N¹,N³-bis(pentafluorobenzyl)-5-hydroxymethyluracil | 126128-80-1

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 二嗪类
• 英文名称: N¹,N³-bis(pentafluorobenzyl)-5-hydroxymethyluracil
• 英文别名: 5-(hydroxymethyl)-1,3-bis[(2,3,4,5,6-pentafluorophenyl)methyl]pyrimidine-2,4-dione
• CAS: 126128-80-1
• 化学式: C₁₉H₈F₁₀N₂O₃
• 分子量: 502.268
• InChiKey: CHOXVHMHFKIEKM-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.99
• 重原子数：
  34.0
• 可旋转键数：
  5.0
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.16
• 拓扑面积：
  64.23
• 氢给体数：
  1.0
• 氢受体数：
  5.0

反应信息

• 作为反应物：
  描述：

  N¹,N³-bis(pentafluorobenzyl)-5-hydroxymethyluracil 、 α-溴-2,3,4,5,6-五氟甲基苯酸酯 生成 5-[(2,3,4,5,6-pentafluorophenyl)methoxymethyl]-1,3-bis[(2,3,4,5,6-pentafluorophenyl)methyl]pyrimidine-2,4-dione
  参考文献：
  名称：

  KRESBACH, GERHARD M.;ITANI, MOHAMED;SAHA, MANASI;ROGERS, EUGENE J.;VOUROS+, J. CHROMATOGR., 476,(1989) C. 423-438

  摘要：

  DOI：
• 作为产物：
  描述：

  5-羟甲基脲嘧啶 、 α-溴-2,3,4,5,6-五氟甲基苯酸酯 在 N,N-二异丙基乙胺 作用下， 以 甲醇 为溶剂， 反应 1.0h， 生成 N¹,N³-bis(pentafluorobenzyl)-5-hydroxymethyluracil
  参考文献：
  名称：

  Measurement of urinary excretion of 5-hydroxymethyluracil in human by GC/NICI/MS:

  摘要：

  5-Hydroxymethyluracil (5-HMU) is derived from radiation in addition to endogenous oxidative DNA damage and it is one of the most abundant DNA adducts. Human 5-HMU-DNA-glycosylase has been shown to repair this lesion. Whether urinary levels of 5-HMU is a valid biomarker for oxidative DNA damage in vivo has been investigated. However, controversial results on its relation to cigarette smoking were reported. To facilitate analysis of urinary 5-HMU in epidemiological studies, a highly sensitive and specific assay based on stable isotope dilution gas chromatography/negative ion chemical ionization/mass spectrometry was developed. The limit of detection for N-1,N-3-bis(pentafluorobenzyl)-HMU is 10 fg (20 amol) (S/N= 4) injected on column and the limit of quantification in urine was 0.7 nM of 5-HMU. Using as little as 10 muL of human urine samples, levels of urinary 5-HMU in 21 healthy volunteers were accurately quantified. No correlation was observed between urinary 5-HMU levels and cigarette smoking. However, there was a statistically significant association between urinary levels of 5-HMU and thiobarbituric acid-reactive substances (r = 0.71, p = 0.0003). In addition, urinary 5-HMU levels also correlated with urinary levels of 1,N-6-ethenoadenine (r = 0.54, p = 0.01). These findings suggest that this assay should be valuable in assessing the role of urinary 5-HMU as a biomarker of oxidative DNA damage and repair. (C) 2004 Elsevier Ireland Ltd. All rights reserved.

  DOI：

  10.1016/j.toxlet.2004.11.009