2-<1-β-D-Glucosyl>-3-oxo-5,6-diphenyl-pyridazin-4-carbonitril | 10428-11-2

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: 2-<1-β-D-Glucosyl>-3-oxo-5,6-diphenyl-pyridazin-4-carbonitril
• 英文别名: 4-cyano-5,6-diphenyl-N(2)-(β-D-glucopyranosyl)-pyridazin-3-one；2-β-D-glucopyranosyl-3-oxo-5,6-diphenyl-2,3-dihydro-pyridazine-4-carbonitrile；3-oxo-5,6-diphenyl-2-[(2R,3R,4S,5S,6R)-3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]pyridazine-4-carbonitrile
• CAS: 10428-11-2
• 化学式: C₂₃H₂₁N₃O₆
• 分子量: 435.436
• InChiKey: HIRINROLJZZUFX-JTLUYSSBSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  0.9
• 重原子数：
  32
• 可旋转键数：
  4
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.26
• 拓扑面积：
  147
• 氢给体数：
  4
• 氢受体数：
  8

反应信息

• 作为产物：
  描述：

  3-Oxo-5,6-diphenyl-2--pyridazin-4-carbonitril 在 水 、 三乙胺 作用下， 以 甲醇 为溶剂， 以85%的产率得到2-<1-β-D-Glucosyl>-3-oxo-5,6-diphenyl-pyridazin-4-carbonitril
  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

文献信息

• Synthesis and Antibacterial Activity of Some Glucosyl- and Ribosyl-Pyridazin-3-ones
  作者：H. A. El-Sayed、A. H. Moustafa、A. Z. Haikal、E. S. H. El-Ashry

  DOI：10.1080/15257770902831011

  日期：2009.4.28

  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.