5-ethoxy-4-ethyloxazole | 15937-91-4

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 唑类
• 英文名称: 5-ethoxy-4-ethyloxazole
• 英文别名: 4-Ethyl-5-ethoxy-oxazol；5-Ethoxy-4-ethyl-1,3-oxazole；5-ethoxy-4-ethyl-1,3-oxazole
• CAS: 15937-91-4
• 化学式: C₇H₁₁NO₂
• 分子量: 141.17
• InChiKey: OHSCSQSIELNURQ-UHFFFAOYSA-N

物化性质

• 沸点：
  190.1±20.0 °C(Predicted)
• 密度：
  1.017±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  1.8
• 重原子数：
  10
• 可旋转键数：
  3
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.57
• 拓扑面积：
  35.3
• 氢给体数：
  0
• 氢受体数：
  3

反应信息

• 作为反应物：
  描述：

  5-ethoxy-4-ethyloxazole 、 丙烯酸 以40%的产率得到2-ethyl-3-hydroxy-4-pyridinecarboxylic acid
  参考文献：
  名称：

  Peroxisome proliferator-activated receptor-γ mediates the anti-inflammatory effect of 3-hydroxy-4-pyridinecarboxylic acid derivatives: Synthesis and biological evaluation

  摘要：

  Seven 3-hydroxy-4-pyridinecarboxylic acid derivatives (HPs), aza-analogues of salicylic acid and structurally close to other potent inflammatory pyridine compounds such as aminopyridinylmethanols and aminopyridinamines, were synthesized, and their anti-inflammatory activity was evaluated. The synthesis was performed by adopting a general procedure involving an intramolecular Diels-Alder cycloaddition of oxazoles with acrylic acid to form various substituted pyridinic acids. The newly synthesized HPs did not exhibit cytotoxic activity on human monocytes-derived macrophages at concentrations up to 10(2) mu M. Anti-inflammatory activity of the compounds was screened in vitro by evaluating the capability to inhibit cytokines release from lipopolysaccharide (LPS) stimulated human macrophages. 3-Hydroxy-1-methyl-4-pyridinecarboxylic acid (24) was found to be the most active HP. At 10 mu M concentration, HP 24 reduced LPS-induced and nuclear factor-kappa B activation and cyclooxygenase-2 expression, while increased intracellular reactive oxygen species generation and peroxisome proliferator-activated receptor (PPAR-gamma) mRNA transcript level. Indeed, pre-treatment of LPS-exposed human macrophages with PPAR-gamma specific antagonist completely prevented HP 24-induced TNF-alpha and IL8 down regulation, demonstrating that the PPAR gamma pathway is mandatory for the HP 24 anti-inflammatory effect. Finally, daily treatment with HP 24 ameliorated the outcome of DSS-induced colitis in mice, significantly reducing colonic MPO activity and IL-1 beta tissue levels. (C) 2013 Elsevier Masson SAS. All rights reserved.

  DOI：

  10.1016/j.ejmech.2013.01.024
• 作为产物：
  描述：

  ethyl 2-aminobutyrate 在 四磷十氧化物 、 magnesium oxide 作用下， 以 氯仿 为溶剂， 反应 22.0h， 生成 5-ethoxy-4-ethyloxazole
  参考文献：
  名称：

  Peroxisome proliferator-activated receptor-γ mediates the anti-inflammatory effect of 3-hydroxy-4-pyridinecarboxylic acid derivatives: Synthesis and biological evaluation

  摘要：

  Seven 3-hydroxy-4-pyridinecarboxylic acid derivatives (HPs), aza-analogues of salicylic acid and structurally close to other potent inflammatory pyridine compounds such as aminopyridinylmethanols and aminopyridinamines, were synthesized, and their anti-inflammatory activity was evaluated. The synthesis was performed by adopting a general procedure involving an intramolecular Diels-Alder cycloaddition of oxazoles with acrylic acid to form various substituted pyridinic acids. The newly synthesized HPs did not exhibit cytotoxic activity on human monocytes-derived macrophages at concentrations up to 10(2) mu M. Anti-inflammatory activity of the compounds was screened in vitro by evaluating the capability to inhibit cytokines release from lipopolysaccharide (LPS) stimulated human macrophages. 3-Hydroxy-1-methyl-4-pyridinecarboxylic acid (24) was found to be the most active HP. At 10 mu M concentration, HP 24 reduced LPS-induced and nuclear factor-kappa B activation and cyclooxygenase-2 expression, while increased intracellular reactive oxygen species generation and peroxisome proliferator-activated receptor (PPAR-gamma) mRNA transcript level. Indeed, pre-treatment of LPS-exposed human macrophages with PPAR-gamma specific antagonist completely prevented HP 24-induced TNF-alpha and IL8 down regulation, demonstrating that the PPAR gamma pathway is mandatory for the HP 24 anti-inflammatory effect. Finally, daily treatment with HP 24 ameliorated the outcome of DSS-induced colitis in mice, significantly reducing colonic MPO activity and IL-1 beta tissue levels. (C) 2013 Elsevier Masson SAS. All rights reserved.

  DOI：

  10.1016/j.ejmech.2013.01.024

文献信息

• Vitamin B₂ Analogs. Synthesis and Biological Activity of Homologs of Pyridoxal 5′-Phosphate
  作者：Peter F. Muhlradt、Y. Morino、Esmond E. Snell

  DOI：10.1021/jm00315a012

  日期：1967.5