3-(4-((3-benzyl-2-chloropyridin-4-yl)ethynyl)phenyl)propanoic acid | 1334589-75-1

• 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-((3-benzyl-2-chloropyridin-4-yl)ethynyl)phenyl)propanoic acid
• 英文别名: 3-[4-[2-(3-Benzyl-2-chloropyridin-4-yl)ethynyl]phenyl]propanoic acid
• CAS: 1334589-75-1
• 化学式: C₂₃H₁₈ClNO₂
• 分子量: 375.854
• InChiKey: KLPGEXLWBNHHIB-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  5.5
• 重原子数：
  27
• 可旋转键数：
  7
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.13
• 拓扑面积：
  50.2
• 氢给体数：
  1
• 氢受体数：
  3

反应信息

• 作为产物：
  描述：

  3-溴-2-氯吡啶 在 copper(l) iodide 、 sodium tetrachloropalladate(II) 、 lithium hydroxide monohydrate 、 四甲基乙二胺 、 lithium diisopropyl amide 、 2-二叔丁基膦-1-苯基吲哚 作用下， 以 四氢呋喃 、 水 为溶剂， 生成 3-(4-((3-benzyl-2-chloropyridin-4-yl)ethynyl)phenyl)propanoic acid
  参考文献：
  名称：

  Identification of a Potent and Selective Free Fatty Acid Receptor 1 (FFA1/GPR40) Agonist with Favorable Physicochemical and in Vitro ADME Properties

  摘要：

  The free fatty acid receptor 1 (FFA1, also known as GPR40) enhances glucose-stimulated insulin secretion from pancreatic beta-cells and is recognized as an interesting new target for treatment of type 2 diabetes. Several series of selective FFA1 agonists are already known. Most of these are derived from free fatty acids (FFAs) or glitazones and are relatively lipophilic. Aiming for the development of potent, selective, and less lipophilic FFA1 agonists, the terminal phenyl of a known compound series was replaced by nitrogen containing heterocycles. This resulted in the identification of 37, a selective FFA1 agonist with potent activity on recombinant human FFA1 receptors and on the rat insulinoma cell line INS-1E, optimal lipophilicity, and excellent in vitro permeability and metabolic stability.

  DOI：

  10.1021/jm2005699

文献信息

• Identification of a Potent and Selective Free Fatty Acid Receptor 1 (FFA1/GPR40) Agonist with Favorable Physicochemical and in Vitro ADME Properties
  作者：Elisabeth Christiansen、Christian Urban、Manuel Grundmann、Maria E. Due-Hansen、Ellen Hagesaether、Johannes Schmidt、Leonardo Pardo、Susanne Ullrich、Evi Kostenis、Matthias Kassack、Trond Ulven

  DOI：10.1021/jm2005699

  日期：2011.10.13

  The free fatty acid receptor 1 (FFA1, also known as GPR40) enhances glucose-stimulated insulin secretion from pancreatic beta-cells and is recognized as an interesting new target for treatment of type 2 diabetes. Several series of selective FFA1 agonists are already known. Most of these are derived from free fatty acids (FFAs) or glitazones and are relatively lipophilic. Aiming for the development of potent, selective, and less lipophilic FFA1 agonists, the terminal phenyl of a known compound series was replaced by nitrogen containing heterocycles. This resulted in the identification of 37, a selective FFA1 agonist with potent activity on recombinant human FFA1 receptors and on the rat insulinoma cell line INS-1E, optimal lipophilicity, and excellent in vitro permeability and metabolic stability.