methyl 2-(2-(1-(2,4-dichlorophenylamino)-1-oxobutan-2-yl)-2,3,4,5-tetrahydro-1H-benzo[c]azepin-8-yloxy)acetate | 1266113-57-8

• 分子结构分类: 有机化合物 - 有机酸及其衍生物 - 羧酸及其衍生物
• 英文名称: methyl 2-(2-(1-(2,4-dichlorophenylamino)-1-oxobutan-2-yl)-2,3,4,5-tetrahydro-1H-benzo[c]azepin-8-yloxy)acetate
• CAS: 1266113-57-8
• 化学式: C₂₃H₂₆Cl₂N₂O₄
• 分子量: 465.376
• InChiKey: PNRCMTZADFCSJC-NRFANRHFSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  4.71
• 重原子数：
  31.0
• 可旋转键数：
  7.0
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.39
• 拓扑面积：
  67.87
• 氢给体数：
  1.0
• 氢受体数：
  5.0

反应信息

• 作为反应物：
  描述：

  methyl 2-(2-(1-(2,4-dichlorophenylamino)-1-oxobutan-2-yl)-2,3,4,5-tetrahydro-1H-benzo[c]azepin-8-yloxy)acetate 在 三氟乙酸 作用下， 以 二氯甲烷 为溶剂， 以46%的产率得到2-(2-(1-(2,4-dichlorophenylamino)-1-oxobutan-2-yl)-2,3,4,5-tetrahydro-1H-benzo[c]azepin-8-yloxy)acetic acid
  参考文献：
  名称：

  Synthesis and biological evaluation of N-alkylated 8-oxybenz[c]azepine derivatives as selective PPARδ agonists

  摘要：

  We describe the discovery of small molecule benzazepine derivatives as agonists of human peroxisome proliferator-activated receptor delta (PPAR delta) that displayed excellent selectivity over the PPAR delta and PPAR gamma subtypes. Compound 8 displayed good PK in the rat and efficacy in upregulation of pyruvate dehydrogenase kinase, isozyme 4 (PDK4) mRNA in human primary myotubes, a biomarker for increased fatty acid oxidation. (C) 2010 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.bmcl.2010.10.083
• 作为产物：
  描述：

  2-bromo-N-(2,4-dichlorophenyl)butanamide 、 methyl 2-((2,3,4,5-tetrahydro-1H-benzo[c]azepin-8-yl)oxy)acetate 在 potassium carbonate 、 sodium iodide 作用下， 以 N,N-二甲基甲酰胺 为溶剂， 反应 18.0h， 以22%的产率得到methyl 2-(2-(1-(2,4-dichlorophenylamino)-1-oxobutan-2-yl)-2,3,4,5-tetrahydro-1H-benzo[c]azepin-8-yloxy)acetate
  参考文献：
  名称：

  Synthesis and biological evaluation of N-alkylated 8-oxybenz[c]azepine derivatives as selective PPARδ agonists

  摘要：

  We describe the discovery of small molecule benzazepine derivatives as agonists of human peroxisome proliferator-activated receptor delta (PPAR delta) that displayed excellent selectivity over the PPAR delta and PPAR gamma subtypes. Compound 8 displayed good PK in the rat and efficacy in upregulation of pyruvate dehydrogenase kinase, isozyme 4 (PDK4) mRNA in human primary myotubes, a biomarker for increased fatty acid oxidation. (C) 2010 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.bmcl.2010.10.083