5-N,6-S-[N'-[4-(7'-diethylaminocoumarin-3'-ylcarboxamido)butyl]iminomethylidene]-6-thionojirimycin | 1257263-18-5

• 分子结构分类: 有机化合物 - 苯丙烷和聚酮 - 香豆素及其衍生物
• 英文名称: 5-N,6-S-[N'-[4-(7'-diethylaminocoumarin-3'-ylcarboxamido)butyl]iminomethylidene]-6-thionojirimycin
• CAS: 1257263-18-5
• 化学式: C₂₅H₃₄N₄O₇S
• 分子量: 534.634
• InChiKey: PLWHWFDUSJEVFM-OXUVVOBNSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  0.34
• 重原子数：
  37.0
• 可旋转键数：
  9.0
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.56
• 拓扑面积：
  159.07
• 氢给体数：
  5.0
• 氢受体数：
  10.0

反应信息

• 作为产物：
  描述：

  5-N,6-S-[N'-(4-amino)butyliminomethylidene]-6-thio-nojirimycin hydrochloride 、 7-(二乙基氨基)香豆素-3-羧酸 在 O-(benzotriazol-1-yl)-N,N,N',N'-tetramethyluronium tetrafluoroborate 、 三乙胺 作用下， 以 N,N-二甲基甲酰胺 为溶剂， 反应 1.0h， 以53%的产率得到5-N,6-S-[N'-[4-(7'-diethylaminocoumarin-3'-ylcarboxamido)butyl]iminomethylidene]-6-thionojirimycin
  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