1,2-bis((4-nitro-2-(trifluoromethyl)phenyl)piperazin-1-yl)ethane

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 二嗪烷类
• 英文名称: 1,2-bis((4-nitro-2-(trifluoromethyl)phenyl)piperazin-1-yl)ethane
• 英文别名: 1-[4-Nitro-2-(trifluoromethyl)phenyl]-4-[2-[4-[4-nitro-2-(trifluoromethyl)phenyl]piperazin-1-yl]ethyl]piperazine；1-[4-nitro-2-(trifluoromethyl)phenyl]-4-[2-[4-[4-nitro-2-(trifluoromethyl)phenyl]piperazin-1-yl]ethyl]piperazine
• 化学式: C₂₄H₂₆F₆N₆O₄
• 分子量: 576.499
• InChiKey: QYRIRLQFUVELKP-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  4.9
• 重原子数：
  40
• 可旋转键数：
  5
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.5
• 拓扑面积：
  105
• 氢给体数：
  0
• 氢受体数：
  14

反应信息

• 作为产物：
  描述：

  1-(4-硝基-2-三氟甲基苯基)-哌嗪 、 1-溴-2-氯乙烷 在 potassium carbonate 作用下， 以 乙腈 为溶剂， 反应 5.25h， 以70%的产率得到1,2-bis((4-nitro-2-(trifluoromethyl)phenyl)piperazin-1-yl)ethane
  参考文献：
  名称：

  Novel aryl piperazines for alleviation of ‘andropause’ associated prostatic disorders and depression

  摘要：

  A series of seventeen piperazine derivatives have been synthesized and biologically evaluated for the management of andropause-associated prostatic disorders and depression. Five compounds 16,19, 20, 21 and 22 significantly inhibited proliferation of androgen-sensitive LNCaP prostatic cell line with EC50 values of 12.4 mu M, 15.6 11.8 mu M, 10.4 mu M, 12.2 mu M respectively and decreased Ca2+ entry through adrenergic-receptor alpha(1A) blocking activity. Anti-androgenic behaviour of compound 19 and 22 was evident by decreased luciferase activity. The high EC50 value in AR-negative cells PC3 and DU145 suggested that the cytotoxicity of compounds was due to AR down regulation. Compound 19 reduced the prostate weight of rats by 53.8%. Further, forced-swimming and tail-suspension tests revealed antidepressant-like activity of compound 19, lacking effects on neuromuscular co-ordination. In silico ADMET predictions revealed that the compound 19 had good oral absorption, aqueous solubility, non-hepatotoxic and good affinity for plasma protein binding. Pharmacokinetic and tissue uptake of 19 at 10 mg/kg demonstrated an oral bioavailability of 35.4%. In silico docking studies predicted similar binding pattern of compound 19 on androgen receptor as hydroxyflutamide. Compound 19 appears to be a unique scaffold with promising activities against androgen associated prostatic disorders in males like prostate cancer and BPH and associated depression. (C) 2017 Elsevier Masson SAS. All rights reserved.

  DOI：

  10.1016/j.ejmech.2017.03.036