2-acetamido-9H-fluoren-1-yl (((2R,3S,5R)-5-(2-amino-6-oxo-1H-purin-9(6H)-yl)-3-hydroxytetrahydrofuran-2-yl)methyl) succinate | 134737-00-1

• 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: 2-acetamido-9H-fluoren-1-yl (((2R,3S,5R)-5-(2-amino-6-oxo-1H-purin-9(6H)-yl)-3-hydroxytetrahydrofuran-2-yl)methyl) succinate
• 英文别名: Succinic acid 2-acetylamino-9H-fluoren-1-yl ester (2R,3S,5R)-5-(2-amino-6-oxo-1,6-dihydro-purin-9-yl)-3-hydroxy-tetrahydro-furan-2-ylmethyl ester
• CAS: 134737-00-1
• 化学式: C₂₉H₂₈N₆O₈
• 分子量: 588.577
• InChiKey: ZDKYBFVMCUIYGM-BHDDXSALSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  1.81
• 重原子数：
  43.0
• 可旋转键数：
  8.0
• 环数：
  6.0
• sp3杂化的碳原子比例：
  0.31
• 拓扑面积：
  200.75
• 氢给体数：
  4.0
• 氢受体数：
  12.0

反应信息

• 作为产物：
  描述：

  4-O-[acetyl(9H-fluoren-2-yl)amino] 1-O-[[(2R,3S,5R)-5-(2-amino-6-oxo-1H-purin-9-yl)-3-hydroxyoxolan-2-yl]methyl] butanedioate 在 phosphate buffer 作用下， 以65%的产率得到Succinic acid mono-((2R,3S,5R)-5-{8-[acetyl-(9H-fluoren-2-yl)-amino]-2-amino-6-oxo-1,6-dihydro-purin-9-yl}-3-hydroxy-tetrahydro-furan-2-ylmethyl) ester
  参考文献：
  名称：

  Interaction and reactivity of carcinogenic N-acetyl-N-(acyloxy)-2-aminofluorene with deoxyguanosine. An intramolecular approach

  摘要：

  Solvolysis of 3 in water-acetone mixtures yields the ''adduct'' 4 (65% in water) with product and rate data consistent with the hypothesis that hydrophobic guanine-fluorene stacking, similar to that which occurs when the carcinogenic aminofluorene metabolite is intercalated in DNA, is responsible for selective binding of the carcinogen at the C-8 guanine center.

  DOI：

  10.1021/jo00016a001