5-(2,3,4,6-tetra-O-acetyl-β-D-glucopyranosyl)tetrahydropyrimidin-2(1H)-one | 1401077-98-2

• 分子结构分类: 有机化合物 - 有机酸及其衍生物 - 羧酸及其衍生物
• 英文名称: 5-(2,3,4,6-tetra-O-acetyl-β-D-glucopyranosyl)tetrahydropyrimidin-2(1H)-one
• CAS: 1401077-98-2
• 化学式: C₁₈H₂₆N₂O₁₀
• 分子量: 430.412
• InChiKey: RASANJCWKNOEOQ-ALYAQQCSSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  -0.96
• 重原子数：
  30.0
• 可旋转键数：
  6.0
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.72
• 拓扑面积：
  155.56
• 氢给体数：
  2.0
• 氢受体数：
  10.0

反应信息

• 作为反应物：
  描述：

  5-(2,3,4,6-tetra-O-acetyl-β-D-glucopyranosyl)tetrahydropyrimidin-2(1H)-one 在 sodium methylate 作用下， 以 甲醇 、 二氯甲烷 为溶剂， 反应 48.0h， 以99%的产率得到5-(β-D-glucopyranosyl)tetrahydropyrimidin-2(1H)-one
  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
• 作为产物：
  描述：

  2-(2,3,4,6-tetra-O-acetyl-β-D-glucopyranosyl)malononitrile 在 platinum(IV) oxide 、 氢气 、 三甲基铝 作用下， 以 乙醇 、 二氯甲烷 、 氯仿 为溶剂， 45.0 ℃ 、101.33 kPa 条件下， 反应 0.25h， 生成 5-(2,3,4,6-tetra-O-acetyl-β-D-glucopyranosyl)tetrahydropyrimidin-2(1H)-one
  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