N-[4-[2-[[2-[4-(1H-Imidazol-1-yl)phenoxy]ethyl](phenylmethyl)amino]-1-oxoethyl]phenyl]methanesulfonamide | 128263-79-6

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: N-[4-[2-[[2-[4-(1H-Imidazol-1-yl)phenoxy]ethyl](phenylmethyl)amino]-1-oxoethyl]phenyl]methanesulfonamide
• 英文别名: N-[4-[2-[benzyl-[2-(4-imidazol-1-ylphenoxy)ethyl]amino]acetyl]phenyl]methanesulfonamide
• CAS: 128263-79-6
• 化学式: C₂₇H₂₈N₄O₄S
• 分子量: 504.61
• InChiKey: ATDAFTHLQMHCJC-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.6
• 重原子数：
  36
• 可旋转键数：
  12
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.19
• 拓扑面积：
  102
• 氢给体数：
  1
• 氢受体数：
  7

反应信息

• 作为反应物：
  描述：

  N-[4-[2-[[2-[4-(1H-Imidazol-1-yl)phenoxy]ethyl](phenylmethyl)amino]-1-oxoethyl]phenyl]methanesulfonamide 在 palladium dihydroxide 盐酸 、 氢气 作用下， 反应 8.0h， 生成 N-[4-[1-hydroxy-2-[[2-[4-(1H-imidazol-1-yl)phenoxy]ethyl]amino]ethyl]phenyl]methanesulfonamide
  参考文献：
  名称：

  Synthesis of novel (aryloxy)propanolamines and related compounds possessing both class II and class III antiarrhythmic activity

  摘要：

  Several (aryloxy)propanolamines and related compounds (i.e. 5-13, 16-18, 20-24, 27-33, 35, 37-39, 41, and 42) were synthesized and investigated for their class III electrophysiological activity and class II (beta-blocking) effects with use of in vitro and in vivo models. Structure-activity relationships are discussed for a series of 30 compounds. A number of these compounds prolonged the action potential duration at 95% repolarization of isolated canine cardiac Purkinje fibers by 20% (C20APD95) at concentrations of less than 1.0 microM, with no significant effects on cardiac conduction. beta-Adrenergic receptor binding studies showed that some of these compounds were 2-20 times more potent for cardiac beta 1 receptors than for beta 2 receptors. In particular, compounds 32, 41, 1, and especially (S)-1 were found to be orally active class III agents in anesthetized mongrel dogs (1 or 3 mg/kg, id) and efficacious at suppressing programmed electrical stimulation induced arrhythmias in halothane-anesthetized dogs. The profile of these compounds was similar to that found for sotalol. Compound (S)-1, which was more potent than sotalol in the PES study and equieffective in the halothane/epinephrine dog model, is being investigated further as a combined class III/II antiarrhythmic agent.

  DOI：

  10.1021/jm00172a033
• 作为产物：
  描述：

  N-[4-(2-bromoacetyl)phenyl]methanesulfonamide 、 2-<4-(1H-imidazol-1-yl)phenoxy>-N-(phenylmethyl)ethanamine dihydrochloride 在 N,N-二异丙基乙胺 作用下， 以 乙腈 为溶剂， 反应 17.0h， 生成 N-[4-[2-[[2-[4-(1H-Imidazol-1-yl)phenoxy]ethyl](phenylmethyl)amino]-1-oxoethyl]phenyl]methanesulfonamide
  参考文献：
  名称：

  Synthesis of novel (aryloxy)propanolamines and related compounds possessing both class II and class III antiarrhythmic activity

  摘要：

  Several (aryloxy)propanolamines and related compounds (i.e. 5-13, 16-18, 20-24, 27-33, 35, 37-39, 41, and 42) were synthesized and investigated for their class III electrophysiological activity and class II (beta-blocking) effects with use of in vitro and in vivo models. Structure-activity relationships are discussed for a series of 30 compounds. A number of these compounds prolonged the action potential duration at 95% repolarization of isolated canine cardiac Purkinje fibers by 20% (C20APD95) at concentrations of less than 1.0 microM, with no significant effects on cardiac conduction. beta-Adrenergic receptor binding studies showed that some of these compounds were 2-20 times more potent for cardiac beta 1 receptors than for beta 2 receptors. In particular, compounds 32, 41, 1, and especially (S)-1 were found to be orally active class III agents in anesthetized mongrel dogs (1 or 3 mg/kg, id) and efficacious at suppressing programmed electrical stimulation induced arrhythmias in halothane-anesthetized dogs. The profile of these compounds was similar to that found for sotalol. Compound (S)-1, which was more potent than sotalol in the PES study and equieffective in the halothane/epinephrine dog model, is being investigated further as a combined class III/II antiarrhythmic agent.

  DOI：

  10.1021/jm00172a033

文献信息

• Derivatized alkanolamines as cardiovascular agents
  申请人：SCHERING AKTIENGESELLSCHAFT

  公开号：EP0358284A2

  公开（公告）日：1990-03-14

  Novel derivatized alkanolamines of the following structural formula are described as useful cardiovascular agents. Most especially described is their usefulness as cardiovascular agents exhibiting an antiarrhythmic effect. Said antiarrhythmic effect is of a combination Class II/Class III variety. Pharmaceutical formulations containing such compounds are also described.

  结构式如下的新型衍生化烷醇胺 被描述为有用的心血管制剂。尤其是它们作为心血管药剂具有抗心律失常的作用。所述抗心律失常作用为 II 类/III 类联合作用。还描述了含有此类化合物的药物制剂。
• US5051423A
  申请人：——

  公开号：US5051423A

  公开（公告）日：1991-09-24
• Synthesis of novel (aryloxy)propanolamines and related compounds possessing both class II and class III antiarrhythmic activity
  作者：Randall Lis、Thomas K. Morgan、Anthony J. Marisca、Robert P. Gomez、Joan M. Lind、David D. Davey、Gary B. Phillips、Mark E. Sullivan

  DOI：10.1021/jm00172a033

  日期：1990.10

  Several (aryloxy)propanolamines and related compounds (i.e. 5-13, 16-18, 20-24, 27-33, 35, 37-39, 41, and 42) were synthesized and investigated for their class III electrophysiological activity and class II (beta-blocking) effects with use of in vitro and in vivo models. Structure-activity relationships are discussed for a series of 30 compounds. A number of these compounds prolonged the action potential duration at 95% repolarization of isolated canine cardiac Purkinje fibers by 20% (C20APD95) at concentrations of less than 1.0 microM, with no significant effects on cardiac conduction. beta-Adrenergic receptor binding studies showed that some of these compounds were 2-20 times more potent for cardiac beta 1 receptors than for beta 2 receptors. In particular, compounds 32, 41, 1, and especially (S)-1 were found to be orally active class III agents in anesthetized mongrel dogs (1 or 3 mg/kg, id) and efficacious at suppressing programmed electrical stimulation induced arrhythmias in halothane-anesthetized dogs. The profile of these compounds was similar to that found for sotalol. Compound (S)-1, which was more potent than sotalol in the PES study and equieffective in the halothane/epinephrine dog model, is being investigated further as a combined class III/II antiarrhythmic agent.