1-(3,4,6-tri-O-acetyl-1,5-anhydro-2-deoxy-D-galactitol-2-yl)-4-(4-nitrophenyloxy)methyl-1,2,3-triazole | 1196658-72-6

• 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-(3,4,6-tri-O-acetyl-1,5-anhydro-2-deoxy-D-galactitol-2-yl)-4-(4-nitrophenyloxy)methyl-1,2,3-triazole
• CAS: 1196658-72-6
• 化学式: C₂₁H₂₄N₄O₁₀
• 分子量: 492.442
• InChiKey: WTMMNYMLMBWKDQ-BQJUDKOJSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  1.13
• 重原子数：
  35.0
• 可旋转键数：
  9.0
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.48
• 拓扑面积：
  171.21
• 氢给体数：
  0.0
• 氢受体数：
  13.0

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-nitrophenyloxy)methyl-1,2,3-triazole 在 甲醇 、 sodium 作用下， 反应 3.0h， 以33%的产率得到1-(1,5-anhydro-2-deoxy-D-galactitol-2-yl)-4-(4-nitrophenoxy)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：

  3,4,6-tri-O-acetyl-1,5-anhydro-2-azido-2-deoxy-D-galactitol 、 1-nitro-4-(prop-2-ynyloxy)benzene 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95%的产率得到1-(3,4,6-tri-O-acetyl-1,5-anhydro-2-deoxy-D-galactitol-2-yl)-4-(4-nitrophenyloxy)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