TUG-424 | 1082058-99-8

• 分子结构分类: 有机化合物 - 苯丙烷和聚酮 - 苯丙酸
• 英文名称: TUG-424
• 英文别名: 3-(4-(o-Tolylethynyl)phenyl)propanoic acid；3-[4-[2-(2-methylphenyl)ethynyl]phenyl]propanoic acid
• CAS: 1082058-99-8
• 化学式: C₁₈H₁₆O₂
• 分子量: 264.324
• InChiKey: FODHWOBAQBTTFS-UHFFFAOYSA-N

物化性质

• 沸点：
  448.1±38.0 °C(Predicted)
• 密度：
  1.17±0.1 g/cm3(Predicted)
• 溶解度：
  二甲基亚砜：>10mg/mL

计算性质

• 辛醇/水分配系数(LogP)：
  4.1
• 重原子数：
  20
• 可旋转键数：
  5
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.17
• 拓扑面积：
  37.3
• 氢给体数：
  1
• 氢受体数：
  2

反应信息

• 作为产物：
  描述：

  methyl 3-(4-(o-tolylethynyl)phenyl)propanoate 在 lithium hydroxide 作用下， 以 1,4-二氧六环 、 水 为溶剂， 以100%的产率得到TUG-424
  参考文献：
  名称：

  A Rapid and Efficient Sonogashira Protocol and Improved Synthesis of Free Fatty Acid 1 (FFA1) Receptor Agonists

  摘要：

  A protocol for rapid and efficient Pd/Cu-catalyzed coupling of aryl bromides and iodides to terminal alkynes has been developed with use of 2-(di-tert-butylphosphino)-N-phenylindole (cataCXium PIntB) as ligand in TMEDA and water. The new protocol successfully couples substrates which failed with standard Sonogashira conditions, and enables an efficient general synthetic route to free fatty acid 1 (FFA1) receptor ligands from 3-(4-bromophenyl)-propionic acid.

  DOI：

  10.1021/jo902533p

文献信息

• [EN] COMPOUNDS FOR THE TREATMENT OF METABOLIC DISEASES<br/>[FR] COMPOSÉS DESTINÉS AU TRAITEMENT DE TROUBLES MÉTABOLIQUES
  申请人：UNIV SYDDANSK

  公开号：WO2010012650A1

  公开（公告）日：2010-02-04

  There is provided novel 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 Il diabetes, hypertension, ketoacidosis, obesity, glucose intolerance, and hypercholesterolemia and related disorders associated with abnormally high or low plasma lipoprotein, triglyceride or glucose levels.

  提供了一种新型化合物，能够调节G蛋白偶联受体GPR40，包括该化合物的组合物和使用方法，用于控制体内胰岛素水平，治疗II型糖尿病、高血压、酮症、肥胖症、葡萄糖不耐受症和与异常高或低血浆脂蛋白、甘油三酯或葡萄糖水平相关的相关疾病。
• COMPOUNDS FOR THE TREATMENT OF METABOLIC DISEASES
  申请人：Ulven Trond

  公开号：US20110152315A1

  公开（公告）日：2011-06-23

  There is provided novel 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 I1 diabetes, hypertension, ketoacidosis, obesity, glucose intolerance, and hypercholesterolemia and related disorders associated with abnormally high or low plasma lipoprotein, triglyceride or glucose levels.

  提供了一种新的化合物，能够调节G蛋白偶联受体GPR40，包括该化合物的组合物以及使用它们的方法，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、葡萄糖耐受性不良以及与异常高或低血浆脂蛋白、甘油三酯或葡萄糖水平有关的相关疾病。
• [EN] PHENYLALANINE COMPOUND HAVING NITROGEN HETEROCYCLIC LINK, PHARMACEUTICAL COMPOSITION THEREOF, PREPARATION METHOD THEREFOR, AND USE THEREOF<br/>[FR] COMPOSÉ DE PHÉNYLALANINE AYANT UN GROUPE DE LIAISON HÉTÉROCYCLIQUE AZOTÉ, COMPOSITION PHARMACEUTIQUE ASSOCIÉE, SON PROCÉDÉ DE PRÉPARATION ET SON UTILISATION
  申请人：SHANGHAI INST MATERIA MEDICA

  公开号：WO2014169817A1

  公开（公告）日：2014-10-23

  提供一种具有显著的降血糖和调节糖脂代谢活性的含氮杂环链接的苯丙酸类化合物、其药学上可接受的盐或立体异构体，含有所述化合物的药物组合物，以及所述化合物在制备糖尿病及糖脂代谢紊乱的药物中的用途，尤其是在制备治疗Π型糖尿病药物中的用途。所述化合物具有通式I所示结构。
• Discovery of Potent and Selective Agonists for the Free Fatty Acid Receptor 1 (FFA₁/GPR40), a Potential Target for the Treatment of Type II Diabetes
  作者：Elisabeth Christiansen、Christian Urban、Nicole Merten、Kathrin Liebscher、Kasper K. Karlsen、Alexandra Hamacher、Andreas Spinrath、Andrew D. Bond、Christel Drewke、Susanne Ullrich、Matthias U. Kassack、Evi Kostenis、Trond Ulven

  DOI：10.1021/jm8010178

  日期：2008.11.27

  A series of 4-phenethynyldihydrocinnamic acid agonists of the free fatty acid receptor 1 (FFA(1)) has been discovered and explored. The preferred compound 20 (TUG-424, EC50 = 32 nM) significantly increased glucose-stimulated insulin secretion at 100 nM and may serve to explore the role of FFA(1) in metabolic diseases such as diabetes or obesity.
• LOW CALORIC FAT REPLACERS
  申请人：Damak Sami

  公开号：US20130071547A1

  公开（公告）日：2013-03-21

  The present invention relates in general to field of food and drinks. In particular, in relates to formulations that mimic the taste of fat but that are lower in calories. One embodiment of the present invention relates to the use of at least one non-fat agonist of GPR40 for imparting a fatty taste to a food product.