1-(3-bromopropyl)-6-methoxynaphthalene | 874624-42-7

• 分子结构分类: 有机化合物 - 苯类化合物 - 萘
• 英文名称: 1-(3-bromopropyl)-6-methoxynaphthalene
• CAS: 874624-42-7
• 化学式: C₁₄H₁₅BrO
• 分子量: 279.176
• InChiKey: DZEUMQOGSIFRNB-UHFFFAOYSA-N

物化性质

• 沸点：
  367.5±17.0 °C(Predicted)
• 密度：
  1.329±0.06 g/cm3(Predicted)

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：

  2,2,6,6-四甲基哌啶 、 1-(3-bromopropyl)-6-methoxynaphthalene 在 sodium carbonate 、 potassium iodide 作用下， 以 乙腈 为溶剂， 反应 48.0h， 以15%的产率得到1-[3-(6-Methoxynaphthalen-1-yl)propyl]-2,2,6,6-tetramethylpiperidine
  参考文献：
  名称：

  Investigation of σ receptors agonist/antagonist activity through N-(6-methoxytetralin-1-yl)- and N-(6-methoxynaphthalen-1-yl)alkyl derivatives of polymethylpiperidines

  摘要：

  A series of polymethyl-substituted piperidines linked to either a 6-methoxy-1,2,3,4-tetrahydronaphthalen-l-yl or a 6-methoxynaphthalen-1-yl moiety was generated with the aim of verifying a previously generated hypothesis: tetralin and naphthalene nuclei confer opposite activity at the sigma(1) receptor. Compounds 6, 9 and 10 displayed appreciable affinity at both sigma subtypes, but none of the novel compounds displayed significant antiproliferative activity in MCF7wt and MCF7 sigma 1 cell lines. The effect on bradikynin-triggered Ca2+ mobilization was studied as a methodology to suggest a receptors mediated activity. (C) 2013 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.bmc.2013.01.034
• 作为产物：
  描述：

  1-(3-bromo-n-propyl)-6-methoxy-1,2,3,4-tetrahydronaphthalene 在 2,3-二氯-5,6-二氰基-1,4-苯醌 作用下， 以65%的产率得到1-(3-bromopropyl)-6-methoxynaphthalene
  参考文献：
  名称：

  N- [ω-（6-甲氧基萘-1-基）烷基]衍生物的哌啶环上的甲基取代基，作为在sigma（1）受体上的选择性结合和活性的探针。

  摘要：

  制备了各种甲基哌啶的N-（6-甲氧基-1,2,3,4-四氢萘-1-基）丙基和N-（6-甲氧基萘-1-基）丙基衍生物以及它们的高级同源丁基衍生物。 。带有单甲基或双甲基二甲基基团的哌啶部分被用作探针，通过在sigma（1）和sigma（2）受体以及Delta（8）-Delta（7）固醇异构酶的放射性配体结合测定来探索sigma-subtype亲和力和选择性（SI）网站。4-甲基衍生物31是最有效的sigma（1）配体（K（i）= 0.030 nM），具有良好的选择性（相对于sigma（2）受体和SI位点分别为597倍和268倍），而3,3-二甲基衍生物26（K（i）= 0.35 nM）是相对于sigma（2）受体最具选择性的（680倍）。两种化合物都可以作为PET实验的工具。此外，

  DOI：

  10.1021/jm050654o

文献信息

• Methyl Substitution on the Piperidine Ring of <i>N</i>-[ω-(6-Methoxynaphthalen-1-yl)alkyl] Derivatives as a Probe for Selective Binding and Activity at the σ₁ Receptor
  作者：Francesco Berardi、Savina Ferorelli、Carmen Abate、Maria P. Pedone、Nicola A. Colabufo、Marialessandra Contino、Roberto Perrone

  DOI：10.1021/jm050654o

  日期：2005.12.1

  pyl derivatives as well as their upper homologous butyl derivatives of various methylpiperidines were prepared. The piperidine moiety bearing monomethyl or geminal dimethyl groups was employed as a probe to explore sigma-subtype affinities and selectivities by radioligand binding assays at sigma(1) and sigma(2) receptors and the Delta(8)-Delta(7) sterol isomerase (SI) site. 4-Methyl derivative 31 was

  制备了各种甲基哌啶的N-（6-甲氧基-1,2,3,4-四氢萘-1-基）丙基和N-（6-甲氧基萘-1-基）丙基衍生物以及它们的高级同源丁基衍生物。 。带有单甲基或双甲基二甲基基团的哌啶部分被用作探针，通过在sigma（1）和sigma（2）受体以及Delta（8）-Delta（7）固醇异构酶的放射性配体结合测定来探索sigma-subtype亲和力和选择性（SI）网站。4-甲基衍生物31是最有效的sigma（1）配体（K（i）= 0.030 nM），具有良好的选择性（相对于sigma（2）受体和SI位点分别为597倍和268倍），而3,3-二甲基衍生物26（K（i）= 0.35 nM）是相对于sigma（2）受体最具选择性的（680倍）。两种化合物都可以作为PET实验的工具。此外，
• Investigation of σ receptors agonist/antagonist activity through N-(6-methoxytetralin-1-yl)- and N-(6-methoxynaphthalen-1-yl)alkyl derivatives of polymethylpiperidines
  作者：Mauro Niso、Carmen Abate、Savina Ferorelli、Giuseppe Cassano、Giuseppe Gasparre、Roberto Perrone、Francesco Berardi

  DOI：10.1016/j.bmc.2013.01.034

  日期：2013.4

  A series of polymethyl-substituted piperidines linked to either a 6-methoxy-1,2,3,4-tetrahydronaphthalen-l-yl or a 6-methoxynaphthalen-1-yl moiety was generated with the aim of verifying a previously generated hypothesis: tetralin and naphthalene nuclei confer opposite activity at the sigma(1) receptor. Compounds 6, 9 and 10 displayed appreciable affinity at both sigma subtypes, but none of the novel compounds displayed significant antiproliferative activity in MCF7wt and MCF7 sigma 1 cell lines. The effect on bradikynin-triggered Ca2+ mobilization was studied as a methodology to suggest a receptors mediated activity. (C) 2013 Elsevier Ltd. All rights reserved.
• 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。