α-1-C-allyl-1,5-dideoxy-1,5-imino-D-xylitol

• 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: α-1-C-allyl-1,5-dideoxy-1,5-imino-D-xylitol
• 英文别名: (2R,3S,4S,5R)-2-prop-2-enylpiperidine-3,4,5-triol
• 化学式: C₈H₁₅NO₃
• 分子量: 173.212
• InChiKey: WHCAXHJJCMTBKC-NGJRWZKOSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  -1.1
• 重原子数：
  12
• 可旋转键数：
  2
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.75
• 拓扑面积：
  72.7
• 氢给体数：
  4
• 氢受体数：
  4

反应信息

• 作为反应物：
  描述：

  正辛醛 、 α-1-C-allyl-1,5-dideoxy-1,5-imino-D-xylitol 在 sodium cyanoborohydride 、 溶剂黄146 作用下， 以 乙醇 为溶剂， 反应 5.0h， 以74%的产率得到α-1-C-allyl-N-(octyl)-1,5-dideoxy-1,5-imino-D-xylitol
  参考文献：
  名称：

  Iminosugars as a new class of cholinesterase inhibitors

  摘要：

  To further extend the scope of iminosugar biological activity, a systematic structure-activity relationship investigation has been performed by synthesizing and evaluating as cholinesterase inhibitors a library of twenty-three iminoalditols with different substitutions and stereochemistry patterns. These compounds have been evaluated in vitro for the inhibition of cholinesterases (different sources of acetylcholinesterase and butyrylcholinesterase). Some compounds have IC50 values in the micromolar range and display significant inhibition selectivity for butyrylcholinesterase over acetylcholinesterase. These are the first examples of iminosugar-based inhibitors of cholinesterases. (C) 2015 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.bmcl.2014.12.071
• 作为产物：
  描述：

  (1R)-1-C-allyl-2,3,4-tri-O-benzyl-1,5-dideoxy-1,5-imino-D-xylitol 在 三氯化硼 作用下， 以 二氯甲烷 为溶剂， 反应 4.0h， 以49%的产率得到α-1-C-allyl-1,5-dideoxy-1,5-imino-D-xylitol
  参考文献：
  名称：

  Iminosugars as a new class of cholinesterase inhibitors

  摘要：

  To further extend the scope of iminosugar biological activity, a systematic structure-activity relationship investigation has been performed by synthesizing and evaluating as cholinesterase inhibitors a library of twenty-three iminoalditols with different substitutions and stereochemistry patterns. These compounds have been evaluated in vitro for the inhibition of cholinesterases (different sources of acetylcholinesterase and butyrylcholinesterase). Some compounds have IC50 values in the micromolar range and display significant inhibition selectivity for butyrylcholinesterase over acetylcholinesterase. These are the first examples of iminosugar-based inhibitors of cholinesterases. (C) 2015 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.bmcl.2014.12.071

文献信息

• Iminosugars as a new class of cholinesterase inhibitors
  作者：Camille Decroocq、Fabien Stauffert、Olivier Pamlard、Farah Oulaïdi、Estelle Gallienne、Olivier R. Martin、Catherine Guillou、Philippe Compain

  DOI：10.1016/j.bmcl.2014.12.071

  日期：2015.2

  To further extend the scope of iminosugar biological activity, a systematic structure-activity relationship investigation has been performed by synthesizing and evaluating as cholinesterase inhibitors a library of twenty-three iminoalditols with different substitutions and stereochemistry patterns. These compounds have been evaluated in vitro for the inhibition of cholinesterases (different sources of acetylcholinesterase and butyrylcholinesterase). Some compounds have IC50 values in the micromolar range and display significant inhibition selectivity for butyrylcholinesterase over acetylcholinesterase. These are the first examples of iminosugar-based inhibitors of cholinesterases. (C) 2015 Elsevier Ltd. All rights reserved.