4-cyano-5,6-diphenyl-N(2)-(2,3,5-tri-O-acetyl-β-D-ribofuranosyl)-pyridazin-3-one | 1185467-06-4

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 二嗪类
• 英文名称: 4-cyano-5,6-diphenyl-N(2)-(2,3,5-tri-O-acetyl-β-D-ribofuranosyl)-pyridazin-3-one
• 英文别名: [(2R,3R,4R,5R)-3,4-diacetyloxy-5-(5-cyano-6-oxo-3,4-diphenylpyridazin-1-yl)oxolan-2-yl]methyl acetate
• CAS: 1185467-06-4
• 化学式: C₂₈H₂₅N₃O₈
• 分子量: 531.522
• InChiKey: POZSLBKBWIIYEB-WKZNCHQYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.7
• 重原子数：
  39
• 可旋转键数：
  10
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.29
• 拓扑面积：
  145
• 氢给体数：
  0
• 氢受体数：
  10

反应信息

• 作为反应物：
  描述：

  4-cyano-5,6-diphenyl-N(2)-(2,3,5-tri-O-acetyl-β-D-ribofuranosyl)-pyridazin-3-one 在 水 、 三乙胺 作用下， 以 甲醇 为溶剂， 以85%的产率得到4-cyano-5,6-diphenyl-N(2)-(β-D-ribofuranosyl)-pyridazin-3-one
  参考文献：
  名称：

  Synthesis and Antibacterial Activity of Some Glucosyl- and Ribosyl-Pyridazin-3-ones

  摘要：

  Reaction of 5,6-diphenylpyridazin-3(2H)-one 1a,b with 2,3,4,6-tetra-O-acetyl--D-glucopyranosyl bromide 2 in K2CO3/acetone gave 5,6-diphenyl-N2-(2',3',4',6'-tetra-O-acetyl--D-glucopyranosyl)pyridazin-3-one 5a,b. The same nucleosides 5a,b were obtained by reaction of 1a,b with peracetylated glucose 3 under MW irradiation. Mercuration of 1a,b followed by reaction with glucosyl bromide 2 gave the same nucleosides 5a,b. The riboside 4-cyano-5,6-diphenyl-N2-(2',3',5'-tri-O-acetyl--D-ribofuranosyl)-pyridazin-3-one 8 was obtained by reaction of 4-cyanopyridazinone 1b with peracetylated ribose 7 under MW irradiation. The deprotected nucleosides 6a,b and 9 were obtained by stirring of 5a,b and 8 in methanol and TEA/H2O. The structure was confirmed using 1H and 13C-NMR spectra. Selected members of these compounds were screened for antibacterial activity.

  DOI：

  10.1080/15257770902831011
• 作为产物：
  描述：

  2,3-二氢-3-氧代-5,6-二苯基-4-哒嗪甲腈 、 四乙酰核糖 在 silica gel 作用下， 反应 0.05h， 以78%的产率得到4-cyano-5,6-diphenyl-N(2)-(2,3,5-tri-O-acetyl-β-D-ribofuranosyl)-pyridazin-3-one
  参考文献：
  名称：

  Synthesis and Antibacterial Activity of Some Glucosyl- and Ribosyl-Pyridazin-3-ones

  摘要：

  Reaction of 5,6-diphenylpyridazin-3(2H)-one 1a,b with 2,3,4,6-tetra-O-acetyl--D-glucopyranosyl bromide 2 in K2CO3/acetone gave 5,6-diphenyl-N2-(2',3',4',6'-tetra-O-acetyl--D-glucopyranosyl)pyridazin-3-one 5a,b. The same nucleosides 5a,b were obtained by reaction of 1a,b with peracetylated glucose 3 under MW irradiation. Mercuration of 1a,b followed by reaction with glucosyl bromide 2 gave the same nucleosides 5a,b. The riboside 4-cyano-5,6-diphenyl-N2-(2',3',5'-tri-O-acetyl--D-ribofuranosyl)-pyridazin-3-one 8 was obtained by reaction of 4-cyanopyridazinone 1b with peracetylated ribose 7 under MW irradiation. The deprotected nucleosides 6a,b and 9 were obtained by stirring of 5a,b and 8 in methanol and TEA/H2O. The structure was confirmed using 1H and 13C-NMR spectra. Selected members of these compounds were screened for antibacterial activity.

  DOI：

  10.1080/15257770902831011