(Z)-3,4-dibromo-5-(4-(pyridin-2-ylmethoxy)benzylidene)furan-2(5H)-one

• 分子结构分类: 有机化合物 - 苯类化合物 - 苯酚醚
• 英文名称: (Z)-3,4-dibromo-5-(4-(pyridin-2-ylmethoxy)benzylidene)furan-2(5H)-one
• 英文别名: (5Z)-3,4-dibromo-5-[[4-(pyridin-2-ylmethoxy)phenyl]methylidene]furan-2-one
• 化学式: C₁₇H₁₁Br₂NO₃
• 分子量: 437.087
• InChiKey: QRNWQFRSONLXNU-ZROIWOOFSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  4.1
• 重原子数：
  23
• 可旋转键数：
  4
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.06
• 拓扑面积：
  48.4
• 氢给体数：
  0
• 氢受体数：
  4

反应信息

• 作为产物：
  描述：

  2-吡啶甲醇 、 3,4-dibromo-5-(4-hydroxybenzylidene)furan-2(5H)-one 在 三苯基膦 、 偶氮二甲酸二乙酯 作用下， 以 四氢呋喃 为溶剂， 反应 24.5h， 以87%的产率得到(Z)-3,4-dibromo-5-(4-(pyridin-2-ylmethoxy)benzylidene)furan-2(5H)-one
  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

文献信息

• Design, synthesis and anti-inflammatory evaluation of novel 5-benzylidene-3,4-dihalo-furan-2-one derivatives
  作者：Fang Wang、Jun-Rong Sun、Mei-Yan Huang、Hui-Ying Wang、Ping-Hua Sun、Jing Lin、Wei-Min Chen

  DOI：10.1016/j.ejmech.2013.10.074

  日期：2014.1

  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.