1-(3-bromopropyl)-5-methoxynaphthalene | 385810-79-7

• 分子结构分类: 有机化合物 - 苯类化合物 - 萘
• 英文名称: 1-(3-bromopropyl)-5-methoxynaphthalene
• CAS: 385810-79-7
• 化学式: C₁₄H₁₅BrO
• 分子量: 279.176
• InChiKey: QFJROTMRCJHOKL-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  4.5
• 重原子数：
  16
• 可旋转键数：
  4
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.29
• 拓扑面积：
  9.2
• 氢给体数：
  0
• 氢受体数：
  1

反应信息

• 作为反应物：
  描述：

  1-环己基哌嗪 、 1-(3-bromopropyl)-5-methoxynaphthalene 在 sodium carbonate 作用下， 以 乙腈 为溶剂， 生成 1-cyclohexyl-4-[3-(5-methoxy-naphthalen-1-yl)-propyl]-piperazine
  参考文献：
  名称：

  1-环己基哌嗪的4-（四氢-1-基）-和4-（萘-1-基）烷基衍生物作为具有激动剂sigma2活性的sigma受体配体。

  摘要：

  与sigma（2）受体配体1-cyclohexyl-4- [3-（5-甲氧基-1,2,3,4-四氢萘-1-基）丙基]哌嗪有关的几种1-cyclohexylpiperazine衍生物（33，K（i合成＝ 0.34nM）并在放射性配体结合测定中测试，以尝试结构亲和关系研究。中间烷基链长度和四氢化萘核上的甲氧基位置是变化的。还制备了一些萘类似物。在几乎所有化合物的sigma（2）受体结合物中都发现了高亲和力，其中一些化合物在亚纳摩尔范围内显示出K（i）值，但是发现了低sigma（2）/ sigma（1）选择性。具有三个（32和43）或五个亚甲基（39和46）的中间烷基链的化合物显示出最高的sigma（2）亲和力。发现具有四亚甲基链的化合物具有相当高的sigma（1）受体亲和力。36（K（i）= 0.036 nM）和45（K（i）= 0.22 nM）显示出良好的sigma（1）/ sigma（2）

  DOI：

  10.1021/jm031026e
• 作为产物：
  描述：

  1-(3-bromopropyl)-5-methoxy-1,2,3,4-tetrahydronaphthalene 在 2,3-二氯-5,6-二氰基-1,4-苯醌 作用下， 以 甲苯 为溶剂， 反应 4.0h， 以65%的产率得到1-(3-bromopropyl)-5-methoxynaphthalene
  参考文献：
  名称：

  1-环己基哌嗪的4-（四氢-1-基）-和4-（萘-1-基）烷基衍生物作为具有激动剂sigma2活性的sigma受体配体。

  摘要：

  与sigma（2）受体配体1-cyclohexyl-4- [3-（5-甲氧基-1,2,3,4-四氢萘-1-基）丙基]哌嗪有关的几种1-cyclohexylpiperazine衍生物（33，K（i合成＝ 0.34nM）并在放射性配体结合测定中测试，以尝试结构亲和关系研究。中间烷基链长度和四氢化萘核上的甲氧基位置是变化的。还制备了一些萘类似物。在几乎所有化合物的sigma（2）受体结合物中都发现了高亲和力，其中一些化合物在亚纳摩尔范围内显示出K（i）值，但是发现了低sigma（2）/ sigma（1）选择性。具有三个（32和43）或五个亚甲基（39和46）的中间烷基链的化合物显示出最高的sigma（2）亲和力。发现具有四亚甲基链的化合物具有相当高的sigma（1）受体亲和力。36（K（i）= 0.036 nM）和45（K（i）= 0.22 nM）显示出良好的sigma（1）/ sigma（2）

  DOI：

  10.1021/jm031026e

文献信息

• 4-(Tetralin-1-yl)- and 4-(Naphthalen-1-yl)alkyl Derivatives of 1-Cyclohexylpiperazine as σ Receptor Ligands with Agonist σ₂ Activity
  作者：Francesco Berardi、Savina Ferorelli、Carmen Abate、Nicola Antonio Colabufo、Marialessandra Contino、Roberto Perrone、Vincenzo Tortorella

  DOI：10.1021/jm031026e

  日期：2004.4.1

  Several 1-cyclohexylpiperazine derivatives related to sigma(2) receptor ligand 1-cyclohexyl-4-[3-(5-methoxy-1,2,3,4-tetrahydronaphthalen-1-yl)propyl]piperazine (33, K(i) = 0.34 nM) were synthesized and tested in radioligand binding assays, to attempt a structure-affinity relationship study. Intermediate alkyl chain length and methoxyl group position on the tetralin nucleus were varied. A few naphthalene

