Ethyl 7-hydroxy-2-methyl-3,4-dihydrochromene-2-carboxylate | 717901-19-4

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 苯并吡喃
• 英文名称: Ethyl 7-hydroxy-2-methyl-3,4-dihydrochromene-2-carboxylate
• CAS: 717901-19-4
• 化学式: C₁₃H₁₆O₄
• 分子量: 236.268
• InChiKey: ZQUVGOXTQFGONJ-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.4
• 重原子数：
  17
• 可旋转键数：
  3
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.46
• 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：

  Ethyl 7-hydroxy-2-methyl-3,4-dihydrochromene-2-carboxylate 在 sodium hydroxide 、 caesium carbonate 作用下， 以 N,N-二甲基甲酰胺 、 异丙醇 为溶剂， 反应 5.0h， 生成 7-(4-(2-Propyl-4-phenoxyphenoxy)butoxy)-2-methylchromane-2-carboxylic acid
  参考文献：
  名称：

  (2R)-2-Ethylchromane-2-carboxylic Acids:  Discovery of Novel PPARα/γ Dual Agonists as Antihyperglycemic and Hypolipidemic Agents

  摘要：

  A series of chromane-2-carboxylic acid derivatives was synthesized and evaluated for PPAR agonist activities. A structure-activity relationship was developed toward PPARalpha/gamma dual agonism. As a result, (2R)-7-{3-[2-chloro-4-(4-fluorophenoxy)phenoxy]propoxy}-2-ethylchromane-2-carboxylic acid (48) was identified as a potent, structurally novel, selective PPARalpha/gamma dual agonist. Compound 48 exhibited substantial antihyperglycemic and hypolipidemic activities when orally administered in three different animal models: the db/db mouse type 2 diabetes model, a Syrian hamster lipid model, and a dog lipid model.

  DOI：

  10.1021/jm030621d
• 作为产物：
  描述：

  ethyl 7-hydroxychromane-2-carboxylate 在 palladium on activated charcoal 六甲基磷酰三胺 、 氢气 、 sodium hexamethyldisilazane 、 potassium carbonate 作用下， 以 四氢呋喃 、 乙醇 、 水 、 丙酮 为溶剂， -78.0~20.0 ℃ 、344.74 kPa 条件下， 反应 61.0h， 生成 Ethyl 7-hydroxy-2-methyl-3,4-dihydrochromene-2-carboxylate
  参考文献：
  名称：

  (2R)-2-Ethylchromane-2-carboxylic Acids:  Discovery of Novel PPARα/γ Dual Agonists as Antihyperglycemic and Hypolipidemic Agents

  摘要：

  A series of chromane-2-carboxylic acid derivatives was synthesized and evaluated for PPAR agonist activities. A structure-activity relationship was developed toward PPARalpha/gamma dual agonism. As a result, (2R)-7-{3-[2-chloro-4-(4-fluorophenoxy)phenoxy]propoxy}-2-ethylchromane-2-carboxylic acid (48) was identified as a potent, structurally novel, selective PPARalpha/gamma dual agonist. Compound 48 exhibited substantial antihyperglycemic and hypolipidemic activities when orally administered in three different animal models: the db/db mouse type 2 diabetes model, a Syrian hamster lipid model, and a dog lipid model.

  DOI：

  10.1021/jm030621d

文献信息

• (2<i>R</i>)-2-Ethylchromane-2-carboxylic Acids:  Discovery of Novel PPARα/γ Dual Agonists as Antihyperglycemic and Hypolipidemic Agents
  作者：Hiroo Koyama、Daniel J. Miller、Julia K. Boueres、Ranjit C. Desai、A. Brian Jones、Joel P. Berger、Karen L. MacNaul、Linda J. Kelly、Thomas W. Doebber、Margaret S. Wu、Gaochao Zhou、Pei-ran Wang、Marc C. Ippolito、Yu-Sheng Chao、Arun K. Agrawal、Ronald Franklin、James V. Heck、Samuel D. Wright、David E. Moller、Soumya P. Sahoo

  DOI：10.1021/jm030621d

  日期：2004.6.1

  A series of chromane-2-carboxylic acid derivatives was synthesized and evaluated for PPAR agonist activities. A structure-activity relationship was developed toward PPARalpha/gamma dual agonism. As a result, (2R)-7-3-[2-chloro-4-(4-fluorophenoxy)phenoxy]propoxy}-2-ethylchromane-2-carboxylic acid (48) was identified as a potent, structurally novel, selective PPARalpha/gamma dual agonist. Compound 48 exhibited substantial antihyperglycemic and hypolipidemic activities when orally administered in three different animal models: the db/db mouse type 2 diabetes model, a Syrian hamster lipid model, and a dog lipid model.