4-(4-chlorophenyl)-1-piperazinopentanenitrile | 258882-52-9

• 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-chlorophenyl)-1-piperazinopentanenitrile
• 英文别名: 5-[4-(4-Chlorophenyl)piperazin-1-yl]pentanenitrile
• CAS: 258882-52-9
• 化学式: C₁₅H₂₀ClN₃
• 分子量: 277.797
• InChiKey: ABOGPTCNMWSNIZ-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.9
• 重原子数：
  19
• 可旋转键数：
  5
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.53
• 拓扑面积：
  30.3
• 氢给体数：
  0
• 氢受体数：
  3

反应信息

• 作为反应物：
  描述：

  4-(4-chlorophenyl)-1-piperazinopentanenitrile 在 dimethyl sulfide borane 作用下， 以 四氢呋喃 为溶剂， 反应 1.0h， 以100%的产率得到4-(4-chlorophenyl)-1-piperazinepentanamine
  参考文献：
  名称：

  A Structure−Affinity Relationship Study on Derivatives of N-[2-[4-(4-Chlorophenyl)piperazin-1-yl]ethyl]-3-methoxybenzamide, a High-Affinity and Selective D₄ Receptor Ligand

  摘要：

  N-[2-[4-(4-Chlorophenyl)piperazin-1-yl]ethyl]-3-methoxybenzamide (1), a high-affinity and selective dopamine D-4 receptor ligand, was chosen as a lead, and structural modifications were done on its amide bond and on its alkyl chain linking the benzamide moiety to the piperazine ring and by preparing some semirigid analogues. The binding profile at dopamine D-4 and dopamine D-2, serotonin 5-HT1A, and adrenergic ar receptors of 16 new compounds was determined. From the results emerged that the modification of the amide bond and the elongation of the intermediate alkyl chain caused a decrease in dopamine D-4 receptor affinity. All prepared semirigid analogues displayed D-4 receptor affinity values in the same range of the opened counterparts.

  DOI：

  10.1021/jm991138z
• 作为产物：
  描述：

  1-(4-氯苯基)哌嗪 、 5-氯戊腈 在 potassium carbonate 作用下， 以 乙腈 为溶剂， 以83%的产率得到4-(4-chlorophenyl)-1-piperazinopentanenitrile
  参考文献：
  名称：

  A Structure−Affinity Relationship Study on Derivatives of N-[2-[4-(4-Chlorophenyl)piperazin-1-yl]ethyl]-3-methoxybenzamide, a High-Affinity and Selective D₄ Receptor Ligand

  摘要：

  N-[2-[4-(4-Chlorophenyl)piperazin-1-yl]ethyl]-3-methoxybenzamide (1), a high-affinity and selective dopamine D-4 receptor ligand, was chosen as a lead, and structural modifications were done on its amide bond and on its alkyl chain linking the benzamide moiety to the piperazine ring and by preparing some semirigid analogues. The binding profile at dopamine D-4 and dopamine D-2, serotonin 5-HT1A, and adrenergic ar receptors of 16 new compounds was determined. From the results emerged that the modification of the amide bond and the elongation of the intermediate alkyl chain caused a decrease in dopamine D-4 receptor affinity. All prepared semirigid analogues displayed D-4 receptor affinity values in the same range of the opened counterparts.

  DOI：

  10.1021/jm991138z

文献信息

• A Structure−Affinity Relationship Study on Derivatives of <i>N</i>-[2-[4-(4-Chlorophenyl)piperazin-1-yl]ethyl]-3-methoxybenzamide, a High-Affinity and Selective D₄ Receptor Ligand
  作者：Roberto Perrone、Francesco Berardi、Nicola A. Colabufo、Marcello Leopoldo、Vincenzo Tortorella

  DOI：10.1021/jm991138z

  日期：2000.1.1

  N-[2-[4-(4-Chlorophenyl)piperazin-1-yl]ethyl]-3-methoxybenzamide (1), a high-affinity and selective dopamine D-4 receptor ligand, was chosen as a lead, and structural modifications were done on its amide bond and on its alkyl chain linking the benzamide moiety to the piperazine ring and by preparing some semirigid analogues. The binding profile at dopamine D-4 and dopamine D-2, serotonin 5-HT1A, and adrenergic ar receptors of 16 new compounds was determined. From the results emerged that the modification of the amide bond and the elongation of the intermediate alkyl chain caused a decrease in dopamine D-4 receptor affinity. All prepared semirigid analogues displayed D-4 receptor affinity values in the same range of the opened counterparts.