6-(5-Dimethylamino-naphthalene-1-sulfonylamino)-hexanoic acid methyl ester | 351351-89-8

• 分子结构分类: 有机化合物 - 苯类化合物 - 萘
• 英文名称: 6-(5-Dimethylamino-naphthalene-1-sulfonylamino)-hexanoic acid methyl ester
• 英文别名: Methyl 6-[[5-(dimethylamino)naphthalen-1-yl]sulfonylamino]hexanoate；methyl 6-[[5-(dimethylamino)naphthalen-1-yl]sulfonylamino]hexanoate
• CAS: 351351-89-8
• 化学式: C₁₉H₂₆N₂O₄S
• 分子量: 378.492
• InChiKey: DUTFPGGNNKLIQW-UHFFFAOYSA-N

物化性质

• 沸点：
  516.9±60.0 °C(Predicted)
• 密度：
  1.202±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  3.3
• 重原子数：
  26
• 可旋转键数：
  10
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.42
• 拓扑面积：
  84.1
• 氢给体数：
  1
• 氢受体数：
  6

反应信息

• 作为反应物：
  描述：

  6-(5-Dimethylamino-naphthalene-1-sulfonylamino)-hexanoic acid methyl ester 在 水 、 sodium hydroxide 作用下， 以 1,4-二氧六环 、 水 为溶剂， 反应 24.0h， 生成 6-({[5-(二甲基氨基)-1-萘基]磺酰基}氨基)己酸
  参考文献：
  名称：

  Fluorescent-tagged sp2-iminosugars with potent β-glucosidase inhibitory activity

  摘要：

  New fluorescently-labelled sp(2)-iminosugars based on the 5N,6S-[N'-(4-aminobutyl)iminomethylidene]-6-thionojirimycin skeleton have been synthesized as photoprobes to monitor glycosidase binding. Dansyl, dapoxyl and coumarin fluorophores were appended to the terminal amino group at the N'-substituent by either sulfonamide or amide bridging reaction. All the conjugates behaved as strong (low micromolar to nanomolar) and selective inhibitors of beta-glucosidases (almonds and bovine liver) and naringinase, in agreement with the inhibition pattern previously encountered for related iso(thio)urea-type bicyclic sp(2)-iminosugars. The presence of the fluorescent probe allows real-time and continuous monitoring of beta-glucosidase inhibition by fluorescence resonance energy transfer (FRET), taking advantage of the intrinsic tryptophan-associated fluorescence of the protein. (C) 2010 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.bmc.2010.09.003
• 作为产物：
  描述：

  丹酰氯 、 6-氨基己酸甲酯 盐酸盐 在 三乙胺 作用下， 以 二氯甲烷 为溶剂， 反应 18.0h， 生成 6-(5-Dimethylamino-naphthalene-1-sulfonylamino)-hexanoic acid methyl ester
  参考文献：
  名称：

  Fluorescent-tagged sp2-iminosugars with potent β-glucosidase inhibitory activity

  摘要：

  New fluorescently-labelled sp(2)-iminosugars based on the 5N,6S-[N'-(4-aminobutyl)iminomethylidene]-6-thionojirimycin skeleton have been synthesized as photoprobes to monitor glycosidase binding. Dansyl, dapoxyl and coumarin fluorophores were appended to the terminal amino group at the N'-substituent by either sulfonamide or amide bridging reaction. All the conjugates behaved as strong (low micromolar to nanomolar) and selective inhibitors of beta-glucosidases (almonds and bovine liver) and naringinase, in agreement with the inhibition pattern previously encountered for related iso(thio)urea-type bicyclic sp(2)-iminosugars. The presence of the fluorescent probe allows real-time and continuous monitoring of beta-glucosidase inhibition by fluorescence resonance energy transfer (FRET), taking advantage of the intrinsic tryptophan-associated fluorescence of the protein. (C) 2010 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.bmc.2010.09.003

文献信息

• Powerful probes for glycosidases
  作者：Albin Hermetter、Hubert Scholze、Arnold E. Stütz、Stephen G. Withers、Tanja M. Wrodnigg

  DOI：10.1016/s0960-894x(01)00209-8

  日期：2001.5

  1-Amino-1,2,5-trideoxy-2,5-imino-D-mannitol was fluorescently tagged by reaction with dansyl chloride at N-1 or by attachment of a dansyl amide bearing spacer to this centre. Compounds obtained are highly potent inhibitors of beta -glucosidase exhibiting K-i values in the single figure nanosmolar range. The 1-N-dansyl substituted inhibitor was successfully exploited for binding studies with beta -glucosidase from Agrobacterium sp. employing fluorescence spectrometric methods. (C) 2001 Elsevier Science Ltd. All rights reserved.