Methyl 2-[[5,7-dipropyl-3-(trifluoromethyl)-1,2-benzoxazol-6-yl]oxy]propanoate | 475271-39-7

• 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: Methyl 2-[[5,7-dipropyl-3-(trifluoromethyl)-1,2-benzoxazol-6-yl]oxy]propanoate
• CAS: 475271-39-7
• 化学式: C₁₈H₂₂F₃NO₄
• 分子量: 373.372
• InChiKey: ZSCIJJSBMFZXHV-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  5.6
• 重原子数：
  26
• 可旋转键数：
  8
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.56
• 拓扑面积：
  61.6
• 氢给体数：
  0
• 氢受体数：
  8

反应信息

• 作为反应物：
  描述：

  Methyl 2-[[5,7-dipropyl-3-(trifluoromethyl)-1,2-benzoxazol-6-yl]oxy]propanoate 在 六甲基磷酰三胺 、 sodium hydroxide 、 lithium diisopropyl amide 作用下， 以 四氢呋喃 、 甲醇 、 环己烷 为溶剂， 反应 4.75h， 生成 2-(5,7-Dipropyl-3-trifluoromethyl-benzo[d]isoxazol-6-yloxy)-2-methyl-butyric acid
  参考文献：
  名称：

  Discovery of a Novel Series of Peroxisome Proliferator-Activated Receptor α/γ Dual Agonists for the Treatment of Type 2 Diabetes and Dyslipidemia

  摘要：

  A series of 2-aryloxy-2-methyl-propionic acid compounds and related analogues were designed, synthesized, and evaluated for their PPAR agonist activities. 2-[(5,7-Dipropyl-3-trifluoromethyl)-benzisoxazol-6-yloxy]-2-methylpropionic acid (4) was identified as a PPAR alpha/gamma dual agonist with relative PPAR alpha selectivity and demonstrated potent efficacy in lowering both glucose and lipids in animal models without causing body weight gain. The PPAR alpha activity of 4 appeared to have played a significant role in lowering glucose levels in db/db mice.

  DOI：

  10.1021/jm048993p
• 作为产物：
  描述：

  2,4-di-n-propylbenzene-1,3-diol 在 吡啶 、 三氯化铝 、 盐酸羟胺 、 sodium acetate 、 caesium carbonate 、 三乙胺 作用下， 以 甲醇 、 二氯甲烷 、 N,N-二甲基甲酰胺 为溶剂， 反应 7.0h， 生成 Methyl 2-[[5,7-dipropyl-3-(trifluoromethyl)-1,2-benzoxazol-6-yl]oxy]propanoate
  参考文献：
  名称：

  Discovery of a Novel Series of Peroxisome Proliferator-Activated Receptor α/γ Dual Agonists for the Treatment of Type 2 Diabetes and Dyslipidemia

  摘要：

  A series of 2-aryloxy-2-methyl-propionic acid compounds and related analogues were designed, synthesized, and evaluated for their PPAR agonist activities. 2-[(5,7-Dipropyl-3-trifluoromethyl)-benzisoxazol-6-yloxy]-2-methylpropionic acid (4) was identified as a PPAR alpha/gamma dual agonist with relative PPAR alpha selectivity and demonstrated potent efficacy in lowering both glucose and lipids in animal models without causing body weight gain. The PPAR alpha activity of 4 appeared to have played a significant role in lowering glucose levels in db/db mice.

  DOI：

  10.1021/jm048993p

文献信息

• Aryloxyacetic acids for diabetes and lipid disorders
  申请人：——

  公开号：US20020173663A1

  公开（公告）日：2002-11-21

  A class of aryloxyacetic acids 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.

  一类芳基羟基乙酸类化合物包括对PPARα和/或γ具有强效激动作用的化合物，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、高血脂症、高胆固醇血症、高甘油三酯血症、动脉粥样硬化、肥胖、血管再狭窄、炎症以及其他PPARα和/或γ介导的疾病、疾病和病况中具有用处。
• US6569879B2
  申请人：——

  公开号：US6569879B2

  公开（公告）日：2003-05-27