5-(β-D-glucopyranosyl)-2-phenyl-1,3,4-oxadiazole | 1179326-61-4

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: 5-(β-D-glucopyranosyl)-2-phenyl-1,3,4-oxadiazole
• 英文别名: (2R,3S,4S,5R,6R)-2-(hydroxymethyl)-6-(5-phenyl-1,3,4-oxadiazol-2-yl)oxane-3,4,5-triol
• CAS: 1179326-61-4
• 化学式: C₁₄H₁₆N₂O₆
• 分子量: 308.291
• InChiKey: MKDOCLRSYSSLSH-RMPHRYRLSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  -1
• 重原子数：
  22
• 可旋转键数：
  3
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.43
• 拓扑面积：
  129
• 氢给体数：
  4
• 氢受体数：
  8

反应信息

• 作为产物：
  描述：

  2-phenyl-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-phenyl-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

文献信息

• Synthesis and structure–activity relationships of C-glycosylated oxadiazoles as inhibitors of glycogen phosphorylase
  作者：Marietta Tóth、Sándor Kun、Éva Bokor、Mahmoud Benltifa、Gaylord Tallec、Sébastien Vidal、Tibor Docsa、Pál Gergely、László Somsák、Jean-Pierre Praly

  DOI：10.1016/j.bmc.2009.04.036

  日期：2009.7

  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.