(4-Mercapto-phenoxy)-acetic Acid Methyl Ester | 1706-60-1

• 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: (4-Mercapto-phenoxy)-acetic Acid Methyl Ester
• 英文别名: methyl (4-mercaptophenoxy)acetate；Methyl 2-(4-sulfanylphenoxy)acetate
• CAS: 1706-60-1
• 化学式: C₉H₁₀O₃S
• 分子量: 198.243
• InChiKey: OLWMUEMPOVOVLB-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  1.6
• 重原子数：
  13
• 可旋转键数：
  4
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.22
• 拓扑面积：
  36.5
• 氢给体数：
  1
• 氢受体数：
  4

反应信息

• 作为反应物：
  描述：

  (4-Mercapto-phenoxy)-acetic Acid Methyl Ester 在 双氧水 、 碳酸氢钠 作用下， 以 甲醇 、 水 、 溶剂黄146 为溶剂， 反应 4.0h， 生成 [4-(4-methyl-thiazole-2-sulfonyl)-phenoxy]-acetic acid methyl ester
  参考文献：
  名称：

  Tippe,A. et al., Roczniki Chemii, 1975, vol. 49, p. 1609 - 1614

  摘要：

  DOI：
• 作为产物：
  描述：

  2-(4-羟基苯氧基)乙酸甲酯 在 甲醇 、 4-二甲氨基吡啶 、 sodium methylate 、 三乙胺 作用下， 以 1,4-二氧六环 为溶剂， 反应 32.0h， 生成 (4-Mercapto-phenoxy)-acetic Acid Methyl Ester
  参考文献：
  名称：

  Novel selective small molecule agonists for peroxisome proliferator-activated receptor δ (PPARδ)—synthesis and biological activity

  摘要：

  We report the synthesis and biological activity of a new series of small molecule agonists of the human Peroxisome Proliferator-Activated Receptor delta (PPARdelta). Several hits were identified from our original libraries containing lipophilic carboxylic acids. Optimization of these hits by structure-guided design led to 7k (GW501516) and 71 (GW0742), which shows an EC50 Of 1.1 nM against PPARdelta with 1000-fold selectivity over the other human subtypes. (C) 2003 Elsevier Science Ltd. All rights reserved.

  DOI：

  10.1016/s0960-894x(03)00207-5

文献信息

• Compounds that modulate PPAR activity and methods of preparation
  申请人：——

  公开号：US20040209936A1

  公开（公告）日：2004-10-21

  This invention relates to compounds that alter PPAR activity. The invention also relates to pharmaceutically acceptable salts of the compounds, pharmaceutically acceptable compositions comprising the compounds or their salts, and methods of using them as therapeutic agents for treating or preventing dyslipidemia, hypercholesterolemia, obesity, hyperglycemia, atherosclerosis, hypertriglyceridemia and hyperinsulinemia in a mammal. The present invention also relates to methods for making the disclosed compounds.

  这项发明涉及改变PPAR活性的化合物。该发明还涉及这些化合物的药用盐、包含这些化合物或其盐的药用组合物，以及将它们用作治疗或预防哺乳动物中的脂质代谢异常、高胆固醇血症、肥胖、高血糖、动脉粥样硬化、高甘油三酯血症和高胰岛素血症的治疗剂的方法。本发明还涉及制备所述化合物的方法。
• Compounds that modulate PPAR activity and methods for their preparation
  申请人：——

  公开号：US20030225158A1

  公开（公告）日：2003-12-04

  This invention discloses compounds that alter PPAR activity. The invention also discloses pharmaceutically acceptable salts of the compounds, pharmaceutically acceptable compositions comprising the compounds or their salts, and methods of using them as therapeutic agents for treating or preventing disipidemia, hypercholesteremia, obesity, eating disorders, hyperglycemia, atherosclerosis, hypertriglyceridemia, hyperinsulinemia and diabetes in a mammal as well as methods of supressing appetite and modulating leptin levels in a mammal. The present invention also discloses methods for making the disclosed compounds.

