N⁶-(1-nitropyren-6-yl)deoxyadenosine

• 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: N⁶-(1-nitropyren-6-yl)deoxyadenosine
• 英文别名: (2R,3S,5R)-2-(hydroxymethyl)-5-[6-[(6-nitropyren-1-yl)amino]purin-9-yl]oxolan-3-ol
• 化学式: C₂₆H₂₀N₆O₅
• 分子量: 496.482
• InChiKey: IEBSYFOAROBIEO-PWRODBHTSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  4.3
• 重原子数：
  37
• 可旋转键数：
  4
• 环数：
  7.0
• sp3杂化的碳原子比例：
  0.19
• 拓扑面积：
  151
• 氢给体数：
  3
• 氢受体数：
  9

反应信息

• 作为产物：
  描述：

  1-氟芘 在 硝酸 、 potassium carbonate 、 三氟乙酸 作用下， 以 四氢呋喃 、 水 、 溶剂黄146 、 二甲基亚砜 为溶剂， 反应 24.5h， 生成 N⁶-(1-nitropyren-6-yl)deoxyadenosine
  参考文献：
  名称：

  Synthesis of N-(1-Nitropyren-6-yl and 8-yl)-2'-deoxyribonucleosides

  摘要：

  A new type of 1-nitropyrene-DNA adduct via addition-elimination reaction was synthesized. Treatment of fluorinated 1-nitropyrene with 3'- and 5'-O-protected 2'-deoxyribonucleoside in dimethyl sulfoxide at 140 degrees C afforded N-(1-nitropyren-6-yl or 8-yl)-2'-deoxyribonucleoside. These DNA adducts resulted from addition of the exocyclic amino group of deoxynucleosides to the fluorinated carbon of the fluoro-1-nitropyrene following elimination of fluoride anion. This is the first report that describes the 1-nitropyrene-DNA adducts in which aromatic ring moiety of 1-nitropyrene is covalently linked to the exocyclic amino group of the deoxyribonucleoside. From our findings, we suggest that the addition-elimination reaction may be responsible for the formation mechanism of the putative 1-nitropyrene-DNA adducts in vivo.

  DOI：

  10.1021/tx00047a009

文献信息

• Synthesis of N-(1-Nitropyren-6-yl and 8-yl)-2'-deoxyribonucleosides
  作者：Tomoharu Sano、Kunimitsu Kaya

  DOI：10.1021/tx00047a009

  日期：1995.7

  A new type of 1-nitropyrene-DNA adduct via addition-elimination reaction was synthesized. Treatment of fluorinated 1-nitropyrene with 3'- and 5'-O-protected 2'-deoxyribonucleoside in dimethyl sulfoxide at 140 degrees C afforded N-(1-nitropyren-6-yl or 8-yl)-2'-deoxyribonucleoside. These DNA adducts resulted from addition of the exocyclic amino group of deoxynucleosides to the fluorinated carbon of the fluoro-1-nitropyrene following elimination of fluoride anion. This is the first report that describes the 1-nitropyrene-DNA adducts in which aromatic ring moiety of 1-nitropyrene is covalently linked to the exocyclic amino group of the deoxyribonucleoside. From our findings, we suggest that the addition-elimination reaction may be responsible for the formation mechanism of the putative 1-nitropyrene-DNA adducts in vivo.