N-{5-[N'-(p-methoxyphenyl)selenoureido]pentyl}-1-deoxynojirimycin

• 分子结构分类: 有机化合物 - 苯类化合物 - 苯酚醚
• 英文名称: N-{5-[N'-(p-methoxyphenyl)selenoureido]pentyl}-1-deoxynojirimycin
• 化学式: C₁₉H₃₁N₃O₅Se
• 分子量: 460.432
• InChiKey: PGINPPCQVNOZSO-XMTFNYHQSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  -1.12
• 重原子数：
  28.0
• 可旋转键数：
  11.0
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.63
• 拓扑面积：
  117.45
• 氢给体数：
  6.0
• 氢受体数：
  8.0

反应信息

• 作为产物：
  描述：

  1-脱氧野尻霉素 在 氢气 、 potassium carbonate 作用下， 以 甲醇 、 N,N-二甲基甲酰胺 为溶剂， 反应 29.5h， 生成 N-{5-[N'-(p-methoxyphenyl)selenoureido]pentyl}-1-deoxynojirimycin
  参考文献：
  名称：

  Selenoureido-iminosugars: A new family of multitarget drugs

  摘要：

  Herein we report the synthesis of N-alkylated deoxynojirimycin derivatives decorated with a selenoureido motif at the hydrocarbon tether as an example of unprecedented multitarget agents. Title compounds were designed as dual drugs for taclding simultaneously the Gaucher disease (by selective inhibition of beta-glucosidase, K-i = 1.6-5.5 mu M, with improved potency and selectivity compared to deoxynojirimycin) and its neurological complications (by inhibiting AChE, K-i up to 5.8 mu M). Moreover, an excellent mimicry of the selenoenzyme glutathione peroxidase was also found for the catalytic scavenging of H2O2 (K-cat/K-uncat up to 640) using PhSH as a cofactor, with improved activity compared to known positive controls, like (PhSe)(2) and ebselen; therefore, such compounds are also excellent scavengers of peroxides, an example of reactive oxygen species present at high concentrations in patients of Gaucher disease and neurological disorders. (C) 2016 Elsevier Masson SAS. All rights reserved.

  DOI：

  10.1016/j.ejmech.2016.07.021

文献信息

• Selenoureido-iminosugars: A new family of multitarget drugs
  作者：Jacob Ingemar Olsen、Gabriela B. Plata、José M. Padrón、Óscar López、Mikael Bols、José G. Fernández-Bolaños

  DOI：10.1016/j.ejmech.2016.07.021

  日期：2016.11

  Herein we report the synthesis of N-alkylated deoxynojirimycin derivatives decorated with a selenoureido motif at the hydrocarbon tether as an example of unprecedented multitarget agents. Title compounds were designed as dual drugs for taclding simultaneously the Gaucher disease (by selective inhibition of beta-glucosidase, K-i = 1.6-5.5 mu M, with improved potency and selectivity compared to deoxynojirimycin) and its neurological complications (by inhibiting AChE, K-i up to 5.8 mu M). Moreover, an excellent mimicry of the selenoenzyme glutathione peroxidase was also found for the catalytic scavenging of H2O2 (K-cat/K-uncat up to 640) using PhSH as a cofactor, with improved activity compared to known positive controls, like (PhSe)(2) and ebselen; therefore, such compounds are also excellent scavengers of peroxides, an example of reactive oxygen species present at high concentrations in patients of Gaucher disease and neurological disorders. (C) 2016 Elsevier Masson SAS. All rights reserved.