2-Ethyl-5-methoxy-2,3-dihydro-benzofuran-2-carboxylic acid methyl ester | 863970-95-0

• 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: 2-Ethyl-5-methoxy-2,3-dihydro-benzofuran-2-carboxylic acid methyl ester
• 英文别名: methyl 2-ethyl-5-methoxy-3H-1-benzofuran-2-carboxylate
• CAS: 863970-95-0
• 化学式: C₁₃H₁₆O₄
• 分子量: 236.268
• InChiKey: QHHOHSSRZLTZMQ-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.6
• 重原子数：
  17
• 可旋转键数：
  4
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.46
• 拓扑面积：
  44.8
• 氢给体数：
  0
• 氢受体数：
  4

反应信息

• 作为反应物：
  描述：

  2-Ethyl-5-methoxy-2,3-dihydro-benzofuran-2-carboxylic acid methyl ester 在 sodium hydroxide 作用下， 以 甲醇 为溶剂， 反应 1.0h， 生成 2-Ethyl-5-methoxy-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 六甲基磷酰三胺 、 氢气 、 lithium hexamethyldisilazane 作用下， 以 四氢呋喃 、 乙醇 为溶剂， -78.0~25.0 ℃ 、310.26 kPa 条件下， 反应 72.0h， 生成 2-Ethyl-5-methoxy-2,3-dihydro-benzofuran-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

• PPAR ALPHA SELECTIVE COMPOUNDS FOR THE TREATMENT OF DYSLIPIDEMIA AND OTHER LIPID DISORDERS
  申请人：Merck & Co., Inc.

  公开号：EP1539136B1

  公开（公告）日：2008-07-09
• US7524882B2
  申请人：——

  公开号：US7524882B2

  公开（公告）日：2009-04-28
• 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.