3-(1-piperazinylmethyl)-1-tetralone | 169304-32-9

• 分子结构分类: 有机化合物 - 苯类化合物 - 四氢化萘
• 英文名称: 3-(1-piperazinylmethyl)-1-tetralone
• 英文别名: 3-(1-piperazinylmethyl)tetralone；1(2H)-Naphthalenone, 3,4-dihydro-3-(1-piperazinylmethyl)-；3-(piperazin-1-ylmethyl)-3,4-dihydro-2H-naphthalen-1-one
• CAS: 169304-32-9
• 化学式: C₁₅H₂₀N₂O
• 分子量: 244.337
• InChiKey: YICFCGVANOMLFK-UHFFFAOYSA-N

物化性质

• 沸点：
  400.1±25.0 °C(Predicted)
• 密度：
  1?+-.0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  1.3
• 重原子数：
  18
• 可旋转键数：
  2
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.53
• 拓扑面积：
  32.3
• 氢给体数：
  1
• 氢受体数：
  3

反应信息

• 作为反应物：
  描述：

  3-(1-piperazinylmethyl)-1-tetralone 在 氢氧化钾 、 一水合肼 作用下， 以 二乙二醇 为溶剂， 以63%的产率得到2-(piperazinylmethyl)tetraline
  参考文献：
  名称：

  Piperazinomethyl Tetralines: Synthesis and Affinities for D1, D2 and 5-HT2A Receptors.

  摘要：

  从 β-（溴甲基）-γ-苯基丁酸甲酯及其间氟衍生物开始，我们制备了 2-[4-[3-（对氟苯甲酰基）-1-丙基]哌嗪-1-基甲基]四氢萘 (QF0105B) 和相应的 7-氟衍生物 (QF0106B)。体外评估了这些化合物对 D1 和 D2 多巴胺受体以及 5-HT2A 受体的亲和力。QF0105B 和 QF0106B 对 D2 受体的亲和力低于氟哌啶醇（抑制 [3H]spiperone 结合的 pKi 值分别为 7.72、7.06 和 8.30），但这三种化合物对 5-HT2A 受体的亲和力相似（抑制 [3H]ketanserine 结合的 pKi 值分别为 7.70、7.36 和 7.70）。

  DOI：

  10.1248/cpb.43.1234
• 作为产物：
  描述：

  3-苯丙烯溴酸酯 在 palladium on activated charcoal PPA 、 氢气 、 溶剂黄146 作用下， 以 甲醇 、 水 为溶剂， 65.0~120.0 ℃ 、253.31 kPa 条件下， 反应 3.5h， 生成 3-(1-piperazinylmethyl)-1-tetralone
  参考文献：
  名称：

  Synthesis and Structure−Activity Relationships of 1-Aralkyl-4-Benzylpiperidine and 1-Aralkyl-4-Benzylpiperazine Derivatives as Potent σ Ligands

  摘要：

  In the attempt to define more accurately structure-affinity relationships for sigma(1) and sigma(2) ligands, we synthesized and tested on sigma subtype receptors a series of aralkyl derivatives of 4-benzylpiperidine, in which the effect of modifications on the aralkyl moiety was studied in a systematic way. The affinity of the compounds here described varied to a great extent, with a sigma(2)/sigma(1), selectivity ranging from 0.1 to 9. Thus, to confirm the ability of the piperazine derivative to bind to sigma(1) receptors in a different way than piperidines, we synthesized and tested a series of piperazine compounds; the comparison of their affinity with that of the corresponding piperidines strongly supports the possibility of a different binding mode. While the compounds here described are on the whole selective for a vs serotonin 5-HT1A and dopamine D-2 receptors, 9aa, 9ba and 9ab possess a remarkable affinity for both a and 5-HT1A receptors, with K-i in the nanomolar range, and are selective with respect to D2 receptors. They displayed also a partial agonist profile in a human 5-HT1A [S-35]GTPgammaS binding assay, suggesting their potential use as atypical antipsychotic agents.

  DOI：

  10.1021/jm049433t

文献信息

• Synthesis and Structure−Activity Relationships of 1-Aralkyl-4-Benzylpiperidine and 1-Aralkyl-4-Benzylpiperazine Derivatives as Potent σ Ligands
  作者：Luca Costantino、Francesca Gandolfi、Claudia Sorbi、Silvia Franchini、Orazio Prezzavento、Franco Vittorio、Giuseppe Ronsisvalle、Amedeo Leonardi、Elena Poggesi、Livio Brasili

  DOI：10.1021/jm049433t

  日期：2005.1.1

  In the attempt to define more accurately structure-affinity relationships for sigma(1) and sigma(2) ligands, we synthesized and tested on sigma subtype receptors a series of aralkyl derivatives of 4-benzylpiperidine, in which the effect of modifications on the aralkyl moiety was studied in a systematic way. The affinity of the compounds here described varied to a great extent, with a sigma(2)/sigma(1), selectivity ranging from 0.1 to 9. Thus, to confirm the ability of the piperazine derivative to bind to sigma(1) receptors in a different way than piperidines, we synthesized and tested a series of piperazine compounds; the comparison of their affinity with that of the corresponding piperidines strongly supports the possibility of a different binding mode. While the compounds here described are on the whole selective for a vs serotonin 5-HT1A and dopamine D-2 receptors, 9aa, 9ba and 9ab possess a remarkable affinity for both a and 5-HT1A receptors, with K-i in the nanomolar range, and are selective with respect to D2 receptors. They displayed also a partial agonist profile in a human 5-HT1A [S-35]GTPgammaS binding assay, suggesting their potential use as atypical antipsychotic agents.
• Piperazinomethyl Tetralines: Synthesis and Affinities for D1, D2 and 5-HT2A Receptors.
  作者：Enrique RAVINA、Jose CID、Jesus NEGREIRA、Maria E. CASTRO、Victor M. MOLDES、Tomas G-FERREIRO、Elizabeth ROSA、Jose MACALLEJA、Maria L. DE CEBALLOS

  DOI：10.1248/cpb.43.1234

  日期：——

  Starting from the methyl ester of β-(bromomethyl)-γ-phenylbutyric acid and its m-fluoro derivative, we have prepared 2-[4[3-(p-fluorobenzoyl)-1-propyl]piperazin-1-ylmethyl]tetraline (QF0105B) and the corresponding 7-fluoro derivative (QF0106B). The affinities of these compounds for D1 and D2 dopamine and 5-HT2A receptors was evaluated in vitro. The afinities of QF0105B and QF0106B for D2 receptors are less than that of haloperidol (pKi's for inhibition of [3H]spiperone binding : 7.72, 7.06 and 8.30, respectively) but all three compounds have similar affinities for 5-HT2A receptors (pKi'S for inhibition of [3H]ketanserine binding : 7.70, 7.36 and 7.70, respectively).

  从 β-（溴甲基）-γ-苯基丁酸甲酯及其间氟衍生物开始，我们制备了 2-[4-[3-（对氟苯甲酰基）-1-丙基]哌嗪-1-基甲基]四氢萘 (QF0105B) 和相应的 7-氟衍生物 (QF0106B)。体外评估了这些化合物对 D1 和 D2 多巴胺受体以及 5-HT2A 受体的亲和力。QF0105B 和 QF0106B 对 D2 受体的亲和力低于氟哌啶醇（抑制 [3H]spiperone 结合的 pKi 值分别为 7.72、7.06 和 8.30），但这三种化合物对 5-HT2A 受体的亲和力相似（抑制 [3H]ketanserine 结合的 pKi 值分别为 7.70、7.36 和 7.70）。