(3R,4R,5R)‑1‑(6‑aminohexyl)‑5‑(hydroxymethyl)piperidine‑3,4‑diol | 885484-47-9

• 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: (3R,4R,5R)‑1‑(6‑aminohexyl)‑5‑(hydroxymethyl)piperidine‑3,4‑diol
• 英文别名: N‑(6‑aminohexyl)isofagomine；(3R,4R,5R)-1-(6-Amino-hexyl)-5-hydroxymethyl-piperidine-3,4-diol；(3r,4r,5r)-1-(6-Aminohexyl)-5-(hydroxymethyl)piperidine-3,4-diol；(3R,4R,5R)-1-(6-aminohexyl)-5-(hydroxymethyl)piperidine-3,4-diol
• CAS: 885484-47-9
• 化学式: C₁₂H₂₆N₂O₃
• 分子量: 246.35
• InChiKey: KGWBQKXDNCIMGO-IJLUTSLNSA-N

物化性质

• 沸点：
  429.4±28.0 °C(Predicted)
• 密度：
  1.133±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  -0.85
• 重原子数：
  17.0
• 可旋转键数：
  7.0
• 环数：
  1.0
• sp3杂化的碳原子比例：
  1.0
• 拓扑面积：
  89.95
• 氢给体数：
  4.0
• 氢受体数：
  5.0

反应信息

• 作为反应物：
  描述：

  (3R,4R,5R)‑1‑(6‑aminohexyl)‑5‑(hydroxymethyl)piperidine‑3,4‑diol 、 丹酰氯 在 三乙胺 作用下， 以 N,N-二甲基甲酰胺 为溶剂， 生成 N‑[6‑[(3R,4R,5R)‑3,4‑dihydroxy‑5‑(hydroxymethyl)piperidin‑1‑yl]hexyl]‑5‑(dimethylamino)naphthalene‑1‑sulfonamide
  参考文献：
  名称：

  Fluorescent glycosidase inhibiting 1,5-dideoxy-1,5-iminoalditols

  摘要：

  1,5-Dideoxy-1,5-iminoalditols of various configurations as well as isofagomine were N-alkylated with non-polar straight chain spacer-arms by a set of simple standard procedures. The spacer-arms' terminal functional groups, primary amines, were employed to introduce fluorescent tags such as dansyl and dapoxyl moieties. Resulting derivatives in the D-xylo, D-gluco, D-galacto as well as GlcNAc series showed distinctly improved glycosidase inhibitory activities compared to parent compounds and are designed to be useful analytical tools. (C) 2006 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.bmcl.2006.01.095
• 作为产物：
  描述：

  6-溴己腈 在 镍 氢气 、 sodium carbonate 作用下， 以 甲醇 、 N,N-二甲基甲酰胺 为溶剂， 40.0 ℃ 、5.0 MPa 条件下， 反应 96.0h， 生成 (3R,4R,5R)‑1‑(6‑aminohexyl)‑5‑(hydroxymethyl)piperidine‑3,4‑diol
  参考文献：
  名称：

  Fluorescent glycosidase inhibiting 1,5-dideoxy-1,5-iminoalditols

  摘要：

  1,5-Dideoxy-1,5-iminoalditols of various configurations as well as isofagomine were N-alkylated with non-polar straight chain spacer-arms by a set of simple standard procedures. The spacer-arms' terminal functional groups, primary amines, were employed to introduce fluorescent tags such as dansyl and dapoxyl moieties. Resulting derivatives in the D-xylo, D-gluco, D-galacto as well as GlcNAc series showed distinctly improved glycosidase inhibitory activities compared to parent compounds and are designed to be useful analytical tools. (C) 2006 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.bmcl.2006.01.095

文献信息

• A remarkable change in inhibition potency and selectivity of isofagomine by simple N-modification
  作者：André Culum、Herwig Prasch、Tobias Dorn、Roland Fischer、Ema Gardić、Franziska Schmutz、Magdalena Steinbrugger、Arnold E. Stütz、Patrick Weber、Tanja M. Wrodnigg、Martin Thonhofer

  DOI：10.1007/s00706-024-03210-7

  日期：2025.1

  Herein, we present an alternative and elegant synthetic approach toward powerful β-glucosidase inhibitor isofagomine. Derivatizations of the ring nitrogen provided a selected set of N-modified isofagomine analogues. Biological evaluation of these compounds showed a remarkable change in potency as well as α/β-preference for various glycosidases from different sources when compared to the parent compound isofagomine. Overall, the conducted N-modification improved the potency against α-glucosidase from Saccharomyces cerevisiae (GH13). Coming along, significant diminished activities toward GH1 family β-glucosidases from three different sources have been observed for all tested derivatives. Moreover, and contrary to isofagomine, deactivations of β-galactosidase from Escherichia coli (GH2) as well as α-mannosidase from Canavalia ensiformis (GH38) have not been verified for this series of compounds. Graphical abstract