2-(1-naphthyl)-5-(2,3,4,6-tetra-O-benzoyl-β-D-glucopyranosyl)-1,3,4-oxadiazole | 1179326-56-7

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: 2-(1-naphthyl)-5-(2,3,4,6-tetra-O-benzoyl-β-D-glucopyranosyl)-1,3,4-oxadiazole
• CAS: 1179326-56-7
• 化学式: C₄₆H₃₄N₂O₁₀
• 分子量: 774.783
• InChiKey: JDKKCSHNKJNRFN-JSMBFNCYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  7.86
• 重原子数：
  58.0
• 可旋转键数：
  11.0
• 环数：
  8.0
• sp3杂化的碳原子比例：
  0.13
• 拓扑面积：
  153.35
• 氢给体数：
  0.0
• 氢受体数：
  12.0

反应信息

• 作为反应物：
  描述：

  2-(1-naphthyl)-5-(2,3,4,6-tetra-O-benzoyl-β-D-glucopyranosyl)-1,3,4-oxadiazole 在 sodium methylate 、 Amberlyst 15 作用下， 以 甲醇 、 氯仿 为溶剂， 以91%的产率得到5-(β-D-glucopyranosyl)-2-(1-naphthyl)-1,3,4-oxadiazole
  参考文献：
  名称：

  Synthesis and structure–activity relationships of C-glycosylated oxadiazoles as inhibitors of glycogen phosphorylase

  摘要：

  A series of per-O-benzoylated 5-beta-D-glucopyranosyl-2-substituted-1,3,4-oxadiazoles was prepared by acylation of the corresponding 5-(beta-D-glucopyranosyl) tetrazole. As an alternative, oxidation of 2,6-anhydro-aldose benzoylhydrazones by iodobenzene I, I-diacetate afforded the same oxadiazoles. 1,3-Dipolar cycloaddition of nitrile oxides to per-O-benzoylated beta-D-glucopyranosyl cyanide gave the corresponding 5-beta-D-glucopyranosyl-3-substituted-1,2,4-oxadiazoles. The O-benzoyl protecting groups were removed by base-catalyzed transesterification. The 1,3,4-oxadiazoles were practically inefficient as inhibitors of rabbit muscle glycogen phosphorylase b while the 1,2,4-oxadiazoles displayed inhibitory activities in the micromolar range. The best inhibitors were the 5-beta-D-glucopyranosyl-3-(4-methylphenyl-and -2-naphthyl)- 1,2,4-oxadiazoles (K-i = 8.8 and 11.6 mu M, respectively). A detailed analysis of the structure-activity relationships is presented. (C) 2009 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.bmc.2009.04.036
• 作为产物：
  描述：

  5-(2',3',4',6'-tetra-O-benzoyl-β-D-glucopyranosyl)tetrazole 、 1-萘甲酰氯 在 吡啶 作用下， 反应 1.0h， 以75%的产率得到2-(1-naphthyl)-5-(2,3,4,6-tetra-O-benzoyl-β-D-glucopyranosyl)-1,3,4-oxadiazole
  参考文献：
  名称：

  Synthesis and structure–activity relationships of C-glycosylated oxadiazoles as inhibitors of glycogen phosphorylase

  摘要：

  A series of per-O-benzoylated 5-beta-D-glucopyranosyl-2-substituted-1,3,4-oxadiazoles was prepared by acylation of the corresponding 5-(beta-D-glucopyranosyl) tetrazole. As an alternative, oxidation of 2,6-anhydro-aldose benzoylhydrazones by iodobenzene I, I-diacetate afforded the same oxadiazoles. 1,3-Dipolar cycloaddition of nitrile oxides to per-O-benzoylated beta-D-glucopyranosyl cyanide gave the corresponding 5-beta-D-glucopyranosyl-3-substituted-1,2,4-oxadiazoles. The O-benzoyl protecting groups were removed by base-catalyzed transesterification. The 1,3,4-oxadiazoles were practically inefficient as inhibitors of rabbit muscle glycogen phosphorylase b while the 1,2,4-oxadiazoles displayed inhibitory activities in the micromolar range. The best inhibitors were the 5-beta-D-glucopyranosyl-3-(4-methylphenyl-and -2-naphthyl)- 1,2,4-oxadiazoles (K-i = 8.8 and 11.6 mu M, respectively). A detailed analysis of the structure-activity relationships is presented. (C) 2009 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.bmc.2009.04.036