N⁷-NH2Gua | 104826-08-6

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 咪唑并嘧啶类
• 英文名称: N⁷-NH2Gua
• 英文别名: 7-aminoguanine；2,7-diamino-1H-purin-6-one
• CAS: 104826-08-6
• 化学式: C₅H₆N₆O
• 分子量: 166.142
• InChiKey: ACMPGXFTGITPLC-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  -0.8
• 重原子数：
  12
• 可旋转键数：
  0
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.0
• 拓扑面积：
  111
• 氢给体数：
  3
• 氢受体数：
  4

反应信息

• 作为反应物：
  描述：

  N⁷-NH2Gua 在 sodium nitrite 作用下， 以 溶剂黄146 为溶剂， 生成 鸟嘌呤
  参考文献：
  名称：

  Kohda, Kohfuku; Baba, Kunihisa; Kawazoe, Yutaka, Chemical and pharmaceutical bulletin, 1986, vol. 34, # 5, p. 2298 - 2301

  摘要：

  DOI：
• 作为产物：
  描述：

  2'-脱氧鸟苷 在 2,4-二硝基苯基羟胺 作用下， 以 水 、 N,N-二甲基甲酰胺 为溶剂， 反应 96.0h， 以20%的产率得到N⁷-NH2Gua
  参考文献：
  名称：

  Kohda, Kohfuku; Baba, Kunihisa; Kawazoe, Yutaka, Chemical and pharmaceutical bulletin, 1986, vol. 34, # 5, p. 2298 - 2301

  摘要：

  DOI：

文献信息

• Formation and Reactions of <i>N</i>⁷-Aminoguanosine and Derivatives
  作者：F. Peter Guengerich、Ralf G. Mundkowski、Markus Voehler、Fred F. Kadlubar

  DOI：10.1021/tx990094u

  日期：1999.10.1

  Arylamines are mutagens and carcinogens and are thought to initiate tumors by forming adducts with DNA. The major adducts are C-8-guanyl, and we have previously suggested a role for guanyl-N-7 intermediates in the formation process. N-7-Aminoguanosine (Guo) was synthesized and characterized, with the position of the NH2 at N7 established by two-dimensional rotating frame Overhauser enhancement NMR spectroscopy. In DMF, N-7-NH(2)Guo formed C-8-NH(2)Guo and the cyclic product C-8:5'-O-cycloGuo. In aqueous media, these products were formed along with 8-oxo-7,8-dihydroGuo, N-7-NH(2)guanine, and a product characterized as a purine 8,9-ring-opened derivative (N-aminoformamidopyrimidine). The rate of aqueous decomposition of N-7-NH(2)Guo increased with pH, with a t(1/2) of 10 h at pH 7 and a t(1/2) of 2 h at pH 9. The rate of migration of NH2 from N7 to C8 is fast enough to explain the formation of C-8-NH(2)Guo from the reaction of 2,4-dinitrophenoxyamine with Guo but not the formation of C-8-(arylamino)Guo in the reaction of Guo with aryl hydroxylamine esters; however, the fluorenyl moiety may facilitate the proposed rearrangement by stabilizing an incipient negative charge in the transfer. In the reaction of Guo with N-hydroxy-2-aminofluorene and acetylsalicylic acid, a peak with the mass spectrum expected for N-7-(2-aminofluorenyl)Guo was detected early in the reaction and was distinguished from C-8-(2-aminofluorenyl)Guo. NMR experiments with [8-C-13]Guo also provided some additional support for transient formation of N-7-(2-aminofluorenyl)Guo. We conclude that a guanyl-N-7 intermediate is reasonable in the reaction of activated arylamines with nucleic acids, although an exact rate of transfer of an N-7-arylamine group to the C8 position has not yet been quantified. The results provide an explanation for the numerous products associated with modification of DNA by activate arylamines. However, the contribution of "direct" reaction at the guanine C8 atom cannot be excluded.
• KOHDA, KOHFUKU;BABA, KUNIHISA;KAWAZOE, YUTAKA, 14TH SYMP. NUCL. ACIDS CHEM., TOKUSHIMA, OCT. 30TH - NOV. 1ST, 1986, OXFO+
  作者：KOHDA, KOHFUKU、BABA, KUNIHISA、KAWAZOE, YUTAKA

  DOI：——

  日期：——
• Kohda, Kohfuku; Baba, Kunihisa; Kawazoe, Yutaka, Chemical and pharmaceutical bulletin, 1986, vol. 34, # 5, p. 2298 - 2301
  作者：Kohda, Kohfuku、Baba, Kunihisa、Kawazoe, Yutaka

  DOI：——

  日期：——