bis(6-dansylaminohexyl)amine | 1241473-39-1

• 分子结构分类: 有机化合物 - 苯类化合物 - 萘
• 英文名称: bis(6-dansylaminohexyl)amine
• 英文别名: di[6-(N-dansyl-amino)hexyl]amine；5-(dimethylamino)-N-[6-[6-[[5-(dimethylamino)naphthalen-1-yl]sulfonylamino]hexylamino]hexyl]naphthalene-1-sulfonamide
• CAS: 1241473-39-1
• 化学式: C₃₆H₅₁N₅O₄S₂
• 分子量: 681.964
• InChiKey: ZQGKOIWKDDZPBM-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  6.7
• 重原子数：
  47
• 可旋转键数：
  20
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.44
• 拓扑面积：
  128
• 氢给体数：
  3
• 氢受体数：
  9

反应信息

• 作为反应物：
  描述：

  N-[5-(methyloxycarbonyl)pentyl]-1,5-dideoxy-1,5-imino-D-galactitol 、 bis(6-dansylaminohexyl)amine 在 O-(benzotriazol-1-yl)-N,N,N',N'-tetramethyluronium tetrafluoroborate 、 三乙胺 作用下， 以 二氯甲烷 、 N,N-二甲基甲酰胺 为溶剂， 反应 0.17h， 以90 mg的产率得到1-{N,N-bis[(dansylamino)hexyl]aminocarbonylpentyl}-1,5-dideoxy-1,5-imino-D-galactitol
  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：

  N-dansyl-O-mesyl-6-aminohexanol 、 N-(6-氨基己基)-5-二甲基氨基萘-1-磺酰胺 在 sodium carbonate 作用下， 以 N,N-二甲基甲酰胺 为溶剂， 反应 48.0h， 以51%的产率得到bis(6-dansylaminohexyl)amine
  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.
• 1-Deoxy-d-galactonojirimycins with dansyl capped N-substituents as β-galactosidase inhibitors and potential probes for GM1 gangliosidosis affected cell lines
  作者：Richard F.G. Fröhlich、Richard H. Furneaux、Don J. Mahuran、Robert Saf、Arnold E. Stütz、Michael B. Tropak、Jacqueline Wicki、Stephen G. Withers、Tanja M. Wrodnigg

  DOI：10.1016/j.carres.2011.05.010

  日期：2011.9

  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.