2-(diethylamino)-1-(1-naphthalenyl)ethanone oxime | 116855-54-0

• 分子结构分类: 有机化合物 - 苯类化合物 - 萘
• 英文名称: 2-(diethylamino)-1-(1-naphthalenyl)ethanone oxime
• 英文别名: 2-(Diethylamino)-1-(naphthalen-1-yl)ethanone oxime；N-[2-(diethylamino)-1-naphthalen-1-ylethylidene]hydroxylamine
• CAS: 116855-54-0
• 化学式: C₁₆H₂₀N₂O
• 分子量: 256.348
• InChiKey: YJYUDOFPZGFNPU-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.9
• 重原子数：
  19
• 可旋转键数：
  5
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.31
• 拓扑面积：
  35.8
• 氢给体数：
  1
• 氢受体数：
  3

反应信息

• 作为反应物：
  描述：

  2-(diethylamino)-1-(1-naphthalenyl)ethanone oxime 在 lithium aluminium tetrahydride 作用下， 以 四氢呋喃 为溶剂， 反应 16.0h， 生成 N²,N²-diethyl-1-(1-naphthalenyl)-1,2-ethanediamine
  参考文献：
  名称：

  Synthesis and cardiac electrophysiological activity of aryl-substituted derivatives of the class III antiarrhythmic agent sematilide. Potential class I/III agents

  摘要：

  Twelve novel derivatives of the selective class III antiarrhythmic agent sematilide were prepared in an attempt to incorporate both class I and class III electrophysiological properties into a single molecule. Electrophysiological activity was determined by standard microelectrode techniques in canine cardiac Purkinje fibers. Initial assessment of class I efficacy was carried out in a ouabain-induced arrhythmia model in guinea pigs. All of the compounds prolonged action potential duration in Purkinje fibers (class III activity), and three were active against ouabain-induced arrhythmias (class I activity). Selected compounds were evaluated further in dogs for efficacy against arrhythmias occurring 24 h following coronary ligation (automatic arrhythmias) and induced by using programmed electrical stimulation techniques (reentrant arrhythmias). The most effective compounds from the series are 3g and -j, which were effective in both canine models. Molecular modeling and structure-activity relationships are discussed.

  DOI：

  10.1021/jm00164a025
• 作为产物：
  描述：

  2-(diethylamino)-1-(1-naphthalenyl)ethanone 在 氢氧化钾 、 盐酸羟胺 作用下， 以 甲醇 、 水 为溶剂， 反应 17.0h， 以62%的产率得到2-(diethylamino)-1-(1-naphthalenyl)ethanone oxime
  参考文献：
  名称：

  Synthesis and cardiac electrophysiological activity of aryl-substituted derivatives of the class III antiarrhythmic agent sematilide. Potential class I/III agents

  摘要：

  Twelve novel derivatives of the selective class III antiarrhythmic agent sematilide were prepared in an attempt to incorporate both class I and class III electrophysiological properties into a single molecule. Electrophysiological activity was determined by standard microelectrode techniques in canine cardiac Purkinje fibers. Initial assessment of class I efficacy was carried out in a ouabain-induced arrhythmia model in guinea pigs. All of the compounds prolonged action potential duration in Purkinje fibers (class III activity), and three were active against ouabain-induced arrhythmias (class I activity). Selected compounds were evaluated further in dogs for efficacy against arrhythmias occurring 24 h following coronary ligation (automatic arrhythmias) and induced by using programmed electrical stimulation techniques (reentrant arrhythmias). The most effective compounds from the series are 3g and -j, which were effective in both canine models. Molecular modeling and structure-activity relationships are discussed.

  DOI：

  10.1021/jm00164a025

文献信息

• N-(aminoalkyl)-substituted(N or C
  申请人：Schering A.G.

  公开号：US04920116A1

  公开（公告）日：1990-04-24

  N-(aminoalkyl)-substituted(N or C alkyl)-aryl-4-(methylsylfonylamino)benzamides of the formula ##STR1## wherein R is C.sub.1 -C.sub.4 straight chain alkyl, one of R.sub.1, R.sub.2 and R.sub.3 is a phenyl or naphthyl group and the others are hydrogen, --NR.sub.4 R.sub.5 is a secondary or teritary amino group, X and X.sub.1 are hydrogen or alkyl and n is 0 or 1, are useful as antiarrhythmic agents in the treatment of cardiac arrhythmias especially as combination Class I/Class III agents.

  该公式化合物为N-(氨基烷基)-取代(N或C烷基)-芳基-4-(甲基磺酰氨基)苯甲酰胺，其中R为C1-C4直链烷基，R1、R2和R3中的一个为苯基或萘基，另外两个为氢，--NR4R5为二级或三级氨基基团，X和X1为氢或烷基，n为0或1，可用作抗心律失常药物，特别是作为I类/III类联合药物治疗心律失常。