2-[(E)-4-[2-carboxy-5-(trifluoromethyl)phenoxy]-4-oxobut-2-enoyl]oxy-4-(trifluoromethyl)benzoic acid | 1352041-82-7

• 分子结构分类: 有机化合物 - 苯类化合物 - 苯和取代衍生物
• 英文名称: 2-[(E)-4-[2-carboxy-5-(trifluoromethyl)phenoxy]-4-oxobut-2-enoyl]oxy-4-(trifluoromethyl)benzoic acid
• CAS: 1352041-82-7
• 化学式: C₂₀H₁₀F₆O₈
• 分子量: 492.285
• InChiKey: NLDHDGMUDOBRRD-AATRIKPKSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  4.1
• 重原子数：
  34
• 可旋转键数：
  8
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.1
• 拓扑面积：
  127
• 氢给体数：
  2
• 氢受体数：
  14

反应信息

• 作为产物：
  描述：

  反丁烯二酰氯 在 吡啶 作用下， 以 四氢呋喃 为溶剂， 反应 1.0h， 以23%的产率得到2-[(E)-4-[2-carboxy-5-(trifluoromethyl)phenoxy]-4-oxobut-2-enoyl]oxy-4-(trifluoromethyl)benzoic acid
  参考文献：
  名称：

  A novel synthetic HTB derivative, BECT inhibits lipopolysaccharide-mediated inflammatory response by suppressing the p38 MAPK/JNK and NF-κB activation pathways

  摘要：

  Activated microglia cells are well recognized as mediators of neuroinflammation, as they release nitric oxide and pro-inflammatory cytokines in various neuroinflammatory diseases. Thus, suppressing microglial activation may alleviate neuroinflammatory and neurodegenerative processes. In the present study, we synthesized and investigated the anti-neuroinflammatory effect of a novel HTB (2-hydroxy-4-trifuoromethylbenzoic acid) derivative in lipopolysaccharide (LPS)-stimulated microglial cells. Among the synthesized derivatives, the BECT [But-2-enedioic acid bis-(2-carboxy-5-trifluoromethyl-phenyl) ester] significantly decreased production of nitric oxide and other pro-inflammatory cytokines including tumor necrosis factor-a, interleukin-1 beta, and interleukin-6 in microglial cells. BED' also mitigated the expression of inducible nitric oxide synthase and cyclooxygenase-2 at both the mRNA and protein levels. Further mechanistic studies demonstrated that the HTB derivative inhibited phosphorylation of JNK and p38 mitogen-activated protein kinase and nuclear translocation of nuclear factor kappa-B in LPS-stimulated BV-2 microglial cells. Thus BED', our novel synthesized compound have anti-inflammatory activity in microglial cells, and may have therapeutic potential for treating neuroinflammatory diseases. (C) 2014 Institute of Pharmacology, Polish Academy of Sciences. Published by Elsevier Urban & Partner Sp. z o.o. All rights reserved.

  DOI：

  10.1016/j.pharep.2013.08.015

文献信息

• A novel synthetic HTB derivative, BECT inhibits lipopolysaccharide-mediated inflammatory response by suppressing the p38 MAPK/JNK and NF-κB activation pathways
  作者：Seong-Mook Kang、Sandeep Vasant More、Ju-Young Park、Byung-Wook Kim、Park Jeong In、Sung-Hwa Yoon、Dong-Kug Choi

  DOI：10.1016/j.pharep.2013.08.015

  日期：2014.6

  Activated microglia cells are well recognized as mediators of neuroinflammation, as they release nitric oxide and pro-inflammatory cytokines in various neuroinflammatory diseases. Thus, suppressing microglial activation may alleviate neuroinflammatory and neurodegenerative processes. In the present study, we synthesized and investigated the anti-neuroinflammatory effect of a novel HTB (2-hydroxy-4-trifuoromethylbenzoic acid) derivative in lipopolysaccharide (LPS)-stimulated microglial cells. Among the synthesized derivatives, the BECT [But-2-enedioic acid bis-(2-carboxy-5-trifluoromethyl-phenyl) ester] significantly decreased production of nitric oxide and other pro-inflammatory cytokines including tumor necrosis factor-a, interleukin-1 beta, and interleukin-6 in microglial cells. BED' also mitigated the expression of inducible nitric oxide synthase and cyclooxygenase-2 at both the mRNA and protein levels. Further mechanistic studies demonstrated that the HTB derivative inhibited phosphorylation of JNK and p38 mitogen-activated protein kinase and nuclear translocation of nuclear factor kappa-B in LPS-stimulated BV-2 microglial cells. Thus BED', our novel synthesized compound have anti-inflammatory activity in microglial cells, and may have therapeutic potential for treating neuroinflammatory diseases. (C) 2014 Institute of Pharmacology, Polish Academy of Sciences. Published by Elsevier Urban & Partner Sp. z o.o. All rights reserved.