N-[4-(Piperazin-1-yl)phenyl]methanesulfonamide hydrochloride | 112940-54-2

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 二嗪烷类
• 英文名称: N-[4-(Piperazin-1-yl)phenyl]methanesulfonamide hydrochloride
• 英文别名: N-(4-piperazin-1-ylphenyl)methanesulfonamide hydrochloride；1-(4-Methanesulphonamidophenyl)piperazine hydrochloride；N-[(4-piperazin-1-yl)phenyl]methanesulphonamide hydrochloride；N-(4-piperazin-1-ylphenyl)methanesulfonamide;hydrochloride
• CAS: 112940-54-2
• 化学式: C₁₁H₁₇N₃O₂S*ClH
• mdl: MFCD22048034
• 分子量: 291.802
• InChiKey: XTCHLADGBZLOCT-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  -0.08
• 重原子数：
  18
• 可旋转键数：
  3
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.454
• 拓扑面积：
  69.8
• 氢给体数：
  3
• 氢受体数：
  5

反应信息

• 作为反应物：
  描述：

  苯基缩水甘油醚 、 N-[4-(Piperazin-1-yl)phenyl]methanesulfonamide hydrochloride 在 sodium methylate 作用下， 以 甲醇 、 水 为溶剂， 反应 17.0h， 以33%的产率得到N-[4-[4-(2-hydroxy-3-phenoxypropyl)piperazin-1-yl]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-(4-乙酰哌嗪-1-基)苯基]甲磺酰胺 在 盐酸 作用下， 生成 N-[4-(Piperazin-1-yl)phenyl]methanesulfonamide hydrochloride
  参考文献：
  名称：

  4-Substituted-1-(4-alkylsulphonamidophenyl)piperazines as antiarrhythmic

  摘要：

  公式为：##STR1## 的抗心律失常药物及其药用盐，其中R和R.sup.1，相同或不同，为C.sub.1 -C.sub.4烷基，C.sub.3 -C.sub.7环烷基，--CH.sub.2 CH.sub.3，--CH.sub.2 Cl，--CF.sub.3或--NH.sub.2；R.sup.2和R.sup.3，相同或不同，为H，卤素，CF.sub.3，C.sub.1 -C.sub.4烷基或C.sub.1 -C.sub.4烷氧基；X为--CH.sub.2 --，##STR2## 或--CH(OH)--。

  公开号：

  US04797401A1

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。
• Novel N-[4-(aminosubstituted)phenyl]methanesulfonamides and their use as
  申请人：Schering A.G.

  公开号：US04906634A1

  公开（公告）日：1990-03-06

  Novel N-[4-(aminosubstituted)phenyl]methanesulfonamides and their use as cardiovascular agents, especially as antiarrhythmic agents are described. Pharmaceutical formulations containing such compounds are also discussed.

  描述了新型N-[4-(氨基取代)苯基]甲磺酰胺类化合物及其作为心血管药物的用途，特别是作为抗心律失常药物的用途。还讨论了含有这类化合物的药物配方。
• Phenyl piperazine anti-arrhythmia agents
  申请人：Pfizer Inc.

  公开号：US04788196A1

  公开（公告）日：1988-11-29

  A series of pyridyl or imidazolyl substituted phenyl piperazines having utility as anti-arrhythmic agents is disclosed.

  揭示了一系列具有抗心律失常作用的吡啶基或咪唑基取代的苯基哌嗪类化合物。
• Phenyl-piperazine anti-arrhythmia agents
  申请人：Pfizer Limited

  公开号：EP0244115A2

  公开（公告）日：1987-11-04

  Compounds of the formula: and their pharmaceutically acceptable salts, wherein R is R³SO₂NH-, R³CONH-, R¹R²NSO₂- or R¹R²NCO-; R¹ and R² are each independently H or C₁-C₄ alkyl; R³ is C₁-C₄ alkyl, C₃-C₇ cycloalkyl or NR¹R²; and Het is 2, 3 or 4-pyridyl optionally substituted by one or more substituents each independently selected from C₁-C₄ alkyl and NH₂; or 2-imidazolyl optionally substituted by one or more C₁-C₄ alkyl groups, are anti-arrhythmia agents useful for the treatment of cardiac conditions.

  式中的化合物 及其药学上可接受的盐类，其中 R 是 R³SO₂NH-、R³CONH-、R¹R²NSO₂- 或 R¹R²NCO-；R¹和 R² 各自独立地为 H 或 C₁-C₄ 烷基；R³ 是 C₁-C₄ 烷基、C₃-C₇ 环烷基或 NR¹R²；和 Het 是 2、3 或 4-吡啶基，任选被一个或多个各自独立选自 C₁-C₄ 烷基和 NH₂ 的取代基取代；或 2-咪唑基，任选被一个或多个 C₁-C₄ 烷基取代。
• Novel-N-(4-(Aminosubstituted)phenyl) methanesulfonamides and their use as cardiovascular agents
  申请人：SCHERING AKTIENGESELLSCHAFT

  公开号：EP0332570A2

  公开（公告）日：1989-09-13

  Novel N-[4-aminosubstituted)phenyl]methane­sulfonamides and their use as cardiovascular agents, especially as antiarrhythmic agents are described. Pharmaceutical formulations containing such compounds are also discussed.

  介绍了新型 N-[4-氨基取代)苯基]甲磺酰胺类化合物及其作为心血管药物，特别是作为抗心律失常药物的用途。还讨论了含有此类化合物的药物制剂。