N-(5-cyano)-pentyl-1,5-dideoxy-1,5-iminoxylitol | 448926-98-5

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 哌啶类
• 英文名称: N-(5-cyano)-pentyl-1,5-dideoxy-1,5-iminoxylitol
• 英文别名: 6-((3R,4r,5S)-3,4,5-trihydroxypiperidin-1-yl)hexanenitrile
• CAS: 448926-98-5
• 化学式: C₁₁H₂₀N₂O₃
• 分子量: 228.291
• InChiKey: FVDCZAHZVLBOHT-URLYPYJESA-N

计算性质

• 辛醇/水分配系数(LogP)：
  -0.53
• 重原子数：
  16.0
• 可旋转键数：
  5.0
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.91
• 拓扑面积：
  87.72
• 氢给体数：
  3.0
• 氢受体数：
  5.0

反应信息

• 作为反应物：
  描述：

  N-(5-cyano)-pentyl-1,5-dideoxy-1,5-iminoxylitol 在 镍 氢气 、 三乙胺 作用下， 以 甲醇 、 N,N-二甲基甲酰胺 为溶剂， 反应 24.0h， 生成 5-Dimethylamino-naphthalene-1-sulfonic acid [6-((3R,4R,5S)-3,4,5-trihydroxy-piperidin-1-yl)-hexyl]-amide
  参考文献：
  名称：

  Fluorescent glycosidase inhibiting 1,5-dideoxy-1,5-iminoalditols

  摘要：

  1,5-Dideoxy-1,5-iminoalditols of various configurations as well as isofagomine were N-alkylated with non-polar straight chain spacer-arms by a set of simple standard procedures. The spacer-arms' terminal functional groups, primary amines, were employed to introduce fluorescent tags such as dansyl and dapoxyl moieties. Resulting derivatives in the D-xylo, D-gluco, D-galacto as well as GlcNAc series showed distinctly improved glycosidase inhibitory activities compared to parent compounds and are designed to be useful analytical tools. (C) 2006 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.bmcl.2006.01.095
• 作为产物：
  描述：

  1,5-DIDEOXY-1,5-IMINO-XYLITOL 、 6-溴己腈 在 吡啶 作用下， 以 甲醇 为溶剂， 反应 48.0h， 以46%的产率得到N-(5-cyano)-pentyl-1,5-dideoxy-1,5-iminoxylitol
  参考文献：
  名称：

  N-Alkylated Derivatives of 1,5-Dideoxy-1,5-iminoxylitol as Β-Xylosidaseand Β-Glucosidase Inhibitors

  摘要：

  A range of lipophilic derivatives of the D-xylosidase inhibitor 1,5-dideoxy-1,5-iminoxylitol was synthesized by N-alkylation of the parent compound with different alkyl halides. Inhibitory activities of the products obtained were measured with beta-glucosidase from Agrobacterium sp., a family I enzyme, as well as with beta-xylosidase from Thermoanaerobacterium saccharolyticum belonging to family 39 of the glycohydrolases. Whereas the former enzyme, which has low beta-xylosidase activity, was only moderately inhibited, with K-i values in the millimolar range, good inhibition was observed with the latter one. Inhibitors with terminally functionalized N-alkyl chains open up opportunities for novel applications as affinity ligands as well as for various types of tagging for diagnostic purposes.

  DOI：

  10.1007/s007060200028

文献信息

• [EN] GLYCOSIDASE INHIBITORS AND USES THEREOF<br/>[FR] INHIBITEURS DE GLYCOSIDASES ET LEURS UTILISATIONS
  申请人：ALECTOS THERAPEUTICS INC

  公开号：WO2014032184A1

  公开（公告）日：2014-03-06

  The invention provides compounds for inhibiting glycosidases, prodrugs of the compounds, and pharmaceutical compositions including the compounds or prodrugs of the compounds. The invention also provides methods of treating diseases and disorders related to deficiency or overexpression of O-GlcNAcase, accumulation or deficiency of O-GlcNAc.

  该发明提供了用于抑制糖苷酶的化合物，这些化合物的前药，以及包括这些化合物或这些化合物的前药的药物组合物。该发明还提供了用于治疗与O-GlcNAcase缺乏或过度表达、O-GlcNAc的积累或缺乏相关的疾病和障碍的方法。
• GLYCOSIDASE INHIBITORS AND USES THEREOF
  申请人：Alectos Therapeutics Inc.

  公开号：US20150299122A1

  公开（公告）日：2015-10-22

  The invention provides compounds for inhibiting glycosidases, prodrugs of the compounds, and pharmaceutical compositions including the compounds or prodrugs of the compounds. The invention also provides methods of treating diseases and disorders related to deficiency or overexpression of O-GlcNAcase, accumulation or deficiency of O-GlcNAc.

  本发明提供了抑制糖苷酶的化合物，该化合物的前药，以及包括该化合物或该化合物的前药的制药组合物。本发明还提供了治疗与O-GlcNA酶的缺乏或过度表达、O-GlcNAc的积累或缺乏有关的疾病和障碍的方法。