4-(4-chlorophenyl)-1-piperazinepentanamine | 258882-53-0

• 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-piperazinepentanamine
• 英文别名: 5-[4-(4-Chlorophenyl)piperazin-1-yl]pentan-1-amine
• CAS: 258882-53-0
• 化学式: C₁₅H₂₄ClN₃
• 分子量: 281.829
• InChiKey: KTHVLLDHNWSYBB-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.6
• 重原子数：
  19
• 可旋转键数：
  6
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.6
• 拓扑面积：
  32.5
• 氢给体数：
  1
• 氢受体数：
  3

反应信息

• 作为反应物：
  描述：

  间甲氧基苯甲酰氯 、 4-(4-chlorophenyl)-1-piperazinepentanamine 在 碳酸氢钠 作用下， 以 二氯甲烷 为溶剂， 生成 N-{5-[4-(4-Chloro-phenyl)-piperazin-1-yl]-pentyl}-3-methoxy-benzamide
  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：

  5-氯戊腈 在 dimethyl sulfide borane 、 potassium carbonate 作用下， 以 四氢呋喃 、 乙腈 为溶剂， 反应 1.0h， 生成 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

文献信息

• Quinoline- and isoquinoline-sulfonamide derivatives of LCAP as potent CNS multi-receptor—5-HT1A/5-HT2A/5-HT7 and D2/D3/D4—agents: The synthesis and pharmacological evaluation
  作者：Paweł Zajdel、Krzysztof Marciniec、Andrzej Maślankiewicz、Grzegorz Satała、Beata Duszyńska、Andrzej J. Bojarski、Anna Partyka、Magdalena Jastrzębska-Więsek、Dagmara Wróbel、Anna Wesołowska、Maciej Pawłowski

  DOI：10.1016/j.bmc.2011.12.039

  日期：2012.2

  Two series of arylpiperazinyl-alkyl quinoline-, isoquinoline-, naphthalene-sulfonamides with flexible (13-26) and semi-rigid (33-36) alkylene spacer were synthesized and evaluated for 5-HT1A, 5-HT2A, 5-HT6, 5-HT7 and selected compounds for D-2, D-3, D-4 receptors. The compounds with a mixed 5-HT and D receptors profile 16 (N-4-[4-(3-chlorophenyl)-piperazin-1-yl]-butyl}-3-quinolinesulfonamide) and 36 (4-(4-2-[4-(4-chloro-phenyl)-piperazin-1-yl]-ethyl}-piperidine-1-sulfonyl)-isoquinoline), displaying antagonistic activity at 5-HT7, 5-HT2A, D2 postsynaptic sites, produced antidepressant-like effects in the forced swim test in mice and showed significant anxiolytic activity in the plus-maze test in rats. The lead compound 36, a multi-receptor 5-HT2A/5-HT7/D-2/D-3/D-4 agent, also displayed significant antipsychotic properties in the MK-801-induced hyperlocomotor activity in mice. (C) 2011 Elsevier Ltd. All rights reserved.
• Structure–activity relationships and molecular studies of novel arylpiperazinylalkyl purine-2,4-diones and purine-2,4,8-triones with antidepressant and anxiolytic-like activity
  作者：Agnieszka Zagórska、Marcin Kołaczkowski、Adam Bucki、Agata Siwek、Grzegorz Kazek、Grzegorz Satała、Andrzej J. Bojarski、Anna Partyka、Anna Wesołowska、Maciej Pawłowski

  DOI：10.1016/j.ejmech.2015.04.046

  日期：2015.6

  A novel series of arylpiperazinylalkyl purine-2,4-diones (4-27) and purine-2,4,8-triones (31-38) was synthesized and tested to evaluated their affinity for the serotoninergic (5-HT1A, 5-HT6, 5-HT7) and dopaminergic (D2) receptors. Compounds with purine-2,4-dione nucleus generally had affinity values higher than the corresponding purine-2,4,8-trione compounds. A spectrum of receptor activities was observed for compounds with a substituent at the 7-position of the imidazo[2,1-f]purine-2,4-dione system and some potent 5-HT1A (18, 25), 5-HT7 (14) and mixed 5-HT1A/5-HT7 (8, 9) receptor ligands with additional affinity for dopamine D2 receptors (15) has been identified. Moreover, docking studies proved that a substituent at the 7-position of 1,3-dimethyl-(1H,8H)-imidazo[2,1-f]purine-2,4-dione could be essential for receptor affinity and selectivity, especially towards 5-HT1A and 5-HT7. The results of the preliminary pharmacological in vivo studies of selected derivatives of 1,3-dimethyl-(1H,8H)imidazo[2,1-f]purine-2,4-dione, including 9 as a potential anxiolytic, 8 and 15 as potential antidepressants, and 18 and 25 as potential antidepressant and anxiolytic agents. (C) 2015 Elsevier Masson SAS. All rights reserved.
• 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.