2-amino-7-(3,4-dihydroxyphenyl)-9-((2R,4S,5R)-4-hydroxy-5-(hydroxymethyl)tetrahydrofuran-2-yl)-6-oxo-6,9-dihydro-1H-purin-7-ium | 1218925-89-3

• 分子结构分类: 有机化合物 - 核苷、核苷酸和类似物
• 英文名称: 2-amino-7-(3,4-dihydroxyphenyl)-9-((2R,4S,5R)-4-hydroxy-5-(hydroxymethyl)tetrahydrofuran-2-yl)-6-oxo-6,9-dihydro-1H-purin-7-ium
• CAS: 1218925-89-3
• 化学式: C₁₆H₁₈N₅O₆
• 分子量: 376.349
• InChiKey: PUHGUDMBBPIIJM-QJPTWQEYSA-O

计算性质

• 辛醇/水分配系数(LogP)：
  -1.36
• 重原子数：
  27.0
• 可旋转键数：
  3.0
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.31
• 拓扑面积：
  170.73
• 氢给体数：
  6.0
• 氢受体数：
  9.0

反应信息

• 作为产物：
  描述：

  2-苯醌 、 2'-脱氧鸟苷 在 水 、 溶剂黄146 作用下， 以 N,N-二甲基甲酰胺 为溶剂， 反应 1.0h， 生成 2-amino-7-(3,4-dihydroxyphenyl)-1H-purin-6-one 、 2-amino-7-(3,4-dihydroxyphenyl)-9-((2R,4S,5R)-4-hydroxy-5-(hydroxymethyl)tetrahydrofuran-2-yl)-6-oxo-6,9-dihydro-1H-purin-7-ium
  参考文献：
  名称：

  Benzene and dopamine catechol quinones could initiate cancer or neurogenic disease

  摘要：

  Catechol quinones of estrogens react with DNA by 1,4-Michael addition to form depurinating N3Ade and N7Gua adducts. Loss of these adducts from DNA creates apurinic sites that can generate mutations leading to cancer initiation. We compared the reactions of the catechol quinones of the leukemogenic benzene (CAT-Q) and N-acetyldopamine (NADA-Q) with 2'-deoxyguanosine (dG) or DNA. NADA was used to prevent intramolecular cyclization of dopamine quinone. Reaction of CAT-Q or NADA-Q with dG at pH 4 afforded CAT-4-N7dG or NADA-6-N7dG, which lost deoxyribose with a half-life of 3 h to form CAT-4-N7Gua or 4 h to form NADA-6-N7Gua. When CAT-Q or NADA-Q was reacted with DNA, N3Ade adducts were formed and lost from DNA instantaneously, whereas N7Gua adducts were lost over several hours. The maximum yield of adducts in the reaction of CAT-Q or NADA-Q with DNA at pH 4 to 7 was at pH 4. When tyrosinase-activated CAT or NADA was reacted with DNA at pH 5 to 8, adduct levels were much higher (10- to 15-fold), and the highest yield was at pH 5. Reaction of catechol quinones of natural and synthetic estrogens, benzene, naphthalene, and dopamine with DNA to form depurinating adducts is a common feature that may lead to initiation of cancer or neurodegenerative disease. (C) 2009 Elsevier Inc. All rights reserved.

  DOI：

  10.1016/j.freeradbiomed.2009.11.002