2-hydrazinoinosine | 52538-27-9

• 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: 2-hydrazinoinosine
• 英文别名: N²-NH2Guo；2-Hydrazino-inosin；xanthosine 2-hydrazone；9-[(2R,3R,4S,5R)-3,4-dihydroxy-5-(hydroxymethyl)oxolan-2-yl]-2-hydrazinyl-1H-purin-6-one
• CAS: 52538-27-9
• 化学式: C₁₀H₁₄N₆O₅
• 分子量: 298.258
• InChiKey: XXJDHHNIDXTOFH-UUOKFMHZSA-N

物化性质

• 熔点：
  213 °C
• 密度：
  2.29±0.1 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  -2.2
• 重原子数：
  21
• 可旋转键数：
  3
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.5
• 拓扑面积：
  167
• 氢给体数：
  6
• 氢受体数：
  8

反应信息

• 作为产物：
  描述：

  2-氯腺嘌呤核苷 在 盐酸 、 一水合肼 、 sodium nitrite 作用下， 以 乙二醇甲醚 、 水 为溶剂， 反应 4.0h， 生成 2-hydrazinoinosine
  参考文献：
  名称：

  鸟嘌呤的N2氨基化为2-肼基次黄嘌呤，这是一种由肝致癌物2-硝基丙烷产生的新型体内核酸修饰。

  摘要：

  2-硝基丙烷（一种工业化学品和大鼠中的肝致癌物）诱导芳基磺基转移酶介导的肝脏DNA和RNA碱基修饰[Sodum，RS，Sohn，OS，Nie，G.，and Fiala，ES（1994）。Res。毒药。7，344-351]。这些修饰中的两个先前被鉴定为8-氨基鸟嘌呤和8-氧代鸟嘌呤。我们现在报告，迄今尚未确定的第三种核酸修饰的基本部分，即RNA中的RX1和DNA中的DX1，是2-肼基次黄嘌呤（N2-氨基鸟嘌呤）。2-Hyrazrazinoinosine和2-hydrazinodeoxyinosine，是通过采用已公开的程序合成的，分别用2-硝基丙烷处理的大鼠的肝RNA和DNA的RX1和DX1进行共色谱。2-Hyrazrazinoinosine和2-hydrazinodeoxyinosine在溶液中像体内产物RX1和DX1一样不稳定。在中性pH下，次黄嘌呤核苷是分解的主要产物，而在pH等于或大

  DOI：

  10.1021/tx980160c

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.