1-[(3,4-dihydro-6-methoxy-2,2,7,8-tetramethyl-2H-1-benzopyran-5-yl)methyl]-4-[2-(4-nitrophenyl)ethyl]piperazine | 910378-58-4

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 苯并吡喃
• 英文名称: 1-[(3,4-dihydro-6-methoxy-2,2,7,8-tetramethyl-2H-1-benzopyran-5-yl)methyl]-4-[2-(4-nitrophenyl)ethyl]piperazine
• CAS: 910378-58-4
• 化学式: C₂₇H₃₇N₃O₄
• 分子量: 467.608
• InChiKey: GWKDGVSETUFRGO-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  4.68
• 重原子数：
  34.0
• 可旋转键数：
  7.0
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.56
• 拓扑面积：
  68.08
• 氢给体数：
  0.0
• 氢受体数：
  6.0

反应信息

• 作为反应物：
  描述：

  1-[(3,4-dihydro-6-methoxy-2,2,7,8-tetramethyl-2H-1-benzopyran-5-yl)methyl]-4-[2-(4-nitrophenyl)ethyl]piperazine 在 sodium tetrahydroborate 、 copper(l) chloride 作用下， 以 乙醇 为溶剂， 反应 2.0h， 以88%的产率得到4-{2-[4-[(3,4-dihydro-6-methoxy-2,2,7,8-tetramethyl-2H-1-benzopyran-5-yl)methyl]piperazin-1-yl]ethyl}aniline
  参考文献：
  名称：

  Synthesis and biological evaluation of benzopyran analogues bearing class III antiarrhythmic pharmacophores

  摘要：

  We have synthesized a series of compounds combining the hydroxy-benzopyran ring of vitamin E with the methylsulfonylaminophenyl group of class III antiarrhythmic drugs, connected through tertiary amine moieties. Evaluation of the antiarrhythmic and antioxidant activity of the new compounds was carried out on isolated rat heart preparations using the non-recirculating Langendorff mode. The new analogues were present, at 10 mu M concentration, during ischemia and reperfusion. Selected compounds were further studied by a conventional microelectrode method in order to get insight into their cellular mode of action. The most active compound, N-[4-[2-[[2-(3,4-dihydro-6-hydroxy-2,2,7,8-tetramethyl-2H-1-benzopyran-5-yl)ethyl] methylamine]ethyl]phenyl]methanesulfonamide (19a), reduces premature beats, prolongs QT and QRS intervals during ischemia and reperfusion, and reduces MDA content, leading to a fast recovery of the heart. In addition, it exhibits moderate class III antiarrhythmic action. (c) 2006 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.bmc.2006.05.065
• 作为产物：
  描述：

  4-硝基苯乙基溴 在 四丁基碘化铵 、 potassium carbonate 作用下， 以 乙腈 为溶剂， 反应 24.0h， 生成 1-[(3,4-dihydro-6-methoxy-2,2,7,8-tetramethyl-2H-1-benzopyran-5-yl)methyl]-4-[2-(4-nitrophenyl)ethyl]piperazine
  参考文献：
  名称：

  Synthesis and biological evaluation of benzopyran analogues bearing class III antiarrhythmic pharmacophores

  摘要：

  We have synthesized a series of compounds combining the hydroxy-benzopyran ring of vitamin E with the methylsulfonylaminophenyl group of class III antiarrhythmic drugs, connected through tertiary amine moieties. Evaluation of the antiarrhythmic and antioxidant activity of the new compounds was carried out on isolated rat heart preparations using the non-recirculating Langendorff mode. The new analogues were present, at 10 mu M concentration, during ischemia and reperfusion. Selected compounds were further studied by a conventional microelectrode method in order to get insight into their cellular mode of action. The most active compound, N-[4-[2-[[2-(3,4-dihydro-6-hydroxy-2,2,7,8-tetramethyl-2H-1-benzopyran-5-yl)ethyl] methylamine]ethyl]phenyl]methanesulfonamide (19a), reduces premature beats, prolongs QT and QRS intervals during ischemia and reperfusion, and reduces MDA content, leading to a fast recovery of the heart. In addition, it exhibits moderate class III antiarrhythmic action. (c) 2006 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.bmc.2006.05.065