N-(acetylamidino)-N'-(2,3,5-tri-O-benzoyl-β-D-ribosyl)urea | 189131-47-3

• 分子结构分类: 有机化合物 - 苯类化合物 - 苯和取代衍生物
• 英文名称: N-(acetylamidino)-N'-(2,3,5-tri-O-benzoyl-β-D-ribosyl)urea
• CAS: 189131-47-3
• 化学式: C₃₀H₂₈N₄O₉
• 分子量: 588.574
• InChiKey: DWLAIDUAZIBRCQ-ZGFBMJKBSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.18
• 重原子数：
  43.0
• 可旋转键数：
  8.0
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.2
• 拓扑面积：
  184.71
• 氢给体数：
  3.0
• 氢受体数：
  9.0

反应信息

• 作为反应物：
  描述：

  N-(acetylamidino)-N'-(2,3,5-tri-O-benzoyl-β-D-ribosyl)urea 在 三甲基氯硅烷 作用下， 以 三乙胺 、 乙腈 为溶剂， 反应 0.33h， 以84%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
• 作为产物：
  描述：

  2,3,5-tri-O-benzoyl-β-D-ribosyl isocyanate 、 N-乙酰基胍 以 丙酮 为溶剂， 反应 0.5h， 以43%的产率得到N-(acetylamidino)-N'-(2,3,5-tri-O-benzoyl-β-D-ribosyl)urea
  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