[(2R,3R,4R,5R)-5-(2-amino-4-methyl-6-oxo-1,3,5-triazin-1-yl)-3,4-dibenzoyloxyoxolan-2-yl]methyl benzoate | 189129-04-2

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: [(2R,3R,4R,5R)-5-(2-amino-4-methyl-6-oxo-1,3,5-triazin-1-yl)-3,4-dibenzoyloxyoxolan-2-yl]methyl benzoate
• CAS: 189129-04-2
• 化学式: C₃₀H₂₆N₄O₈
• 分子量: 570.558
• InChiKey: FEALENYJOGFDSE-ZGFBMJKBSA-N

物化性质

• 沸点：
  712.7±70.0 °C(Predicted)
• 密度：
  1.41±0.1 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  2.73
• 重原子数：
  42.0
• 可旋转键数：
  8.0
• 环数：
  5.0
• sp3杂化的碳原子比例：
  0.2
• 拓扑面积：
  161.93
• 氢给体数：
  1.0
• 氢受体数：
  12.0

反应信息

• 作为反应物：
  描述：

  [(2R,3R,4R,5R)-5-(2-amino-4-methyl-6-oxo-1,3,5-triazin-1-yl)-3,4-dibenzoyloxyoxolan-2-yl]methyl benzoate 在 sodium methylate 作用下， 以 甲醇 为溶剂， 反应 8.0h， 以70%的产率得到6-Amino-1-((2R,3R,4S,5R)-3,4-dihydroxy-5-hydroxymethyl-tetrahydro-furan-2-yl)-4-methyl-1H-[1,3,5]triazin-2-one
  参考文献：
  名称：

  6-Methyl-5-Azacytidine-Synthesis, Conformational Properties and Biological Activity. A Comparison of Molecular Conformation with 5-Azacytidine

  摘要：

  The title compound was prepared by the isocyanate procedure and the trimethylsilyl method. The measurement of H-1 NMR spectrum of 6-methyl-5-azacytidine (1) revealed a preference of gamma(t) (46%) rotamer around C(5')-C(4') bond, a predominance of N conformation of the ribose ring (K-eq 0.33) and a preference of syn conformation around the C-N glycosyl bond. An analogous measurement of 5-azacytidine has shown a preference of gamma(+) (60%) rotamer around the C(5')-C(4') bond, a predominance of N conformation of the ribose ring (K-eq 0.41) and a preference of anti conformation around the C-N glycosyl bond. 6-Methyl-5-azacytidine (1) inhibits the growth of bacteria E. coli to the extent of 85% at 4000 mu M concentration and the growth of LoVo/L, a human colon carcinoma cell line, to the extent of 30% at 100 mu M concentration but did not inhibit L1210 cells at less than or equal to 100 mu M concentration. 6-Methyl-5-azacytidine (1) exhibited no in vitro antiviral activity at less than or equal to 1 mu M concentration.

  DOI：

  10.1080/07328319708002528
• 作为产物：
  描述：

  1-乙酰氧基-2,3,5-三苯甲酰氧基-1-beta-D-呋喃核糖 、 (4-Methyl-6-trimethylsilanyloxy-[1,3,5]triazin-2-yl)-trimethylsilanyl-amine 在 四氯化锡 作用下， 以 1,2-二氯乙烷 为溶剂， 反应 0.5h， 以40%的产率得到2',3',5'-tri-O-benzoyl-6-methyl-5-azacytidine
  参考文献：
  名称：

  6-Methyl-5-Azacytidine-Synthesis, Conformational Properties and Biological Activity. A Comparison of Molecular Conformation with 5-Azacytidine

  摘要：

  The title compound was prepared by the isocyanate procedure and the trimethylsilyl method. The measurement of H-1 NMR spectrum of 6-methyl-5-azacytidine (1) revealed a preference of gamma(t) (46%) rotamer around C(5')-C(4') bond, a predominance of N conformation of the ribose ring (K-eq 0.33) and a preference of syn conformation around the C-N glycosyl bond. An analogous measurement of 5-azacytidine has shown a preference of gamma(+) (60%) rotamer around the C(5')-C(4') bond, a predominance of N conformation of the ribose ring (K-eq 0.41) and a preference of anti conformation around the C-N glycosyl bond. 6-Methyl-5-azacytidine (1) inhibits the growth of bacteria E. coli to the extent of 85% at 4000 mu M concentration and the growth of LoVo/L, a human colon carcinoma cell line, to the extent of 30% at 100 mu M concentration but did not inhibit L1210 cells at less than or equal to 100 mu M concentration. 6-Methyl-5-azacytidine (1) exhibited no in vitro antiviral activity at less than or equal to 1 mu M concentration.

  DOI：

  10.1080/07328319708002528