3-methyl-1-<2-<4-<(methylsulfonyl)amino>phenyl>-2-oxoethyl>-1H-imidazolium chloride | 97163-47-8

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: 3-methyl-1-<2-<4-<(methylsulfonyl)amino>phenyl>-2-oxoethyl>-1H-imidazolium chloride
• 英文别名: N-[4-[2-(3-methylimidazol-3-ium-1-yl)acetyl]phenyl]methanesulfonamide;chloride
• CAS: 97163-47-8
• 化学式: C₁₃H₁₆N₃O₃S*Cl
• 分子量: 329.807
• InChiKey: JQWURBUZZPSJGE-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  -2.43
• 重原子数：
  21
• 可旋转键数：
  5
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.23
• 拓扑面积：
  80.4
• 氢给体数：
  1
• 氢受体数：
  5

反应信息

• 作为反应物：
  描述：

  3-methyl-1-<2-<4-<(methylsulfonyl)amino>phenyl>-2-oxoethyl>-1H-imidazolium chloride 在 palladium on activated charcoal 氢气 作用下， 以 水 为溶剂， 反应 5.0h， 以78%的产率得到(+/-)-1-<2-hydroxy-2-<4-<(methylsulfonyl)amino>-phenyl>ethyl>-3-methyl-1H-imidazolium chloride
  参考文献：
  名称：

  Synthesis and antiarrhythmic activity of novel 3-alkyl-1-[.omega.-[4-[(alkylsulfonyl)amino]phenyl]-.omega.-hydroxyalkyl]-1H-imidazolium salts and related compounds

  摘要：

  Novel 3-alkyl-1-[omega-[4-[(alkylsulfonyl)amino]phenyl]-omega-hydroxyalkyl]-1H -imidazolium salts were synthesized and investigated for their class III electrophysiological activity on isolated canine cardiac Purkinje fibers and ventricular muscle tissue. Structure-activity relationships are discussed for a series of 25 compounds. Compound 3, 1-[2-hydroxy-2-[4-[(methylsulfonyl)amino]phenyl]ethyl]-3-methyl-1H- imidazolium chloride, prolonged the functional refractory period in anesthetized dogs when given intraduodenally and was also effective in preventing reentrant ventricular tachycardia induced by programmed electrical stimulation when administered intravenously in anesthetized dogs 24 h after an acute myocardial infarction. Both enantiomers of 3 were synthesized. No enantioselectivity was found in the electrophysiological effects of 3.

  DOI：

  10.1021/jm00387a020
• 作为产物：
  描述：

  N-苯基甲磺酰胺 在 三氯化铝 作用下， 以 二氯甲烷 、 乙腈 为溶剂， 反应 24.0h， 生成 3-methyl-1-<2-<4-<(methylsulfonyl)amino>phenyl>-2-oxoethyl>-1H-imidazolium chloride
  参考文献：
  名称：

  Synthesis and antiarrhythmic activity of novel 3-alkyl-1-[.omega.-[4-[(alkylsulfonyl)amino]phenyl]-.omega.-hydroxyalkyl]-1H-imidazolium salts and related compounds

  摘要：

  Novel 3-alkyl-1-[omega-[4-[(alkylsulfonyl)amino]phenyl]-omega-hydroxyalkyl]-1H -imidazolium salts were synthesized and investigated for their class III electrophysiological activity on isolated canine cardiac Purkinje fibers and ventricular muscle tissue. Structure-activity relationships are discussed for a series of 25 compounds. Compound 3, 1-[2-hydroxy-2-[4-[(methylsulfonyl)amino]phenyl]ethyl]-3-methyl-1H- imidazolium chloride, prolonged the functional refractory period in anesthetized dogs when given intraduodenally and was also effective in preventing reentrant ventricular tachycardia induced by programmed electrical stimulation when administered intravenously in anesthetized dogs 24 h after an acute myocardial infarction. Both enantiomers of 3 were synthesized. No enantioselectivity was found in the electrophysiological effects of 3.

  DOI：

  10.1021/jm00387a020

文献信息

• LIS R.; MORGAN T. K., JR.; DE VITA R. J.; DAVEY D. D.; LUMMA W. C.; WOHL +, J. MED. CHEM., 30,(1987) N 4, 696-704
  作者：LIS R.、 MORGAN T. K., JR.、 DE VITA R. J.、 DAVEY D. D.、 LUMMA W. C.、 WOHL +

  DOI：——

  日期：——
• Imidazolium salts, intermediates thereto and their use
  申请人：SCHERING AKTIENGESELLSCHAFT

  公开号：EP0131302B1

  公开（公告）日：1992-01-29
• US4613609A
  申请人：——

  公开号：US4613609A

  公开（公告）日：1986-09-23
• US4689341A
  申请人：——

  公开号：US4689341A

  公开（公告）日：1987-08-25
• Synthesis and antiarrhythmic activity of novel 3-alkyl-1-[.omega.-[4-[(alkylsulfonyl)amino]phenyl]-.omega.-hydroxyalkyl]-1H-imidazolium salts and related compounds
  作者：Randall Lis、Thomas K. Morgan、Robert J. DeVita、David D. Davey、William C. Lumma、Ronald A. Wohl、Julius Diamond、Samuel S. Wong、Mark E. Sullivan

  DOI：10.1021/jm00387a020

  日期：1987.4

  Novel 3-alkyl-1-[omega-[4-[(alkylsulfonyl)amino]phenyl]-omega-hydroxyalkyl]-1H -imidazolium salts were synthesized and investigated for their class III electrophysiological activity on isolated canine cardiac Purkinje fibers and ventricular muscle tissue. Structure-activity relationships are discussed for a series of 25 compounds. Compound 3, 1-[2-hydroxy-2-[4-[(methylsulfonyl)amino]phenyl]ethyl]-3-methyl-1H- imidazolium chloride, prolonged the functional refractory period in anesthetized dogs when given intraduodenally and was also effective in preventing reentrant ventricular tachycardia induced by programmed electrical stimulation when administered intravenously in anesthetized dogs 24 h after an acute myocardial infarction. Both enantiomers of 3 were synthesized. No enantioselectivity was found in the electrophysiological effects of 3.