(β-D-glucopyranosyl)-di-[3-(p-tolyl)-1,2,4-oxadiazol-5-yl]methane | 1401078-02-1

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: (β-D-glucopyranosyl)-di-[3-(p-tolyl)-1,2,4-oxadiazol-5-yl]methane
• 英文别名: (2S,3R,4R,5S,6R)-2-[bis[3-(4-methylphenyl)-1,2,4-oxadiazol-5-yl]methyl]-6-(hydroxymethyl)oxane-3,4,5-triol
• CAS: 1401078-02-1
• 化学式: C₂₅H₂₆N₄O₇
• 分子量: 494.504
• InChiKey: QHUNDUSKCNPOJU-RQXATKFSSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2
• 重原子数：
  36
• 可旋转键数：
  6
• 环数：
  5.0
• sp3杂化的碳原子比例：
  0.36
• 拓扑面积：
  168
• 氢给体数：
  4
• 氢受体数：
  11

反应信息

• 作为产物：
  描述：

  2-(2,3,4,6-tetra-O-acetyl-β-D-glucopyranosyl)malononitrile 在 三乙胺 作用下， 以 甲醇 、 水 、 甲苯 为溶剂， 反应 84.0h， 生成 (β-D-glucopyranosyl)-di-[3-(p-tolyl)-1,2,4-oxadiazol-5-yl]methane
  参考文献：
  名称：

  C-Glucosylated malonitrile as a key intermediate towards carbohydrate-based glycogen phosphorylase inhibitors

  摘要：

  Glycogen utilization involves glycogen phosphorylase, an enzyme which appears to be a potential target for the regulation of glycaemia, as the liver isoform is a major player for hepatic glucose output. A single C-glucosylated malonitrile allowed for the synthesis of three glucose-based derivatives namely bis-oxadiazoles, bis-amides and a C-glucosylated tetrahydropyrimidin-2-one. When evaluated as glycogen phosphorylase inhibitors, two of the synthesized compounds displayed inhibition in the sub-millimolar range. In silico studies revealed that only one out of the bis-amides obtained and the C-glucosylated tetrahydropyrimidin- 2-one may bind at the catalytic site. (C) 2012 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.bmc.2012.07.033

文献信息

• C-Glucosylated malonitrile as a key intermediate towards carbohydrate-based glycogen phosphorylase inhibitors
  作者：Sophie Feuillastre、Aikaterini S. Chajistamatiou、Constantinos Potamitis、Maria Zervou、Panagiotis Zoumpoulakis、Evangelia D. Chrysina、Jean-Pierre Praly、Sébastien Vidal

  DOI：10.1016/j.bmc.2012.07.033

  日期：2012.9

  Glycogen utilization involves glycogen phosphorylase, an enzyme which appears to be a potential target for the regulation of glycaemia, as the liver isoform is a major player for hepatic glucose output. A single C-glucosylated malonitrile allowed for the synthesis of three glucose-based derivatives namely bis-oxadiazoles, bis-amides and a C-glucosylated tetrahydropyrimidin-2-one. When evaluated as glycogen phosphorylase inhibitors, two of the synthesized compounds displayed inhibition in the sub-millimolar range. In silico studies revealed that only one out of the bis-amides obtained and the C-glucosylated tetrahydropyrimidin- 2-one may bind at the catalytic site. (C) 2012 Elsevier Ltd. All rights reserved.