2-bromo-4-[4-(3-fluoro-2-methoxyphenyl)piperidin-1-yl]pyridine-3-carbonitrile | 1403598-31-1

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 哌啶类
• 英文名称: 2-bromo-4-[4-(3-fluoro-2-methoxyphenyl)piperidin-1-yl]pyridine-3-carbonitrile
• 英文别名: 2-Bromo-4-[4-(3-fluoro-2-methoxyphenyl)piperidin-1-yl]pyridine-3-carbonitrile
• CAS: 1403598-31-1
• 化学式: C₁₈H₁₇BrFN₃O
• 分子量: 390.255
• InChiKey: AKGSAVCAHUPUTM-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  4
• 重原子数：
  24
• 可旋转键数：
  3
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.33
• 拓扑面积：
  49.2
• 氢给体数：
  0
• 氢受体数：
  5

反应信息

• 作为反应物：
  描述：

  2-bromo-4-[4-(3-fluoro-2-methoxyphenyl)piperidin-1-yl]pyridine-3-carbonitrile 在 肼 作用下， 以 四氢呋喃 为溶剂， 反应 0.25h， 以75%的产率得到4-[4-(3-fluoro-2-methoxyphenyl)piperidin-1-yl]-2-hydrazinopyridine-3-carbonitrile
  参考文献：
  名称：

  Synthesis, Evaluation, and Radiolabeling of New Potent Positive Allosteric Modulators of the Metabotropic Glutamate Receptor 2 as Potential Tracers for Positron Emission Tomography Imaging

  摘要：

  The synthesis and in vitro and in vivo evaluation of a new series of 7-(phenylpiperidinyl)-1,2,4-triazolo[4,3-a]pyridines, which were conveniently radiolabeled with carbon-11, as potential positron emission tomography (PET) radiotracers for in vivo imaging of the allosteric binding site of the metabotropic glutamate (mGlu) receptor subtype 2 are described. The synthesized compounds proved to be potent and selective positive allosteric modulators (PAMs) of the mGlu receptor 2 (mGluR2) in a [S-35]GTP gamma S binding assay and were able to displace an mGluR2 PAM radioligand, which we had previously developed, with IC50 values in the low nanomolar range. The most promising candidates were radiolabeled and subjected to biodistribution studies and radiometabolite analysis in rats. Preliminary small-animal PET (mu PET) studies in rats indicated that [C-11]20f binds specifically and reversibly to an mGluR2 allosteric site, strongly suggesting that it is a promising candidate for PET imaging of mGluR2 in the brain.

  DOI：

  10.1021/jm300912k
• 作为产物：
  描述：

  2-溴-6-氟苯甲醚 在 盐酸 、 四(三苯基膦)钯 、 10 wt% Pd(OH)2 on carbon 、 氢气 、 sodium hydride 、 potassium carbonate 作用下， 以 1,4-二氧六环 、 甲醇 、 乙醇 、 N,N-二甲基甲酰胺 、 异丙醇 、 mineral oil 为溶剂， 反应 2.75h， 生成 2-bromo-4-[4-(3-fluoro-2-methoxyphenyl)piperidin-1-yl]pyridine-3-carbonitrile
  参考文献：
  名称：

  Synthesis, Evaluation, and Radiolabeling of New Potent Positive Allosteric Modulators of the Metabotropic Glutamate Receptor 2 as Potential Tracers for Positron Emission Tomography Imaging

  摘要：

  The synthesis and in vitro and in vivo evaluation of a new series of 7-(phenylpiperidinyl)-1,2,4-triazolo[4,3-a]pyridines, which were conveniently radiolabeled with carbon-11, as potential positron emission tomography (PET) radiotracers for in vivo imaging of the allosteric binding site of the metabotropic glutamate (mGlu) receptor subtype 2 are described. The synthesized compounds proved to be potent and selective positive allosteric modulators (PAMs) of the mGlu receptor 2 (mGluR2) in a [S-35]GTP gamma S binding assay and were able to displace an mGluR2 PAM radioligand, which we had previously developed, with IC50 values in the low nanomolar range. The most promising candidates were radiolabeled and subjected to biodistribution studies and radiometabolite analysis in rats. Preliminary small-animal PET (mu PET) studies in rats indicated that [C-11]20f binds specifically and reversibly to an mGluR2 allosteric site, strongly suggesting that it is a promising candidate for PET imaging of mGluR2 in the brain.

  DOI：

  10.1021/jm300912k