1-(1,5-anhydro-2-deoxy-D-galactitol-2-yl)-4-(4-trifluoromethylsulfonamidophenoxy)methyl-1,2,3-triazole | 1196658-81-7

• 分子结构分类: 有机化合物 - 苯类化合物 - 苯和取代衍生物
• 英文名称: 1-(1,5-anhydro-2-deoxy-D-galactitol-2-yl)-4-(4-trifluoromethylsulfonamidophenoxy)methyl-1,2,3-triazole
• 英文别名: N-[4-[[1-[(3S,4R,5R,6R)-4,5-dihydroxy-6-(hydroxymethyl)oxan-3-yl]triazol-4-yl]methoxy]phenyl]-1,1,1-trifluoromethanesulfonamide
• CAS: 1196658-81-7
• 化学式: C₁₆H₁₉F₃N₄O₇S
• 分子量: 468.411
• InChiKey: VXSHQHBIVSXIMC-YJNKXOJESA-N

计算性质

• 辛醇/水分配系数(LogP)：
  -0.3
• 重原子数：
  31
• 可旋转键数：
  7
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.5
• 拓扑面积：
  164
• 氢给体数：
  4
• 氢受体数：
  13

反应信息

• 作为产物：
  描述：

  1-(3,4,6-tri-O-acetyl-1,5-anhydro-2-deoxy-D-galactitol-2-yl)-4-(trifluoromethylsulfonamidophenyloxy)methyl-1,2,3-triazole 在 甲醇 、 sodium 作用下， 反应 3.0h， 以73%的产率得到1-(1,5-anhydro-2-deoxy-D-galactitol-2-yl)-4-(4-trifluoromethylsulfonamidophenoxy)methyl-1,2,3-triazole
  参考文献：
  名称：

  Design, synthesis and evaluation of monovalent ligands for the asialoglycoprotein receptor (ASGP-R)

  摘要：

  A series of novel aryl-substituted triazolyl D-galactosamine derivatives was synthesized as ligands for the carbohydrate recognition domain of the major subunit H1 (H1-CRD) of the human asialoglycoprotein receptor (ASGP-R). The compounds were biologically evaluated with a newly developed competitive binding assay, surface plasmon resonance and by a competitive NMR binding experiment. With compound 1b, a new ligand with a twofold improved affinity to the best so far known D-GalNAc was identified. This small, drug-like ligand can be used as targeting device for drug delivery to hepatocytes. (C) 2009 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.bmc.2009.08.049

文献信息

• Design, synthesis and evaluation of monovalent ligands for the asialoglycoprotein receptor (ASGP-R)
  作者：Daniela Stokmaier、Oleg Khorev、Brian Cutting、Rita Born、Daniel Ricklin、Thomas O.G. Ernst、Fabienne Böni、Kathrin Schwingruber、Martin Gentner、Matthias Wittwer、Morena Spreafico、Angelo Vedani、Said Rabbani、Oliver Schwardt、Beat Ernst

  DOI：10.1016/j.bmc.2009.08.049

  日期：2009.10

  A series of novel aryl-substituted triazolyl D-galactosamine derivatives was synthesized as ligands for the carbohydrate recognition domain of the major subunit H1 (H1-CRD) of the human asialoglycoprotein receptor (ASGP-R). The compounds were biologically evaluated with a newly developed competitive binding assay, surface plasmon resonance and by a competitive NMR binding experiment. With compound 1b, a new ligand with a twofold improved affinity to the best so far known D-GalNAc was identified. This small, drug-like ligand can be used as targeting device for drug delivery to hepatocytes. (C) 2009 Elsevier Ltd. All rights reserved.