N-(2-aminoethyl)-4-(1H-imidazol-1-yl)benzamide | 125903-44-8

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 唑类
• 英文名称: N-(2-aminoethyl)-4-(1H-imidazol-1-yl)benzamide
• 英文别名: N-(2-aminoethyl)-4-imidazol-1-ylbenzamide
• CAS: 125903-44-8
• 化学式: C₁₂H₁₄N₄O
• 分子量: 230.269
• InChiKey: RVRQKBILOQZRIG-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  0
• 重原子数：
  17
• 可旋转键数：
  4
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.17
• 拓扑面积：
  72.9
• 氢给体数：
  2
• 氢受体数：
  3

反应信息

• 作为反应物：
  描述：

  2,3-环氧丙基-4-甲氧基苯基醚 、 N-(2-aminoethyl)-4-(1H-imidazol-1-yl)benzamide 在 氮气 、 乙醇 作用下， 以 甲醇 为溶剂， 反应 24.0h， 生成 N-[2-[[2-Hydroxy-3-(4-methoxyphenoxy)propyl]amino]ethyl]-4-(1H-imidazol-1-yl)benzamide
  参考文献：
  名称：

  Derivatized alkanolamines as cardiovascular agents

  摘要：

  本发明涉及以下结构式的新型衍生烷基胺类化合物，其被描述为有用的心血管药物。尤其是描述了它们作为表现出抗心律失常效果的心血管药物的有用性。所述的抗心律失常效果是一种II类/III类的组合。还描述了含有这种化合物的制药配方。

  公开号：

  US05051423A1
• 作为产物：
  描述：

  4-(1H-咪唑-1-基)苯甲酸甲酯 、 乙二胺 反应 24.0h， 生成 N-(2-aminoethyl)-4-(1H-imidazol-1-yl)benzamide
  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

文献信息

• Synthesis and cardiac electrophysiological activity of N-substituted-4-(1H-imidazol-1-yl)benzamides - new selective class III agents
  作者：Thomas K. Morgan、Randall Lis、William C. Lumma、Klaus Nickisch、Ronald A. Wohl、Gary B. Phillips、Robert P. Gomez、John W. Lampe、Susan V. Di Meo

  DOI：10.1021/jm00166a003

  日期：1990.4

  The synthesis and cardiac electrophysiological activity of 18 N-substituted imidazolylbenzamides or benzene-sulfonamides are described. Compounds 6a,d,f-k and 11 exhibited potency in the in vitro Purkinje fiber assay comparable to that of N-[2-(diethylamino)ethyl]-4- [(methylsulfonyl)amino]benzamide (1, sematilide), a potent selective class III agent which is undergoing clinical trials. These data

  描述了18种N-取代的咪唑基苯甲酰胺或苯磺酰胺的合成和心脏电生理活性。化合物6a，d，fk和11在体外Purkinje纤维测定中显示出与N- [2-（二乙基氨基）乙基] -4-[（甲基磺酰基）氨基]苯甲酰胺（1，sematilide）相当的效能。正在进行临床试验的III类药物。这些数据表明1H-咪唑-1-基部分是甲基磺酰氨基的可行替代物，用于在N-取代的苯甲酰胺系列中产生III类电生理活性。在两个折返性心律不齐的体内模型中进一步研究了N- [2-（二乙氨基）乙基] -4-（1H-咪唑-1-基）苯甲酰胺二盐酸盐（6a），显示出与1。
• MORGAN, THOMAS K. (JR);LIS, RANDALL;LUMMA, WILLIAM C. (JR);NICKISCH, KLAU+, J. MED. CHEM., 33,(1990) N, C. 1091-1097
  作者：MORGAN, THOMAS K. (JR)、LIS, RANDALL、LUMMA, WILLIAM C. (JR)、NICKISCH, KLAU+

  DOI：——

  日期：——
• 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.