  该发明揭示了可以改变PPAR活性的化合物。该发明还揭示了这些化合物的药用可接受盐、含有这些化合物或其盐的药用可接受组合物，以及将它们用作治疗或预防哺乳动物的失脂血症、高胆固醇血症、肥胖症、进食障碍、高血糖、动脉粥样硬化、高甘油三酯血症、高胰岛素血症和糖尿病的治疗剂的方法，以及在哺乳动物中抑制食欲和调节瘦素水平的方法。本发明还揭示了制备所述化合物的方法。
• Insights into the mechanism of the site-selective sequential palladium-catalyzed cross-coupling reactions of dibromothiophenes/dibromothiazoles and arylboronic acids. Synthesis of PPARβ/δ agonists
  作者：Raquel Pereira、Audrey Furst、Beatriz Iglesias、Pierre Germain、Hinrich Gronemeyer、Angel R. de Lera

  DOI：10.1039/b612235c

  日期：——

  A reactivity study, aided by NMR spectroscopy, allowed a mechanistic rationale to be postulated for the palladium-catalyzed regioselective coupling of arylboronic acid (and arylstannane where feasible) at the position next to the sulfur atom in functionalized dibromothiophenes and dibromothiazoles. The analysis of the NMR spectra (using 19F from the boronic acid CF3 group and 31P from the phosphine of the catalyst as probes) of the entire reaction starting from the dibromoheterocycles allowed the qualitative proposal that the transmetalation is the rate-limiting step for both sequential substitution processes. The extremely facile oxidative addition at the C–Br bond next to the sulfur atom of the heterocycle instead determines the positional selectivity. An additional Stille reaction then replaced the second halogen, providing the trisubstituted heterocyclic scaffolds of PPAR ligands, which displayed PPARβ/δ agonist activity, as revealed by reporter assays in living cells.

  一项反应性研究，借助 NMR 光谱学，使得能够提出一种机制推断，用于钯催化的区域选择性偶联反应，即在功能化的二溴噻吩和二溴噻唑中，芳基硼酸（以及可行的芳基锡化合物）在硫原子相邻位置的偶联。对整个反应的 NMR 光谱（使用来自硼酸 CF3 组的 19F 和催化剂的膦的 31P 作为探针）进行分析表明，跨金属转移是两种顺序取代过程的速率限制步骤。异环次的 C–Br 键的极其容易的氧化加成决定了位置选择性。随后，通过额外的 Stille 反应替代第二卤素，提供了具有 PPAR 配体特征的三取代杂环支架，这些支架在活细胞中的报告酶测试中显示出 PPARβ/δ 激动剂活性。
• COMPOUNDS THAT MODULATE PPAR ACTIVITY AND METHODS FOR THEIR PREPARATION
  申请人：Auerbach J. Bruce

  公开号：US20050153996A1

  公开（公告）日：2005-07-14

  This invention discloses compounds that alter PPAR activity. The invention also discloses pharmaceutically acceptable salts of the compounds, pharmaceutically acceptable compositions comprising the compounds or their salts, and methods of using them as therapeutic agents for treating or preventing disipidemia, hypercholesteremia, obesity, eating disorders, hyperglycemia, atherosclerosis, hypertriglyceridemia, hyperinsulinemia and diabetes in a mammal as well as methods of supressing appetite and modulating leptin levels in a mammal. The present invention also discloses methods for making the disclosed compounds.

  本发明揭示了能够改变PPAR活性的化合物。本发明还揭示了这些化合物的药学上可接受的盐，包含这些化合物或其盐的药学上可接受的组合物，以及将它们用作治疗或预防哺乳动物的失脂症、高胆固醇血症、肥胖症、进食障碍、高血糖、动脉硬化、高三酰甘油血症、高胰岛素血症和糖尿病的治疗剂的方法，以及在哺乳动物中抑制食欲和调节瘦素水平的方法。本发明还揭示了制备所述化合物的方法。
• Synthesis of the PPARβ/δ-selective agonist GW501516 and C4-thiazole-substituted analogs
  作者：Raquel Pereira、Claudine Gaudon、Beatriz Iglesias、Pierre Germain、Hinrich Gronemeyer、Angel R. de Lera

  DOI：10.1016/j.bmcl.2005.09.060

  日期：2006.1

  Sequential, position-selective, Pd-catalyzed cross-coupling reactions of 2,4-dibromo-5-hydroxymethylthiazole provided the scaffold for the synthesis of GW501516, the most potent PPAR beta/delta agonist yet described, and equally selective analogs at the thiazole-C4 position. (c) 2005 Elsevier Ltd. All rights reserved.