1-ethyl-4-{4-[α-(1-tricyclo[3.3.1.1(3,7)]decyl)phenylmethyl]phenyl}piperazine | 1041003-31-9

• 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: 1-ethyl-4-{4-[α-(1-tricyclo[3.3.1.1(3,7)]decyl)phenylmethyl]phenyl}piperazine
• 英文别名: 1-[4-[1-Adamantyl(phenyl)methyl]phenyl]-4-ethylpiperazine
• CAS: 1041003-31-9
• 化学式: C₂₉H₃₈N₂
• 分子量: 414.634
• InChiKey: YVRGGVNLKYVRQU-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  7.4
• 重原子数：
  31
• 可旋转键数：
  5
• 环数：
  7.0
• sp3杂化的碳原子比例：
  0.59
• 拓扑面积：
  6.5
• 氢给体数：
  0
• 氢受体数：
  2

反应信息

• 作为产物：
  描述：

  N-乙基哌嗪 、 α-(1-adamantyl)benzhydryl chloride 反应 12.0h， 以41%的产率得到1-ethyl-4-{4-[α-(1-tricyclo[3.3.1.1(3,7)]decyl)phenylmethyl]phenyl}piperazine
  参考文献：
  名称：

  Synthesis, σ1, σ2-receptors binding affinity and antiproliferative action of new C1-substituted adamantanes

  摘要：

  The synthesis of N-{4-[a-(1-adamantyl)benzyl]phenyl}piperazines 2a-e is described. The in vitro antiproliferative activity of most compounds against main cancer cell lines is significant. The sigma(1),sigma(2)-receptors and sodium channels binding affinity of compounds 2 were investigated. One of the most active analogs, 2a, had an interesting in vivo anticancer profile against the BxPC-3 and Mia-Paca-2 pancreas cancer cell lines with caspase-3 activation, which was associated with an anagelsic activity against the neuropathic pain. (C) 2012 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.bmc.2012.03.038

文献信息

• SIGMA(s)-RECEPTOR LIGANDS WITH ANTI-APOPTOTIC AND/OR PRO-APOPTOTIC PROPERTIES OVER CELLULAR BIOCHEMICAL MECHANISMS, WITH NEUROPROTECTIVE, ANTI-CANCER, ANTI-METASTATIC AND ANTI-(CHRONIC) INFLAMMATORY ACTION
  申请人：Vamvakides Alexandre

  公开号：US20100069484A1

  公开（公告）日：2010-03-18

  The present invention involves new and original sigma receptors ligands : (Mono- or di-alkylaminoalkyl)-γ-butyrolactones, their analogues aminotetrahydrofuranes, the (1-adamantyl)phenyl(s) alkylamines, the N,N Dialkyl α-[(adamantyl-1)benzyloxy-2] alkylamines and the 3-cyclopentyl adamantyl-amines or alkylamines or -alkyl phenylamines, their enantiomers or diastereoisomers and their pharmaceutically acceptable salts, with pro-apoptotic and/or anti-apoptotic properties over cellular bio-chemical mechanisms, with anti-cancer, anti-metastatic, anti-(chronic) inflammatory, neuro-protective, anticonvulsive, antidepressive and nooanaleptic or sedative action.
• Synthesis, σ1, σ2-receptors binding affinity and antiproliferative action of new C1-substituted adamantanes
  作者：Stefanos Riganas、Ioannis Papanastasiou、George B. Foscolos、Andrew Tsotinis、Jean-Jacques Bourguignon、Guillaume Serin、Jean-François Mirjolet、Kostas Dimas、Vassilios N. Kourafalos、Andreas Eleutheriades、Vassilios I. Moutsos、Humaira Khan、Stavroula Georgakopoulou、Angeliki Zaniou、Margarita Prassa、Maria Theodoropoulou、Stavroula Pondiki、Alexandre Vamvakides

  DOI：10.1016/j.bmc.2012.03.038

  日期：2012.5

  The synthesis of N-4-[a-(1-adamantyl)benzyl]phenyl}piperazines 2a-e is described. The in vitro antiproliferative activity of most compounds against main cancer cell lines is significant. The sigma(1),sigma(2)-receptors and sodium channels binding affinity of compounds 2 were investigated. One of the most active analogs, 2a, had an interesting in vivo anticancer profile against the BxPC-3 and Mia-Paca-2 pancreas cancer cell lines with caspase-3 activation, which was associated with an anagelsic activity against the neuropathic pain. (C) 2012 Elsevier Ltd. All rights reserved.