3-(2-fluoro-4-((2-((3-(methylsulfonyl)propoxy)methyl)phenyl)ethynyl)phenyl)propanoic acid | 1429427-36-0

• 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-(2-fluoro-4-((2-((3-(methylsulfonyl)propoxy)methyl)phenyl)ethynyl)phenyl)propanoic acid
• 英文别名: 3-[2-Fluoro-4-[2-[2-(3-methylsulfonylpropoxymethyl)phenyl]ethynyl]phenyl]propanoic acid；3-[2-fluoro-4-[2-[2-(3-methylsulfonylpropoxymethyl)phenyl]ethynyl]phenyl]propanoic acid
• CAS: 1429427-36-0
• 化学式: C₂₂H₂₃FO₅S
• 分子量: 418.486
• InChiKey: NPKSNKFRLYXDLG-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.2
• 重原子数：
  29
• 可旋转键数：
  11
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.32
• 拓扑面积：
  89
• 氢给体数：
  1
• 氢受体数：
  6

反应信息

• 作为产物：
  描述：

  ethyl (E)-3-(4-bromo-2-fluorophenyl)acrylate 在 sodium tetrahydroborate 、 copper(l) iodide 、 sodium tetrachloropalladate(II) 、 四甲基乙二胺 、 potassium carbonate 、 cobalt(II) chloride 、 lithium hydroxide 、 2-二叔丁基膦-1-苯基吲哚 作用下， 以 四氢呋喃 、 甲醇 、 水 为溶剂， 反应 3.0h， 生成 3-(2-fluoro-4-((2-((3-(methylsulfonyl)propoxy)methyl)phenyl)ethynyl)phenyl)propanoic acid
  参考文献：
  名称：

  Discovery of TUG-770: A Highly Potent Free Fatty Acid Receptor 1 (FFA1/GPR40) Agonist for Treatment of Type 2 Diabetes

  摘要：

  Free fatty acid receptor 1 (FFA1 or GPR40) enhances glucose-stimulated insulin secretion from pancreatic beta-cells and currently attracts high interest as a new target for the treatment of type 2 diabetes. We here report the discovery of a highly potent FFA1 agonist with favorable physicochemical and pharmacokinetic properties. The compound efficiently normalizes glucose tolerance in diet-induced obese mice, an effect that is fully sustained after 29 days of chronic dosing.

  DOI：

  10.1021/ml4000673

文献信息

• Discovery of TUG-770: A Highly Potent Free Fatty Acid Receptor 1 (FFA1/GPR40) Agonist for Treatment of Type 2 Diabetes
  作者：Elisabeth Christiansen、Steffen V. F. Hansen、Christian Urban、Brian D. Hudson、Edward T. Wargent、Manuel Grundmann、Laura Jenkins、Mohamed Zaibi、Claire J. Stocker、Susanne Ullrich、Evi Kostenis、Matthias U. Kassack、Graeme Milligan、Michael A. Cawthorne、Trond Ulven

  DOI：10.1021/ml4000673

  日期：2013.5.9

  Free fatty acid receptor 1 (FFA1 or GPR40) enhances glucose-stimulated insulin secretion from pancreatic beta-cells and currently attracts high interest as a new target for the treatment of type 2 diabetes. We here report the discovery of a highly potent FFA1 agonist with favorable physicochemical and pharmacokinetic properties. The compound efficiently normalizes glucose tolerance in diet-induced obese mice, an effect that is fully sustained after 29 days of chronic dosing.