2-acetamido-1,4-imino-1,2,4-trideoxy-L-ribitol | 1207673-89-9

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 吡咯烷类
• 英文名称: 2-acetamido-1,4-imino-1,2,4-trideoxy-L-ribitol
• 英文别名: 2-acetamido-1,2,4-trideoxy-1,4-imino-1-ribitol；N-[(3R,4R,5S)-4-Hydroxy-5-(hydroxymethyl)pyrrolidin-3-yl]acetamide
• CAS: 1207673-89-9
• 化学式: C₇H₁₄N₂O₃
• 分子量: 174.2
• InChiKey: CIBNSHFFZNRICG-DSYKOEDSSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  -1.7
• 重原子数：
  12
• 可旋转键数：
  2
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.86
• 拓扑面积：
  81.6
• 氢给体数：
  4
• 氢受体数：
  4

反应信息

• 作为产物：
  描述：

  2-acetamido-N-benzyl-1,4-imino-1,2,4-trideoxy-L-ribitol 在 氢气 、 钯 作用下， 以 1,4-二氧六环 、 水 为溶剂， 反应 18.0h， 以88%的产率得到2-acetamido-1,4-imino-1,2,4-trideoxy-L-ribitol
  参考文献：
  名称：

  Enantiomeric 2-acetamido-1,4-dideoxy-1,4-iminoribitols as potential pyrrolidine hexosaminidase inhibitors

  摘要：

  摘要 2-乙酰氨基-1,4-亚氨基-1,2,4-三脱氧-D-核糖醇（DRBNAc）和对映体 LRBNAc 分别由 L- 和 D-lyxonolactone 制备而成，是潜在的己糖胺酸酶抑制剂。无论是 N-苄基-DRBNAc 还是 N-苄基-LRBNAc，都没有显示出对 α 或 β-己糖胺酶或任何其他糖苷酶的抑制作用。

  DOI：

  10.1016/j.crci.2010.03.020

文献信息

• TREATMENT OF LYSOSOMAL STORAGE DISORDERS AND OTHER PROTEOSTATIC DISEASES
  申请人：De Moor Olivier

  公开号：US20110237538A1

  公开（公告）日：2011-09-29

  Described are various compounds, in particular iminosugars, and methods for the treatment of proteostatic diseases, in particular lysosomal storage disorders. The compound may be a pharmacoperone of an enzyme selected from: (a) Acid alpha-glucosidase; (b) Acid beta-glucosidase; (c) glucocerebrosidase; (d) alpha-Galactosidase A; (e) Acid beta-galactosidase; (f) beta-Hexosaminidase A; (g) beta-Hexosaminidase B; (h) Acid sphingomyelinase; (i) Galactocerebrosidase; (j) Acid ceramidase; (k) Arylsulfatase A; (l) alpha-L-Iduronidase; (m) Iduronate-2-sulfatase; (n) Heparan N-sulfatase; (o) alpha-N-Acetylglucosaminidase; (p) Acetyl-CoA: alpha-glucosaminide N-acetyltransferase; (q) N-Acetylglucosamine-6-sulfate sulfatase; (r) N-Acetylgalactosamine-6-sulfate sulfatase; (s) Acid beta-galactosidase; (t) Arylsulfatase B; (u) beta-Glucuronidase; (v) Acid alpha-mannosidase; (w) Acid beta-mannosidase; (x) Acid alpha-L-fucosidase; (y) Sialidase; and (z) alpha-N-acetylgalactosaminidase.
• Enantiomeric 2-acetamido-1,4-dideoxy-1,4-iminoribitols as potential pyrrolidine hexosaminidase inhibitors
  作者：J.S. Shane Rountree、Terry D. Butters、Raymond A. Dwek、George W.J. Fleet

  DOI：10.1016/j.crci.2010.03.020

  日期：2011.1

  Résumé 2-Acetamido-1,4-imino-1,2,4-trideoxy-D-ribitol (DRBNAc) and the enantiomeric LRBNAc were prepared as potential hexosaminidase inhibitors from L- and D-lyxonolactone, respectively. Neither N-benzyl-DRBNAc nor N-benzyl-LRBNAc showed any inhibition of α- or β-hexosaminidases or any other glycosidase.

  摘要 2-乙酰氨基-1,4-亚氨基-1,2,4-三脱氧-D-核糖醇（DRBNAc）和对映体 LRBNAc 分别由 L- 和 D-lyxonolactone 制备而成，是潜在的己糖胺酸酶抑制剂。无论是 N-苄基-DRBNAc 还是 N-苄基-LRBNAc，都没有显示出对 α 或 β-己糖胺酶或任何其他糖苷酶的抑制作用。