N,N-diethyl-N'-<2,6-bis(1-methylethyl)phenyl>-1,2-ethanediamine | 116855-49-3

• 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: N,N-diethyl-N'-<2,6-bis(1-methylethyl)phenyl>-1,2-ethanediamine
• 英文别名: N-(2,6-diisopropylphenyl)-N′,N′-diethylethane-1,2-diamine；N,N-Diethyl-N'-(2,6-bis(1-methylethyl)phenyl)-1,2-ethanediamine；N-[2,6-di(propan-2-yl)phenyl]-N',N'-diethylethane-1,2-diamine
• CAS: 116855-49-3
• 化学式: C₁₈H₃₂N₂
• 分子量: 276.465
• InChiKey: DIIWPKXGWUOTPD-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  4.9
• 重原子数：
  20
• 可旋转键数：
  8
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.67
• 拓扑面积：
  15.3
• 氢给体数：
  1
• 氢受体数：
  2

反应信息

• 作为反应物：
  描述：

  N,N-diethyl-N'-<2,6-bis(1-methylethyl)phenyl>-1,2-ethanediamine 生成 N-<2-(diethylamino)ethyl>-N-<2,6-bis(1-methylethyl)phenyl>-4-<(methylsulfonyl)amino>benzamide hydrochloride
  参考文献：
  名称：

  N-(aminoalkyl)-substituted(N or C

  摘要：

  公式为##STR1##的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C.sub.1-C.sub.4直链烷基，R.sub.1、R.sub.2和R.sub.3中的一个为苯基或萘基，其余为氢，--NR.sub.4 R.sub.5为二级或三级氨基基团，X和X.sub.1为氢或烷基，n为0或1，可用于治疗心律失常，特别是作为I类/III类联合药物。

  公开号：

  US04920116A1
• 作为产物：
  描述：

  2-氯-N-(2,6-二异丙基苯基)乙酰胺 在 lithium aluminium tetrahydride 作用下， 以 四氢呋喃 、 乙醇 为溶剂， 反应 30.0h， 生成 N,N-diethyl-N'-<2,6-bis(1-methylethyl)phenyl>-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

文献信息

• Versatile Bulky <i>N</i> , <i>N</i> ′, <i>N</i> ′‐Substituted 1,2‐Ethanediamine Ligands and Their Lithium, Aluminium, and Gallium Derivatives
  作者：Robert Kretschmer、Maximilian Dehmel、Michael Bodensteiner

  DOI：10.1002/ejic.201601355

  日期：2017.2.3

  Sterically demanding N,N',N'-substituted 1,2-ethanediamine ligands have been prepared from commercially available starting materials by applying a facile one-step procedure. These ligands offer advantages compared to known systems: a suppressed delocalization due to the saturated backbone inhibits a noninnocent behaviour and the low symmetry of the related metal complexes makes them potential candidates

  空间要求高的 N,N',N'-取代的 1,2-乙二胺配体已通过应用简便的一步程序从市售的起始材料中制备。与已知系统相比，这些配体具有优势：由于饱和主链而抑制的离域化抑制了非无辜行为，并且相关金属配合物的低对称性使它们成为不对称催化的潜在候选者。配体很容易转化为相应的锂衍生物 4，而锂衍生物 4 又作为起始材料分别获得相应的二氯化铝和二氯化镓 5 和 6。此外，Al(CH3)(3) 的去质子化产生相关的二甲基丙烷 7。所有主族元素化合物都已通过单 X 射线晶体学和光谱方法进行了研究。
• ARYL-N-AMINOALKYL-4-(SULFONAMIDO)BENZAMIDES, ANTIARRHYTMIC AGENTS AND COMPOSITIONS THEREOF
  申请人：SCHERING AKTIENGESELLSCHAFT

  公开号：EP0324791A1

  公开（公告）日：1989-07-26
• US4920116A
  申请人：——

  公开号：US4920116A

  公开（公告）日：1990-04-24
• [EN] ARYL-N-AMINOALKYL-4-(SULFONAMIDO)BENZAMIDES, ANTIARRHYTMIC AGENTS AND COMPOSITIONS THEREOF
  申请人：SCHERING AKTIENGESELLSCHAFT

  公开号：WO1988002362A1

  公开（公告）日：1988-04-07

  (EN) Novel aryl-N-aminoalkyl-4-(sulfonamido)benzamides are described as useful antiarrhytmic agents. Their use in the treatment of cardiac arrhytmias especially as combination class I/class III agents is described. Pharmaceutical formulations containing such compounds are also disclosed.(FR) Les aryl-N-aminoalkyl-4-(sulfonamido)benzamides décrites sont utiles en tant qu'agents antiarythmiques. Leur utilisation dans le traitement d'arrythmie cardiaque, spécialement comme agents de la combinaison de la classe I et de la classe III est décrite. Des compositions pharmaceutiques contenant de tels composés sont également décrites.
• Synthesis and cardiac electrophysiological activity of aryl-substituted derivatives of the class III antiarrhythmic agent sematilide. Potential class I/III agents
  作者：Gary B. Phillips、Thomas K. Morgan、Klaus Nickisch、Joan M. Lind、Robert P. Gomez、Ronald A. Wohl、Thomas M. Argentieri、Mark E. Sullivan

  DOI：10.1021/jm00164a025

  日期：1990.2

  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.