(Z)-3,4-dichloro-5-(3-methoxy-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-dichloro-5-(3-methoxy-4-(pyridin-2-ylmethoxy)benzylidene)furan-2(5H)-one
• 英文别名: (5Z)-3,4-dichloro-5-[[3-methoxy-4-(pyridin-2-ylmethoxy)phenyl]methylidene]furan-2-one
• 化学式: C₁₈H₁₃Cl₂NO₄
• 分子量: 378.212
• InChiKey: TVOYMUJQDNCTLS-DHDCSXOGSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.9
• 重原子数：
  25
• 可旋转键数：
  5
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.11
• 拓扑面积：
  57.6
• 氢给体数：
  0
• 氢受体数：
  5

反应信息

• 作为产物：
  描述：

  香草醛 在 溶剂黄146 、 三苯基膦 、 2-甲基哌啶 、 偶氮二甲酸二乙酯 作用下， 以 四氢呋喃 、 甲苯 为溶剂， 反应 26.5h， 生成 (Z)-3,4-dichloro-5-(3-methoxy-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.