1-(6-chloro-4-methylamino-imidazo[4,5-c]pyridin-1-yl)-β-D-1-deoxy-ribofuranose | 55385-39-2

• 分子结构分类: 有机化合物 - 核苷、核苷酸和类似物
• 英文名称: 1-(6-chloro-4-methylamino-imidazo[4,5-c]pyridin-1-yl)-β-D-1-deoxy-ribofuranose
• CAS: 55385-39-2
• 化学式: C₁₂H₁₅ClN₄O₄
• 分子量: 314.728
• InChiKey: VSKLYYCTCHFQCS-XYHAGOFUSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  -0.26
• 重原子数：
  21.0
• 可旋转键数：
  3.0
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.5
• 拓扑面积：
  112.66
• 氢给体数：
  4.0
• 氢受体数：
  8.0

反应信息

• 作为反应物：
  描述：

  1-(6-chloro-4-methylamino-imidazo[4,5-c]pyridin-1-yl)-β-D-1-deoxy-ribofuranose 在 磷酸三甲酯 、 三氯氧磷 、 水 、 三乙胺 、 碳酸氢铵 作用下， 以 水 为溶剂， 反应 3.0h， 以88%的产率得到azane;[(2R,3S,4R,5R)-5-[6-chloro-4-(methylamino)imidazo[4,5-c]pyridin-1-yl]-3,4-dihydroxyoxolan-2-yl]methyl dihydrogen phosphate
  参考文献：
  名称：

  Frontal Affinity Chromatography−Mass Spectrometry Useful for Characterization of New Ligands for GPR17 Receptor

  摘要：

  The application of frontal affinity chromatography mass spectrometry (FAC-MS), along with molecular modeling studies, to the screening of potential drug candidates toward the recently deorphanized G-protein-coupled receptor (GPCR) GPR17 is shown. GPR17 is dually activated by uracil nucleotides and cysteinyl-leukotrienes, and is expressed in organs typically undergoing ischemic damage (i.e., brain, heart and kidney), thus representing a new pharmacological target for acute and chronic neurodegeneration. GPR17 was entrapped on an immobilized artificial membrane (IAM), and this stationary phase was used to screen a library of nucleotide derivatives by FAC-MS to select high affinity ligands. The chromatographic results have been validated with a reference functional assay ([S-35]GTP gamma S binding assay). The receptor nucleotide-binding site was studied by setting up a column where a mutated GPR17 receptor (Arg255Ile) has been immobilized. The chromatographic behavior of the tested nucleotide derivatives together with in silico studies have been used to gain insights into the structure requirement of GPR17 ligands.

  DOI：

  10.1021/jm901691y