[4-(2-bromo-ethoxy)-3-iodo-phenyl]-(2-butyl-benzofuran-3-yl)-methanone | 96027-83-7

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: [4-(2-bromo-ethoxy)-3-iodo-phenyl]-(2-butyl-benzofuran-3-yl)-methanone
• 英文别名: 2-n-Butyl-3-[4-(2-bromo-ethoxy)-3-iodo-benzoyl]-benzofuran；[4-(2-Bromoethoxy)-3-iodophenyl]-(2-butyl-1-benzofuran-3-yl)methanone
• CAS: 96027-83-7
• 化学式: C₂₁H₂₀BrIO₃
• 分子量: 527.197
• InChiKey: QJECRIYPDXNKMV-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  6.9
• 重原子数：
  26
• 可旋转键数：
  8
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.29
• 拓扑面积：
  39.4
• 氢给体数：
  0
• 氢受体数：
  3

反应信息

• 作为反应物：
  描述：

  [4-(2-bromo-ethoxy)-3-iodo-phenyl]-(2-butyl-benzofuran-3-yl)-methanone 在 sodium azide 作用下， 以 N,N-二甲基甲酰胺 为溶剂， 反应 2.0h， 生成 [4-(2-azido-ethoxy)-3-iodo-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
• 作为产物：
  描述：

  1,2-二溴乙烷 、 (2-丁基-1-苯并呋喃-3-基)(4-羟基-3-碘苯基)甲酮 在 potassium carbonate 作用下， 以 N,N-二甲基甲酰胺 为溶剂， 反应 2.0h， 以63%的产率得到[4-(2-bromo-ethoxy)-3-iodo-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

文献信息

• US4575513A
  申请人：——

  公开号：US4575513A

  公开（公告）日：1986-03-11
• US4661514A
  申请人：——

  公开号：US4661514A

  公开（公告）日：1987-04-28
• US4791137A
  申请人：——

  公开号：US4791137A

  公开（公告）日：1988-12-13