N-dansyl-O-mesyl-6-aminohexanol | 1241473-35-7

• 分子结构分类: 有机化合物 - 苯类化合物 - 萘
• 英文名称: N-dansyl-O-mesyl-6-aminohexanol
• 英文别名: N-dansyl-O-mesyl-6-aminohexan-1-ol；6-[[5-(Dimethylamino)naphthalen-1-yl]sulfonylamino]hexyl methanesulfonate；6-[[5-(dimethylamino)naphthalen-1-yl]sulfonylamino]hexyl methanesulfonate
• CAS: 1241473-35-7
• 化学式: C₁₉H₂₈N₂O₅S₂
• 分子量: 428.574
• InChiKey: LFMZNCZOMGKYJD-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.72
• 重原子数：
  28.0
• 可旋转键数：
  11.0
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.47
• 拓扑面积：
  92.78
• 氢给体数：
  1.0
• 氢受体数：
  6.0

反应信息

• 作为反应物：
  描述：

  N-dansyl-O-mesyl-6-aminohexanol 在 盐酸 、 水 、 sodium carbonate 作用下， 以 N,N-二甲基甲酰胺 为溶剂， 反应 47.0h， 生成 1-{N,N-bis[6-(dansylamino)hexyl]aminohexyl}-1,5-dideoxy-1,5-imino-D-galactitol tetrahydrochloride
  参考文献：
  名称：

  1-Deoxy-d-galactonojirimycins with dansyl capped N-substituents as β-galactosidase inhibitors and potential probes for GM1 gangliosidosis affected cell lines

  摘要：

  Two simple and reliably accessible intermediates, N-carboxypentyl- and N-aminohexyl-1-deoxy-D-galactonojirimycin were employed for the synthesis of a set of terminally N-dansyl substituted derivatives. Reaction of the terminal carboxylic acid of N-carboxypentyl-1-deoxy-D-galactonojirimycin with N-dansyl-1,6-diaminohexane provided the chain-extended fluorescent derivative. Employing bis(6-dansylaminohexyl)amine, the corresponding branched di-N-dansyl compound was obtained. Partially protected N-aminohexyl-1-deoxy-D-galactonojirimycin served as intermediate for two additional chain-extended fluorescent 1-deoxy-D-galactonojirimycin (1-DGJ) derivatives featuring terminal dansyl groups in the N-alkyl substituent. These new compounds are strong inhibitors of D-galactosidases and may serve as leads en route to pharmacological chaperones for GM1-gangliosidosis. (C) 2011 Published by Elsevier Ltd.

  DOI：

  10.1016/j.carres.2011.05.010
• 作为产物：
  描述：

  甲基磺酰氯 、 5-(二甲氨基)-N-(6-羟基己基)萘-1-磺酰胺 在 三乙胺 作用下， 以 二氯甲烷 为溶剂， 以92%的产率得到N-dansyl-O-mesyl-6-aminohexanol
  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