2-氨基-1,7-二氢-7-(2-羟基丙基)-6H-嘌呤-6-酮 | 56247-84-8

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 咪唑并嘧啶类
• 中文名称: 2-氨基-1,7-二氢-7-(2-羟基丙基)-6H-嘌呤-6-酮
• 英文名称: N-7-(2-Hydroxypropyl)gaunine
• 英文别名: N-7-(2-Hydroxyprop-1-yl)guanine；7-(2-Hydroxy-propyl)-guanine；2-amino-7-(2-hydroxy-propyl)-1,7-dihydro-purin-6-one；7-(2-Hydroxypropyl)guanine；2-amino-7-(2-hydroxypropyl)-1H-purin-6-one
• CAS: 56247-84-8
• 化学式: C₈H₁₁N₅O₂
• 分子量: 209.208
• InChiKey: JVWVMKYNORDKGP-UHFFFAOYSA-N

物化性质

• 熔点：
  >300°C
• 溶解度：
  可溶于DMSO、水（少量）

计算性质

• 辛醇/水分配系数(LogP)：
  -1.4
• 重原子数：
  15
• 可旋转键数：
  2
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.38
• 拓扑面积：
  106
• 氢给体数：
  3
• 氢受体数：
  4

反应信息

• 作为产物：
  描述：

  鸟苷 、 methyloxirane 在 溶剂黄146 、 盐酸 作用下， 反应 5.5h， 生成 2-氨基-1,7-二氢-7-(2-羟基丙基)-6H-嘌呤-6-酮
  参考文献：
  名称：

  比较人血红蛋白的N末端缬氨酸和人DNA的N-7鸟嘌呤在体外形成乙烯，丙烯和苯乙烯7,8-氧化物的加合物。

  摘要：

  环氧化合物在大分子的各种亲核位点（如血红蛋白和DNA）反应。为了研究环氧乙烷（EO），环氧丙烷（PO）和苯乙烯7,8-氧化物（SO）在其中两个位置上的反应速率常数，即血红蛋白中的N末端缬氨酸和N-7鸟嘌呤中的DNA是这项研究的主要目标。这两个反应性位点分别是研究最多的血红蛋白和DNA加合物。因此，还进一步关注了体外测定的反应常数在体内的适用性。Hb [分别为2.7 l（mol Hb h）-1和1.0 l（mol Hb h）-1]中EO和PO与N末端缬氨酸之间的二级速率常数的测定与文献值一致。与N-7-鸟嘌呤[16x10（-3）l（mol DNA核苷酸h）-1和7的反应常数。[分别为7x10（-3）l（mol DNA核苷酸h）-1]低于以前发表的值，可能是由于所使用的方法不同。使用体外获得的值对体内情况进行建模可得到EO和PO的一致图片。相反，对于SO，N末端缬氨酸[1.5 l（mol Hb

  DOI：

  10.1016/s1383-5718(98)00106-5

文献信息

• Tandem mass spectrometric approaches for the analysis of alkylguanines in human urine
  作者：J. R. Cushnir、S. Naylor、J. H. Lamb、P. B. Farmer

  DOI：10.1002/oms.1210280514

  日期：1993.5

  AbstractHuman exposure to carcinogenic alkylating agents can lead to the formation of covalently bound adducts in DNA, some of which are excreted in urine as alkylated purines following DNA degradation and repair. Tandem mass spectrometric methods have been developed for the qualitative and quantitative determination of such alkylpurines in human urine. Short‐chain alkyl‐ and hydroxyalkylguanines have been synthesized with the substituents at theN‐7‐,O6‐ andN2‐positions of guanine. Examination of the product ion scans of their molecular ions (electron impact (EI) ionization) revealed that the ion atm/z151, [guanine]+, was common to all of the alkylguanines studied, with the exception of the methylated analogues. Precursor ion scans of this ion on partially purified human urine extracts showed the presence of several ions (e.g.m/z179, 195) which were consistent with molecular ions for alkylguanines. The presence of these and other constituents was confirmed by product ion spectra of molecular ions (EI and fast atom bombardment), and by high‐performance liquid chromatographic separation prior to tandem mass spectrometry (MS/MS). Evidence was obtained for the presence ofN‐7‐methyl‐,N2‐dimethyl‐,N2‐dimethyl‐,N2‐ethyl‐ andN‐7‐(2‐hydroxyethyl)guanine. Quantitative methods were established for these five alkyl guanines using gas chromatography mass spectrometry (GC/MS) and GC/MS/MS. Deuterated internal standards were synthesized and added to the urine prior to extraction of alkylpurines by Sep‐Pak cartridge chromatography. The products were converted into theirtert‐butyldimethylsilyl derivatives and analysed by selected ion monitoring (SIM) of [M – 57]+or by multiple reaction monitoring (MRM) of the fragmentation M+˙→ [M – 57]+. The MRM method yielded values forN‐7‐methylguanine of 2.57 ± S.D. 1.32 mg day−1(n= 6),N2‐methylguanine of 0.31 ± 0.10 mg day−1(n= 10) andN2‐dimethylguanine of 0.21 ± 0.23 mg day−1(n= 10).N2‐Ethyl‐ andN‐7‐(2‐hydroxyethyl)guanine could only be detected by SIM at levels of ∼0.5 and 2 μg day−1, respectively. The MRM analyses, although inherently less sensitive than the SIM analyses, exhibit greater selectivity and consequently fewer contaminant ions.
• Comparison of ethylene, propylene and styrene 7,8-oxide in vitro adduct formation on N-terminal valine in human haemoglobin and on N-7-guanine in human DNA
  作者：W Pauwels、H Veulemans

  DOI：10.1016/s1383-5718(98)00106-5

  日期：1998.9

  nucleophilic sites in macromolecules such as haemoglobin and DNA. To study the reaction rate constants of ethylene oxide (EO), propylene oxide (PO) and styrene 7,8-oxide (SO) towards two of these positions, i.e., the N-terminal valine in haemoglobin and N-7-guanine in DNA was the central aim of this investigation. These two reactive sites are the most studied haemoglobin and DNA adducts, respectively. Further

  环氧化合物在大分子的各种亲核位点（如血红蛋白和DNA）反应。为了研究环氧乙烷（EO），环氧丙烷（PO）和苯乙烯7,8-氧化物（SO）在其中两个位置上的反应速率常数，即血红蛋白中的N末端缬氨酸和N-7鸟嘌呤中的DNA是这项研究的主要目标。这两个反应性位点分别是研究最多的血红蛋白和DNA加合物。因此，还进一步关注了体外测定的反应常数在体内的适用性。Hb [分别为2.7 l（mol Hb h）-1和1.0 l（mol Hb h）-1]中EO和PO与N末端缬氨酸之间的二级速率常数的测定与文献值一致。与N-7-鸟嘌呤[16x10（-3）l（mol DNA核苷酸h）-1和7的反应常数。[分别为7x10（-3）l（mol DNA核苷酸h）-1]低于以前发表的值，可能是由于所使用的方法不同。使用体外获得的值对体内情况进行建模可得到EO和PO的一致图片。相反，对于SO，N末端缬氨酸[1.5 l（mol Hb