1-(2,4-dimethoxyquinolin-3-yl)-3-methylbutane-2,3-diol | 1564261-93-3

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 喹啉及其衍生物
• 英文名称: 1-(2,4-dimethoxyquinolin-3-yl)-3-methylbutane-2,3-diol
• CAS: 1564261-93-3
• 化学式: C₁₆H₂₁NO₄
• 分子量: 291.347
• InChiKey: RDEDVVAWEJCOLP-UHFFFAOYSA-N

物化性质

• 沸点：
  437.1±40.0 °C(predicted)
• 密度：
  1.201±0.06 g/cm3(Temp: 20 °C; Press: 760 Torr)(predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  1.93
• 重原子数：
  21.0
• 可旋转键数：
  5.0
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.44
• 拓扑面积：
  71.81
• 氢给体数：
  2.0
• 氢受体数：
  5.0

反应信息

• 作为产物：
  描述：

  3-((3,3-dimethyloxiran-2-yl)methyl)-2,4-dimethoxyquinoline 在 potassium hydroxide 作用下， 以 二甲基亚砜 为溶剂， 反应 20.0h， 以45%的产率得到5-methoxy-2,2-dimethyl-4a,10b-dihydro-2H-pyrano[3,2-c]quinoline
  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