1-<4-<(methylsulfonyl)amino>benzoyl>piperazine | 129872-46-4

• 分子结构分类: 有机化合物 - 苯类化合物 - 苯和取代衍生物
• 英文名称: 1-<4-<(methylsulfonyl)amino>benzoyl>piperazine
• 英文别名: 1-[4-[(methylsulfonyl)amino]benzoyl]piperazine；N-[4-(piperazine-1-carbonyl)phenyl]methanesulfonamide
• CAS: 129872-46-4
• 化学式: C₁₂H₁₇N₃O₃S
• 分子量: 283.351
• InChiKey: RGXMBHUPSBXTKS-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  -0.3
• 重原子数：
  19
• 可旋转键数：
  3
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.42
• 拓扑面积：
  86.9
• 氢给体数：
  2
• 氢受体数：
  5

反应信息

• 作为反应物：
  描述：

  1-<4-<(methylsulfonyl)amino>benzoyl>piperazine 、 [[P-(2-甲氧基乙基)苯氧基]甲基]环氧乙烷 以 甲醇 为溶剂， 反应 46.0h， 生成 1-[2-hydroxy-3-[4-(2-methoxyethyl)phenoxy]propyl]-4-[4-[(methylsulfonyl)amino]benzoyl]piperazine
  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-[(4-benzylpiperazin-1-yl)carbonyl]phenyl}methanesulfonamide 生成 1-<4-<(methylsulfonyl)amino>benzoyl>piperazine
  参考文献：
  名称：

  LIS, RANDALL;MORGAN, THOMAS K. (JR);MARISCA, ANTHONY J.;GOMEZ, ROBERT P.;+, J. MED. CHEM., 33,(1990) N0, C. 2883-2891

  摘要：

  DOI：

文献信息

• Derivatized alkanolamines as cardiovascular agents
  申请人：Schering AG

  公开号：US05051423A1

  公开（公告）日：1991-09-24

  Novel derivatized alkanolamines of the following structural formula ##STR1## 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.

  以下结构式##STR1##的新型衍生烷醇胺被描述为有用的心血管药物。特别描述了它们作为表现出抗心律失常作用的心血管药物的有用性。所述的抗心律失常作用属于II类/III类结合型。还描述了含有这类化合物的药物配方。
• LIS, RANDALL;MORGAN, THOMAS K. (JR);MARISCA, ANTHONY J.;GOMEZ, ROBERT P.;+, J. MED. CHEM., 33,(1990) N0, C. 2883-2891
  作者：LIS, RANDALL、MORGAN, THOMAS K. (JR)、MARISCA, ANTHONY J.、GOMEZ, ROBERT P.、+

  DOI：——

  日期：——
• US5051423A
  申请人：——

  公开号：US5051423A

  公开（公告）日：1991-09-24
• [EN] DERIVATIZED ALKANOLAMINES AS CARDIOVASCULAR AGENTS
  申请人：SCHERING AKTIENGESELLSCHAFT BERLIN AND BERGKAMEN

  公开号：WO1990000548A2

  公开（公告）日：1990-01-25

  (EN) Novel derivatized alkanolamines of structural formula (I) 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.(FR) La présente invention se rapporte à de nouvelles alcanolamines dérivées représentées par la formule structurelle (I) et utiles comme agents cardiovasculaires. Est particulièrement décrite leur utilité comme agents cardiovasculaires comportant une action anti-arythmie. Le type d'action anti-arythmie décrite est une variété de combinaison de classe II/classe III. Des formules pharmaceutiques contenant de tels composés sont également décrites.
• 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.