3-phenyl-5-(2,3,4,6-tetra-O-benzoyl-β-D-glucopyranosyl)-1,2,4-oxadiazole

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: 3-phenyl-5-(2,3,4,6-tetra-O-benzoyl-β-D-glucopyranosyl)-1,2,4-oxadiazole
• 英文别名: [(2R,3R,4S,5R,6R)-3,4,5-tribenzoyloxy-6-(3-phenyl-1,2,4-oxadiazol-5-yl)oxan-2-yl]methyl benzoate
• 化学式: C₄₂H₃₂N₂O₁₀
• 分子量: 724.723
• InChiKey: RBKPRSSRKUKMRC-SQGINLDNSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  7.8
• 重原子数：
  54
• 可旋转键数：
  15
• 环数：
  7.0
• sp3杂化的碳原子比例：
  0.14
• 拓扑面积：
  153
• 氢给体数：
  0
• 氢受体数：
  12

反应信息

• 作为反应物：
  描述：

  3-phenyl-5-(2,3,4,6-tetra-O-benzoyl-β-D-glucopyranosyl)-1,2,4-oxadiazole 在 1,8-二氮杂双环[5.4.0]十一碳-7-烯 作用下， 以 二氯甲烷 为溶剂， 反应 24.0h， 以78%的产率得到3-phenyl-5-(3',4',6'-tri-O-benzoyl-2'-deoxy-d-arabino-hex-1'-enopyranosyl)-1,2,4-oxadiazole
  参考文献：
  名称：

  C-(2-Deoxy-d-arabino-hex-1-enopyranosyl)-oxadiazoles: synthesis of possible isomers and their evaluation as glycogen phosphorylase inhibitors

  摘要：

  Synthetic methods were elaborated for D-glucals attached to oxadiazoles by a C-C bond. Introduction of the double bond was effected by either DBU induced elimination of PhCOOH from the O-perbenzoylated glucopyranosyl precursors or Zn/N-methylimidazole mediated reductive elimination from the 1-bromoglucopyranosyl starting compounds. Alternatively, heterocyclizations of 2-deoxy-D-arabino-hex-1-enopyranosyl cyanide were also carried out. Test compounds were obtained by Zemplen debenzoylation, however, none of them showed significant inhibition of rabbit muscle glycogen phosphorylase b. (C) 2015 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.carres.2015.04.016
• 作为产物：
  描述：

  benzohydroximoyl chloride 、 (2R,3R,4R,5S,6S)-2-[(苯甲酰氧基)甲基]-6-氰基四氢-2H-吡喃-3,4,5-三基三苯甲酸酯 在 三乙胺 作用下， 以 甲苯 为溶剂， 以94%的产率得到3-phenyl-5-(2,3,4,6-tetra-O-benzoyl-β-D-glucopyranosyl)-1,2,4-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

• 1,3-Dipolar cycloaddition reactions on carbohydrate-based templates: synthesis of spiro-isoxazolines and 1,2,4-oxadiazoles as glycogen phosphorylase inhibitors
  作者：Mahmoud Benltifa、Sébastien Vidal、David Gueyrard、Peter G. Goekjian、Moncef Msaddek、Jean-Pierre Praly

  DOI：10.1016/j.tetlet.2006.06.058

  日期：2006.8

  1, 3-Dipolar cycloaddition of aryl nitrile oxides to benzyl/acetyl-protected exo-glucals and to a benzoylated glucosyl cyanide led in high yield to spiro-isoxazolines and to 3-aryl-5-glucosyl-1,2,4-oxadiazoles, respectively. The choice of the protective groups was important to the outcome of the cycloaddition and for the deprotection of the adducts. Cleavage of the ester protecting groups (acetyl, benzoyl) provided water-soluble spiro-isoxazolines and 3-aryl-5-glucosyl-1,2,4-oxadiazoles, evaluated as glycogen phosphorylase inhibitors. Preliminary tests showed IC50 values in the mu M range. (c) 2006 Elsevier Ltd. All rights reserved.
• 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.
• C-(2-Deoxy-d-arabino-hex-1-enopyranosyl)-oxadiazoles: synthesis of possible isomers and their evaluation as glycogen phosphorylase inhibitors
  作者：Éva Bokor、Eszter Szennyes、Tibor Csupász、Nóra Tóth、Tibor Docsa、Pál Gergely、László Somsák

  DOI：10.1016/j.carres.2015.04.016

  日期：2015.8

  Synthetic methods were elaborated for D-glucals attached to oxadiazoles by a C-C bond. Introduction of the double bond was effected by either DBU induced elimination of PhCOOH from the O-perbenzoylated glucopyranosyl precursors or Zn/N-methylimidazole mediated reductive elimination from the 1-bromoglucopyranosyl starting compounds. Alternatively, heterocyclizations of 2-deoxy-D-arabino-hex-1-enopyranosyl cyanide were also carried out. Test compounds were obtained by Zemplen debenzoylation, however, none of them showed significant inhibition of rabbit muscle glycogen phosphorylase b. (C) 2015 Elsevier Ltd. All rights reserved.