1-(4-甲氧基-2-甲基苯基)-哌嗪 | 59803-92-8

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 二嗪烷类
• 中文名称: 1-(4-甲氧基-2-甲基苯基)-哌嗪
• 英文名称: 1-(4-(methoxy)-2-(methyl)phenyl)piperazine
• 英文别名: 4-(4'-methoxy-2'-methylphenyl)piperazine；1-(4-Methoxy-2-methyl-phenyl)-piperazine；1-(4-methoxy-2-methylphenyl)piperazine
• CAS: 59803-92-8
• 化学式: C₁₂H₁₈N₂O
• 分子量: 206.288
• InChiKey: QACLELNFVSMAIZ-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.2
• 重原子数：
  15
• 可旋转键数：
  2
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.5
• 拓扑面积：
  24.5
• 氢给体数：
  1
• 氢受体数：
  3

反应信息

• 作为反应物：
  描述：

  1-(4-甲氧基-2-甲基苯基)-哌嗪 、 1-(3-bromopropylcarbamoyl)-6-(3,4-difluorophenyl)-5-methoxycarbonyl-4-methyl-2-oxo-1,2,3,6-tetrahydropyrimidine 在 碳酸氢钠 、 potassium iodide 作用下， 以 丙酮 为溶剂， 反应 10.0h， 生成 4-(3,4-Difluoro-phenyl)-3-{3-[4-(4-methoxy-2-methyl-phenyl)-piperazin-1-yl]-propylcarbamoyl}-6-methyl-2-oxo-1,2,3,4-tetrahydro-pyrimidine-5-carboxylic acid methyl ester
  参考文献：
  名称：

  Design and Synthesis of Novel α_1a Adrenoceptor-Selective Antagonists. 3. Approaches To Eliminate Opioid Agonist Metabolites by Using Substituted Phenylpiperazine Side Chains

  摘要：

  Dihydropyrimidinones, such as 1, represent a novel class of alpha(1a) adrenoceptor antagonists with potential for the treatment of benign prostatic hyperplasia (BPH) (see part 1 of this series). Analysis of the metabolites of 1 revealed that 4-methoxycarbonyl-4-phenylpiperidine is formed as the major metabolite and is an agonist at the mu-opioid receptor. To circumvent any potential liability resulting from the metabolite, we decided to identify alternate templates devoid of agonist activity at the mu-opioid receptor to replace the 4-methoxycarbonyl-4-phenylpiperidine moiety. The present study describes the synthesis and SAR of dihydropyrimidinones linked to substituted 4-phenylpiperazine containing side chains. Compound (+)-38 was identified as a lead compound with a binding and functional profile comparable to that of 1. The putative metabolite 2-carboxamidophenylpiperazine has negligible affinity for the mu-opioid receptor.

  DOI：

  10.1021/jm990202+
• 作为产物：
  描述：

  二(2-氯乙基)胺盐酸盐 、 2-甲基-4-甲氧基苯胺 在 potassium carbonate 作用下， 以 二乙二醇二甲醚 为溶剂， 反应 18.0h， 以60%的产率得到1-(4-甲氧基-2-甲基苯基)-哌嗪
  参考文献：
  名称：

  Structure−Activity Relationships for the Binding of Arylpiperazines and Arylbiguanides at 5-HT₃ Serotonin Receptors

  摘要：

  Arylpiperazines are nonselective agents that bind at 5-HT3 serotonin receptors with moderate to high affinity, whereas 1-phenylbiguanide is a low-affinity but more selective 5-HT3 agonist. In an attempt to enhance the affinity of the latter agent, and working with the assumption that similarities might exist between the binding of the two types of agents, we formulated structure-activity relationships for the binding of the arylpiperazines and then incorporated those substituents, leading to high affinity for the arylpiperazines, into 1-phenylbiguanide. A subsequent investigation examined the structure-activity relationships of the arylbiguanides and identified arylguanidines as a novel class of 5-HT3 ligands. Although curious similarities exist between the structure-activity relationships of the arylpiperazines, arylbiguanides, and arylguanidines, it cannot be concluded that all three series of compounds are binding in the same manner. Furthermore, upon investigating pairs of compounds in the three series, the arylpiperazines behaved as 5-HT3 antagonists (von Bezold-Jarisch assay) whereas the arylbiguanides and arylguanidines acted as 5-HT3 agonists.

