1-[(2R,4S,5R)-4-hydroxy-5-(hydroxymethyl)oxolan-2-yl]-3-[(2-hydroxy-5-methylphenyl)methyl]-4-iminopyrimidin-2-one | 1268266-47-2

• 分子结构分类: 有机化合物 - 核苷、核苷酸和类似物 - 嘧啶核苷
• 英文名称: 1-[(2R,4S,5R)-4-hydroxy-5-(hydroxymethyl)oxolan-2-yl]-3-[(2-hydroxy-5-methylphenyl)methyl]-4-iminopyrimidin-2-one
• CAS: 1268266-47-2
• 化学式: C₁₇H₂₁N₃O₅
• 分子量: 347.371
• InChiKey: KFCWICAQPZDUIE-SQWLQELKSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  0.4
• 重原子数：
  25
• 可旋转键数：
  4
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.41
• 拓扑面积：
  117
• 氢给体数：
  4
• 氢受体数：
  6

反应信息

• 作为反应物：
  描述：

  1-[(2R,4S,5R)-4-hydroxy-5-(hydroxymethyl)oxolan-2-yl]-3-[(2-hydroxy-5-methylphenyl)methyl]-4-iminopyrimidin-2-one 在 [双(三氟乙酰氧基)碘]苯 作用下， 生成
  参考文献：
  名称：

  Oxidative Quenching of Quinone Methide Adducts Reveals Transient Products of Reversible Alkylation in Duplex DNA

  摘要：

  ortho-Quinone methides (ortho-QM) and para-quinone methides are generated by xenobiotic metabolism of numerous compounds including environmental toxins and therapeutic agents. These intermediates are highly electrophilic and have the potential to alkylate DNA. Assessing their genotoxicity can be difficult when all or some of their resulting adducts form reversibly. Stable adducts are most easily detected but are not necessarily the most prevalent products formed initially as DNA repair commences. Selective oxidation of ortho-QM-DNA adducts by bis[(trifluoroacetoxy)iodo]benzene (BTI) rapidly quenches their reversibility to prevent QM regeneration and allows for observation of the kinetic products. The resulting derivatives persist through standard enzymatic digestion, chromatography, and mass spectral analysis. The structural standards required for this approach have been synthesized and confirmed by two-dimensional NMR spectroscopy. The adducts of dA N-6, dG NI, dG N-2, and guanine N7 are converted to the expected para-quinol derivatives within 5 min after addition of BTI under aqueous conditions (pH 7). Concurrently, the adduct of dA N1 forms a Spiro derivative comparable to that characterized previously after oxidation of the corresponding dC N3 adduct. By application of this oxidative quenching strategy, the dC N3 and dA NI adducts have been identified as the dominant products formed by both single- and double-stranded DNA under initial conditions. As expected, however, these labile adducts dissipate within 24 h if not quenched with BTI. Still, the products favored by kinetics are responsible for inducing the first response to ortho-QM exposure in cells, and hence, they are also key to establishing the relationship between biological activity and molecular structure.

  DOI：

  10.1021/tx500152d
• 作为产物：
  描述：

  2-(tert-butyldimethylsilyl)oxy-5-methylbenzaldehyde 在 potassium fluoride 、 硼烷四氢呋喃络合物 、 三溴化磷 作用下， 以 四氢呋喃 、 二氯甲烷 、 N,N-二甲基甲酰胺 、 乙腈 为溶剂， 反应 4.41h， 生成 1-[(2R,4S,5R)-4-hydroxy-5-(hydroxymethyl)oxolan-2-yl]-3-[(2-hydroxy-5-methylphenyl)methyl]-4-iminopyrimidin-2-one
  参考文献：
  名称：

  捕获在邻-醌醌甲硫氨酸和2'-脱氧胞苷之间形成的不稳定加合物

  摘要：

  双[（三氟乙酰氧基）碘]苯（BTI）的选择性氧化为有效地捕集在生理条件下dC和邻醌甲基化物（QM）之间可逆形成的加合物提供了一个有效的陷阱。由4-甲基-o - QM和2'-脱氧胞苷生成的模型加合物通过分子内环化和芳香性的丧失迅速转化为用于量化QM烷基化的特征产物。然而，BTI引起了令人惊讶的重排，该重排是由在QM的4位缺少烷基取代基的衍生物的过氧化驱动的。

  DOI：

  10.1021/ol200071p