4-(4-(7-phenoxyheptyl)piperazin-1-yl)butan-1-amine | 1383629-87-5

• 分子结构分类: 有机化合物 - 苯类化合物 - 苯酚醚
• 英文名称: 4-(4-(7-phenoxyheptyl)piperazin-1-yl)butan-1-amine
• 英文别名: 1-[7-Phenoxyheptyl)-4-(4-aminobutyl]piperazine；4-[4-(7-phenoxyheptyl)piperazin-1-yl]butan-1-amine
• CAS: 1383629-87-5
• 化学式: C₂₁H₃₇N₃O
• 分子量: 347.544
• InChiKey: GLIWPDHUHGSFQT-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.5
• 重原子数：
  25
• 可旋转键数：
  13
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.71
• 拓扑面积：
  41.7
• 氢给体数：
  1
• 氢受体数：
  4

反应信息

• 作为反应物：
  描述：

  4-(4-(7-phenoxyheptyl)piperazin-1-yl)butan-1-amine 在 lithium aluminium tetrahydride 、 乙酸酐 、 三乙胺 作用下， 以 乙醚 、 二氯甲烷 为溶剂， 反应 3.0h， 生成
  参考文献：
  名称：

  1-Phenoxyalkyl-4-[(N,N-disubstitutedamino)alkyl]piperazine derivatives as non-imidazole histamine H3-antagonists

  摘要：

  In this study, a series of 1-phenoxyalkyl-4-[(N,N-disubstitutedamino)alkyl]piperazine derivatives has been prepared and in vitro tested as H-3-receptor antagonists (electrically evoked contraction of the guinea pig jejunum). All compounds investigated show moderate in vitro affinities. The most potent antagonists in this series are the compounds 9b, 1b, 1f, and 1l, which exhibit, independently of the substituent at the end of -N- moiety, almost the same level of affinity (pA (2) = 7.18, pA (2) = 7.27, pA (2) = 7.13, pA (2) = 7.12, respectively). The histaminergic H-1 antagonism of the aforementioned four products was established on the isolated guinea pig ileum by conventional methods; the pA (2) values were compared with the potency of pyrilamine. None of them shows any H-1-antagonistic activity (pA (2) < 4; for pyrilamine pA (2) = 9.35).

  DOI：

  10.1007/s00044-012-0090-2
• 作为产物：
  描述：

  1-bromo-7-phenoxyheptane 在 lithium aluminium tetrahydride 、 potassium carbonate 作用下， 以 甲醇 、 乙醚 、 乙腈 为溶剂， 反应 46.5h， 生成 4-(4-(7-phenoxyheptyl)piperazin-1-yl)butan-1-amine
  参考文献：
  名称：

  1-Phenoxyalkyl-4-[(N,N-disubstitutedamino)alkyl]piperazine derivatives as non-imidazole histamine H3-antagonists

  摘要：

  In this study, a series of 1-phenoxyalkyl-4-[(N,N-disubstitutedamino)alkyl]piperazine derivatives has been prepared and in vitro tested as H-3-receptor antagonists (electrically evoked contraction of the guinea pig jejunum). All compounds investigated show moderate in vitro affinities. The most potent antagonists in this series are the compounds 9b, 1b, 1f, and 1l, which exhibit, independently of the substituent at the end of -N- moiety, almost the same level of affinity (pA (2) = 7.18, pA (2) = 7.27, pA (2) = 7.13, pA (2) = 7.12, respectively). The histaminergic H-1 antagonism of the aforementioned four products was established on the isolated guinea pig ileum by conventional methods; the pA (2) values were compared with the potency of pyrilamine. None of them shows any H-1-antagonistic activity (pA (2) < 4; for pyrilamine pA (2) = 9.35).

  DOI：

  10.1007/s00044-012-0090-2

文献信息

• Design, synthesis, and<i>in vitro</i>and<i>in vivo</i>characterization of 1-{4-[4-(substituted)piperazin-1-yl]butyl}guanidines and their piperidine analogues as histamine H₃receptor antagonists
  作者：Marek Staszewski、Anna Stasiak、Tadeusz Karcz、Daniel McNaught Flores、Wiesława Agnieszka Fogel、Katarzyna Kieć-Kononowicz、Rob Leurs、Krzysztof Walczyński

  DOI：10.1039/c8md00527c

  日期：——

  antagonistic activity against the histamine H3 receptor. Additionally, the most active compounds 1a, 1c, and 1d were evaluated for their affinity to the rat histamine H3 receptor and the human histamine H3 and H4 receptors. It was also shown that compounds 1a, 1c and 1d, given parenterally for five days, reduced the food intake of rats and did not influence the brain histamine or noradrenaline concentrations;

  以前，我们已经证明 1-取代的-[4-(7-苯氧基庚基哌嗪-1-基)丁基]胍在苄基部分的第 4 位具有吸电子取代基，对豚鼠空肠组胺 H3 受体具有很高的体外亲和力。 pA 2 范围为 8.49 至 8.43。在这里，我们提供了哌啶环（化合物 2a 和 2b）取代哌嗪支架的影响的数据，将苄基和 4-三氟甲基苄基取代基从胍部分的位置 1 移动到 3（化合物 2c 和 2d），其中降低胍碱度（化合物 2e），以及存在于先导化合物 1b 和 1c 中的单个合成子（化合物 2f-h）对组胺 H3 受体拮抗活性的影响。此外，最活跃的化合物 1a、1c、评估了 1d 和 1d 对大鼠组胺 H3 受体和人组胺 H3 和 H4 受体的亲和力。还表明，化合物 1a、1c 和 1d，肠胃外给药 5 天，减少了大鼠的食物摄入，并且不影响脑组胺或去甲肾上腺素浓度；然而，分别在给予化合物 1a 和 1c 的大鼠中发现血清素和多巴胺浓度显着降低。