N-[(dansylamino)hexyl]aminocarbonylpentyl-1,5-dideoxy-1,5-imino-D-galactitol | 1320341-35-2

• 分子结构分类: 有机化合物 - 苯类化合物 - 萘
• 英文名称: N-[(dansylamino)hexyl]aminocarbonylpentyl-1,5-dideoxy-1,5-imino-D-galactitol
• 英文别名: N-[6-[[5-(dimethylamino)naphthalen-1-yl]sulfonylamino]hexyl]-6-[(2R,3S,4R,5S)-3,4,5-trihydroxy-2-(hydroxymethyl)piperidin-1-yl]hexanamide
• CAS: 1320341-35-2
• 化学式: C₃₀H₄₈N₄O₇S
• 分子量: 608.8
• InChiKey: FFECDIPLJGSHMF-MOXFVITDSA-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：

  (6-甲氧基-6-氧代己基)胺 在 盐酸 、 甲醇 、 20% palladium(II) hydroxide on carbon 、 水 、 氢气 、 sodium hydroxide 作用下， 以 甲醇 、 二氯甲烷 为溶剂， 20.0 ℃ 、101.33 kPa 条件下， 反应 75.0h， 生成 N-[(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

文献信息

• A fluorescent probe for GM1 gangliosidosis related β-galactosidase: N-(Dansylamino)hexylaminocarbonylpentyl-1,5-dideoxy-1,5-imino-d-galactitol
  作者：Richard F.G. Fröhlich、Katrin Fantur、Richard H. Furneaux、Eduard Paschke、Arnold E. Stütz、Jacqueline Wicki、Stephen G. Withers、Tanja M. Wrodnigg

  DOI：10.1016/j.bmcl.2011.09.012

  日期：2011.11

  N-(Dansylamino)hexylaminocarbonylpentyl-1,5-dideoxy-1,5-imino-D-galactitol, a strong competitive inhibitor of beta-galactosidase, enhances residual beta-galactosidase activities in fibroblasts and serves as lead en route to diagnostic compounds for tracking the fate of mutant beta-gal as well as aberrant GM1 gangliosides by live cell imaging. (C) 2011 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.