2-(4-benzhydrylpiperazin-1-yl)-1-(4-bromophenyl)ethanol

• 分子结构分类: 有机化合物 - 苯类化合物 - 苯和取代衍生物
• 英文名称: 2-(4-benzhydrylpiperazin-1-yl)-1-(4-bromophenyl)ethanol
• 化学式: C₂₅H₂₇BrN₂O
• 分子量: 451.406
• InChiKey: PCJGPMGDUSSPRY-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  4.8
• 重原子数：
  29
• 可旋转键数：
  6
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.28
• 拓扑面积：
  26.7
• 氢给体数：
  1
• 氢受体数：
  3

反应信息

• 作为产物：
  描述：

  1-benzhydryl-4-(4-bromophenacyl)piperazine 在 sodium tetrahydroborate 作用下， 以 乙醇 为溶剂， 以78%的产率得到2-(4-benzhydrylpiperazin-1-yl)-1-(4-bromophenyl)ethanol
  参考文献：
  名称：

  Compounds Interacting with the Neuroexcitatory Amino Acids: Synthesis of 2-(4-Aralkylpiperazine-1-yl)-1-arylethanols

  摘要：

  氨基酮Ia - If和III被合成。它们的还原产生相应的醇IIa - IIf，IVa和IVb。这些通过生化和行为药理学方法进行评估。

  DOI：

  10.1135/cccc19940658

文献信息

• Synthesis and Structure-Activity Relationships of 2-(4-Benzhydryl-1-piperazinyl)-1-phenylethanols as New Calcium Blocker.
  作者：Yutaka NOMURA、Tomio YAMAKAWA、Koichiro NISHIOKA、Tomohiro OMURA、Norihisa MIYAKE、Mitsuo MASAKI、Hiroyuki NOHIRA

  DOI：10.1248/cpb.43.241

  日期：——

  A series of 2-(4-benzhydryl-1-piperazinyl)-1-phenylethanols (4) was synthesized and evaluated for calcium entry-blocking activity, assessed as inhibitory activity on calcium current in rat hippocampal pyramidal neurons by using a patch-clamp technique (10-5 M), and cerebral visodilating activity, assessed in terms of increase of vertebral blood flow after intravenous administration (1 mg/kg) in anesthetized dogs. Alkoxy substituents on the phenyl ring of the phenylethanol moiety conferred potent calcium entry-blocking activity and potent cerebral vesodilating activity.Among these compounds, 4i (NC-1100) was selected as the best analog. Some pharmacological properties of 4i are presented.

  一系列2-(4-二苯甲基-1-哌嗪基)-1-苯乙醇（4）被合成并评估了它们阻止钙进入的活性，这种活性通过使用膜片钳技术（10-5 M）在鼠海马椎体神经元中测定钙电流的抑制活性，以及脑血管舒张活性，这种活性根据静脉给药后（1 mg/kg）在麻醉狗中椎动脉血流增加的程度来评估。苯乙醇部分的苯环上的烷氧基取代赋予了强大的阻止钙进入的活性和强大的脑血管舒张活性。在这些化合物中，4i（NC-1100）被选为最佳类似物。一些4i的药理特性被呈现。
• Compounds Interacting with the Neuroexcitatory Amino Acids: Synthesis of 2-(4-Aralkylpiperazine-1-yl)-1-arylethanols
  作者：Alexandra Šilhánková、Karel Dobrovský、Ivan Krejčí、Zdeněk Polívka

  DOI：10.1135/cccc19940658

  日期：——

  Amino ketones Ia - If and III were synthesized. Their reduction gave corresponding alcohols IIa - IIf, IVa and IVb. These were evaluated by methods of biochemical and behavioural pharmacology.

  氨基酮Ia - If和III被合成。它们的还原产生相应的醇IIa - IIf，IVa和IVb。这些通过生化和行为药理学方法进行评估。
• 苯基哌嗪衍生物及其制备方法与用途
  申请人：山东理工大学

  公开号：CN103804322B

  公开（公告）日：2016-05-18

  本发明属于有机合成领域，具体涉及一种苯基哌嗪衍生物及其制备方法与用途。将2,4’-二溴苯乙酮、取代哌嗪、碳酸钾与乙腈置于带有回流装置的圆底烧瓶中，油浴加热，回流反应，然后滤去沉淀，蒸干滤液，用水和乙酸乙酯萃取，保留有机层，无水硫酸钠干燥后蒸干得到产物；将产物与NaBH4进行反应，反应溶剂为乙醇，常温反应，反应完全后蒸干溶剂，用水和乙酸乙酯萃取，保留有机溶剂层，无水硫酸钠干燥后蒸干得到苯基哌嗪衍生物。本发明将具有良好抗癌活性的2,4’-二溴苯乙酮引入苯基哌嗪环，制备含有溴苯乙酮的苯基哌嗪类衍生物。苯基哌嗪衍生物对癌细胞生长有明显的抑制作用，可以应用于制备抗癌药物。
• Discovery of phenylpiperazine derivatives as IGF-1R inhibitor with potent antiproliferative properties in vitro
  作者：Feng-Jiao Guo、Juan Sun、Li-Li Gao、Xin-Yi Wang、Yang Zhang、Shao-Song Qian、Hai-Liang Zhu

  DOI：10.1016/j.bmcl.2015.01.011

  日期：2015.3

  A series of phenylpiperazine derivatives (3a-3q) were designed and synthesized. In vitro assays indicated that several phenylpiperazine derivatives had excellent antiproliferative properties against four cancer cell lines including multidrug-resistant cancer cell lines, with IC50 values in the low micromolar range. The average IC50 of the most active compound 3b is 0.024 mu M to the MCF-7 cell line. In addition, the mechanism of action of these new analogues was investigated by molecular docking studies, insulin-like growth factor 1-receptor (IGF-1R) kinase assay and apoptosis induced assay. These studies confirmed that these new phenylpiperazine derivatives maintain their mechanisms of action by disrupting IGF-1R kinase. (C) 2015 Elsevier Ltd. All rights reserved.