O⁶-(4-nitrophenyl)hypoxanthine | 66085-18-5

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: O⁶-(4-nitrophenyl)hypoxanthine
• 英文别名: 6-(4-nitro-phenoxy)-7(9)H-purine；6-(4-nitrophenoxy)-7H-purine
• CAS: 66085-18-5
• 化学式: C₁₁H₇N₅O₃
• 分子量: 257.208
• InChiKey: YTBDOBCHNAMFEO-UHFFFAOYSA-N

物化性质

• 沸点：
  413.6±55.0 °C(Predicted)
• 密度：
  1.66±0.1 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  1.8
• 重原子数：
  19
• 可旋转键数：
  2
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.0
• 拓扑面积：
  110
• 氢给体数：
  1
• 氢受体数：
  6

反应信息

• 作为产物：
  描述：

  6-氯嘌呤核苷 在 三氟乙酸 作用下， 以 高氯酸 、 N,N-二甲基甲酰胺 为溶剂， 反应 29.0h， 生成 O⁶-(4-nitrophenyl)hypoxanthine
  参考文献：
  名称：

  O⁶-(4-Nitrophenyl)inosine and -Guanosine as Chromogenic Substrates for Adenosine Deaminase

  摘要：

  O-6-(4-Nitrophenyl)inosine (1a), O-6-(4-nitrophenyl)guanosine (1c) and O-6-(4-methylumbelliferonyl)inosine (2) were obtained by reaction of 6-chloro-9-(beta-D-ribofuranosyl)purine (3a) or 2-amino-6-chloro-9-(beta-D-ribofuranosyl)purine (3c) with sodium salts of 4-nitrophenol or 4-methylumbelliferone in N,N-dimethylformamide. Similarly, 6-chloro-9-(beta-D-2,3-isopropylideneribofuranosyl)purine (3b) was transformed to 2',3'-O-isopropylidene-O-6-(4-nitrophenyl)inosine (1b). Deprotection of 1b with CF3COOH gave compound 1a and O-6-(4-nitrophenyl)hypoxanthine (4). Compounds la and Ic are substrates for adenosine deaminase releasing 4-nitrophenol which is readily detected visually or spectrophotometrically. Rate and extent of hydrolysis of 1a are significantly increased in the presence of purine nucleoside phosphorylase but xanthine oxidase has no influence. A potential fluorogenic analogue 2 is not a substrate for adenosine deaminase.

  DOI：

  10.1080/07328319608002410