2-(but-1-ynyl)-6-chloro-9-methyl-9H-purine | 1443762-87-5

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 咪唑并嘧啶类
• 英文名称: 2-(but-1-ynyl)-6-chloro-9-methyl-9H-purine
• 英文别名: 2-But-1-ynyl-6-chloro-9-methylpurine；2-but-1-ynyl-6-chloro-9-methylpurine
• CAS: 1443762-87-5
• 化学式: C₁₀H₉ClN₄
• 分子量: 220.661
• InChiKey: ZROCYFIKGALOCK-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.2
• 重原子数：
  15
• 可旋转键数：
  1
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.3
• 拓扑面积：
  43.6
• 氢给体数：
  0
• 氢受体数：
  3

反应信息

• 作为反应物：
  描述：

  2-(but-1-ynyl)-6-chloro-9-methyl-9H-purine 在 sodium tetrahydroborate 、 氨 、 异丁胺 、 四氯化钛 、 2,4,6-三甲基苯胺 作用下， 以 1,4-二氧六环 、 甲醇 、 二氯甲烷 、 水 、 甲苯 为溶剂， 反应 32.0h， 生成 1-(6-amino-9-methyl-9H-purin-2-yl)butan-2-ol
  参考文献：
  名称：

  Synthesis and Biological Evaluation of Metabolites of 2-n-Butyl-9-methyl-8-[1,2,3]triazol-2-yl-9H-purin-6-ylamine (ST1535), A Potent Antagonist of the A_2A Adenosine Receptor for the Treatment of Parkinson’s Disease

  摘要：

  The synthesis and preliminary in vitro evaluation of five metabolites of the A(2A) antagonist ST1535 (1) are reported. The metabolites, originating in vivo from enzymatic oxidation of 2-butyl group of parent compound, were synthesized from 6-chloro-2-iodo-9-methyl-9H-purine (2) by selective C-C bond formation via halogen/magnesium exchange and/or palladium-catalyzed reactions. The metabolites behaved in vitro as antagonist, ligands of cloned human A(2A), receptor with affinities (K-i 7.5-53 nM) comparable to that of compound 1 (K-i 10.7 nM), thus showing that the long duration of action of 1 could be in part due to its metabolites. General behavior after oral administration in mice was also analyzed.

  DOI：

  10.1021/jm400491x
• 作为产物：
  描述：

  1-丁炔 、 6-chloro-2-iodo-9-methyl-9H-purine 在 bis-triphenylphosphine-palladium(II) chloride 、 copper(l) iodide 、 三乙胺 作用下， 以 1,4-二氧六环 为溶剂， 反应 1.5h， 以84%的产率得到2-(but-1-ynyl)-6-chloro-9-methyl-9H-purine
  参考文献：
  名称：

  Synthesis and Biological Evaluation of Metabolites of 2-n-Butyl-9-methyl-8-[1,2,3]triazol-2-yl-9H-purin-6-ylamine (ST1535), A Potent Antagonist of the A_2A Adenosine Receptor for the Treatment of Parkinson’s Disease

  摘要：

  The synthesis and preliminary in vitro evaluation of five metabolites of the A(2A) antagonist ST1535 (1) are reported. The metabolites, originating in vivo from enzymatic oxidation of 2-butyl group of parent compound, were synthesized from 6-chloro-2-iodo-9-methyl-9H-purine (2) by selective C-C bond formation via halogen/magnesium exchange and/or palladium-catalyzed reactions. The metabolites behaved in vitro as antagonist, ligands of cloned human A(2A), receptor with affinities (K-i 7.5-53 nM) comparable to that of compound 1 (K-i 10.7 nM), thus showing that the long duration of action of 1 could be in part due to its metabolites. General behavior after oral administration in mice was also analyzed.

  DOI：

  10.1021/jm400491x