{(4-methoxyphenoxycarbonyl)-[4-(5-methyl-2-(4-methylphenyl)oxazol-4-yl)-butyl]-amino}acetic acid | 1101858-40-5

• 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-methoxyphenoxycarbonyl)-[4-(5-methyl-2-(4-methylphenyl)oxazol-4-yl)-butyl]-amino}acetic acid
• 英文别名: 2-[(4-Methoxyphenoxy)carbonyl-[4-[5-methyl-2-(4-methylphenyl)-1,3-oxazol-4-yl]butyl]amino]acetic acid
• CAS: 1101858-40-5
• 化学式: C₂₅H₂₈N₂O₆
• 分子量: 452.507
• InChiKey: DVLJBLURDLJJDP-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  4.8
• 重原子数：
  33
• 可旋转键数：
  11
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.32
• 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-(4-(5-methyl-2-(p-tolyl)oxazol-4-yl)butyl)glycinate 在 lithium hydroxide monohydrate 、 水 作用下， 以 四氢呋喃 、 甲醇 为溶剂， 反应 3.0h， 以96%的产率得到{(4-methoxyphenoxycarbonyl)-[4-(5-methyl-2-(4-methylphenyl)oxazol-4-yl)-butyl]-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

文献信息

• Modulation of PPAR receptor subtype selectivity of the ligands: Aliphatic chain vs aromatic ring as a spacer between pharmacophore and the lipophilic moiety
  作者：Harikishore Pingali、Mukul Jain、Shailesh Shah、Pravin Patil、Pankaj Makadia、Pandurang Zaware、Kalapatapu V.V.M. Sairam、Jeevankumar Jamili、Ashish Goel、Megha Patel、Pankaj Patel

  DOI：10.1016/j.bmcl.2008.10.062

  日期：2008.12

  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.