{4-[2-(benzyl-ethyl-amino)-ethoxy]-3,5-diiodo-phenyl}-(2-butyl-benzofuran-3-yl)-methanone | 1096359-59-9

• 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]-3,5-diiodo-phenyl}-(2-butyl-benzofuran-3-yl)-methanone
• CAS: 1096359-59-9
• 化学式: C₃₀H₃₁I₂NO₃
• 分子量: 707.39
• InChiKey: DYWNZQWAYFYDNL-UHFFFAOYSA-N

物化性质

• 沸点：
  700.1±60.0 °C(Predicted)
• 密度：
  1.563±0.06 g/cm3(Temp: 20 °C; Press: 760 Torr)(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  8.12
• 重原子数：
  36.0
• 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]-3,5-diiodo-phenyl}-(2-butyl-benzofuran-3-yl)-methanone 在 1-氯乙基氯甲酸酯 、 盐酸 作用下， 以 1,2-二氯乙烷 、 甲醇 、 水 、 乙酸乙酯 为溶剂， 反应 3.0h， 生成 去乙基胺碘酮盐酸盐
  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-(3,5-二碘-4-羟基苯甲酰)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40%的产率得到{4-[2-(benzyl-ethyl-amino)-ethoxy]-3,5-diiodo-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