2-β-D-ribofuranosyl-(2',3’,5’-tri-O-acetyl)-N5-acetylamino-1,2,4-triazin-3(2H)-one | 20757-65-7

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: 2-β-D-ribofuranosyl-(2',3’,5’-tri-O-acetyl)-N5-acetylamino-1,2,4-triazin-3(2H)-one
• 英文别名: N4-acetyl-6-aza-triacetylcytidine；N,O-tetraacetyl-6-azacytidine；5-acetylamino-2-(tri-O-acetyl-β-D-ribofuranosyl)-2H-[1,2,4]triazin-3-one；N⁴-Acetyl-2',3',5'-tri-O-acetyl-6-aza-cytidin；N(4)-Acetyl-2',3',5'-tri-O-acetyl-6-aza-cytidin；N(49-Acetyl-2',3',5'-tri-O-acetyl-6-aza-cytidin；[(2R,3R,4R,5R)-5-(5-acetamido-3-oxo-1,2,4-triazin-2-yl)-3,4-diacetyloxyoxolan-2-yl]methyl acetate
• CAS: 20757-65-7
• 化学式: C₁₆H₂₀N₄O₉
• 分子量: 412.356
• InChiKey: KPWRZHUNKUNRSC-NMFUWQPSSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  -0.3
• 重原子数：
  29
• 可旋转键数：
  9
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.56
• 拓扑面积：
  162
• 氢给体数：
  1
• 氢受体数：
  10

反应信息

• 作为产物：
  描述：

  四乙酰核糖 在 吡啶 、 ammonium hydroxide 、 三甲基氯硅烷 、 四氯化锡 、 六甲基二硅氮烷 作用下， 以 乙醇 、 乙腈 为溶剂， 生成 2-β-D-ribofuranosyl-(2',3’,5’-tri-O-acetyl)-N5-acetylamino-1,2,4-triazin-3(2H)-one
  参考文献：
  名称：

  Synthesis and Comparative Study of Anti-Adenoviral Activity of 6-Azacytidine and Its Analogues

  摘要：

  This paper presents the results of synthesis and study of cytotoxicity and the anti-adenoviral activity of new N4-derivatives of 6-azacytidine and its alpha-L-glycopyranosyl analogues obtained by the simplified one-pot version of the silyl condensation method. The resulting acylated 4-methylmercapto-1,2,4-triazin-3(2H)-one glycosides then underwent the amination and/or ammonolysis to provide 6-azacytidine glycoside analogues (2-6, 12, 15, 17) and compounds with modifications at both base and sugar fragments (11, 15). The evaluation of cytotoxicity and antiviral activity of new compounds against AdV5 showed high selectivity indexes for N4-methyl-6-azacytidine (2) and N,O-tetraacetyl-6-azacytidine (8). High anti-adenoviral activity of N4-methyl-6-azacytidine as well as very low cytotoxicity may suggest its further investigation as potential compound for the therapy of AdV infection.

  DOI：

  10.1080/15257770.2015.1034363

文献信息

• Synthesis and Comparative Study of Anti-Adenoviral Activity of 6-Azacytidine and Its Analogues
  作者：Inna Alexeeva、Lydia Nosach、Larisa Palchykovska、Lyubov Usenko、Olga Povnitsa

  DOI：10.1080/15257770.2015.1034363

  日期：2015.8.3

  This paper presents the results of synthesis and study of cytotoxicity and the anti-adenoviral activity of new N4-derivatives of 6-azacytidine and its alpha-L-glycopyranosyl analogues obtained by the simplified one-pot version of the silyl condensation method. The resulting acylated 4-methylmercapto-1,2,4-triazin-3(2H)-one glycosides then underwent the amination and/or ammonolysis to provide 6-azacytidine glycoside analogues (2-6, 12, 15, 17) and compounds with modifications at both base and sugar fragments (11, 15). The evaluation of cytotoxicity and antiviral activity of new compounds against AdV5 showed high selectivity indexes for N4-methyl-6-azacytidine (2) and N,O-tetraacetyl-6-azacytidine (8). High anti-adenoviral activity of N4-methyl-6-azacytidine as well as very low cytotoxicity may suggest its further investigation as potential compound for the therapy of AdV infection.