1-(3,4,6-tri-O-acetyl-1,5-anhydro-2-deoxy-D-galactitol-2-yl)-4-(4-cyanophenoxy)methyl-1,2,3-triazole | 1196658-71-5

• 分子结构分类: 有机化合物 - 有机酸及其衍生物 - 羧酸及其衍生物
• 英文名称: 1-(3,4,6-tri-O-acetyl-1,5-anhydro-2-deoxy-D-galactitol-2-yl)-4-(4-cyanophenoxy)methyl-1,2,3-triazole
• CAS: 1196658-71-5
• 化学式: C₂₂H₂₄N₄O₈
• 分子量: 472.455
• InChiKey: FNONKTNDUDPYJF-CBPXPLCBSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  1.1
• 重原子数：
  34.0
• 可旋转键数：
  8.0
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.45
• 拓扑面积：
  151.86
• 氢给体数：
  0.0
• 氢受体数：
  12.0

反应信息

• 作为反应物：
  描述：

  1-(3,4,6-tri-O-acetyl-1,5-anhydro-2-deoxy-D-galactitol-2-yl)-4-(4-cyanophenoxy)methyl-1,2,3-triazole 在 水 、 三乙胺 作用下， 以 甲醇 为溶剂， 以81%的产率得到1-(1,5-anhydro-2-deoxy-D-galactitol-2-yl)-4-(4-cyanophenoxy)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
• 作为产物：
  描述：

  4-(2-丙炔氧基)苯甲腈 、 3,4,6-tri-O-acetyl-1,5-anhydro-2-azido-2-deoxy-D-galactitol 在 N,N-二异丙基乙胺 、 copper(l) chloride 作用下， 以 二氯甲烷 为溶剂， 反应 24.0h， 以98%的产率得到1-(3,4,6-tri-O-acetyl-1,5-anhydro-2-deoxy-D-galactitol-2-yl)-4-(4-cyanophenoxy)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