5-bromo-2-(2-fluoroethoxy)benzoic acid | 1269797-09-2

• 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: 5-bromo-2-(2-fluoroethoxy)benzoic acid
• CAS: 1269797-09-2
• 化学式: C₉H₈BrFO₃
• 分子量: 263.063
• InChiKey: FDPDRXOUVHWRKD-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.3
• 重原子数：
  14
• 可旋转键数：
  4
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.22
• 拓扑面积：
  46.5
• 氢给体数：
  1
• 氢受体数：
  4

反应信息

• 作为反应物：
  描述：

  4-(4-(2-methoxy)phenylpiperazin-1-yl)-trans-but-2-en-1-amine 、 5-bromo-2-(2-fluoroethoxy)benzoic acid 在 1-羟基苯并三唑 、 N,N'-二环己基碳二亚胺 作用下， 以 二氯甲烷 为溶剂， 以35%的产率得到5-bromo-2-(2-fluoroethoxy)-N-(4-(4-(2-methoxyphenyl)piperazin-1-yl)-trans-butyl-2-enyl)benzamide
  参考文献：
  名称：

  Synthesis and Pharmacological Evaluation of Fluorine-Containing D₃ Dopamine Receptor Ligands

  摘要：

  A series of fluorine-containing N-(2-methoxyphenyl)piperazine and N-(2-fluoroethoxy)piperazine analogues were synthesized, and their affinities for human dopamine D-2, D-3, and D-4 receptors were determined. Radioligand binding studies identified five compounds, 18a, 20a, 20c, 20e, and 21e, which bind with high affinity at D-3 (K-i = 0.17-5 nM) and moderate to high selectivity for D-3 VS D-2 receptors (ranging from similar to 25-to 163-fold). These compounds were also evaluated for intrinsic activity at D-2 and D3 receptors using a forskolin-dependent adenylyl cyclase assay. This panel of compounds exhibits varying receptor subtype binding selectivity and intrinsic activity at D-2 VS D-3 receptors. These compounds may be useful for behavioral pharmacology studies on the role of D-2-like dopamine receptors in neuropsychiatric and neurological disorders. Furthermore, compound 20e, which has the highest binding affinity and selectivity for the D-3 receptor (K-i = 0.17 nM for D-3, 163-fold selectivity for D-3 VS D-2 receptors), represents a candidate fluorine-18 radiotracer for in vivo PET imaging studies on the regulation of D-3 receptor expression.

  DOI：

  10.1021/jm101323b
• 作为产物：
  描述：

  5-溴水杨酸 在 硫酸 、 水 、 potassium carbonate 、 sodium hydroxide 作用下， 以 甲醇 、 丙酮 为溶剂， 生成 5-bromo-2-(2-fluoroethoxy)benzoic acid
  参考文献：
  名称：

  Synthesis and Pharmacological Evaluation of Fluorine-Containing D₃ Dopamine Receptor Ligands

  摘要：

  A series of fluorine-containing N-(2-methoxyphenyl)piperazine and N-(2-fluoroethoxy)piperazine analogues were synthesized, and their affinities for human dopamine D-2, D-3, and D-4 receptors were determined. Radioligand binding studies identified five compounds, 18a, 20a, 20c, 20e, and 21e, which bind with high affinity at D-3 (K-i = 0.17-5 nM) and moderate to high selectivity for D-3 VS D-2 receptors (ranging from similar to 25-to 163-fold). These compounds were also evaluated for intrinsic activity at D-2 and D3 receptors using a forskolin-dependent adenylyl cyclase assay. This panel of compounds exhibits varying receptor subtype binding selectivity and intrinsic activity at D-2 VS D-3 receptors. These compounds may be useful for behavioral pharmacology studies on the role of D-2-like dopamine receptors in neuropsychiatric and neurological disorders. Furthermore, compound 20e, which has the highest binding affinity and selectivity for the D-3 receptor (K-i = 0.17 nM for D-3, 163-fold selectivity for D-3 VS D-2 receptors), represents a candidate fluorine-18 radiotracer for in vivo PET imaging studies on the regulation of D-3 receptor expression.

  DOI：

  10.1021/jm101323b

文献信息

• Synthesis and Pharmacological Evaluation of Fluorine-Containing D₃ Dopamine Receptor Ligands
  作者：Zhude Tu、Shihong Li、Jinquan Cui、Jinbin Xu、Michelle Taylor、David Ho、Robert R. Luedtke、Robert H. Mach

  DOI：10.1021/jm101323b

  日期：2011.3.24

  A series of fluorine-containing N-(2-methoxyphenyl)piperazine and N-(2-fluoroethoxy)piperazine analogues were synthesized, and their affinities for human dopamine D-2, D-3, and D-4 receptors were determined. Radioligand binding studies identified five compounds, 18a, 20a, 20c, 20e, and 21e, which bind with high affinity at D-3 (K-i = 0.17-5 nM) and moderate to high selectivity for D-3 VS D-2 receptors (ranging from similar to 25-to 163-fold). These compounds were also evaluated for intrinsic activity at D-2 and D3 receptors using a forskolin-dependent adenylyl cyclase assay. This panel of compounds exhibits varying receptor subtype binding selectivity and intrinsic activity at D-2 VS D-3 receptors. These compounds may be useful for behavioral pharmacology studies on the role of D-2-like dopamine receptors in neuropsychiatric and neurological disorders. Furthermore, compound 20e, which has the highest binding affinity and selectivity for the D-3 receptor (K-i = 0.17 nM for D-3, 163-fold selectivity for D-3 VS D-2 receptors), represents a candidate fluorine-18 radiotracer for in vivo PET imaging studies on the regulation of D-3 receptor expression.