N-butyl-7-O-β-D-glucopyranosyl-α-homonojirimycin

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: N-butyl-7-O-β-D-glucopyranosyl-α-homonojirimycin
• 英文别名: (2R,3R,4S,5S,6R)-1-butyl-2-(hydroxymethyl)-6-[[(2R,3R,4S,5S,6R)-3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxymethyl]piperidine-3,4,5-triol
• 化学式: C₁₇H₃₃NO₁₀
• 分子量: 411.45
• InChiKey: LMSOOPJUZDCJRQ-YBVXMOICSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  -2.8
• 重原子数：
  28
• 可旋转键数：
  8
• 环数：
  2.0
• sp3杂化的碳原子比例：
  1.0
• 拓扑面积：
  184
• 氢给体数：
  8
• 氢受体数：
  11

反应信息

• 作为产物：
  描述：

  正溴丁烷 、 7-O-β-D-吡喃葡萄糖基-Alpha-后莫野尻霉素 在 potassium carbonate 作用下， 以 N,N-二甲基甲酰胺 为溶剂， 反应 24.0h， 以49 mg的产率得到N-butyl-7-O-β-D-glucopyranosyl-α-homonojirimycin
  参考文献：
  名称：

  α-Glucosidase-inhibitory iminosugars from the leaves of Suregada glomerulata

  摘要：

  A water extract of the leaves of Suregada glomerulata (Euphorbiaceae) was found to inhibit rat small intestinal alpha-glucosidase. An examination of the extract afforded 20 iminosugars including one pyrrolidine and 19 piperidines. The structures of the 10 new compounds (11-20) were determined by NMR, and MS spectroscopic data analyses, and chemical correlations. The novelty of the identified compounds mainly stems from the loss of a hydroxy at C-4 and the presence of an 8-hydroxyoctyl side chain. Nine N-alkyl derivatives including N-methyl (1a, 8a, and 13a), N-butyl (1b, 2b, and 9b) and N,N-dimethyl (1c, 2c, and 9c) were synthesized. The compounds were tested for rat small intestinal a-glucosidase inhibitory activity. In total, 15 compounds, including compounds 11, 12, 15, and 19 and the three derivatives 8a, 9b, and 13a, showed inhibitory activity with IC50 values less than 40 mu M. In vivo results showed that total alkaloids of S. glomerulata (10 mg/kg) and four major iminosugars 1, 2, 3, and 9 (10 mg/kg) can lower the postprandial blood glucose level after sucrose and starch load in healthy male ICR mice. (C) 2013 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.bmc.2013.07.048

文献信息

• α-Glucosidase-inhibitory iminosugars from the leaves of Suregada glomerulata
  作者：Ren-Yi Yan、Hong-Qing Wang、Chao Liu、Jie Kang、Ruo-Yun Chen

  DOI：10.1016/j.bmc.2013.07.048

  日期：2013.11

  A water extract of the leaves of Suregada glomerulata (Euphorbiaceae) was found to inhibit rat small intestinal alpha-glucosidase. An examination of the extract afforded 20 iminosugars including one pyrrolidine and 19 piperidines. The structures of the 10 new compounds (11-20) were determined by NMR, and MS spectroscopic data analyses, and chemical correlations. The novelty of the identified compounds mainly stems from the loss of a hydroxy at C-4 and the presence of an 8-hydroxyoctyl side chain. Nine N-alkyl derivatives including N-methyl (1a, 8a, and 13a), N-butyl (1b, 2b, and 9b) and N,N-dimethyl (1c, 2c, and 9c) were synthesized. The compounds were tested for rat small intestinal a-glucosidase inhibitory activity. In total, 15 compounds, including compounds 11, 12, 15, and 19 and the three derivatives 8a, 9b, and 13a, showed inhibitory activity with IC50 values less than 40 mu M. In vivo results showed that total alkaloids of S. glomerulata (10 mg/kg) and four major iminosugars 1, 2, 3, and 9 (10 mg/kg) can lower the postprandial blood glucose level after sucrose and starch load in healthy male ICR mice. (C) 2013 Elsevier Ltd. All rights reserved.