2-(4-Brom-butoxy)-β-phenyl-propiophenon | 2525-99-7

• 分子结构分类: 有机化合物 - 苯丙烷和聚酮 - 直链 1,3-二芳基丙烷
• 英文名称: 2-(4-Brom-butoxy)-β-phenyl-propiophenon
• 英文别名: 1-[2-(4-Bromobutoxy)phenyl]-3-phenylpropan-1-one
• CAS: 2525-99-7
• 化学式: C₁₉H₂₁BrO₂
• 分子量: 361.279
• InChiKey: UTEPYLJAAIBQTN-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  4.9
• 重原子数：
  22
• 可旋转键数：
  9
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.32
• 拓扑面积：
  26.3
• 氢给体数：
  0
• 氢受体数：
  2

反应信息

• 作为反应物：
  描述：

  哌啶 、 2-(4-Brom-butoxy)-β-phenyl-propiophenon 反应 0.5h， 以84.5%的产率得到GPV 195
  参考文献：
  名称：

  Studies on propafenone-type modulators of multidrug resistance VI. Synthesis and pharmacological activity of compounds with varied spacer length between the central aromatic ring and the nitrogen atom

  摘要：

  A series of propafenone-type modulators of multidrug resistance (MDR) with varied spacer length between the central aromatic ring and the positively chargeable nitrogen atom was synthesized and tested for their ability to block P-glycoprotein-mediated transport of daunomycin out of tumor cells. Synthesis was achieved by O-alkylation of o-hydroxy-3-phenylpropiophenone with dibromoalkanes and subsequent nucleophilic substitution of the bromine with piperidine. All compounds showed high MDR-modulating activity with EC50 values from 1.45-0.15 mu M Generally, activity increased with increasing number of methylene groups, whereby it reaches a plateau for compounds with more than five methylene groups between the ether oxygen and the nitrogen atom. (C) 1998 Elsevier Science S.A. All rights reserved.

  DOI：

  10.1016/s0014-827x(98)00035-4
• 作为产物：
  描述：

  1,4-二溴丁烷 、 2'-羟基-3-苯基苯丙酮 在 sodium ethanolate 作用下， 以 乙醇 为溶剂， 反应 4.0h， 以5.4%的产率得到1.4-Bis-[2-(3-phenyl-propionyl)-phenoxy]-butan
  参考文献：
  名称：

  Studies on propafenone-type modulators of multidrug resistance VI. Synthesis and pharmacological activity of compounds with varied spacer length between the central aromatic ring and the nitrogen atom

  摘要：

  A series of propafenone-type modulators of multidrug resistance (MDR) with varied spacer length between the central aromatic ring and the positively chargeable nitrogen atom was synthesized and tested for their ability to block P-glycoprotein-mediated transport of daunomycin out of tumor cells. Synthesis was achieved by O-alkylation of o-hydroxy-3-phenylpropiophenone with dibromoalkanes and subsequent nucleophilic substitution of the bromine with piperidine. All compounds showed high MDR-modulating activity with EC50 values from 1.45-0.15 mu M Generally, activity increased with increasing number of methylene groups, whereby it reaches a plateau for compounds with more than five methylene groups between the ether oxygen and the nitrogen atom. (C) 1998 Elsevier Science S.A. All rights reserved.

  DOI：

  10.1016/s0014-827x(98)00035-4

文献信息

• Studies on propafenone-type modulators of multidrug resistance VI. Synthesis and pharmacological activity of compounds with varied spacer length between the central aromatic ring and the nitrogen atom
  作者：Peter Chiba、Danilo Annibali、Manuela Hitzler、Elisabeth Richter、Gerhard Ecker

  DOI：10.1016/s0014-827x(98)00035-4

  日期：1998.5

  A series of propafenone-type modulators of multidrug resistance (MDR) with varied spacer length between the central aromatic ring and the positively chargeable nitrogen atom was synthesized and tested for their ability to block P-glycoprotein-mediated transport of daunomycin out of tumor cells. Synthesis was achieved by O-alkylation of o-hydroxy-3-phenylpropiophenone with dibromoalkanes and subsequent nucleophilic substitution of the bromine with piperidine. All compounds showed high MDR-modulating activity with EC50 values from 1.45-0.15 mu M Generally, activity increased with increasing number of methylene groups, whereby it reaches a plateau for compounds with more than five methylene groups between the ether oxygen and the nitrogen atom. (C) 1998 Elsevier Science S.A. All rights reserved.