5-乙氧基-1,3-恶唑-4-羧酸乙酯 | 14423-15-5

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 唑类
• 中文名称: 5-乙氧基-1,3-恶唑-4-羧酸乙酯
• 英文名称: 5-ethoxyoxazole-4-carboxylic acid ethyl ester
• 英文别名: ethyl 5-ethoxyoxazole-4-carboxylate；5-ethoxy-4-ethoxycarbonyloxazole；4-carboxyethyl-5-ethoxyoxazole；5-ethoxy-oxazole-4-carboxylic acid ethyl ester；5-Aethoxy-oxazol-4-carbonsaeure-aethylester；5-Ethoxy-oxazol-4-carbonsaeureethylester；4-Oxazolecarboxylic acid, 5-ethoxy-, ethyl ester；ethyl 5-ethoxy-1,3-oxazole-4-carboxylate
• CAS: 14423-15-5
• 化学式: C₈H₁₁NO₄
• 分子量: 185.18
• InChiKey: LFBNBGOBQMFXIF-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  1.6
• 重原子数：
  13
• 可旋转键数：
  5
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.5
• 拓扑面积：
  61.6
• 氢给体数：
  0
• 氢受体数：
  5

反应信息

• 作为反应物：
  描述：

  5-乙氧基-1,3-恶唑-4-羧酸乙酯 在 lithium aluminium tetrahydride 作用下， 以 乙醚 为溶剂， 反应 20.0h， 以40%的产率得到(5-ethoxyoxazol-4-yl)methanol
  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：

  丙二酸2-氨基-1-乙酯 在 盐酸 、 四磷十氧化物 、 magnesium oxide 作用下， 以 氯仿 、 水 为溶剂， 反应 28.5h， 生成 5-乙氧基-1,3-恶唑-4-羧酸乙酯
  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

• Hoppe,D., Angewandte Chemie, 1974, vol. 86, p. 878 - 893
  作者：Hoppe,D.

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• Schroeder,R. et al., Justus Liebigs Annalen der Chemie, 1975, p. 533 - 546
  作者：Schroeder,R. et al.

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• Johnsen, Bjoern A.; Undheim, Kjell, Acta chemica Scandinavica. Series B: Organic chemistry and biochemistry, 1983, vol. 37, # 2, p. 127 - 132
  作者：Johnsen, Bjoern A.、Undheim, Kjell

  DOI：——

  日期：——
• Reaction of 1-tosyloxyaziridine-2,2-diacarboxylic ester with triethylamine
  作者：A. V. Prosyanik、P. N. Belov、V. I. Markov

  DOI：10.1007/bf00505968

  日期：1984.12
• JOHNSEN, B. A.;UNDHEIM, K., ACTA CHEM. SCAND., 1983, 37, N 2, 127-132
  作者：JOHNSEN, B. A.、UNDHEIM, K.

  DOI：——

  日期：——