4-(4-cyanophenyl)-N-[2-(dimethylamino)ethyl]-1-piperazinecarboxamide | 117518-28-2

• 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: 4-(4-cyanophenyl)-N-[2-(dimethylamino)ethyl]-1-piperazinecarboxamide
• 英文别名: 4-(4-cyanophenyl)-N-[2-(dimethylamino)ethyl]piperazine-1-carboxamide
• CAS: 117518-28-2
• 化学式: C₁₆H₂₃N₅O
• 分子量: 301.392
• InChiKey: NBNNMKQJNBWORK-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  0.9
• 重原子数：
  22
• 可旋转键数：
  4
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.5
• 拓扑面积：
  62.6
• 氢给体数：
  1
• 氢受体数：
  4

反应信息

• 作为产物：
  描述：

  N,N-二甲基乙二胺 、 N,N'-羰基二咪唑 、 4-哌嗪基苯甲腈 生成 4-(4-cyanophenyl)-N-[2-(dimethylamino)ethyl]-1-piperazinecarboxamide
  参考文献：
  名称：

  Synthesis and antiallergy activity of N-[2-(dimethylamino)ethyl]-4-aryl-1-piperazinecarboxamide derivatives

  摘要：

  A series of N-[2-(dimethylamino)ethyl]-4-aryl-1-piperazinecarboxamides was synthesized and evaluated for antiallergy activity. Several derivatives had activity in the passive foot anaphylaxis (PFA) assay, an IgE-mediated model useful in the detection of compounds possessing antiallergic activity, but no derivative tested had activity at 10 mg/kg in the guinea pig anaphylaxis (GPA) assay. One analogue, N-[2-(dimethylamino)ethyl]-4-(4-fluorophenyl)-1-piperazinecarboxamide , had an IC50 = 310 nM for inhibition of tritiated mepyramine binding to H1 histaminic receptors isolated from guinea pig cerebral cortex.

  DOI：

  10.1021/jm00169a037

文献信息

• 4-Aryl-N-[2-(dialkylamino and heterocyclicamino) alkyl]-1-piperazinecarboxamides and their use as anti allergy agents
  申请人：A.H. ROBINS COMPANY, INCORPORATED

  公开号：EP0277725A2

  公开（公告）日：1988-08-10

  Novel 4-aryl-N-[2-(dialkylamino and heterocyclic­amino)alkyl]-1-piperazinecarboxamides of the formula: wherein B is oxygen or sulfur; Ar is selected from Or 2, 3 or 4-pyridyl; X is selected from hydrogen, halogen, loweralkyl, loweralkoxy, amino, dimethylamino, nitro, trifluoromethyl, cyano, acetyl, acetylamino, aminocarbonyl, carboxy or loweralkylcarboxylic acid ester; Y is selected from hydrogen, halogen, loweralkyl, loweralkoxy, nitro, trifluoromethyl, cyano, acetylamino, aminocarbonyl, carboxy or loweralkyl carboxylic acid ester; Z is selected from hydrogen, loweralkyl or loweralkoxy; Q is selected from m is 1 to 3 inclusive; n is zero or 1; p is zero to 3 inclusive; R¹, R² and R³ are loweralkyl and may be the same or different, or R¹ and R² taken together with the adjacent nitrogen atom may form a heterocyclic residue; and the pharmaceutically acceptable salts thereof are disclosed. The compounds are useful in a method of combating allergic response associated with anaphylactic sensitivity in animals and humans.

  式中的新型 4-芳基-N-[2-(二烷基氨基和杂环氨基)烷基]-1-哌嗪甲酰胺： 其中 B 是氧或硫；Ar 选自 或2、3或4-吡啶基；X选自氢、卤素、低级烷基、低级烷氧基、氨基、二甲基氨基、硝基、三氟甲基、氰基、乙酰基、乙酰氨基、氨基羰基、羧基或低级烷基羧酸酯；Y 选自氢、卤素、低级烷基、低级烷氧基、硝基、三氟甲基、氰基、乙酰氨基、 氨基羰基、羧基或低级烷基羧酸酯； Z 选自氢、低级烷基或低级烷氧基； Q 选自 R¹、R²和R³为低级烷基，可以相同或不同，或者R¹和R²与相邻的氮原子一起可形成杂环残基；以及公开了其药学上可接受的盐。这些化合物可用于防治动物和人类与过敏反应相关的过敏反应。
• US4960776A
  申请人：——

  公开号：US4960776A

  公开（公告）日：1990-10-02
• Synthesis and antiallergy activity of N-[2-(dimethylamino)ethyl]-4-aryl-1-piperazinecarboxamide derivatives
  作者：David A. Walsh、Jerry B. Green、Stephen K. Franzyshen、Joseph C. Nolan、John M. Yanni

  DOI：10.1021/jm00169a037

  日期：1990.7

  A series of N-[2-(dimethylamino)ethyl]-4-aryl-1-piperazinecarboxamides was synthesized and evaluated for antiallergy activity. Several derivatives had activity in the passive foot anaphylaxis (PFA) assay, an IgE-mediated model useful in the detection of compounds possessing antiallergic activity, but no derivative tested had activity at 10 mg/kg in the guinea pig anaphylaxis (GPA) assay. One analogue, N-[2-(dimethylamino)ethyl]-4-(4-fluorophenyl)-1-piperazinecarboxamide , had an IC50 = 310 nM for inhibition of tritiated mepyramine binding to H1 histaminic receptors isolated from guinea pig cerebral cortex.