(2R,3S,4R,5R)-2-(hydroxymethyl)-5-(6-((4-iodophenyl)amino)-9H-purin-9-yl)tetrahydrofuran-3,4-diol | 107799-06-4

• 分子结构分类: 有机化合物 - 核苷、核苷酸和类似物 - 嘌呤核苷
• 英文名称: (2R,3S,4R,5R)-2-(hydroxymethyl)-5-(6-((4-iodophenyl)amino)-9H-purin-9-yl)tetrahydrofuran-3,4-diol
• 英文别名: (2R,3S,4R,5R)-2-Hydroxymethyl-5-[6-(4-iodo-phenylamino)-purin-9-yl]-tetrahydro-furan-3,4-diol；(2R,3S,4R,5R)-2-(hydroxymethyl)-5-[6-(4-iodoanilino)purin-9-yl]oxolane-3,4-diol
• CAS: 107799-06-4
• 化学式: C₁₆H₁₆IN₅O₄
• 分子量: 469.239
• InChiKey: WDGFDTMMTJGMAN-XNIJJKJLSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  1.8
• 重原子数：
  26
• 可旋转键数：
  4
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.31
• 拓扑面积：
  126
• 氢给体数：
  4
• 氢受体数：
  8

反应信息

• 作为反应物：
  描述：

  (2R,3S,4R,5R)-2-(hydroxymethyl)-5-(6-((4-iodophenyl)amino)-9H-purin-9-yl)tetrahydrofuran-3,4-diol 在 哌啶 、 bis-triphenylphosphine-palladium(II) chloride 、 copper(l) iodide 、 (benzotriazo-1-yloxy)tris(dimethylamino)phosphonium hexafluorophosphate 、 三乙胺 作用下， 以 四氢呋喃 、 N,N-二甲基甲酰胺 为溶剂， 反应 9.5h， 生成 N-(4-(4-((9-((2R,3R,4S,5R)-3,4-dihydroxy-5-(hydroxymethyl)tetrahydrofuran-2-yl)-9H-purin-6-yl)amino)phenyl)but-3-yn-1-yl)benzamide
  参考文献：
  名称：

  Examining the Role of the Linker in Bitopic N⁶-Substituted Adenosine Derivatives Acting as Biased Adenosine A₁ Receptor Agonists

  摘要：

  DOI：

  10.1021/acs.jmedchem.2c00320
• 作为产物：
  描述：

  6-氯嘌呤核苷 、 对碘苯胺 在 calcium carbonate 作用下， 以 乙醇 为溶剂， 生成 (2R,3S,4R,5R)-2-(hydroxymethyl)-5-(6-((4-iodophenyl)amino)-9H-purin-9-yl)tetrahydrofuran-3,4-diol
  参考文献：
  名称：

  N6-Phenyladenosines: pronounced effect of phenyl substituents on affinity for A2 adenosine receptors

  摘要：

  A number of N6-phenyladenosines with various substitutions on the phenyl ring have been synthesized and tested for their affinities toward brain A1 and A2 adenosine receptors. Compounds with meta substituents, such as (m-hydroxy- and m-iodophenyl)adenosine, were found to have high A1 selectivity. Meta substitution caused a selective decrease in the affinity of these compounds for A2 receptors. The results suggest that, in contrast to what is commonly held, certain N6-substituents have pronounced effects on affinity for brain A2 adenosine receptors. Thus, brain A2 receptors may have a well-defined region that recognizes N6-substitutions.

  DOI：

  10.1021/jm00388a039