ethyl 7-hydroxy-2-ethylchromane-2-carboxylate | 717901-09-2

• 物质功能分类: 化学试剂 - 有机试剂 - 酯类
• 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-ethylchromane-2-carboxylate
• 英文别名: Ethyl 2-ethyl-7-hydroxy-3,4-dihydro-2H-1-benzopyran-2-carboxylate；ethyl 2-ethyl-7-hydroxy-3,4-dihydrochromene-2-carboxylate
• CAS: 717901-09-2
• 化学式: C₁₄H₁₈O₄
• 分子量: 250.295
• InChiKey: QPXLREAUUJPEBM-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3
• 重原子数：
  18
• 可旋转键数：
  4
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.5
• 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-ethylchromane-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-(3-(2-Fluoro-4-phenoxyphenoxy)propoxy)-2-ethylchromane-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-ethylchromane-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

• Benzopyrancarboxylic acid derivatives for the treatment of diabetes and lipid disorders
  申请人：——

  公开号：US20020103242A1

  公开（公告）日：2002-08-01

  A class of benzopyrancarboxylic acid derivatives comprises compounds that are potent agonists of PPAR alpha and/or gamma, and are therefore useful in the treatment, control or prevention of non-insulin dependent diabetes mellitus (NIDDM), hyperglycemia, dyslipidemia, hyperlipidemia, hypercholesterolemia, hypertriglyceridemia, atherosclerosis, obesity, vascular restenosis, inflammation, and other PPAR alpha and/or gamma mediated diseases, disorders and conditions.

  一类苯并吡喃羧酸衍生物包括具有强效PPAR alpha和/或gamma激动剂作用的化合物，因此在治疗、控制或预防非胰岛素依赖型糖尿病（NIDDM）、高血糖、血脂异常、高脂血症、高胆固醇血症、高三酸甘油脂血症、动脉粥样硬化、肥胖、血管再狭窄、炎症以及其他PPAR alpha和/或gamma介导的疾病、疾病和疾病状态中具有用处。
• BENZOPYRANCARBOXYLIC ACID DERIVATIVES FOR THE TREATMENT OF DIABETES AND LIPID DISORDERS
  申请人：Merck & Co., Inc.

  公开号：EP1347755A2

  公开（公告）日：2003-10-01
• US6713508B2
  申请人：——

  公开号：US6713508B2

  公开（公告）日：2004-03-30
• [EN] BENZOPYRANCARBOXYLIC ACID DERIVATIVES FOR THE TREATMENT OF DIABETES AND LIPID DISORDERS<br/>[FR] DERIVES D'ACIDE BENZOPYRANOCARBOXYLIQUE POUR TRAITER LE DIABETE ET D'AUTRES TROUBLES LIPIDIQUES
  申请人：MERCK & CO INC

  公开号：WO2002060434A2

  公开（公告）日：2002-08-08

  A class of benzopyrancarboxylic acid derivatives of formula I comprises compounds that are potent agonists of PPAR alpha and/or gamma, and are therefore useful in the treatment, control or prevention of non-insulin dependent diabetes mellitus (NIDDM), hyperglycemia, dyslipidemia, hyperlipidemia, hypercholesterolemia, hypertriglyceridemia, atherosclerosis, obesity, vascular restenosis, inflammation, and other PPAR alpha and/or gamma mediated diseases, disorders and conditions.
• (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.