1-{6-[N-[6-(dansylamino)hexyl]-N-(octanoyl)amino]hexyl}-3,4-O-isopropylidene-1,5-dideoxy-1,5-imino-D-galactitol | 1320341-46-5

• 分子结构分类: 有机化合物 - 苯类化合物 - 萘
• 英文名称: 1-{6-[N-[6-(dansylamino)hexyl]-N-(octanoyl)amino]hexyl}-3,4-O-isopropylidene-1,5-dideoxy-1,5-imino-D-galactitol
• CAS: 1320341-46-5
• 化学式: C₄₁H₆₈N₄O₇S
• 分子量: 761.08
• InChiKey: PXBRAODSIBOHEK-NZHLCYFPSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  6.05
• 重原子数：
  53.0
• 可旋转键数：
  24.0
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.73
• 拓扑面积：
  131.88
• 氢给体数：
  3.0
• 氢受体数：
  9.0

反应信息

• 作为反应物：
  描述：

  1-{6-[N-[6-(dansylamino)hexyl]-N-(octanoyl)amino]hexyl}-3,4-O-isopropylidene-1,5-dideoxy-1,5-imino-D-galactitol 在 盐酸 、 水 作用下， 反应 2.0h， 以100%的产率得到1-{6-[N-[6-(dansylamino)hexyl]-N-(octanoyl)amino]hexyl}-1,5-dideoxy-1,5-imino-D-galactitol dihydrochloride
  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 在 吡啶 、 sodium carbonate 作用下， 以 二氯甲烷 、 N,N-二甲基甲酰胺 为溶剂， 反应 44.5h， 生成 1-{6-[N-[6-(dansylamino)hexyl]-N-(octanoyl)amino]hexyl}-3,4-O-isopropylidene-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