4-[2-(4-methoxyphenyl)phenyl]-N-(pyridin-2-ylmethyl)piperazinehexanamide | 1414942-03-2

• 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-[2-(4-methoxyphenyl)phenyl]-N-(pyridin-2-ylmethyl)piperazinehexanamide
• 英文别名: 4-[2-(4-methoxyphenyl)phenyl]-N-(pyridin-2-ylmethyl)piperazinohexanamide；4-[2-(4-methoxyphenyl)phenyl]-N-(2-pyridinylmethyl)-1-piperazinehexanamide；4-[2-(4-Methoxyphenyl)phenyl]-N-(2-pyridinylmethyl)-1-piperazinehexanamide；6-[4-[2-(4-methoxyphenyl)phenyl]piperazin-1-yl]-N-(pyridin-2-ylmethyl)hexanamide
• CAS: 1414942-03-2
• 化学式: C₂₉H₃₆N₄O₂
• 分子量: 472.63
• InChiKey: JSQKAYZTFGCBNA-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  4.2
• 重原子数：
  35
• 可旋转键数：
  11
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.38
• 拓扑面积：
  57.7
• 氢给体数：
  1
• 氢受体数：
  5

反应信息

• 作为产物：
  描述：

  2-氨甲基吡啶 、 6-溴己酰氯 在 potassium carbonate 、 sodium hydroxide 作用下， 以 二氯甲烷 、 水 、 乙腈 为溶剂， 生成 4-[2-(4-methoxyphenyl)phenyl]-N-(pyridin-2-ylmethyl)piperazinehexanamide
  参考文献：
  名称：

  对5-HT 7受体进行脑成像的潜在正电子发射断层扫描（PET）放射配体的设计，合成，放射性标记和体内评估

  摘要：

  在这里，我们描述了一组与高亲和性5-羟色胺5-HT 7受体激动剂N-（4-氰基苯基甲基）-4-（2-二苯基）-1-哌嗪己酰胺（6，LP-211）。的具体结构进行了修饰，以保持亲和力靶受体和以改进对5-HT的选择性进行1A和肾上腺素能α 1个受体。合成的化合物具有化学特征，可以使用正电子发射体放射性同位素（碳11或氟18）进行标记，并且亲脂性在认为对脑部穿透和低非特异性结合最合适的范围内。4- [2-（4-甲氧基苯基）苯基] -N-（吡啶-4-基甲基）哌嗪己酰胺（23a）和N-吡啶-4-基甲基-3- [4- [2-（4-（4-甲氧基苯基）苯基]哌嗪-1-基]乙氧基]丙酰胺（26a）被标记。在带有碳原子11的甲氧基上。正电子发射断层扫描（PET）分析显示，[ 11 C] -23a和[ 11 C] -26a是P-糖蛋白（P-gp）底物，并迅速代谢，导致大脑摄取不良。这些特征不是通过体外测试来预测的。

  DOI：

  10.1016/j.bmc.2014.01.016

文献信息

• [EN] NEW 1-ARYLPIPERAZINIC LIGANDS OF 5-HT7 RECEPTOR AND USE THEREOF<br/>[FR] NOUVEAUX LIGANDS 1-ARYLPIPÉRAZINIQUES DE RÉCEPTEUR 5-HT7 ET UTILISATION DE CEUX-CI
  申请人：UNIV BARI

  公开号：WO2012159662A1

  公开（公告）日：2012-11-29

  The invention relates to a new class of compounds able to inhibit with high affinity and selectivity the 5-HT7 receptor. The invention also relates to the utilization of such compounds as medicaments useful in the treatment and prevention of 5-HT7 receptor relating disorders of the central nervous system. The invention also relates to the isotopically labeled compounds for use in vivo diagnosis or imaging of a 5-HT7 condition.

