methyl (E)-3-(2-fluoro-4-(3-methylpent-3-en-1-yn-1-yl)phenyl)propanoate | 1402601-96-0

• 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: methyl (E)-3-(2-fluoro-4-(3-methylpent-3-en-1-yn-1-yl)phenyl)propanoate
• 英文别名: Methyl (E)-3-(2-fluoro-4-(3-methylpent-3-en-1-yn-1-yl)phenyl)propanoate；methyl 3-[2-fluoro-4-[(E)-3-methylpent-3-en-1-ynyl]phenyl]propanoate
• CAS: 1402601-96-0
• 化学式: C₁₆H₁₇FO₂
• 分子量: 260.308
• InChiKey: NJZSTTOJVKYOIL-UUILKARUSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  4.1
• 重原子数：
  19
• 可旋转键数：
  6
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.31
• 拓扑面积：
  26.3
• 氢给体数：
  0
• 氢受体数：
  3

反应信息

• 作为反应物：
  描述：

  methyl (E)-3-(2-fluoro-4-(3-methylpent-3-en-1-yn-1-yl)phenyl)propanoate 在 lithium hydroxide monohydrate 、 水 作用下， 以 四氢呋喃 为溶剂， 以92%的产率得到(E)-3-(2-fluoro-4-(3-methylpent-3-en-1-yn-1-yl)phenyl)propanoic acid
  参考文献：
  名称：

  Discovery of a Potent Free Fatty Acid 1 Receptor Agonist with Low Lipophilicity, Low Polar Surface Area, and Robust in Vivo Efficacy

  摘要：

  The free fatty acid receptor 1 (FFA1 or GPR40) is established as an interesting potential target for treatment of type 2 diabetes. However, to obtain optimal ligands, it may be necessary to limit both lipophilicity and polar surface area, translating to a need for small compounds. We here describe the identification of 24, a potent FFA1 agonist with low lipophilicity and very high ligand efficiency that exhibit robust glucose lowering effect.

  DOI：

  10.1021/acs.jmedchem.5b01962
• 作为产物：
  描述：

  2-溴-cis-2-丁烯 、 methyl 3-(4-ethynyl-2-fluorophenyl)propanoate 在 copper(l) iodide 、 sodium tetrachloropalladate(II) 、 四甲基乙二胺 、 2-二叔丁基膦-1-苯基吲哚 作用下， 以 水 为溶剂， 以64%的产率得到methyl (E)-3-(2-fluoro-4-(3-methylpent-3-en-1-yn-1-yl)phenyl)propanoate
  参考文献：
  名称：

  Discovery of a Potent Free Fatty Acid 1 Receptor Agonist with Low Lipophilicity, Low Polar Surface Area, and Robust in Vivo Efficacy

  摘要：

  The free fatty acid receptor 1 (FFA1 or GPR40) is established as an interesting potential target for treatment of type 2 diabetes. However, to obtain optimal ligands, it may be necessary to limit both lipophilicity and polar surface area, translating to a need for small compounds. We here describe the identification of 24, a potent FFA1 agonist with low lipophilicity and very high ligand efficiency that exhibit robust glucose lowering effect.

  DOI：

  10.1021/acs.jmedchem.5b01962

文献信息

• ORTHO-FLUORO SUBSTITUTED COMPOUNDS FOR THE TREATMENT OF METABOLIC DISEASES
  申请人：Ulven Trond

  公开号：US20140058125A1

  公开（公告）日：2014-02-27

  There is provided novel fluoro-substituted compounds capable of modulating the G-protein-coupled receptor GPR40, compositions comprising the compounds, and methods for their use for controlling insulin levels in vivo and for the treatment of conditions such as type II diabetes, hypertension, ketoacidosis, obesity, glucose intolerance, and hypercholesterolemia and related disorders associated with abnormally high or low plasma lipoprotein, triglyceride or glucose levels.

  本发明提供了一种新型的氟取代化合物，能够调节G蛋白偶联受体GPR40，包括该化合物的组合物，以及其使用方法，用于控制体内胰岛素水平和治疗诸如2型糖尿病、高血压、酮症酸中毒、肥胖症、葡萄糖不耐受症和与异常高或低的血浆脂蛋白、甘油三酯或葡萄糖水平相关的疾病。
• Discovery of a Potent Free Fatty Acid 1 Receptor Agonist with Low Lipophilicity, Low Polar Surface Area, and Robust in Vivo Efficacy
  作者：Steffen V. F. Hansen、Elisabeth Christiansen、Christian Urban、Brian D. Hudson、Claire J. Stocker、Maria E. Due-Hansen、Ed T. Wargent、Bharat Shimpukade、Reinaldo Almeida、Christer S. Ejsing、Michael A. Cawthorne、Matthias U. Kassack、Graeme Milligan、Trond Ulven

  DOI：10.1021/acs.jmedchem.5b01962

  日期：2016.3.24

  The free fatty acid receptor 1 (FFA1 or GPR40) is established as an interesting potential target for treatment of type 2 diabetes. However, to obtain optimal ligands, it may be necessary to limit both lipophilicity and polar surface area, translating to a need for small compounds. We here describe the identification of 24, a potent FFA1 agonist with low lipophilicity and very high ligand efficiency that exhibit robust glucose lowering effect.