2-(4-(4-nitro-2-(trifluoromethyl)phenyl)piperazin-1-yl)pyrimidine | 1259332-92-7

• 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: 2-(4-(4-nitro-2-(trifluoromethyl)phenyl)piperazin-1-yl)pyrimidine
• 英文别名: 2-[4-[4-Nitro-2-(trifluoromethyl)phenyl]piperazin-1-yl]pyrimidine
• CAS: 1259332-92-7
• 化学式: C₁₅H₁₄F₃N₅O₂
• 分子量: 353.304
• InChiKey: NXYONIYYGZVYFR-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3
• 重原子数：
  25
• 可旋转键数：
  2
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.33
• 拓扑面积：
  78.1
• 氢给体数：
  0
• 氢受体数：
  9

反应信息

• 作为产物：
  描述：

  1-(2-嘧啶基)哌嗪 、 2-氯-5-硝基三氟甲苯 在 三乙胺 作用下， 以75%的产率得到2-(4-(4-nitro-2-(trifluoromethyl)phenyl)piperazin-1-yl)pyrimidine
  参考文献：
  名称：

  Arylpiperazines for Management of Benign Prostatic Hyperplasia: Design, Synthesis, Quantitative Structure−Activity Relationships, and Pharmacokinetic Studies

  摘要：

  A series of 27 aryl/heteroaryl/aralkyl/aroyl piperazines were synthesized, and most of these compounds reduced prostate weight of mature rats by 15-47% Three compounds, 10, 12, and 18, had better activity profile (reduced prostate weight by 47%, 43%, and 39%, respectively) than the standard drug flutamide (24% reduction) QSAR suggested structures with more cyclic and branched moieties, increased topological separation of 0 and N therein, and reduced solvation connectivity index for better activity Pharmacokinetic study with compound 10 at an oral dose of 10 0 mg/kg indicated good absorption, negligible extrahepatic elimination, and rapid distribution to the target organ (prostate) but restricted entry through the blood brain barrier A 10-fold decrease in PSA and 15-fold increase in ER-beta gene expressions of human prostate cancer cells (LNCaP) by compound 10 in vitro indicated AR and ER-beta mediated actions The findings may stimulate further explorations of identified lead for the management of benign prostatic hyperplasia

  DOI：

  10.1021/jm101163m

文献信息

• Arylpiperazines for Management of Benign Prostatic Hyperplasia: Design, Synthesis, Quantitative Structure−Activity Relationships, and Pharmacokinetic Studies
  作者：Amit Sarswat、Rajeev Kumar、Lalit Kumar、Nand Lal、Smriti Sharma、Yenamandra S. Prabhakar、Shailendra K. Pandey、Jawahar Lal、Vikas Verma、Ashish Jain、Jagdamba P. Maikhuri、Diwakar Dalela、Kirti、Gopal Gupta、Vishnu L. Sharma

  DOI：10.1021/jm101163m

  日期：2011.1.13

  A series of 27 aryl/heteroaryl/aralkyl/aroyl piperazines were synthesized, and most of these compounds reduced prostate weight of mature rats by 15-47% Three compounds, 10, 12, and 18, had better activity profile (reduced prostate weight by 47%, 43%, and 39%, respectively) than the standard drug flutamide (24% reduction) QSAR suggested structures with more cyclic and branched moieties, increased topological separation of 0 and N therein, and reduced solvation connectivity index for better activity Pharmacokinetic study with compound 10 at an oral dose of 10 0 mg/kg indicated good absorption, negligible extrahepatic elimination, and rapid distribution to the target organ (prostate) but restricted entry through the blood brain barrier A 10-fold decrease in PSA and 15-fold increase in ER-beta gene expressions of human prostate cancer cells (LNCaP) by compound 10 in vitro indicated AR and ER-beta mediated actions The findings may stimulate further explorations of identified lead for the management of benign prostatic hyperplasia