N-((2R,3R,4R,5R)-3,4-Dihydroxy-5-hydroxymethyl-piperidin-2-ylmethyl)-acetamide | 682771-51-3

• 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-((2R,3R,4R,5R)-3,4-Dihydroxy-5-hydroxymethyl-piperidin-2-ylmethyl)-acetamide
• 英文别名: N-[[(2R,3R,4R,5R)-3,4-dihydroxy-5-(hydroxymethyl)piperidin-2-yl]methyl]acetamide
• CAS: 682771-51-3
• 化学式: C₉H₁₈N₂O₄
• 分子量: 218.253
• InChiKey: QGBVLKXVGKVLMU-FNCVBFRFSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  -1.6
• 重原子数：
  15
• 可旋转键数：
  3
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.89
• 拓扑面积：
  102
• 氢给体数：
  5
• 氢受体数：
  5

反应信息

• 作为产物：
  描述：

  6-acetamido-N-benzyl-3,4-di-O-benzyl-2-C-benzyloxymethyl-1,2,5,6-tetradeoxy-1,5-imino-D-glucitol 在 palladium on activated charcoal 氢气 作用下， 以 N,N-二甲基甲酰胺 为溶剂， 反应 16.0h， 以94%的产率得到N-((2R,3R,4R,5R)-3,4-Dihydroxy-5-hydroxymethyl-piperidin-2-ylmethyl)-acetamide
  参考文献：
  名称：

  Design and synthesis of 2-acetamidomethyl derivatives of isofagomine as potential inhibitors of human lysosomal β-hexosaminidases

  摘要：

  As part of a program towards the development of specific inhibitors of human lysosomal beta-hexosaminidase for use as chemical chaperones in therapy of G(M2) gangliosidosis related diseases, the synthesis of 2-acetamidomethyl derivatives of isofagomine has been undertaken. Key event in this synthesis is the conversion of a C-2 substituted gluconolactone derivative into the corresponding lactam, followed by reduction to the corresponding amine. The 1-N-imino-2 acetamidomethyl derivative 5 proved to be a rather selective inhibitor with a K-i of 2.4 muM for homogenate of human spleen lysosomal beta-hexosaminidase. (C) 2004 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.bmc.2003.12.040

文献信息

• Design and synthesis of 2-acetamidomethyl derivatives of isofagomine as potential inhibitors of human lysosomal β-hexosaminidases
  作者：Richard J.B.H.N van den Berg、Wilma Donker-Koopman、Jacques H van Boom、Hans M.F.G Aerts、Daan Noort

  DOI：10.1016/j.bmc.2003.12.040

  日期：2004.3

  As part of a program towards the development of specific inhibitors of human lysosomal beta-hexosaminidase for use as chemical chaperones in therapy of G(M2) gangliosidosis related diseases, the synthesis of 2-acetamidomethyl derivatives of isofagomine has been undertaken. Key event in this synthesis is the conversion of a C-2 substituted gluconolactone derivative into the corresponding lactam, followed by reduction to the corresponding amine. The 1-N-imino-2 acetamidomethyl derivative 5 proved to be a rather selective inhibitor with a K-i of 2.4 muM for homogenate of human spleen lysosomal beta-hexosaminidase. (C) 2004 Elsevier Ltd. All rights reserved.