7-(β-D-ribofuranosyl)-6-oxo-6,7-dihydro-4H-pyrimido[1,6-a]pyrimidine-3-carbaldehyde

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: 7-(β-D-ribofuranosyl)-6-oxo-6,7-dihydro-4H-pyrimido[1,6-a]pyrimidine-3-carbaldehyde
• 英文别名: 7-[(2R,3R,4S,5R)-3,4-dihydroxy-5-(hydroxymethyl)oxolan-2-yl]-6-oxo-4H-pyrimido[1,2-c]pyrimidine-3-carbaldehyde
• 化学式: C₁₃H₁₅N₃O₆
• 分子量: 309.279
• InChiKey: HRYFRKPTCIHNPH-HJQYOEGKSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  -2.9
• 重原子数：
  22
• 可旋转键数：
  3
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.46
• 拓扑面积：
  123
• 氢给体数：
  3
• 氢受体数：
  7

反应信息

• 作为产物：
  描述：

  聚合甲醛 、 1,1,3,3-四甲氧基丙烷 、 胞苷 在 盐酸 作用下， 以 various solvent(s) 为溶剂， 反应 72.0h， 以3.0 mg的产率得到7-(β-D-ribofuranosyl)-6-oxo-6,7-dihydro-4H-pyrimido[1,6-a]pyrimidine-3-carbaldehyde
  参考文献：
  名称：

  Identification of Conjugate Adducts Formed in the Reactions of Malonaldehyde-Acetaldehyde and Malonaldehyde-Formaldehyde with Cytidine

  摘要：

  Malonaldehyde was reacted with cytidine in buffered aqueous solutions in the presence of acetaldehyde or formaldehyde. The reaction mixtures were analyzed by HPLC, and the products were isolated by preparative C18 chromatography and structurally characterized by UV absorbance, fluorescence emission, H-1 and C-13 NMR spectroscopy, and mass spectrometry. The major adducts formed in the reaction of malonaldehyde and acetaldehyde were identified as 7-(beta-D-ribofuranosyl)-4-methyl-6-oxo-6,7-dihydro-4H-pyrimido[1,6-a]pyrimidine-3-carbaldehyde (M(1)AA-Cyd) and 1-(beta-D-ribofuranosyl)-4-(3,5-diformyl-4-methyl-1,4-dihydro-1-pyridyl)pyrimidine (M(2)AA-Cyd). In the reaction of malonaldehyde and formaldehyde, the major product was identified as 7-(beta-D-ribofuranosyl)-6-oxo-6,7-dihydro-4H-pyrimido[1,6-a] pyrimidine-3-carbaldehyde (M(1)FA-Cyd). The highest yields of M(1)AA-Cyd and M(2)AA-Cyd, 3.2 and 0.5 mol%, respectively, were obtained in the reaction performed at pH 4.6 and 37 degreesC for 8 days, while M(1)FA-Cyd was produced at a yield of 0.3 mol% after 3 days of reaction at pH 4.0 and 37 degreesC. The products consist of units derived from malonaldehyde and acetaldehyde (M(1)AA-Cyd and M(2)AA-Cyd) or from malonaldehyde and formaldehyde (M(1)FA-Cyd), and are thus further examples of nucleoside modifications containing structural elements derived from aldehyde condensation reactions. Trace amounts of the adducts may be formed at physiological conditions and may be involved in the mutagenicity of the studied aldehydes.

  DOI：

  10.1021/tx010122k

文献信息

• Pluskota-Karwatka; Munter; Le Curieux, Polish Journal of Chemistry, 2007, vol. 81, # 5-6, p. 1147 - 1157
  作者：Pluskota-Karwatka、Munter、Le Curieux、Sjoeholm、Koroniak、Kronberg

  DOI：——

  日期：——
• Identification of Conjugate Adducts Formed in the Reactions of Malonaldehyde-Acetaldehyde and Malonaldehyde-Formaldehyde with Cytidine
  作者：Donata Pluskota-Karwatka、Frank Le Curieux、Tony Munter、Rainer Sjöholm、Leif Kronberg

  DOI：10.1021/tx010122k

  日期：2002.2.1

  Malonaldehyde was reacted with cytidine in buffered aqueous solutions in the presence of acetaldehyde or formaldehyde. The reaction mixtures were analyzed by HPLC, and the products were isolated by preparative C18 chromatography and structurally characterized by UV absorbance, fluorescence emission, H-1 and C-13 NMR spectroscopy, and mass spectrometry. The major adducts formed in the reaction of malonaldehyde and acetaldehyde were identified as 7-(beta-D-ribofuranosyl)-4-methyl-6-oxo-6,7-dihydro-4H-pyrimido[1,6-a]pyrimidine-3-carbaldehyde (M(1)AA-Cyd) and 1-(beta-D-ribofuranosyl)-4-(3,5-diformyl-4-methyl-1,4-dihydro-1-pyridyl)pyrimidine (M(2)AA-Cyd). In the reaction of malonaldehyde and formaldehyde, the major product was identified as 7-(beta-D-ribofuranosyl)-6-oxo-6,7-dihydro-4H-pyrimido[1,6-a] pyrimidine-3-carbaldehyde (M(1)FA-Cyd). The highest yields of M(1)AA-Cyd and M(2)AA-Cyd, 3.2 and 0.5 mol%, respectively, were obtained in the reaction performed at pH 4.6 and 37 degreesC for 8 days, while M(1)FA-Cyd was produced at a yield of 0.3 mol% after 3 days of reaction at pH 4.0 and 37 degreesC. The products consist of units derived from malonaldehyde and acetaldehyde (M(1)AA-Cyd and M(2)AA-Cyd) or from malonaldehyde and formaldehyde (M(1)FA-Cyd), and are thus further examples of nucleoside modifications containing structural elements derived from aldehyde condensation reactions. Trace amounts of the adducts may be formed at physiological conditions and may be involved in the mutagenicity of the studied aldehydes.