N-(2-hydroxyethyl)-1-deoxynojirimycin hydrochloride | 1204250-58-7

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 哌啶类
• 英文名称: N-(2-hydroxyethyl)-1-deoxynojirimycin hydrochloride
• 英文别名: miglitol hydrochloride；(2R,3R,4R,5S)-1-(2-hydroxyethyl)-2-(hydroxymethyl)piperidine-3,4,5-triol;hydrochloride
• CAS: 1204250-58-7
• 化学式: C₈H₁₇NO₅*ClH
• 分子量: 243.688
• InChiKey: QHWGCVIAMMMOPR-FNYDNKIFSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  -2.84
• 重原子数：
  15
• 可旋转键数：
  3
• 环数：
  1.0
• sp3杂化的碳原子比例：
  1.0
• 拓扑面积：
  104
• 氢给体数：
  6
• 氢受体数：
  6

安全信息

• 储存条件：
  -20°C储存

反应信息

• 作为产物：
  描述：

  米格列醇 在 盐酸 作用下， 以 水 为溶剂， 反应 1.0h， 以1.865 g的产率得到N-(2-hydroxyethyl)-1-deoxynojirimycin hydrochloride
  参考文献：
  名称：

  Dual-Action Lipophilic Iminosugar Improves Glycemic Control in Obese Rodents by Reduction of Visceral Glycosphingolipids and Buffering of Carbohydrate Assimilation

  摘要：

  The lipophilic iminosugar N-[5-(adamantan-1-ylmethoxy)pentyl]-1-deoxynojirimycin (2, AMP-DNM) potently controls hyperglycemia in obese rodent models of insulin resistance. The reduction of visceral glycosphingolipids by 2 is thought to underlie its beneficial action. It cannot, however, be excluded that concomitant inhibition of intestinal glycosidases and associated buffering of carbohydrate assimilation add to this. To firmly establish the mode of action or 2, we developed a panel of lipophilic iminosugars varying in configuration at C-4/C-5 and N-substitution of the iminosugar. From these we identified the L-ido derivative of 2, L-ido-AMP-DNM (4), as a selective inhibitor of glycosphingolipid synthesis. Compound 4 lowered visceral glycosphingolipids in ob/ob mice and ZDF rats on a par with 2. In contrast to 2, 4 did not inhibit sucrase activity or sucrose assimilation. Treatment with 4 was significantly less effective in reducing blood glucose and HbAlc. We conclude that the combination of reduction of glycosphingolipids in tissue and buffering of carbohydrate assimilation by 2 produces a superior glucose homeostasis.

  DOI：

  10.1021/jm901281m

文献信息

• Dual-Action Lipophilic Iminosugar Improves Glycemic Control in Obese Rodents by Reduction of Visceral Glycosphingolipids and Buffering of Carbohydrate Assimilation
  作者：Tom Wennekes、Alfred J. Meijer、Albert K. Groen、Rolf G. Boot、Johanna E. Groener、Marco van Eijk、Roelof Ottenhoff、Nora Bijl、Karen Ghauharali、Hang Song、Tom J. O’Shea、Hanlan Liu、Nelson Yew、Diane Copeland、Richard J. van den Berg、Gijsbert A. van der Marel、Herman S. Overkleeft、Johannes M. Aerts

  DOI：10.1021/jm901281m

  日期：2010.1.28

  The lipophilic iminosugar N-[5-(adamantan-1-ylmethoxy)pentyl]-1-deoxynojirimycin (2, AMP-DNM) potently controls hyperglycemia in obese rodent models of insulin resistance. The reduction of visceral glycosphingolipids by 2 is thought to underlie its beneficial action. It cannot, however, be excluded that concomitant inhibition of intestinal glycosidases and associated buffering of carbohydrate assimilation add to this. To firmly establish the mode of action or 2, we developed a panel of lipophilic iminosugars varying in configuration at C-4/C-5 and N-substitution of the iminosugar. From these we identified the L-ido derivative of 2, L-ido-AMP-DNM (4), as a selective inhibitor of glycosphingolipid synthesis. Compound 4 lowered visceral glycosphingolipids in ob/ob mice and ZDF rats on a par with 2. In contrast to 2, 4 did not inhibit sucrase activity or sucrose assimilation. Treatment with 4 was significantly less effective in reducing blood glucose and HbAlc. We conclude that the combination of reduction of glycosphingolipids in tissue and buffering of carbohydrate assimilation by 2 produces a superior glucose homeostasis.