(S)-3-[4-(6-isopropoxypyridin-3-yloxy)phenyl]-1-methylpropylamine | 1204484-08-1

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: (S)-3-[4-(6-isopropoxypyridin-3-yloxy)phenyl]-1-methylpropylamine
• 英文别名: (2S)-4-[4-(6-propan-2-yloxypyridin-3-yl)oxyphenyl]butan-2-amine
• CAS: 1204484-08-1
• 化学式: C₁₈H₂₄N₂O₂
• 分子量: 300.401
• InChiKey: FTSZCGLTNYJNHN-AWEZNQCLSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.6
• 重原子数：
  22
• 可旋转键数：
  7
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.39
• 拓扑面积：
  57.4
• 氢给体数：
  1
• 氢受体数：
  4

反应信息

• 作为反应物：
  描述：

  (S)-3-[4-(6-isopropoxypyridin-3-yloxy)phenyl]-1-methylpropylamine 、 环丙基甲酰氯 在 三乙胺 作用下， 以 乙酸乙酯 为溶剂， 生成 cyclopropanecarboxylic acid {(S)-3-[4-(6-isopropoxypyridin-3-yloxy)phenyl]-1-methylpropyl}amide
  参考文献：
  名称：

  Identification and Synthesis of Novel Inhibitors of Acetyl-CoA Carboxylase with in Vitro and in Vivo Efficacy on Fat Oxidation

  摘要：

  Acetyl CoA carboxylase isoforms 1 and 2 (ACC1/2) are key enzymes of fat utilization and their inhibition is considered to improve aspects of the metabolic syndrome. To identify pharmacological inhibitors of ACC1/2, a high throughput screen was performed which resulted in the identification of the lead compound 3 (Gargazanli, G.; Lardenois, P.; Frost, J.; George, P. Patent WO9855474 A1, 1998) as a moderate selective ACC2 inhibitor. Optimization of 3 led to 4m (Zoller, G.; Schmoll, D.; Mueller, M.; Haschke, G.; Focken, I. Patent WO2010003624 A2, 2010) as a submicromolar dual ACC1/2 inhibitor of the rat and human isoforms. 4m possessed favorable pharmacokinetic parameters. This compound stimulated fat oxidation in vivo and reduced plasma triglyceride levels in a rodent model after subchronic administration. 4m is a suitable tool compound for the elucidation of the pharmacological potential of ACC1/2 inhibition.

  DOI：

  10.1021/jm101179e
• 作为产物：
  描述：

  2-氯-5-羟基吡啶 在 吡啶 、 bis-triphenylphosphine-palladium(II) chloride 、 copper(l) iodide 、 10% palladium on activated carbon 、 氢气 、 sodium hydride 、 potassium carbonate 、 一水合肼 、 三乙胺 、 copper(II) oxide 作用下， 以 N-甲基吡咯烷酮 、 乙醇 、 乙酸乙酯 、 N,N-二甲基甲酰胺 、 mineral oil 为溶剂， 20.0~150.0 ℃ 、300.01 kPa 条件下， 反应 17.0h， 生成 (S)-3-[4-(6-isopropoxypyridin-3-yloxy)phenyl]-1-methylpropylamine
  参考文献：
  名称：

  Identification and Synthesis of Novel Inhibitors of Acetyl-CoA Carboxylase with in Vitro and in Vivo Efficacy on Fat Oxidation

  摘要：

  Acetyl CoA carboxylase isoforms 1 and 2 (ACC1/2) are key enzymes of fat utilization and their inhibition is considered to improve aspects of the metabolic syndrome. To identify pharmacological inhibitors of ACC1/2, a high throughput screen was performed which resulted in the identification of the lead compound 3 (Gargazanli, G.; Lardenois, P.; Frost, J.; George, P. Patent WO9855474 A1, 1998) as a moderate selective ACC2 inhibitor. Optimization of 3 led to 4m (Zoller, G.; Schmoll, D.; Mueller, M.; Haschke, G.; Focken, I. Patent WO2010003624 A2, 2010) as a submicromolar dual ACC1/2 inhibitor of the rat and human isoforms. 4m possessed favorable pharmacokinetic parameters. This compound stimulated fat oxidation in vivo and reduced plasma triglyceride levels in a rodent model after subchronic administration. 4m is a suitable tool compound for the elucidation of the pharmacological potential of ACC1/2 inhibition.

  DOI：

  10.1021/jm101179e

文献信息

• Identification and Synthesis of Novel Inhibitors of Acetyl-CoA Carboxylase with in Vitro and in Vivo Efficacy on Fat Oxidation
  作者：Stefanie Keil、Marco Müller、Gerhard Zoller、Guido Haschke、Katrin Schroeter、Maike Glien、Sven Ruf、Ingo Focken、Andreas W. Herling、Dieter Schmoll

  DOI：10.1021/jm101179e

  日期：2010.12.23

  Acetyl CoA carboxylase isoforms 1 and 2 (ACC1/2) are key enzymes of fat utilization and their inhibition is considered to improve aspects of the metabolic syndrome. To identify pharmacological inhibitors of ACC1/2, a high throughput screen was performed which resulted in the identification of the lead compound 3 (Gargazanli, G.; Lardenois, P.; Frost, J.; George, P. Patent WO9855474 A1, 1998) as a moderate selective ACC2 inhibitor. Optimization of 3 led to 4m (Zoller, G.; Schmoll, D.; Mueller, M.; Haschke, G.; Focken, I. Patent WO2010003624 A2, 2010) as a submicromolar dual ACC1/2 inhibitor of the rat and human isoforms. 4m possessed favorable pharmacokinetic parameters. This compound stimulated fat oxidation in vivo and reduced plasma triglyceride levels in a rodent model after subchronic administration. 4m is a suitable tool compound for the elucidation of the pharmacological potential of ACC1/2 inhibition.