7-amino-3-[2-[4-(2-bromo-4-fluorobenzoyl)-1-piperidinyl]ethyl]-2,4-(1H,3H)-quinazolinedione | 102745-98-2

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: 7-amino-3-[2-[4-(2-bromo-4-fluorobenzoyl)-1-piperidinyl]ethyl]-2,4-(1H,3H)-quinazolinedione
• 英文别名: 7-amino-3-<2-<4-(2-bromo-4-fluorobenzoyl)-1-piperidinyl>ethyl>-2,4-(1H,3H)-quinazolinedione
• CAS: 102745-98-2
• 化学式: C₂₂H₂₂BrFN₄O₃
• 分子量: 489.344
• InChiKey: KIANWDJESNGGPQ-UHFFFAOYSA-N

物化性质

• 密度：
  1.495±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  2.77
• 重原子数：
  31.0
• 可旋转键数：
  5.0
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.32
• 拓扑面积：
  101.19
• 氢给体数：
  2.0
• 氢受体数：
  6.0

反应信息

• 作为反应物：
  描述：

  7-amino-3-[2-[4-(2-bromo-4-fluorobenzoyl)-1-piperidinyl]ethyl]-2,4-(1H,3H)-quinazolinedione 在 palladium on activated charcoal 、 calcium oxide 噻吩 、 超重氢 作用下， 以 四氢呋喃 为溶剂， 反应 18.0h， 以18%的产率得到7-氨基-3-[2-[4-(4-氟-2-氚苯甲酰基)哌啶-1-基]乙基]-1H-喹唑啉-2,4-二酮
  参考文献：
  名称：

  In vitro labeling of serotonin-S2 receptors. Synthesis and binding characteristics of [3H]-7-aminoketanserin

  摘要：

  [3H]-7-Aminoketanserin (7-amino-3-[2-[4-(2-tritio-4-fluorobenzoyl)-1- piperidinyl]ethyl]-2,4-(1H,3H)-quinazolinedione), an amino derivative of the selective serotonin-S2 antagonist ketanserin, was synthesized and tested for in vitro labeling of serotonin-S2 receptors. The compound showed a very high affinity for both membrane-bound and detergent-solubilized serotonin-S2 receptors with KD values of 0.35 and 2.03 nM, respectively. At nanomolar concentrations, binding to serotonin-S1 sites was totally absent. Serotonin-S2 receptor binding was characterized by a slow dissociation and a very low nonspecific binding. In rat frontal cortex preparations, binding could be displaced by nanomolar concentrations of different serotonin antagonists and micromolar concentrations of serotonin agonists. Compounds with other pharmacological profiles were poorly or not active. Introduction of an amino function in this new radioligand led to a decreased lipophilicity. Therefore, besides being a valuable radioligand for routine binding studies, [3H]-7-aminoketanserin will probably be a good ligand for labeling serotonin-S2 receptors on intact cells.

  DOI：

  10.1021/jm00159a017
• 作为产物：
  描述：

  1-乙酰基哌啶-4-酰基氯 在 盐酸 、 三氯化铝 、 sodium carbonate 、 potassium iodide 作用下， 以 various solvent(s) 为溶剂， 反应 25.0h， 生成 7-amino-3-[2-[4-(2-bromo-4-fluorobenzoyl)-1-piperidinyl]ethyl]-2,4-(1H,3H)-quinazolinedione
  参考文献：
  名称：

  In vitro labeling of serotonin-S2 receptors. Synthesis and binding characteristics of [3H]-7-aminoketanserin

  摘要：

  [3H]-7-Aminoketanserin (7-amino-3-[2-[4-(2-tritio-4-fluorobenzoyl)-1- piperidinyl]ethyl]-2,4-(1H,3H)-quinazolinedione), an amino derivative of the selective serotonin-S2 antagonist ketanserin, was synthesized and tested for in vitro labeling of serotonin-S2 receptors. The compound showed a very high affinity for both membrane-bound and detergent-solubilized serotonin-S2 receptors with KD values of 0.35 and 2.03 nM, respectively. At nanomolar concentrations, binding to serotonin-S1 sites was totally absent. Serotonin-S2 receptor binding was characterized by a slow dissociation and a very low nonspecific binding. In rat frontal cortex preparations, binding could be displaced by nanomolar concentrations of different serotonin antagonists and micromolar concentrations of serotonin agonists. Compounds with other pharmacological profiles were poorly or not active. Introduction of an amino function in this new radioligand led to a decreased lipophilicity. Therefore, besides being a valuable radioligand for routine binding studies, [3H]-7-aminoketanserin will probably be a good ligand for labeling serotonin-S2 receptors on intact cells.

  DOI：

  10.1021/jm00159a017