2-(β-D-ribofuranosyl)-5-methylamino-1,2,4-triazin-3(2H)-one | 878551-34-9

• 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)-5-methylamino-1,2,4-triazin-3(2H)-one
• 英文别名: N4-methyl-6-azacytidine；2-[(2R,3R,4S,5R)-3,4-dihydroxy-5-(hydroxymethyl)oxolan-2-yl]-5-(methylamino)-1,2,4-triazin-3-one
• CAS: 878551-34-9
• 化学式: C₉H₁₄N₄O₅
• 分子量: 258.234
• InChiKey: LAHPMWFZIQCWCX-XVFCMESISA-N

计算性质

• 辛醇/水分配系数(LogP)：
  -2.1
• 重原子数：
  18
• 可旋转键数：
  3
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.67
• 拓扑面积：
  127
• 氢给体数：
  4
• 氢受体数：
  6

反应信息

• 作为产物：
  描述：

  四乙酰核糖 在 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， 反应 16.5h， 生成 2-(β-D-ribofuranosyl)-5-methylamino-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.