  DOI：

  10.1021/jm9603936

文献信息

• [EN] PIPERIDIN-4-YLPIPERAZINE COMPOUNDS FOR THE TREATMENT OF HCV INFECTION<br/>[FR] COMPOSÉS DE PIPÉRIDIN-4-YLPIPÉRAZINE POUR LE TRAITEMENT D'UNE INFECTION À VHC
  申请人：GENOSCIENCE PHARMA

  公开号：WO2010081851A1

  公开（公告）日：2010-07-22

  The invention relates to new piperazine-pieridine compounds having anti-viral activity and particularly anti-HCV activity. The invention further relates to pharmaceutical compositions comprising compounds according to the invention.

  该发明涉及具有抗病毒活性，特别是抗丙型肝炎病毒活性的新哌嗪-哌啶化合物。该发明还涉及包含根据该发明的化合物的药物组合物。
• Design, synthesis and antimicrobial activities of some new quinoline derivatives carrying 1,2,3-triazole moiety
  作者：K.D. Thomas、Airody Vasudeva Adhikari、N. Suchetha Shetty

  DOI：10.1016/j.ejmech.2010.05.030

  日期：2010.9

  A new series of [1-(6-methoxy-2-methylquinolin-4-y1)-1H-1,2,3-triazol-4-yl] methanamine derivatives were synthesized starting from 4-methoxyaniline through multi-step reactions. The title compounds 5a-y were prepared by treating the azide intermediate 4 with propargyl bromide and different alkyl/heterocyclic amines in a sequential three component synthesis. All the new compounds were characterized by spectral and elemental analyses. The newly synthesized final compounds were evaluated for their in vitro antibacterial and antifungal activities against pathogenic strains. The preliminary screening results indicated that most of the compounds demonstrated moderate to very good antibacterial and antifungal activities, comparable to the first-line drugs. (C) 2010 Elsevier Masson SAS. All rights reserved.
• US4094980A
  申请人：——

  公开号：US4094980A

  公开（公告）日：1978-06-13
• USRE44205E1
  申请人：——

  公开号：USRE44205E1

  公开（公告）日：2013-05-07
• Structure−Activity Relationships for the Binding of Arylpiperazines and Arylbiguanides at 5-HT₃ Serotonin Receptors
  作者：Małgorzata Dukat、Ashraf A. Abdel-Rahman、Abd M. Ismaiel、Stacy Ingher、Milt Teitler、Laszlo Gyermek、Richard A. Glennon

  DOI：10.1021/jm9603936

  日期：1996.1.1

  Arylpiperazines are nonselective agents that bind at 5-HT3 serotonin receptors with moderate to high affinity, whereas 1-phenylbiguanide is a low-affinity but more selective 5-HT3 agonist. In an attempt to enhance the affinity of the latter agent, and working with the assumption that similarities might exist between the binding of the two types of agents, we formulated structure-activity relationships for the binding of the arylpiperazines and then incorporated those substituents, leading to high affinity for the arylpiperazines, into 1-phenylbiguanide. A subsequent investigation examined the structure-activity relationships of the arylbiguanides and identified arylguanidines as a novel class of 5-HT3 ligands. Although curious similarities exist between the structure-activity relationships of the arylpiperazines, arylbiguanides, and arylguanidines, it cannot be concluded that all three series of compounds are binding in the same manner. Furthermore, upon investigating pairs of compounds in the three series, the arylpiperazines behaved as 5-HT3 antagonists (von Bezold-Jarisch assay) whereas the arylbiguanides and arylguanidines acted as 5-HT3 agonists.