{(4-methoxy-phenoxycarbonyl)-[6-(5-methyl-2-(4-methylphenyl)oxazol-4-yl)-hexyl]-amino}acetic acid | 1101858-42-7

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 唑类
• 英文名称: {(4-methoxy-phenoxycarbonyl)-[6-(5-methyl-2-(4-methylphenyl)oxazol-4-yl)-hexyl]-amino}acetic acid
• 英文别名: 2-(((4-Methoxyphenoxy)carbonyl)(6-(5-methyl-2-p-tolyloxazol-4-yl)hexyl)amino)acetic acid；2-[(4-methoxyphenoxy)carbonyl-[6-[5-methyl-2-(4-methylphenyl)-1,3-oxazol-4-yl]hexyl]amino]acetic acid
• CAS: 1101858-42-7
• 化学式: C₂₇H₃₂N₂O₆
• 分子量: 480.561
• InChiKey: FVEHPNUUVUGNOQ-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  5.7
• 重原子数：
  35
• 可旋转键数：
  13
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.37
• 拓扑面积：
  102
• 氢给体数：
  1
• 氢受体数：
  7

反应信息

• 作为产物：
  描述：

  ethyl N-((4-methoxyphenoxy)carbonyl)-N-(6-(5-methyl-2-(p-tolyl)oxazol-4-yl)hexyl)glycinate 在 lithium hydroxide monohydrate 、 水 作用下， 以 四氢呋喃 、 甲醇 为溶剂， 反应 3.0h， 以92%的产率得到{(4-methoxy-phenoxycarbonyl)-[6-(5-methyl-2-(4-methylphenyl)oxazol-4-yl)-hexyl]-amino}acetic acid
  参考文献：
  名称：

  Modulation of PPAR receptor subtype selectivity of the ligands: Aliphatic chain vs aromatic ring as a spacer between pharmacophore and the lipophilic moiety

  摘要：

  Oxazole containing glycine and oximinobutyric acid derivatives were synthesized as PPAR alpha agonists by incorporating polymethylene spacer as a replacement of commonly used phenylene group that connects the acidic head with lipophilic tail. Compound 13a was found to be a selective and potent PPAR alpha agonist. Further 1,3-dioxane-2-carboxylic acid derivative 20 was synthesized by replacing the tetramethylene spacer of NS-220, a selective PPAR alpha agonist with phenylene group and found to exhibit PPAR alpha/gamma dual agonism. These results suggest that compounds possessing polymethylene spacer between pharmacophore and lipophilic tail exhibit predominantly PPARa agonism whereas those with an aromatic phenylene spacer shows PPAR alpha/gamma dual agonism. (C) 2008 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.bmcl.2008.10.062