4-(6-amino-9-methyl-9H-purin-2-yl)but-3-yn-2-ol | 1246018-24-5

• 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: 4-(6-amino-9-methyl-9H-purin-2-yl)but-3-yn-2-ol
• 英文别名: 4-(6-amino-9-methylpurin-2-yl)but-3-yn-2-ol
• CAS: 1246018-24-5
• 化学式: C₁₀H₁₁N₅O
• 分子量: 217.23
• InChiKey: JVPHTWLHPCXPHA-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  -0.3
• 重原子数：
  16
• 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：
  89.8
• 氢给体数：
  2
• 氢受体数：
  5

反应信息

• 作为反应物：
  描述：

  4-(6-amino-9-methyl-9H-purin-2-yl)but-3-yn-2-ol 在 10% Pd/C 、 氢气 、 溴 、 caesium carbonate 、 2-碘酰基苯甲酸 作用下， 以 四氢呋喃 、 甲醇 、 乙醇 、 二甲基亚砜 、 N,N-二甲基甲酰胺 为溶剂， -14.0~90.0 ℃ 、405.33 kPa 条件下， 反应 76.33h， 生成 ST4206
  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：

  6-chloro-2-iodo-9-methyl-9H-purine 在 bis-triphenylphosphine-palladium(II) chloride 、 copper(l) iodide 、 氨 、 三乙胺 作用下， 以 1,4-二氧六环 、 水 为溶剂， 反应 17.5h， 生成 4-(6-amino-9-methyl-9H-purin-2-yl)but-3-yn-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

文献信息

• [EN] OXIDATED DERIVATIVES OF TRIAZOLYPURINES USEFUL AS LIGANDS OF THE ADENOSINE A2A RECEPTOR AND THEIR USE AS MEDICAMENTS<br/>[FR] DÉRIVÉS OXYDÉS DE TRIAZOLYPURINES UTILES EN TANT QUE LIGANDS DU RÉCEPTEUR ADÉNOSINIQUE A2A ET LEUR UTILISATION EN TANT QUE MÉDICAMENTS
  申请人：SIGMA TAU IND FARMACEUTI

  公开号：WO2010106145A1

  公开（公告）日：2010-09-23

  The present invention relates to new triazolyl purine derivatives of formula (I), processes for their preparation, and to pharmaceutical compositions containing them for the treatment of neurological disorders or cerebral ischaemia for which inhibition of adenosine A2A receptor will result at improving the health state of a patient.

  本发明涉及公式（I）的新三唑基嘌呤衍生物，其制备方法，以及含有这些衍生物的药物组合物，用于治疗神经系统疾病或脑缺血，通过抑制腺苷A2A受体来改善患者的健康状态。
• OXIDATED DERIVATIVES OF TRIAZOLYLPURINES USEFUL AS LIGANDS OF THE ADENOSINE A2A RECEPTOR AND THEIR USE AS MEDICAMENTS
  申请人：Cabri Walter

  公开号：US20120053191A1

  公开（公告）日：2012-03-01

  The present invention relates to new triazolyl purine derivatives of formula (I), processes for their preparation, and to pharmaceutical compositions containing them for the treatment of neurological disorders or cerebral ischaemia for which inhibition of adenosine A2A receptor will result at improving the health state of a patient.

  本发明涉及式(I)的新三唑基嘌呤衍生物，其制备方法，以及包含它们的制药组合物，用于治疗神经系统疾病或脑缺血，通过抑制腺苷A2A受体来改善患者的健康状况。
• Oxidated derivatives of triazolylpurines useful as ligands of the adenosine A2A receptor and their use as medicaments
  申请人：Cabri Walter

  公开号：US09133197B2

  公开（公告）日：2015-09-15

  The present invention relates to new triazolyl purine derivatives of formula (I), processes for their preparation, and to pharmaceutical compositions containing them for the treatment of neurological disorders or cerebral ischaemia for which inhibition of adenosine A2A receptor will result at improving the health state of a patient.

  本发明涉及公式（I）的新的三唑基嘌呤衍生物、其制备方法以及含有它们的制药组合物，用于治疗神经系统疾病或脑缺血，通过抑制腺苷A2A受体来改善患者的健康状态。
• J. Med. Chem. 2013, 56, 5456-5463
  作者：

  DOI：——

  日期：——
• OXIDATED DERIVATIVES OF TRIAZOLYPURINES USEFUL AS LIGANDS OF THE ADENOSINE A2A RECEPTOR AND THEIR USE AS MEDICAMENTS
  申请人：SIGMA-TAU Industrie Farmaceutiche Riunite S.p.A.

  公开号：EP2408775A1

  公开（公告）日：2012-01-25