3-{4-[(4-Bromobenzyl)oxy]phenyl}propanoic acid | 1236109-58-2

• 分子结构分类: 有机化合物 - 苯丙烷和聚酮 - 苯丙酸
• 英文名称: 3-{4-[(4-Bromobenzyl)oxy]phenyl}propanoic acid
• 英文别名: 3-[4-[(4-bromophenyl)methoxy]phenyl]propanoic acid
• CAS: 1236109-58-2
• 化学式: C₁₆H₁₅BrO₃
• 分子量: 335.197
• InChiKey: VVMPRKZQODSJGQ-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  4.1
• 重原子数：
  20
• 可旋转键数：
  6
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.19
• 拓扑面积：
  46.5
• 氢给体数：
  1
• 氢受体数：
  3

反应信息

• 作为产物：
  描述：

  methyl 3-{4-[(4-bromobenzyl)oxy]phenyl}propanoate 在 水 、 lithium hydroxide 作用下， 以 四氢呋喃 为溶剂， 生成 3-{4-[(4-Bromobenzyl)oxy]phenyl}propanoic acid
  参考文献：
  名称：

  Structure−Activity Study of Dihydrocinnamic Acids and Discovery of the Potent FFA1 (GPR40) Agonist TUG-469

  摘要：

  The free fatty acid 1 receptor (FFA1 or GPR40), which is highly expressed on pancreatic beta-cells and amplifies glucose-stimulated insulin secretion, has emerged as attractive target for the treatment of type 2 diabetes Several FFA1 agonists containing the para-substituted dihydrocinnamic acid moiety are known. We here present a structure-activity relationship study of this compound family suggesting that the central methyleneoxy linker is preferable for the smaller compounds whereas the central methyleneamine linker gives higher potency to the larger compounds. The study resulted in the discovery of the potent and selective full FFA1 agonist TUG-469 (29).

  DOI：

  10.1021/ml100106c

文献信息

• Structure−Activity Study of Dihydrocinnamic Acids and Discovery of the Potent FFA1 (GPR40) Agonist TUG-469
  作者：Elisabeth Christiansen、Maria E. Due-Hansen、Christian Urban、Nicole Merten、Michael Pfleiderer、Kasper K. Karlsen、Sanne S. Rasmussen、Mette Steensgaard、Alexandra Hamacher、Johannes Schmidt、Christel Drewke、Rasmus Koefoed Petersen、Karsten Kristiansen、Susanne Ullrich、Evi Kostenis、Matthias U. Kassack、Trond Ulven

  DOI：10.1021/ml100106c

  日期：2010.10.14

  The free fatty acid 1 receptor (FFA1 or GPR40), which is highly expressed on pancreatic beta-cells and amplifies glucose-stimulated insulin secretion, has emerged as attractive target for the treatment of type 2 diabetes Several FFA1 agonists containing the para-substituted dihydrocinnamic acid moiety are known. We here present a structure-activity relationship study of this compound family suggesting that the central methyleneoxy linker is preferable for the smaller compounds whereas the central methyleneamine linker gives higher potency to the larger compounds. The study resulted in the discovery of the potent and selective full FFA1 agonist TUG-469 (29).