)methoxy)benzylidene) thiazolidine-2,4-dione
• 英文别名: (5Z)-5-[[3-ethoxy-4-[(3,5,6-trimethylpyrazin-2-yl)methoxy]phenyl]methylidene]-1,3-thiazolidine-2,4-dione
• 化学式: C₂₀H₂₁N₃O₄S
• 分子量: 399.47
• InChiKey: LGZKLGBJPAHGJM-NVMNQCDNSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.1
• 重原子数：
  28
• 可旋转键数：
  6
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.3
• 拓扑面积：
  116
• 氢给体数：
  1
• 氢受体数：
  7

反应信息

• 作为产物：
  描述：

  川芎嗪 在 N-溴代丁二酰亚胺(NBS) 、 potassium carbonate 、 溶剂黄146 、 2-甲基哌啶 、 过氧化苯甲酰 作用下， 以 四氯化碳 、 N,N-二甲基甲酰胺 、 甲苯 为溶剂， 反应 24.0h， 生成 (Z)-5-(3-ethoxy-4-((3,5,6-trimethylpyrazin-2-yl)methoxy)benzylidene) thiazolidine-2,4-dione
  参考文献：
  名称：

  Design, synthesis and anti-inflammatory evaluation of novel 5-benzylidene-3,4-dihalo-furan-2-one derivatives

  摘要：

  Rosiglitazone has shown promising anti-inflammation effect. To develop preferable anti-inflammatory agents, twenty-two rosiglitazone analogs were synthesized and their anti-inflammatory activity was evaluated. Among these compounds, 6i and 6k displayed excellent inhibitory activities on the production of inflammatory mediators, including nitric oxide (NO), tumor necrosis factor-alpha (TNF-alpha) and interleukin-6 (IL-6). Furthermore, 6i and 6k showed suppression effects on the nuclear factor-kappa B (NF-kappa B) and mitogen-activated protein kinase (MAPK) pathways, and this suppression effects could be partially reversed by GW9662, which is a peroxisome proliferator-activated receptor gamma (PPAR gamma) antagonist. Additionally, our docking results exhibited the well combination of 6i and 6k to PPAR gamma. So the anti-inflammation activity of 6i and 6k was due at least in part, to their interaction with PPAR gamma. (C) 2013 Elsevier Masson SAS. All rights reserved.

  DOI：

  10.1016/j.ejmech.2013.10.074