{2-[4-(2-butyl-benzofuran-3-carbonyl)-phenoxy]-ethyl}-carbamic acid tert-butyl ester | 1096359-54-4

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: {2-[4-(2-butyl-benzofuran-3-carbonyl)-phenoxy]-ethyl}-carbamic acid tert-butyl ester
• CAS: 1096359-54-4
• 化学式: C₂₆H₃₁NO₅
• 分子量: 437.536
• InChiKey: VOPWLROZAXFMBO-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  5.91
• 重原子数：
  32.0
• 可旋转键数：
  9.0
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.38
• 拓扑面积：
  77.77
• 氢给体数：
  1.0
• 氢受体数：
  5.0

反应信息

• 作为反应物：
  描述：

  {2-[4-(2-butyl-benzofuran-3-carbonyl)-phenoxy]-ethyl}-carbamic acid tert-butyl ester 在 盐酸 作用下， 以 水 、 乙酸乙酯 为溶剂， 以100%的产率得到Didesethyl-dideiodo-amiodarone hydrochloride
  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：

  2-({[(2-甲基-2-丙基)氧基]羰基}氨基)乙基甲烷磺酸酯 、 2-丁基-3-(4-羟基苯甲酰基)苯并呋喃 在 caesium carbonate 作用下， 以 N,N-二甲基甲酰胺 为溶剂， 以68%的产率得到{2-[4-(2-butyl-benzofuran-3-carbonyl)-phenoxy]-ethyl}-carbamic acid tert-butyl ester
  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