  这项发明涉及一类新的化合物，能够以高亲和力和选择性抑制5-HT7受体。该发明还涉及将这类化合物用作药物，用于治疗和预防中枢神经系统与5-HT7受体相关的疾病。该发明还涉及同位素标记的化合物，用于体内诊断或成像5-HT7状况。
• NEW I-ARYLPIPERAZINIC LIGANDS OF 5-HT7 RECEPTOR AND USE THEREOF
  申请人：UNIVERSITA' DEGLI STUDI DI BARI ''ALDO MORO''

  公开号：US20140086834A1

  公开（公告）日：2014-03-27

  The invention relates to a new class of compounds able to inhibit with high affinity and selectivity the 5-HT7 receptor. The invention also relates to the utilization of such compounds as medicaments useful in the treatment and prevention of 5-HT7 receptor relating disorders of the central nervous system. The invention also relates to the isotopically labeled compounds for use in vivo diagnosis or imaging of a 5-HT7 condition.

  该发明涉及一类新的化合物，能够高亲和力和选择性地抑制5-HT7受体。该发明还涉及将这类化合物用作药物，用于治疗和预防中枢神经系统与5-HT7受体相关的疾病。该发明还涉及同位素标记的化合物，用于体内诊断或成像5-HT7状况。
• I-arylpiperazinic ligands of 5-HT7 receptor and use thereof
  申请人：Leopoldo Marcello

  公开号：US09260400B2

  公开（公告）日：2016-02-16

  The invention relates to a new class of compounds able to inhibit with high affinity and selectivity the 5-HT7 receptor and having the following formula IV: wherein W is O; K, L, M and Q is CH or nitrogen; R1 is hydrogen; R2 is hydrogen; and Ar is an aromatic ring with the following formula: wherein X, Y and Z is CH; and R3 is a five- or six-membered ring selected from the group consisting of:

  本发明涉及一种新的化合物类别，能够高亲和力和选择性地抑制5-HT7受体，并具有以下公式IV：其中W为O；K、L、M和Q为CH或氮；R1为氢；R2为氢；而Ar为具有以下公式的芳香环：其中X、Y和Z为CH；而R3为从以下组中选择的五元或六元环：
• New 1-arylpiperazinic ligands of 5-HT7 receptor and use thereof
  申请人：Università degli Studi di Bari "Aldo Moro"

  公开号：EP2816037A2

  公开（公告）日：2014-12-24

  The invention relates to a new class of compounds able to inhibit with high affinity and selectivity the 5-HT7 receptor. The invention also relates to the utilization of such compounds as medicaments useful in the treatment and prevention of 5-HT7 receptor relating disorders of the central nervous system. The invention also relates to the isotopically labeled compounds for use in vivo diagnosis or imaging of a 5-HT7 condition.

  本发明涉及一类能以高亲和力和选择性抑制 5-HT7 受体的新型化合物。本发明还涉及将此类化合物用作治疗和预防与 5-HT7 受体有关的中枢神经系统疾病的药物。本发明还涉及用于 5-HT7 病症体内诊断或成像的同位素标记化合物。
• Novel highly potent serotonin 5-HT7 receptor ligands: Structural modifications to improve pharmacokinetic properties
  作者：Enza Lacivita、Pantaleo Di Pilato、Madia Letizia Stama、Nicola Antonio Colabufo、Francesco Berardi、Roberto Perrone、Bianca De Filippis、Giovanni Laviola、Walter Adriani、Mauro Niso、Marcello Leopoldo

  DOI：10.1016/j.bmcl.2013.09.025

  日期：2013.11

  Here we report the synthesis, pharmacological and pharmacokinetic evaluation of a pilot set of compounds structurally related to the potent and selective 5-HT7 ligand LP-211. Among the studied compounds, N-pyridin-3-ylmethyl-3-[4-[2-(4-methoxyphenyl)phenyl]piperazin-1-yl]ethoxy]propanamide (4b) showed high affinity for 5-HT7 receptors (K-i = 23.8 nM), selectivity over 5-HT1A receptors (>50-fold), in vitro metabolic stability (82%) and weak interaction with P-glycoprotein (BA/AB = 3.3). Compound 4b was injected ip in mice to preliminarily evaluate its distribution between blood and brain. (c) 2013 Elsevier Ltd. All rights reserved.