benzyl 5-bromomethyl-2-n-butoxybenzoate | 943544-04-5

• 分子结构分类: 有机化合物 - 苯类化合物 - 苯和取代衍生物
• 英文名称: benzyl 5-bromomethyl-2-n-butoxybenzoate
• CAS: 943544-04-5
• 化学式: C₁₉H₂₁BrO₃
• 分子量: 377.278
• InChiKey: GFPKDEFIUIBIJM-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  5.12
• 重原子数：
  23.0
• 可旋转键数：
  8.0
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.32
• 拓扑面积：
  35.53
• 氢给体数：
  0.0
• 氢受体数：
  3.0

反应信息

• 作为反应物：
  描述：

  benzyl 5-bromomethyl-2-n-butoxybenzoate 、 (S)-4-benzyl-3-butyryloxazolidin-2-one 在 sodium hexamethyldisilazane 作用下， 以 四氢呋喃 为溶剂， 反应 1.0h， 生成 benzyl 5-[(R)-2-((S)-4-benzyl-2-oxo-oxazolidin-3-ylcarbonyl)butyl]-2-n-butoxybenzoate
  参考文献：
  名称：

  Design, synthesis, and evaluation of potent, structurally novel peroxisome proliferator-activated receptor (PPAR) δ-selective agonists

  摘要：

  A series of 3-(4-alkoxyphenyl)propanoic acid derivatives was prepared as candidate peroxisome proliferator-activated receptor (PPAR) 6-selective agonists, based on our previously discovered potent human PPAR alpha/delta dual agonist TIPP-401 as a lead compound. Structure-activity relationship studies clearly indicated the importance of the chain length of the alkoxy group at the 4-position, and the n-butoxy compound exhibited the most potent PPAR delta transactivation activity and highest PPAR delta selectivity. The (S)-enantiomer of a representative compound exhibited extremely potent PPAR delta transactivation activity, comparable with or somewhat superior to that of the known PPAR delta-selective agonist, GW-501516. The representative compound regulated the expression of genes involved in lipid and glucose homeostasis, and should be useful not only as a chemical tool to study PPAR delta function, but also as a candidate drug for the treatment of metabolic syndrome. (c) 2007 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.bmc.2007.05.023
• 作为产物：
  描述：

  在 三溴化磷 作用下， 以 乙醚 为溶剂， 反应 1.0h， 以70%的产率得到benzyl 5-bromomethyl-2-n-butoxybenzoate
  参考文献：
  名称：

  Design, synthesis, and evaluation of potent, structurally novel peroxisome proliferator-activated receptor (PPAR) δ-selective agonists

  摘要：

  A series of 3-(4-alkoxyphenyl)propanoic acid derivatives was prepared as candidate peroxisome proliferator-activated receptor (PPAR) 6-selective agonists, based on our previously discovered potent human PPAR alpha/delta dual agonist TIPP-401 as a lead compound. Structure-activity relationship studies clearly indicated the importance of the chain length of the alkoxy group at the 4-position, and the n-butoxy compound exhibited the most potent PPAR delta transactivation activity and highest PPAR delta selectivity. The (S)-enantiomer of a representative compound exhibited extremely potent PPAR delta transactivation activity, comparable with or somewhat superior to that of the known PPAR delta-selective agonist, GW-501516. The representative compound regulated the expression of genes involved in lipid and glucose homeostasis, and should be useful not only as a chemical tool to study PPAR delta function, but also as a candidate drug for the treatment of metabolic syndrome. (c) 2007 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.bmc.2007.05.023