(E)-4-(2-methoxy-5-(3-methylbut-1-enyl)phenoxy)-4-oxobutanoic acid | 1564262-13-0

• 分子结构分类: 有机化合物 - 苯类化合物 - 苯酚酯
• 英文名称: (E)-4-(2-methoxy-5-(3-methylbut-1-enyl)phenoxy)-4-oxobutanoic acid
• CAS: 1564262-13-0
• 化学式: C₁₆H₂₀O₅
• 分子量: 292.332
• InChiKey: KXYRZFLJQDAXOZ-SNAWJCMRSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.13
• 重原子数：
  21.0
• 可旋转键数：
  7.0
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.38
• 拓扑面积：
  72.83
• 氢给体数：
  1.0
• 氢受体数：
  4.0

反应信息

• 作为反应物：
  描述：

  2,2-二甲基-2,6-二氢-吡喃并[3,2-c]喹啉-5-酮 、 (E)-4-(2-methoxy-5-(3-methylbut-1-enyl)phenoxy)-4-oxobutanoic acid 以 neat (no solvent) 为溶剂， 反应 16.0h， 以0.56%的产率得到(1RS,2RS,2aRS,10aSR)-2-[4-methoxy-3-(oxobutanoicacid)phenyl]-10,10-dimethyl-1-(1-methylethyl)-1,2,2a,4,10,10a-hexahydro-3Hcyclobuta[4,5]pyrano[3,2-c]quinolin-3-one
  参考文献：
  名称：

  Euodenine A: A Small-Molecule Agonist of Human TLR4

  摘要：

  A small-molecule natural product, euodenine A (1), was identified as an agonist of the human TLR4 receptor. Euodenine A was isolated from the leaves of Euodia asteridula (Rutaceae) found in Papua New Guinea and has an unusual U-shaped structure. It was synthesized along with a series of analogues that exhibit potent and selective agonism of the TLR4 receptor. SAR development around the cyclobutane ring resulted in a 10-fold increase in potency. The natural product demonstrated an extracellular site of action, which requires the extracellular domain of TLR4 to stimulate a NF-kappa B reporter response. 1 is a human-selective agonist that is CD14-independent, and it requires both TLR4 and MD-2 for full efficacy. Testing for immunomodulation in PBMC cells shows the induction of the cytokines IL-8, IL-10, TNF-alpha, and IL-12p40 as well as suppression of IL-5 from activated PBMCs, indicating that compounds like 1 could modulate the Th2 immune response without causing lung damage.

  DOI：

  10.1021/jm401321v
• 作为产物：
  描述：

  异香兰素 在 吡啶 、 4-二甲氨基吡啶 、 silica gel 作用下， 以 1,4-二氧六环 、 乙醚 、 甲苯 为溶剂， 反应 56.0h， 生成 (E)-4-(2-methoxy-5-(3-methylbut-1-enyl)phenoxy)-4-oxobutanoic acid
  参考文献：
  名称：

  Euodenine A: A Small-Molecule Agonist of Human TLR4

  摘要：

  A small-molecule natural product, euodenine A (1), was identified as an agonist of the human TLR4 receptor. Euodenine A was isolated from the leaves of Euodia asteridula (Rutaceae) found in Papua New Guinea and has an unusual U-shaped structure. It was synthesized along with a series of analogues that exhibit potent and selective agonism of the TLR4 receptor. SAR development around the cyclobutane ring resulted in a 10-fold increase in potency. The natural product demonstrated an extracellular site of action, which requires the extracellular domain of TLR4 to stimulate a NF-kappa B reporter response. 1 is a human-selective agonist that is CD14-independent, and it requires both TLR4 and MD-2 for full efficacy. Testing for immunomodulation in PBMC cells shows the induction of the cytokines IL-8, IL-10, TNF-alpha, and IL-12p40 as well as suppression of IL-5 from activated PBMCs, indicating that compounds like 1 could modulate the Th2 immune response without causing lung damage.

  DOI：

  10.1021/jm401321v