4-(4-(3-methoxyphenyl)piperazin-1-yl)butanenitrile | 898533-22-7

• 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-(3-methoxyphenyl)piperazin-1-yl)butanenitrile
• 英文别名: 4-[4-(3-methoxyphenyl)piperazin-1-yl]butanenitrile
• CAS: 898533-22-7
• 化学式: C₁₅H₂₁N₃O
• 分子量: 259.351
• InChiKey: ZEFIJDIDPVEQQK-UHFFFAOYSA-N

物化性质

• 沸点：
  449.1±45.0 °C(Predicted)
• 密度：
  1.077±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  1.9
• 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：
  39.5
• 氢给体数：
  0
• 氢受体数：
  4

反应信息

• 作为反应物：
  描述：

  4-(4-(3-methoxyphenyl)piperazin-1-yl)butanenitrile 在 dimethyl sulfide borane 、 甲醇 作用下， 以 四氢呋喃 为溶剂， 反应 1.0h， 生成 4-(4-(3-methoxyphenyl)piperazin-1-yl)butan-1-amine
  参考文献：
  名称：

  具有最佳亲脂性的潜在正电子发射断层扫描（PET）配体的设计，合成和结合亲和力，用于多巴胺D 3受体的脑成像。第二部分

  摘要：

  在寻找具有潜力开发为脑D 3受体成像的正电子发射断层照相放射配体的化合物时，一系列具有适当亲脂性的N- [4-（4-芳基哌嗪-1-基）丁基]芳基羧酰胺（2

  DOI：

  10.1016/j.bmc.2008.11.044
• 作为产物：
  描述：

  1-(3-甲氧基苯基)哌嗪 、 4-溴丁腈 在 potassium carbonate 作用下， 以 乙腈 为溶剂， 生成 4-(4-(3-methoxyphenyl)piperazin-1-yl)butanenitrile
  参考文献：
  名称：

  具有最佳亲脂性的潜在正电子发射断层扫描（PET）配体的设计，合成和结合亲和力，用于多巴胺D 3受体的脑成像。第二部分

  摘要：

  在寻找具有潜力开发为脑D 3受体成像的正电子发射断层照相放射配体的化合物时，一系列具有适当亲脂性的N- [4-（4-芳基哌嗪-1-基）丁基]芳基羧酰胺（2

  DOI：

  10.1016/j.bmc.2008.11.044

文献信息

• Novel Aryl Piperazine Derivatives With Medical Utility
  申请人：Campiani Giuseppe

  公开号：US20090238761A1

  公开（公告）日：2009-09-24

  This invention provides novel aryl piperazine derivatives having medical utility, in particular as modulators of dopamine and serotonin receptors, preferably the D 3 , D 2 -like and 5-HT 2 receptor subtypes, and in particular useful for the treatment of neuropsychiatric disorders incl. schizophrenia.

  这项发明提供了具有医疗效用的新型芳基哌嗪衍生物，特别是作为多巴胺和5-羟色胺受体的调节剂，优选为D3、D2样和5-HT2受体亚型，特别适用于治疗包括精神分裂症在内的神经精神障碍。
• ARYL PIPERAZINE DERIVATIVES FOR THE TREATMENT OF NEUROPSYCHIATRIC DISORDERS
  申请人：Universita' Degli Studi di Siena

  公开号：EP1836192A2

  公开（公告）日：2007-09-26
• [EN] NOVEL ARYL PIPERAZINE DERIVATIVES WITH MEDICAL UTILITY<br/>[FR] NOUVEAUX DERIVES D'ARYLE PIPERAZINE PRESENTANT UNE UTILITE MEDICALE
  申请人：UNIV SIENA

  公开号：WO2006072608A2

  公开（公告）日：2006-07-13

  [EN] This invention provides novel aryl piperazine derivatives having medical utility, in particular as modulators of dopamine and serotonin receptors, preferably the D₃, D₂-like and 5-HT₂ receptor subtypes, and in particular useful for the treatment of neuropsychiatric disorders incl. schizophrenia.
  [FR] L'invention concerne de nouveaux dérivés d'aryle pipérazine possédant une utilité médicale, en particulier, en tant que modulateurs des récepteurs de dopamine et de sérotonine, de préférence, les sous-types des récepteurs D₃, analogue à D₂ et 5-HT₂, ces dérivés étant, en particulier utiles, pour traiter des troubles neuropsychiatriques, y compris la schizophrénie.
• Targeting Dopamine D₃ and Serotonin 5-HT_1A and 5-HT_2A Receptors for Developing Effective Antipsychotics: Synthesis, Biological Characterization, and Behavioral Studies
  作者：Margherita Brindisi、Stefania Butini、Silvia Franceschini、Simone Brogi、Francesco Trotta、Sindu Ros、Alfredo Cagnotto、Mario Salmona、Alice Casagni、Marco Andreassi、Simona Saponara、Beatrice Gorelli、Pia Weikop、Jens D. Mikkelsen、Jorgen Scheel-Kruger、Karin Sandager-Nielsen、Ettore Novellino、Giuseppe Campiani、Sandra Gemma

  DOI：10.1021/jm501119j

  日期：2014.11.26

  Combination of dopamine D-3 antagonism, serotonin 5-HT1A partial agonism, and antagonism at 5-HT2A leads to a novel approach to potent atypical antipsychotics. Exploitation of the original structureactivity relationships resulted in the identification of safe and effective antipsychotics devoid of extrapyramidal symptoms liability, sedation, and catalepsy. The potential atypical antipsychotic 5bb was selected for further pharmacological investigation. The distribution of c-fos positive cells in the ventral striatum confirmed the atypical antipsychotic profile of 5bb in agreement with behavioral rodent studies. 5bb administered orally demonstrated a biphasic effect on the MK801-induced hyperactivity at dose levels not able to induce sedation, catalepsy, or learning impairment in passive avoidance. In microdialysis studies, 5bb increased the dopamine efflux in the medial prefrontal cortex. Thus, 5bb represents a valuable lead for the development of atypical antipsychotics endowed with a unique pharmacological profile for addressing negative symptoms and cognitive deficits in schizophrenia.
• Design, synthesis, and binding affinities of potential positron emission tomography (PET) ligands with optimal lipophilicity for brain imaging of the dopamine D3 receptor. Part II
  作者：Marcello Leopoldo、Enza Lacivita、Paola De Giorgio、Marialessandra Contino、Francesco Berardi、Roberto Perrone

  DOI：10.1016/j.bmc.2008.11.044

  日期：2009.1

  In the search for compounds with potential for development as positron emission tomography radioligands for brain D3 receptor imaging, a series of N-[4-(4-arylpiperazin-1-yl)butyl]arylcarboxamides with appropriate lipophilicity (2 < log P < 3.5) were synthesized and tested in vitro. Some of the final compounds showed moderate-to-high dopamine D3 receptor affinities but lacked selectivity over D2 receptors

  在寻找具有潜力开发为脑D 3受体成像的正电子发射断层照相放射配体的化合物时，一系列具有适当亲脂性的N- [4-（4-芳基哌嗪-1-基）丁基]芳基羧酰胺（2