2-(4-(2-bromoethoxy)phenyl)benzofuran | 57664-56-9

• 分子结构分类: 有机化合物 - 苯丙烷和聚酮 - 2-芳基苯并呋喃类黄酮
• 英文名称: 2-(4-(2-bromoethoxy)phenyl)benzofuran
• 英文别名: 2-[4'-(2-Bromoethoxy)phenyl]benzofuran；2-[4-(2-bromoethoxy)phenyl]-1-benzofuran
• CAS: 57664-56-9
• 化学式: C₁₆H₁₃BrO₂
• 分子量: 317.182
• InChiKey: UNWTWBWACFCITQ-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  4.7
• 重原子数：
  19
• 可旋转键数：
  4
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.12
• 拓扑面积：
  22.4
• 氢给体数：
  0
• 氢受体数：
  2

反应信息

• 作为反应物：
  描述：

  2-(4-(2-bromoethoxy)phenyl)benzofuran 、 berberrubine 在 potassium carbonate 作用下， 以 N,N-二甲基甲酰胺 为溶剂， 反应 24.0h， 以39%的产率得到9-O-2-(4-(2-ethoxy)phenyl)benzofuran-berberine bromide
  参考文献：
  名称：

  Inhibition of cholinesterase activity and amyloid aggregation by berberine-phenyl-benzoheterocyclic and tacrine-phenyl-benzoheterocyclic hybrids

  摘要：

  A series of berberine-phenyl-benzoheterocyclic (26-29) and tacrine-phenyl-benzoheterocyclic hybrids (44-46) were synthesised and evaluated as multifunctional anti-Alzheimer's disease agents. Compound 44b, tacrine linked with phenyl-benzothiazole by 3-carbon spacers, was the most potent AChE inhibitor with an IC50 value of 0.017 mu M. This compound demonstrated similar A beta aggregation inhibitory activity with cucurmin (51.8% vs 52.1% at 20 mu M, respectively), indicating that this hybrid is an excellent multifunctional drug candidate for AD. (C) 2012 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.bmc.2012.02.059
• 作为产物：
  描述：

  2-(4-甲氧基苯基)苯并呋喃 在 三溴化硼 、 potassium carbonate 作用下， 以 二氯甲烷 、 丙酮 为溶剂， 生成 2-(4-(2-bromoethoxy)phenyl)benzofuran
  参考文献：
  名称：

  Inhibition of cholinesterase activity and amyloid aggregation by berberine-phenyl-benzoheterocyclic and tacrine-phenyl-benzoheterocyclic hybrids

  摘要：

  A series of berberine-phenyl-benzoheterocyclic (26-29) and tacrine-phenyl-benzoheterocyclic hybrids (44-46) were synthesised and evaluated as multifunctional anti-Alzheimer's disease agents. Compound 44b, tacrine linked with phenyl-benzothiazole by 3-carbon spacers, was the most potent AChE inhibitor with an IC50 value of 0.017 mu M. This compound demonstrated similar A beta aggregation inhibitory activity with cucurmin (51.8% vs 52.1% at 20 mu M, respectively), indicating that this hybrid is an excellent multifunctional drug candidate for AD. (C) 2012 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.bmc.2012.02.059

文献信息

• Substituted benzofurans and benzothiophenes
  申请人：SmithKline Corporation

  公开号：US04001426A1

  公开（公告）日：1977-01-04

  The compounds are benzoyl benzofurans and benzothiophenes having pharmacological activity, in particular, coronary vasodilator activity useful for the treatment of angina pectoris and intermediates for the preparation thereof.

  这些化合物是苯并呋喃和苯并噻吩，具有药理活性，特别是冠状动脉扩张剂活性，对治疗心绞痛有用，并可用作其制备的中间体。
• US4001426A
  申请人：——

  公开号：US4001426A

  公开（公告）日：1977-01-04
• Inhibition of cholinesterase activity and amyloid aggregation by berberine-phenyl-benzoheterocyclic and tacrine-phenyl-benzoheterocyclic hybrids
  作者：Ling Huang、Tao Su、Wenjun Shan、Zonghua Luo、Yang Sun、Feng He、Xingshu Li

  DOI：10.1016/j.bmc.2012.02.059

  日期：2012.5

  A series of berberine-phenyl-benzoheterocyclic (26-29) and tacrine-phenyl-benzoheterocyclic hybrids (44-46) were synthesised and evaluated as multifunctional anti-Alzheimer's disease agents. Compound 44b, tacrine linked with phenyl-benzothiazole by 3-carbon spacers, was the most potent AChE inhibitor with an IC50 value of 0.017 mu M. This compound demonstrated similar A beta aggregation inhibitory activity with cucurmin (51.8% vs 52.1% at 20 mu M, respectively), indicating that this hybrid is an excellent multifunctional drug candidate for AD. (C) 2012 Elsevier Ltd. All rights reserved.