3-[5-(3-benzyloxyphenyl)[1,3]dioxan-2-yl]propylamine | 1257243-75-6

• 分子结构分类: 有机化合物 - 苯类化合物 - 苯酚醚
• 英文名称: 3-[5-(3-benzyloxyphenyl)[1,3]dioxan-2-yl]propylamine
• 英文别名: 3-[5-(3-Phenylmethoxyphenyl)-1,3-dioxan-2-yl]propan-1-amine
• CAS: 1257243-75-6
• 化学式: C₂₀H₂₅NO₃
• 分子量: 327.423
• InChiKey: NCBCUTBBCLHCFY-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.9
• 重原子数：
  24
• 可旋转键数：
  7
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.4
• 拓扑面积：
  53.7
• 氢给体数：
  1
• 氢受体数：
  4

反应信息

• 作为反应物：
  描述：

  3-[5-(3-benzyloxyphenyl)[1,3]dioxan-2-yl]propylamine 在 10% palladium on activated carbon 、 氢气 、 三乙胺 、 三苯基膦 、 偶氮二甲酸二乙酯 作用下， 以 四氢呋喃 、 乙醇 、 乙酸乙酯 为溶剂， 20.0 ℃ 、300.01 kPa 条件下， 反应 8.0h， 生成 N-(3-{5-[3-(2-cyclopropylethoxy)phenyl][1,3]dioxan-2-yl}propyl)acetamide
  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-(3-(苄氧基)苯基)乙酸甲酯 在 sodium hydride 、 二异丁基氢化铝 、 对甲苯磺酸 作用下， 以 甲苯 为溶剂， 反应 77.0h， 生成 3-[5-(3-benzyloxyphenyl)[1,3]dioxan-2-yl]propylamine
  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