  与sigma（2）受体配体1-cyclohexyl-4- [3-（5-甲氧基-1,2,3,4-四氢萘-1-基）丙基]哌嗪有关的几种1-cyclohexylpiperazine衍生物（33，K（i合成＝ 0.34nM）并在放射性配体结合测定中测试，以尝试结构亲和关系研究。中间烷基链长度和四氢化萘核上的甲氧基位置是变化的。还制备了一些萘类似物。在几乎所有化合物的sigma（2）受体结合物中都发现了高亲和力，其中一些化合物在亚纳摩尔范围内显示出K（i）值，但是发现了低sigma（2）/ sigma（1）选择性。具有三个（32和43）或五个亚甲基（39和46）的中间烷基链的化合物显示出最高的sigma（2）亲和力。发现具有四亚甲基链的化合物具有相当高的sigma（1）受体亲和力。36（K（i）= 0.036 nM）和45（K（i）= 0.22 nM）显示出良好的sigma（1）/ sigma（2）
• <i>trans</i>-4-[4-(Methoxyphenyl)cyclohexyl]-1-arylpiperazines:  A New Class of Potent and Selective 5-HT_1A Receptor Ligands as Conformationally Constrained Analogues of 4-[3-(5-Methoxy-1,2,3,4-tetrahydronaphthalen-1-yl)propyl]-1- arylpiperazines
  作者：Roberto Perrone、Francesco Berardi、Nicola A. Colabufo、Marcello Leopoldo、Enza Lacivita、Vincenzo Tortorella、Amedeo Leonardi、Elena Poggesi、Rodolfo Testa

  DOI：10.1021/jm010866v

  日期：2001.12.1

  The present paper concerns the influence of conformational parameters on the recognition by rat 5-HT1A receptors of derivatives 4-[3-(5-methoxy-1,2,3,4-tetrahydronaphthalen-1-yl)propyl]-1-(2-pyridinyl)piperazine (1a) and 3-(5-methoxy-1,2,3,4-tetrahydronaphthalen-1-yl)-N-[2-(2-pyridyloxy)ethyl]propanamine (3b), two highly potent and selective 5-HT1A receptor ligands. Fifteen corresponding flexible and rigid analogues were prepared following several synthetic routes and were tested in binding assays with radioligands at 5-HT1A, D-2, and alpha (1) receptors from rat brain membranes. Among the new derivatives emerged trans-4-[4-(3-methoxyphenyl)-cyclohexyl]-1-(2-pyridinyl)piperazine (trans-8a) and trans-N-[4-(3-methoxyphenyl)cyclohexyl]-2-(2-pyridyloxy)ethylamine (trans-8b). These compounds can be-considered as conformationally constrained analogues of compounds 1a and 3a, respectively. In fact, compounds trans-8a and trans-8b showed a marked enhancement in 5-HT1A receptor affinity when compared to the corresponding cis isomers. Because compound trans-8a was a potent and selective 5-HT1A ligand (K-i, nM: 5-HT1A = 0.028, D-2 = 2194, alpha (1) = 767), it was chosen as a lead to prepare other analogues that were tested at 5-HT1A, D-2, and alpha (1) receptors from rat brain membranes, showing high affinity at the 5-HT1A and selectivity vs D-2 and alpha (1) receptors. Selected compounds were tested for their affinity at the human cloned 5-HT1A, alpha (1a), alpha (1b), alpha (1d) receptor subtypes. They were also submitted to the [S-35]GTP gammaS binding assay stimulating the 5-HT1A receptor-mediated G-protein activation, therefore behaving as full or as partial agonists. Finally, the ability of iv administration of trans-8a to induce fore-paw treading in rats was evaluated in comparison with 8-OH-DPAT. Although the affinity (K-i) and in vitro activity (pD'(2)) of trans-8a at the 5-HT1A receptor were higher than those of 8-OH-DPAT, the compound was less potent than the reference standard in inducing the symptom.
• Design and Evaluation of Naphthol- and Carbazole-Containing Fluorescent σ Ligands as Potential Probes for Receptor Binding Studies
  作者：Savina Ferorelli、Carmen Abate、Nicola Antonio Colabufo、Mauro Niso、Carmela Inglese、Francesco Berardi、Roberto Perrone

  DOI：10.1021/jm070373b

  日期：2007.9.1

  Some 3,3-dimethyl-1-(3-naphthylpropyl)piperidine and 1-cyclohexyl-4-(3-naphthylpropyl)piperazine derivatives, structurally containing naphthol as a fluorescent moiety, were prepared for being potentially used as fluorescent sigma ligands. Structurally related analogs were also prepared, where the naphthalene nucleus was replaced by the fluorescent carbazole moiety and chain length was varied. For all

  制备了一些结构上含有萘酚作为荧光部分的3，3-二甲基-1-（3-萘基丙基）哌啶和1-环己基-4-（3-萘基丙基）哌嗪衍生物，它们有可能被用作荧光σ配体。还制备了结构相关的类似物，其中萘核被荧光咔唑部分取代，并且链长变化。对于所有化合物，均测量了对sigma受体和Delta8-Delta7固醇异构酶位点的体外亲和力，并确定了荧光性质。化合物19的sigma受体亲和力（sigma1，Ki = 6.78 nM和sigma2，Ki = 26.4 nM）和荧光特征均给出了最佳结果。因此，它被选择用于sigma受体的体外饱和结合分析。