1-C-(1,4-dideoxy-1,4-imino-D-galactosyl)-2-N-hexadecyl-2-propylamine | 1093187-83-7

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 吡咯烷类
• 英文名称: 1-C-(1,4-dideoxy-1,4-imino-D-galactosyl)-2-N-hexadecyl-2-propylamine
• 英文别名: (2S,3S,4S)-2-[(1S)-1,2-dihydroxyethyl]-5-[2-(hexadecylamino)propyl]pyrrolidine-3,4-diol
• CAS: 1093187-83-7
• 化学式: C₂₅H₅₂N₂O₄
• 分子量: 444.699
• InChiKey: OLUTVIFZMNYQOB-BQOABDRHSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  5.8
• 重原子数：
  31
• 可旋转键数：
  20
• 环数：
  1.0
• sp3杂化的碳原子比例：
  1.0
• 拓扑面积：
  105
• 氢给体数：
  6
• 氢受体数：
  6

反应信息

• 作为产物：
  描述：

  1-C-(2,3,6-tri-O-benzyl-1,4-dideoxy-1,4-imino-D-galactosyl)-2-N-hexadecyl-2-propylamine 在 palladium dihydroxide 、 氢气 作用下， 以 水 、 溶剂黄146 为溶剂， 以92%的产率得到1-C-(1,4-dideoxy-1,4-imino-D-galactosyl)-2-N-hexadecyl-2-propylamine
  参考文献：
  名称：

  Synthesis of iminoalditol analogues of galactofuranosides and their activities against glycosidases

  摘要：

  Iminoalditol analogues of galactofuranosides were synthesized from 1-C-(2'-oxo-propyl)-1,4-dideoxy1,4-imino-D-galactosides and different amines by reductive amination. followed by removal of protecting groups. The activity of these compounds against galactosidases and other glycosidases was investigated. The best inhibitor against beta-galactosidase (bovine liver) is a diastereomeric mixture of an iminoalditol (10h), which contains a hydrophobic hexadecyl aglycon (R=C16H33), whereas no significant inhibitory activity was observed with compounds having a hydrophilic aglycon. Surprisingly, activation of alpha-galactosidase (coffee bean) by 10th was also observed. Because these results were obtained from a mixture of iminoalditols, the inhibition and activation of glycosidases could result from different diastereomers. Crown Copyright (C) 2008 Published by Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.carres.2008.07.013

文献信息

• Synthesis of iminoalditol analogues of galactofuranosides and their activities against glycosidases
  作者：Mahendra Sandbhor、Milan Bhasin、Dean T. Williams、Margaret Hsieh、Shih-Hsiung Wu、Wei Zou

  DOI：10.1016/j.carres.2008.07.013

  日期：2008.11

  Iminoalditol analogues of galactofuranosides were synthesized from 1-C-(2'-oxo-propyl)-1,4-dideoxy1,4-imino-D-galactosides and different amines by reductive amination. followed by removal of protecting groups. The activity of these compounds against galactosidases and other glycosidases was investigated. The best inhibitor against beta-galactosidase (bovine liver) is a diastereomeric mixture of an iminoalditol (10h), which contains a hydrophobic hexadecyl aglycon (R=C16H33), whereas no significant inhibitory activity was observed with compounds having a hydrophilic aglycon. Surprisingly, activation of alpha-galactosidase (coffee bean) by 10th was also observed. Because these results were obtained from a mixture of iminoalditols, the inhibition and activation of glycosidases could result from different diastereomers. Crown Copyright (C) 2008 Published by Elsevier Ltd. All rights reserved.