6-((2R,4S,5R)-4-hydroxy-5-(hydroxymethyl)tetrahydrofuran-2-yl)-3-(2-oxoheptyl)-1,8a-dihydroimidazo[1,2-c]pyrimidin-5(6H)-one | 566943-69-9

• 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: 6-((2R,4S,5R)-4-hydroxy-5-(hydroxymethyl)tetrahydrofuran-2-yl)-3-(2-oxoheptyl)-1,8a-dihydroimidazo[1,2-c]pyrimidin-5(6H)-one
• 英文别名: dC-ONE；6-[(2R,4S,5R)-4-hydroxy-5-(hydroxymethyl)oxolan-2-yl]-3-(2-oxoheptyl)imidazo[1,2-c]pyrimidin-5-one
• CAS: 566943-69-9
• 化学式: C₁₈H₂₅N₃O₅
• 分子量: 363.414
• InChiKey: MVZSJYKSHQNNDA-ZMSDIMECSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  0.83
• 重原子数：
  26.0
• 可旋转键数：
  8.0
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.61
• 拓扑面积：
  106.06
• 氢给体数：
  2.0
• 氢受体数：
  8.0

反应信息

• 作为产物：
  描述：

  2'-脱氧胞嘧啶核苷 、 4-oxo-non-2-enal 以 aq. phosphate buffer 、 乙腈 为溶剂， 反应 48.0h， 生成 6-((2R,4S,5R)-4-hydroxy-5-(hydroxymethyl)tetrahydrofuran-2-yl)-3-(2-oxoheptyl)-1,8a-dihydroimidazo[1,2-c]pyrimidin-5(6H)-one
  参考文献：
  名称：

  Identification of Octenal-Related dA and dC Adducts Formed by Reactions with a Hemin-ω-6-fat Peroxidation Model System

  摘要：

  Deoxynucleosides were reacted in a lipid peroxidation model system, emulsified hemin-ethyl linoleate, and the adducts thus produced were analyzed by HPLC. Substantial amounts of stable adducts were detected in the dA- and dC-reaction mixtures. The structures of the major dA and dC adducts, other than the known 4-oxo-2-nonenal adducts, were determined to be etheno-type adducts, with a C-6 side chain bearing an a-hydroxyl-group. These results suggested that the substance involved in adduct formation is 2,3-epoxyoctanal. This compound showed mutagenicity in Salmonella strains TA 100 and TA 104 without the S-9 mix. In addition, based on the structure of a minor dC adduct, another possibly involved mutagen, 4-oxo-2-octenal, was proposed. These mutagens may be formed during storage and cooking of food, or during digestion, and may be involved in human cancers.

  DOI：

  10.1021/tx400245a