phenyl(4-(pyrimidin-2-yl)piperazin-1-yl)methanone | 545429-39-8

• 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: phenyl(4-(pyrimidin-2-yl)piperazin-1-yl)methanone
• 英文别名: Phenyl-(4-pyrimidin-2-ylpiperazin-1-yl)methanone
• CAS: 545429-39-8
• 化学式: C₁₅H₁₆N₄O
• mdl: MFCD00860992
• 分子量: 268.318
• InChiKey: UVRGBFKYBAZGMZ-UHFFFAOYSA-N

物化性质

• 熔点：
  113-115 °C(Solv: ethyl acetate (141-78-6); hexane (110-54-3))
• 沸点：
  486.0±55.0 °C(Predicted)
• 密度：
  1.240±0.06 g/cm3(Predicted)
• 溶解度：
  >40.2 [ug/mL]

计算性质

• 辛醇/水分配系数(LogP)：
  1.6
• 重原子数：
  20
• 可旋转键数：
  2
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.27
• 拓扑面积：
  49.3
• 氢给体数：
  0
• 氢受体数：
  4

反应信息

• 作为产物：
  描述：

  1-(2-嘧啶基)哌嗪 、 苯甲酰氯 在 三乙胺 作用下， 以 二氯甲烷 为溶剂， 以88%的产率得到phenyl(4-(pyrimidin-2-yl)piperazin-1-yl)methanone
  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