(3E,5E)-3,5-bis(4-hydroxy-3-methoxybenzylidene)-tetrahydropyran-4-one

• 分子结构分类: 有机化合物 - 苯类化合物 - 酚类
• 英文名称: (3E,5E)-3,5-bis(4-hydroxy-3-methoxybenzylidene)-tetrahydropyran-4-one
• 英文别名: (3E,5E)-3,5-bis[(4-hydroxy-3-methoxyphenyl)methylidene]oxan-4-one
• 化学式: C₂₁H₂₀O₆
• 分子量: 368.386
• InChiKey: FNGUUSNEVVYVES-BGPOSVGRSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.7
• 重原子数：
  27
• 可旋转键数：
  4
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.19
• 拓扑面积：
  85.2
• 氢给体数：
  2
• 氢受体数：
  6

反应信息

• 作为产物：
  描述：

  四氢吡喃酮 、 香草醛 以 乙醇 为溶剂， 以53%的产率得到(3E,5E)-3,5-bis(4-hydroxy-3-methoxybenzylidene)-tetrahydropyran-4-one
  参考文献：
  名称：

  New MD2 inhibitors derived from curcumin with improved anti-inflammatory activity

  摘要：

  An overactive Toll-like receptor (TLR) signaling complex is a significant pathogenic factor of acute and chronic inflammatory diseases. The natural product curcumin is reported to inhibit the TLR4 co-receptor, MD2 (myeloid differentiation protein 2), but its low in vivo bioavailability limits its therapeutic potential. We developed new curcumin analogs (MACs) with removal of the beta-diketone moiety and substituted residues in benzene rings, and identify these as potential MD2 inhibitors with improved inhibition potency and stability over that of curcumin. Specifically, MAC 17 and 28 showed the highest anti-inflammatory activity, with >90% inhibition of LPS-stimulated cytokine secretion from macrophages, and protected against LPS-induced acute lung injury and sepsis. The MACs inhibited the TLR4-MD2 signaling complex through competition with LPS for binding on MD2, likely at Arg(90). Our findings indicated that MAC 17 and 28 are promising candidates for future development as therapeutic drugs for inflammatory diseases with an endotoxin etiology. (C) 2018 Elsevier Masson SAS. All rights reserved.

  DOI：

  10.1016/j.ejmech.2018.02.008

文献信息

• [EN] CURCUMIN ANALOGS AND METHODS OF USE THEREOF<br/>[FR] ANALOGUES DE LA CURCUMINE ET PROCÉDÉS D'UTILISATION
  申请人：UNIV RUTGERS

  公开号：WO2012021692A1

  公开（公告）日：2012-02-16

  Curcumin analogs and methods of use thereof are provided.

  提供了姜黄素类似物及其使用方法。