N²-(2-amino-3-methyl-3H-imidazo[4,5-f]quinolin-5-yl)-2'-deoxyguanosine | 142038-29-7

• 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: N²-(2-amino-3-methyl-3H-imidazo[4,5-f]quinolin-5-yl)-2'-deoxyguanosine
• 英文别名: 5-(2'-deoxyguanosin-N²-yl)-2-amino-3-methylimidazo[4,5-f]quinoline；Guanosine, N-(2-amino-3-methyl-3H-imidazo(4,5-f)quinolin-5-yl)-2'-deoxy-；2-[(2-amino-3-methylimidazo[4,5-f]quinolin-5-yl)amino]-9-[(2R,4S,5R)-4-hydroxy-5-(hydroxymethyl)oxolan-2-yl]-1H-purin-6-one
• CAS: 142038-29-7
• 化学式: C₂₁H₂₁N₉O₄
• 分子量: 463.456
• InChiKey: JGGDEQWCMVVRSC-BFHYXJOUSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  -0.4
• 重原子数：
  34
• 可旋转键数：
  4
• 环数：
  6.0
• sp3杂化的碳原子比例：
  0.29
• 拓扑面积：
  178
• 氢给体数：
  5
• 氢受体数：
  9

反应信息

• 作为产物：
  描述：

  [6-Benzyloxy-9-((2R,3aS,9aR)-5,5,7,7-tetraisopropyl-tetrahydro-1,4,6,8-tetraoxa-5,7-disila-cyclopentacycloocten-2-yl)-9H-purin-2-yl]-(3-methyl-2-nitro-3H-imidazo[4,5-f]quinolin-5-yl)-amine 在 palladium on activated charcoal 四丁基氟化铵 、 氢气 作用下， 以 四氢呋喃 、 甲醇 为溶剂， 20.0 ℃ 、101.33 kPa 条件下， 反应 7.0h， 生成 N²-(2-amino-3-methyl-3H-imidazo[4,5-f]quinolin-5-yl)-2'-deoxyguanosine
  参考文献：
  名称：

  Synthesis of the N²-Deoxyguanosine Adduct of the Potent Dietary Mutagen IQ ¹

  摘要：

  After bioactivation, the potent dietary mutagen 2-amino-3-methylimidazo[4,5-f]-quinoline (IQ) reacts with DNA to give two regioisomeric adducts of deoxyguanosine. The synthesis of the minor W-adduct has been achieved utilizing the Buchwald-Hartwig palladium-catalyzed N-2-arylation reaction as the key step.

  DOI：

  10.1021/ol047851m

文献信息

• Synthesis of the <i>N</i>²-Deoxyguanosine Adduct of the Potent Dietary Mutagen IQ ¹
  作者：James S. Stover、Carmelo J. Rizzo

  DOI：10.1021/ol047851m

  日期：2004.12.1

  After bioactivation, the potent dietary mutagen 2-amino-3-methylimidazo[4,5-f]-quinoline (IQ) reacts with DNA to give two regioisomeric adducts of deoxyguanosine. The synthesis of the minor W-adduct has been achieved utilizing the Buchwald-Hartwig palladium-catalyzed N-2-arylation reaction as the key step.