5-hydroxy-2,3-dihydrobenzofuran-2-carboxylic acid methyl ester | 863970-62-1

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 香豆素
• 英文名称: 5-hydroxy-2,3-dihydrobenzofuran-2-carboxylic acid methyl ester
• 英文别名: Methyl 5-hydroxy-2,3-dihydro-1-benzofuran-2-carboxylate
• CAS: 863970-62-1
• 化学式: C₁₀H₁₀O₄
• 分子量: 194.187
• InChiKey: WQQGWHUQZPKEDL-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  1.5
• 重原子数：
  14
• 可旋转键数：
  2
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.3
• 拓扑面积：
  55.8
• 氢给体数：
  1
• 氢受体数：
  4

反应信息

• 作为反应物：
  描述：

  5-hydroxy-2,3-dihydrobenzofuran-2-carboxylic acid methyl ester 在 氢氧化钾 、 caesium carbonate 作用下， 以 甲醇 、 N,N-二甲基甲酰胺 为溶剂， 反应 9.0h， 生成 5-{3-[2-Chloro-4-(2,2,2-trifluoro-ethoxy)-phenoxy]-propoxy}-2,3-dihydro-benzofuran-2-carboxylic acid
  参考文献：
  名称：

  Novel 2,3-Dihydrobenzofuran-2-carboxylic Acids:  Highly Potent and Subtype-Selective PPARα Agonists with Potent Hypolipidemic Activity

  摘要：

  The design and synthesis of a novel class of 2,3-dihydrobenzofuran-2-carboxylic acids as highly potent and subtype-selective PPAR alpha agonists are reported. Systematic study of structure-activity relationships has identified several key structural elements within this class for maintaining the potency and subtype selectivity. Select compounds were evaluated in animal models of dyslipidemia using Syrian hamsters and male Beagle dogs, and all these compounds displayed excellent cholesterol- and triglyceride-lowering activity at dose levels that were much lower than the marketed weak PPAR alpha agonist fenofibrate.

  DOI：

  10.1021/jm050373g
• 作为产物：
  描述：

  5-甲氧基-1-苯并呋喃-2-甲酸甲酯 在 palladium on activated charcoal 氢气 、 三溴化硼 作用下， 以 乙醇 、 二氯甲烷 为溶剂， 反应 73.0h， 生成 5-hydroxy-2,3-dihydrobenzofuran-2-carboxylic acid methyl ester
  参考文献：
  名称：

  Novel 2,3-Dihydrobenzofuran-2-carboxylic Acids:  Highly Potent and Subtype-Selective PPARα Agonists with Potent Hypolipidemic Activity

  摘要：

  The design and synthesis of a novel class of 2,3-dihydrobenzofuran-2-carboxylic acids as highly potent and subtype-selective PPAR alpha agonists are reported. Systematic study of structure-activity relationships has identified several key structural elements within this class for maintaining the potency and subtype selectivity. Select compounds were evaluated in animal models of dyslipidemia using Syrian hamsters and male Beagle dogs, and all these compounds displayed excellent cholesterol- and triglyceride-lowering activity at dose levels that were much lower than the marketed weak PPAR alpha agonist fenofibrate.

  DOI：

  10.1021/jm050373g

文献信息

• COMPOUNDS AND METHODS FOR MODULATING G PROTEIN-COUPLED RECEPTORS
  申请人：Epple Robert

  公开号：US20100035944A1

  公开（公告）日：2010-02-11

  The invention provides compounds and pharmaceutical compositions thereof, which are useful for modulating G protein-coupled receptor 20 (GPR20), and methods for using such compounds to treat, ameliorate or prevent a condition associated with abnormal or deregulated GPR20.

  本发明提供了化合物及其制药组合物，这些化合物对调节G蛋白偶联受体20 (GPR20) 有用，以及使用这些化合物治疗、改善或预防与异常或失调的GPR20相关的疾病的方法。
• US8394841B2
  申请人：——

  公开号：US8394841B2

  公开（公告）日：2013-03-12
• [EN] COMPOUNDS AND METHODS FOR MODULATING G PROTEIN-COUPLED RECEPTORS<br/>[FR] COMPOSÉS ET PROCÉDÉS POUR MODULER DES RÉCEPTEURS COUPLÉS AUX PROTÉINES G
  申请人：IRM LLC

  公开号：WO2008103501A1

  公开（公告）日：2008-08-28

  [EN] The invention provides compounds and pharmaceutical compositions thereof, which are useful for modulating G protein-coupled receptor 20 (GPR20), and methods for using such compounds to treat, ameliorate or prevent a condition associated with abnormal or deregulated GPR20.
  [FR] L'invention concerne des composés et leurs compositions pharmaceutiques, qui sont utiles pour moduler un récepteur 20 couplé aux protéines G (GPR20), et des procédés pour utiliser de tels composés pour traiter, améliorer ou prévenir une affection associée à un GPR20 anormal ou dérégulé.
• Novel 2,3-Dihydrobenzofuran-2-carboxylic Acids:  Highly Potent and Subtype-Selective PPARα Agonists with Potent Hypolipidemic Activity
  作者：Guo Q. Shi、James F. Dropinski、Yong Zhang、Conrad Santini、Soumya P. Sahoo、Joel P. Berger、Karen L. MacNaul、Gaochao Zhou、Arun Agrawal、Raul Alvaro、Tian-quan Cai、Melba Hernandez、Samuel D. Wright、David E. Moller、James V. Heck、Peter T. Meinke

  DOI：10.1021/jm050373g

  日期：2005.8.1

  The design and synthesis of a novel class of 2,3-dihydrobenzofuran-2-carboxylic acids as highly potent and subtype-selective PPAR alpha agonists are reported. Systematic study of structure-activity relationships has identified several key structural elements within this class for maintaining the potency and subtype selectivity. Select compounds were evaluated in animal models of dyslipidemia using Syrian hamsters and male Beagle dogs, and all these compounds displayed excellent cholesterol- and triglyceride-lowering activity at dose levels that were much lower than the marketed weak PPAR alpha agonist fenofibrate.