5,6,7,9-tetrahydro-7-hydroxy-9-oxoimidazo[1,2-a]purine

• 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: 5,6,7,9-tetrahydro-7-hydroxy-9-oxoimidazo[1,2-a]purine
• 英文别名: 7-hydroxy-1,4,6,7-tetrahydroimidazo[1,2-a]purin-9-one
• 化学式: C₇H₇N₅O₂
• 分子量: 193.165
• InChiKey: JISAHYOXPXPVOY-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  -1.2
• 重原子数：
  14
• 可旋转键数：
  0
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.29
• 拓扑面积：
  93.6
• 氢给体数：
  3
• 氢受体数：
  4

反应信息

• 作为产物：
  描述：

  氯乙烯氧化物 、 alkaline earth salt of/the/ methylsulfuric acid 在 N-ethylmorpholine acetate buffer 作用下， 生成 3,5-二氢咪唑并[2,1-b]嘌呤-4-酮 、 1,(N2)-乙烯桥鸟嘌呤 、 3-(2-deoxy-β-D-erythro-pentofuranosyl)-3,5,6,7-tetrahydro-7-hydroxy-9H-imidazo[1,2-a]purin-9-one 、 5,6,7,9-tetrahydro-7-hydroxy-9-oxoimidazo[1,2-a]purine
  参考文献：
  名称：

  Analysis of 1,N²-Ethenoguanine and 5,6,7,9-Tetrahydro-7-hydroxy-9-oxoimidazo[1,2-a]purine in DNA Treated with 2-Chlorooxirane by High Performance Liquid Chromatography/Electrospray Mass Spectrometry and Comparison of Amounts to Other DNA Adducts

  摘要：

  High performance liquid chromatography (HPLC)/electrospray mass spectrometry methods were developed for the analysis of 1/N-2-etheno(epsilon)guanine (Gua) and 5,6,7,9-tetrahydro-7-hydroxy-9-oxoimidazo[1,2-a]purine (HO-ethanoGua) [the cyclized form of N-2-(2-oxoethyl)Gua] and its deoxyribose derivative in DNA. Evidence was provided for the formation of the latter adduct in DNA treated with 2-chlorooxirane, the reactive product formed from the carcinogen vinyl chloride. Measured levels of HO-ethanoGua and HO-ethanodeoxyguanosine were similar, although the assay for the deoxyribosyl derivative has some technical advantages. 3,N-4-epsilon-Deoxycytidine was also estimated in 2-chlorooxirane-treated DNA using HPLC with fluorescence detection. Levels of all known adducts formed from vinyl chloride have now been estimated in DNA treated with 2-chlorooxirane and vary in the order N-7-(2-oxoethyl)Gua >> 1,N-6-epsilon-adenine > HO-ethanoGua > N-2,3-epsilon-Gua > 3,N-4-epsilon-cytosine > 1,N-2-epsilon-Gua. Although in vivo adduct levels may not parallel these due to differential stability and rates of repair, analyses of the adducts in DNA treated with 2-chlorooxirane provide a basis for consideration of the biological effects of these adducts.

  DOI：

  10.1021/tx960124i