N-(dansylamino)hexylaminocarbonylpentyl-1,5-dideoxy-1,5-imino-D-glucitol | 1241473-40-4

• 分子结构分类: 有机化合物 - 苯类化合物 - 萘
• 英文名称: N-(dansylamino)hexylaminocarbonylpentyl-1,5-dideoxy-1,5-imino-D-glucitol
• 英文别名: N-[6-[[5-(dimethylamino)naphthalen-1-yl]sulfonylamino]hexyl]-6-[(2R,3R,4R,5S)-3,4,5-trihydroxy-2-(hydroxymethyl)piperidin-1-yl]hexanamide
• CAS: 1241473-40-4
• 化学式: C₃₀H₄₈N₄O₇S
• 分子量: 608.8
• InChiKey: FFECDIPLJGSHMF-QUKNIHFLSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  1.9
• 重原子数：
  42
• 可旋转键数：
  17
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.63
• 拓扑面积：
  171
• 氢给体数：
  6
• 氢受体数：
  10

反应信息

• 作为产物：
  描述：

  N-5-羧基戊基-1-脱氧野尻霉素 、 N-(6-氨基己基)-5-二甲基氨基萘-1-磺酰胺 在 O-(benzotriazol-1-yl)-N,N,N',N'-tetramethyluronium tetrafluoroborate 、 三乙胺 作用下， 以 N,N-二甲基甲酰胺 为溶剂， 反应 0.17h， 以120 mg的产率得到N-(dansylamino)hexylaminocarbonylpentyl-1,5-dideoxy-1,5-imino-D-glucitol
  参考文献：
  名称：

  1-Deoxynojirimycins with dansyl capped N-substituents as probes for Morbus Gaucher affected cell lines

  摘要：

  Cyclization by double reductive amination of D-xylo-hexos-5-ulose with methyl 6-aminohexanoate gave (methoxycarbonyl)pentyl-1-deoxynojirimycin. Reaction of the terminal carboxylic acid with N-dansyl-1,6-diaminohexane provided the corresponding chain-extended fluorescent derivative. By reaction with bis(6-dansylaminohexyl)amine, the corresponding branched di-N-dansyl compound was obtained. Both compounds are strong inhibitors of D-glucosidases and could also be shown to distinctly improve, at sub-inhibitory concentrations, the activity of beta-glucocerebrosidase in a Gaucher fibroblast (N370S) cell-line through chaperoning of the enzyme to the lysosome. (C) 2010 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.carres.2010.04.015

文献信息

• 1-Deoxynojirimycins with dansyl capped N-substituents as probes for Morbus Gaucher affected cell lines
  作者：Richard F.G. Fröhlich、Richard H. Furneaux、Don J. Mahuran、Brigitte A. Rigat、Arnold E. Stütz、Michael B. Tropak、Jacqueline Wicki、Stephen G. Withers、Tanja M. Wrodnigg

  DOI：10.1016/j.carres.2010.04.015

  日期：2010.7

  Cyclization by double reductive amination of D-xylo-hexos-5-ulose with methyl 6-aminohexanoate gave (methoxycarbonyl)pentyl-1-deoxynojirimycin. Reaction of the terminal carboxylic acid with N-dansyl-1,6-diaminohexane provided the corresponding chain-extended fluorescent derivative. By reaction with bis(6-dansylaminohexyl)amine, the corresponding branched di-N-dansyl compound was obtained. Both compounds are strong inhibitors of D-glucosidases and could also be shown to distinctly improve, at sub-inhibitory concentrations, the activity of beta-glucocerebrosidase in a Gaucher fibroblast (N370S) cell-line through chaperoning of the enzyme to the lysosome. (C) 2010 Elsevier Ltd. All rights reserved.