methyl 3-deoxy-3-(4-propyl-1H-[1,2,3]-triazol-1-yl)-1-thio-β-D-galactopyranoside

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: methyl 3-deoxy-3-(4-propyl-1H-[1,2,3]-triazol-1-yl)-1-thio-β-D-galactopyranoside
• 英文别名: Methyl-3-deoxy-3-(4-propyl-1H-[1,2,3]-triazol-1-yl)-1-thio-beta-D-galactopyranoside；(2R,3R,4S,5R,6S)-2-(hydroxymethyl)-6-methylsulfanyl-4-(4-propyltriazol-1-yl)oxane-3,5-diol
• 化学式: C₁₂H₂₁N₃O₄S
• 分子量: 303.382
• InChiKey: BPLPAEXIUKSCIA-IIRVCBMXSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  0
• 重原子数：
  20
• 可旋转键数：
  5
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.83
• 拓扑面积：
  126
• 氢给体数：
  3
• 氢受体数：
  7

反应信息

• 作为产物：
  描述：

  methyl 3-azido-3-deoxy-1-thio-β-D-galactoside 在 铜 、 N,N-二异丙基乙胺 、 甲胺 作用下， 以 甲苯 为溶剂， 生成 methyl 3-deoxy-3-(4-propyl-1H-[1,2,3]-triazol-1-yl)-1-thio-β-D-galactopyranoside
  参考文献：
  名称：

  3-(1,2,3-Triazol-1-yl)-1-thio-galactosides as small, efficient, and hydrolytically stable inhibitors of galectin-3

  摘要：

  Copper(I)-catalyzed addition of alkynes to methyl 3 -azido-3-deoxy-1-thio-beta-D-galactopyrano side afforded stable and structurally simple 3-deoxy-3-(1H-1,2,3-triazol-1-yl)-1-thio-galactosides carrying a panel of substituents at the triazole C4 in high yields. The 3-(1H-[1,2,3]-triazol-1-yl)-1-thio-galactoside collection synthesized contained inhibitors of the tumor- and inflammation-related galectin-3 with K-d values as low as 107 mu M, which is as potent as the natural disaccharide inhibitors lactose and N-acetyllactosamine. (c) 2005 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.bmcl.2005.05.084

文献信息

• [EN] GALACTOSIDE INHIBITORS FOR THE TREATMENT OF ALPHA-SYNUCLEINOPTHIES<br/>[FR] INHIBITEURS GALACTOSIDES POUR LE TRAITEMENT DES ALPHA-SYNUCLÉINOPATHIES
  申请人：GALECTO BIOTECH AB

  公开号：WO2015155207A1

  公开（公告）日：2015-10-15

  The present invention relates to a pharmaceutical composition for use in a method for treatment or prevention of a-synucleinopathies wherein the composition comprises a molecule for pharmacological modulation of galectin activity in a mammalian brain. The invention also concerns a method for treatment or prevention of a-synucleinopathies in a mammalian subject, the method comprising administering a therapeutically effective amount of at least one composition to the subject, wherein the composition comprises a molecule for pharmacological modulation of galectin activity in a mammalian brain.

  本发明涉及一种药物组合物，用于治疗或预防α-突触核蛋白病，其中该组合物包括一种用于在哺乳动物大脑中调节半乳糖凝集素活性的分子。该发明还涉及一种治疗或预防哺乳动物主体中α-突触核蛋白病的方法，该方法包括向主体中注射至少一种组合物的治疗有效量，其中该组合物包括一种用于在哺乳动物大脑中调节半乳糖凝集素活性的分子。
• NOVEL 3-TRIAZOLYL-GALACTOSIDE INHIBITORS OF GALECTINS
  申请人：Leffler Hakon

  公开号：US20070185041A1

  公开（公告）日：2007-08-09

  The present invention relates to novel compounds, the use of said compounds as a medicament as well as for the manufacture of a medicament for treatment of disorders relating to the binding of galectin to receptors in a mammal. Said galectin is preferably a galectin-3.

  本发明涉及新型化合物，以及将该化合物用作药物以及制造用于治疗哺乳动物中与galectin与受体结合相关的疾病的药物。所述的galectin通常是galectin-3。
• 1H-1,2,3-Triazol-1-yl thiodigalactoside derivatives as high affinity galectin-3 inhibitors
  作者：Bader A. Salameh、Ian Cumpstey、Anders Sundin、Hakon Leffler、Ulf J. Nilsson

  DOI：10.1016/j.bmc.2010.05.040

  日期：2010.7

  Galactose C3-triazole derivatives were synthesized by Cu(I)-catalyzed cycloaddition between acetylenes and galactose C3-azido derivatives. Evaluation against galectin-3, 7, 8N (N-terminal) and 9N (N-terminal) revealed 1,4-disubstituted triazoles to be high-affinity inhibitors of galectin-3 with selectivity over galectin-7, 8N, and 9N. Conformational analysis of 1,4-di-and 1,4,5-tri-substituted galactose C3-triazoles suggested that a triazole C5-substituent interfered sterically with the galectin proteins, which explained their poor affinities compared to the corresponding 1,4-disubstituted triazoles. Introduction of two 1,4-disubstituted triazole moieties onto thiodigalactoside resulted in affinities down to 29 nM for galectin-3. (C) 2010 Elsevier Ltd. All rights reserved.
• GALACTOSIDE INHIBITORS FOR THE TREATMENT OF ALPHA-SYNUCLEINOPTHIES
  申请人：Galecto Biotech AB

  公开号：EP3129032A1

  公开（公告）日：2017-02-15
• Methods, compositions and kits for treating, modulating, or preventing ocular angiogenesis or fibrosis in a subject using a galectin protein inhibitor
  申请人：TUFTS UNIVERSITY

  公开号：US20150320782A1

  公开（公告）日：2015-11-12

  Methods and kits using a pharmaceutical composition for use in inhibiting ocular angiogenesis or fibrosis are provided herein, such that composition includes a pharmaceutically suitable carrier or diluent and an amount of the inhibitor composition effective to inhibit the angiogenesis or the fibrosis by inhibiting expression and/or activity of a galectin protein or a portion thereof.