{4-[2-(benzyl-ethyl-amino)-ethoxy]-phenyl}-(2-butyl-benzofuran-3-yl)-methanone | 1096359-57-7

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: {4-[2-(benzyl-ethyl-amino)-ethoxy]-phenyl}-(2-butyl-benzofuran-3-yl)-methanone
• CAS: 1096359-57-7
• 化学式: C₃₀H₃₃NO₃
• 分子量: 455.597
• InChiKey: DPTNUUALLTVBMV-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  6.91
• 重原子数：
  34.0
• 可旋转键数：
  12.0
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.3
• 拓扑面积：
  42.68
• 氢给体数：
  0.0
• 氢受体数：
  4.0

反应信息

• 作为反应物：
  描述：

  {4-[2-(benzyl-ethyl-amino)-ethoxy]-phenyl}-(2-butyl-benzofuran-3-yl)-methanone 在 palladium 10% on activated carbon 、 氢气 、 盐酸 作用下， 以 乙酸乙酯 、 水 为溶剂， 20.0 ℃ 、101.33 kPa 条件下， 反应 20.0h， 以79%的产率得到Desethyl-dideiodo-amiodarone
  参考文献：
  名称：

  Trace amine-associated receptor 1 (TAAR1) is activated by amiodarone metabolites

  摘要：

  Amiodarone (Cordarone, Wyeth-Ayerst Pharmaceuticals) is a clinically available drug used to treat a wide variety of cardiac arrhythmias. We report here the synthesis and characterization of a panel of potential amiodarone metabolites that have significant structural similarity to thyroid hormone and its metabolites the iodothyronamines. Several of these amiodarone derivatives act as specific agonists of the G protein-coupled receptor (GPCR) trace amine-associated receptor 1 (TAAR(1)). This result demonstrates a novel molecular target for amiodarone derivatives with potential clinical significance. (C) 2008 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.bmcl.2008.08.013
• 作为产物：
  描述：

  benzyl-(2-chloro-ethyl)-ethyl-amine 、 2-丁基-3-(4-羟基苯甲酰基)苯并呋喃 在 sodium iodide 作用下， 以 N,N-二甲基甲酰胺 为溶剂， 反应 24.0h， 以85%的产率得到{4-[2-(benzyl-ethyl-amino)-ethoxy]-phenyl}-(2-butyl-benzofuran-3-yl)-methanone
  参考文献：
  名称：

  Trace amine-associated receptor 1 (TAAR1) is activated by amiodarone metabolites

  摘要：

  Amiodarone (Cordarone, Wyeth-Ayerst Pharmaceuticals) is a clinically available drug used to treat a wide variety of cardiac arrhythmias. We report here the synthesis and characterization of a panel of potential amiodarone metabolites that have significant structural similarity to thyroid hormone and its metabolites the iodothyronamines. Several of these amiodarone derivatives act as specific agonists of the G protein-coupled receptor (GPCR) trace amine-associated receptor 1 (TAAR(1)). This result demonstrates a novel molecular target for amiodarone derivatives with potential clinical significance. (C) 2008 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.bmcl.2008.08.013