2-氨基-5'-溴-3,3'-联吡啶 | 1044503-51-6

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 吡啶及其衍生物
• 中文名称: 2-氨基-5'-溴-3,3'-联吡啶
• 英文名称: 2-amino-5'-bromo-3,3'-bipyridine
• 英文别名: 3-(5-Bromopyridin-3-yl)pyridin-2-amine
• CAS: 1044503-51-6
• 化学式: C₁₀H₈BrN₃
• 分子量: 250.098
• InChiKey: DCAIYIVVBCZSHU-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  1.8
• 重原子数：
  14
• 可旋转键数：
  1
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.0
• 拓扑面积：
  51.8
• 氢给体数：
  1
• 氢受体数：
  3

反应信息

• 作为反应物：
  描述：

  2-氨基-5'-溴-3,3'-联吡啶 、 tert-butyl 7-azabicyclo[2.2.1]hept-2-ene-7-carboxylate 在 四丁基氯化铵 、 palladium diacetate 、 potassium formate 作用下， 以 N,N-二甲基甲酰胺 为溶剂， 反应 68.0h， 以42%的产率得到7-tert-butoxycarbonyl-2-exo-[3'-(2-aminopyridin-3-yl)-5'-pyridinyl]-7-azabicyclo[2.2.1]heptane
  参考文献：
  名称：

  Discovery of (−)-7-Methyl-2-exo-[3′-(6-[¹⁸F]fluoropyridin-2-yl)-5′-pyridinyl]-7-azabicyclo[2.2.1]heptane, a Radiolabeled Antagonist for Cerebral Nicotinic Acetylcholine Receptor (α4β2-nAChR) with Optimal Positron Emission Tomography Imaging Properties

  摘要：

  Several isomers of 7-methyl-2-exo-([F-18]fluoropyridinyl-5'-pyridinyl)-7-azabicyclo[2.2.1]heptane have been developed as radioligands with optimized brain kinetics for PET imaging of nAChR. The binding assay demonstrated that all isomers are beta-nAChR selective ligands with K-i = 0.02-0.3 nM. The experimental lipophilicity values of all isomers were in the. optimal range for the cerebral radioligands (log D-7.4=0.67-0.99). The isomers with higher binding affinity manifested slow baboon brain kinetics, whereas the isomer with the lowest binding affinity (K-i=0.3 nM) ((-)-7-methyl-2-exo-[3'-(6-[F]fluoropyridin-2-yl)-5'-pyridinyl]-7-azabicyclo[2.2.1]heptane, [F-18](-)-6c) and greatest lipophilicity (log D-7.4=0.99) exhibited optimal brain kinetics. [F-18](-)-6c manifests a unique combination of the optimally rapid brain kinetics, high BP and brain uptake, and favorable metabolic profile. Pharmacological studies showed that (-)-6c is an alpha 4 beta 2-nAChR antagonist with low side effects in mice. This combination of imaging properties suggests that [F-18]-(-)-6c is a potentially superior replacement for 2-[F-18]fluoro-A-85380 and 6-[F-18]fluoro-A-85380, the only available nAChR PET radioligands for humans.

  DOI：

  10.1021/jm800323d
• 作为产物：
  描述：

  2-氨基-3-碘吡啶 、 5-溴吡啶-3-硼酸 在 四(三苯基膦)钯 、 potassium carbonate 作用下， 以 乙醇 、 水 、 甲苯 为溶剂， 反应 22.0h， 以81%的产率得到2-氨基-5'-溴-3,3'-联吡啶
  参考文献：
  名称：

  Discovery of (−)-7-Methyl-2-exo-[3′-(6-[¹⁸F]fluoropyridin-2-yl)-5′-pyridinyl]-7-azabicyclo[2.2.1]heptane, a Radiolabeled Antagonist for Cerebral Nicotinic Acetylcholine Receptor (α4β2-nAChR) with Optimal Positron Emission Tomography Imaging Properties

  摘要：

  Several isomers of 7-methyl-2-exo-([F-18]fluoropyridinyl-5'-pyridinyl)-7-azabicyclo[2.2.1]heptane have been developed as radioligands with optimized brain kinetics for PET imaging of nAChR. The binding assay demonstrated that all isomers are beta-nAChR selective ligands with K-i = 0.02-0.3 nM. The experimental lipophilicity values of all isomers were in the. optimal range for the cerebral radioligands (log D-7.4=0.67-0.99). The isomers with higher binding affinity manifested slow baboon brain kinetics, whereas the isomer with the lowest binding affinity (K-i=0.3 nM) ((-)-7-methyl-2-exo-[3'-(6-[F]fluoropyridin-2-yl)-5'-pyridinyl]-7-azabicyclo[2.2.1]heptane, [F-18](-)-6c) and greatest lipophilicity (log D-7.4=0.99) exhibited optimal brain kinetics. [F-18](-)-6c manifests a unique combination of the optimally rapid brain kinetics, high BP and brain uptake, and favorable metabolic profile. Pharmacological studies showed that (-)-6c is an alpha 4 beta 2-nAChR antagonist with low side effects in mice. This combination of imaging properties suggests that [F-18]-(-)-6c is a potentially superior replacement for 2-[F-18]fluoro-A-85380 and 6-[F-18]fluoro-A-85380, the only available nAChR PET radioligands for humans.

  DOI：

  10.1021/jm800323d