{3-[4-amino-6-(2-(benzyloxy)phenyl)-1,3,5-triazin-2-yl]phenyl}(4-methylpiperazin-1-yl)methanone | 1311378-16-1

• 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: {3-[4-amino-6-(2-(benzyloxy)phenyl)-1,3,5-triazin-2-yl]phenyl}(4-methylpiperazin-1-yl)methanone
• 英文别名: {3-[4-amino-6-(2-benzyloxyphenyl)-1,3,5-triazin-2-yl]phenyl}(4-methylpiperazin-1-yl)methanone
• CAS: 1311378-16-1
• 化学式: C₂₈H₂₈N₆O₂
• 分子量: 480.569
• InChiKey: URTQDQLWWXRRGC-UHFFFAOYSA-N

物化性质

• 沸点：
  757.2±70.0 °C(Predicted)
• 密度：
  1?+-.0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  3.75
• 重原子数：
  36.0
• 可旋转键数：
  6.0
• 环数：
  5.0
• sp3杂化的碳原子比例：
  0.21
• 拓扑面积：
  97.47
• 氢给体数：
  1.0
• 氢受体数：
  7.0

反应信息

• 作为反应物：
  描述：

  {3-[4-amino-6-(2-(benzyloxy)phenyl)-1,3,5-triazin-2-yl]phenyl}(4-methylpiperazin-1-yl)methanone 在 1,4-环己二烯 、 20 % Pd(OH)2/C 作用下， 以 乙酸乙酯 为溶剂， 反应 1.0h， 以51%的产率得到{3-[4-amino-6-(2-hydroxyphenyl)-1,3,5-triazin-2-yl]phenyl}(4-methylpiperazin-1-yl)methanone
  参考文献：
  名称：

  Biophysical Mapping of the Adenosine A_2A Receptor

  摘要：

  A new approach to generating information on ligand receptor interactions within the binding pocket of G protein-coupled receptors has been developed, called Biophysical Mapping (BPM). Starting from a stabilized receptor (StaR), minimally engineered for thermostability, additional single mutations are then added at positions that could be involved in small molecule interactions. The StaR and a panel of binding site mutants are captured onto Biacore chips to enable characterization of the binding of small molecule ligands using surface plasmon resonance (SPR) measurement. A matrix of binding data for a set of ligands versus each active site mutation is then generated, providing specific affinity and kinetic information (K-D, k(on), and k(off)) of receptor-ligand interactions. This data set, in combination with molecular modeling and docking, is used to map the small molecule binding site for each class of compounds. Taken together, the many constraints provided by these data identify key protein-ligand interactions and allow the shape of the site to be refined to produce a high quality three-dimensional picture of ligand binding, thereby facilitating structure based drug design. Results of biophysical mapping of the adenosine A(2A) receptor are presented.

  DOI：

  10.1021/jm2003798
• 作为产物：
  描述：

  4-[2-(benzyloxy)phenyl]-6-chloro-1,3,5-triazin-2-amine 、 3-(4-甲基哌嗪-1-羰基)苯硼酸盐酸盐 在 四(三苯基膦)钯 、 sodium carbonate 作用下， 以 1,4-二氧六环 、 水 为溶剂， 反应 16.0h， 以1 g的产率得到{3-[4-amino-6-(2-(benzyloxy)phenyl)-1,3,5-triazin-2-yl]phenyl}(4-methylpiperazin-1-yl)methanone
  参考文献：
  名称：

  Identification of Novel Adenosine A_2A Receptor Antagonists by Virtual Screening

  摘要：

  Virtual screening was performed against experimentally enabled homology models of the adenosine A(2A) receptor, identifying a diverse range of ligand efficient antagonists (hit rate 9%). By use of ligand docking and Biophysical Mapping (BPM), hits and 5 were optimized to potent and selective lead molecules (11-13 from 5, pK(I) = 7.5-8.5, 13- to >100-fold selective versus adenosine A(1); 14-16 from 1, pK(I) = 7.9-9.0, 19- to 59-fold selective).

  DOI：

  10.1021/jm201455y