4-(benzyloxycarbonylamino)-N-{tris[13-hydroxy-2,6,10-trioxatridecyl]methyl}butyramide | 1038802-23-1

• 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: 4-(benzyloxycarbonylamino)-N-{tris[13-hydroxy-2,6,10-trioxatridecyl]methyl}butyramide
• CAS: 1038802-23-1
• 化学式: C₄₃H₇₈N₂O₁₅
• 分子量: 863.097
• InChiKey: VUJZKRFKBOMNQG-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.19
• 重原子数：
  60.0
• 可旋转键数：
  46.0
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.81
• 拓扑面积：
  211.19
• 氢给体数：
  5.0
• 氢受体数：
  15.0

反应信息

• 作为反应物：
  描述：

  4-(benzyloxycarbonylamino)-N-{tris[13-hydroxy-2,6,10-trioxatridecyl]methyl}butyramide 、 ethyl 3,4,6-tri-O-acetyl-2-deoxy-1-thio-2-(2,2,2-trichloroethoxycarbonylamino)-β-D-galactopyranoside 在 DMTST 作用下， 以 二氯甲烷 为溶剂， 反应 72.0h， 以91%的产率得到N-(tris{13-[3,4,6-tri-O-acetyl-2-deoxy-2-(2,2,2-trichloroethoxycarbonylamino)-β-D-galactopyranosyloxy]-2,6,10-trioxatridecyl}methyl)-4-(benzyloxycarbonylamino)butyramide
  参考文献：
  名称：

  Trivalent, Gal/GalNAc-containing ligands designed for the asialoglycoprotein receptor

  摘要：

  A series of novel, fluorescent ligands designed to bind with high affinity and specificity to the asialoglycoprotein receptor (ASGP-R) has been synthesized and tested on human liver cells. The compounds bear three non-reducing, beta-linked Gal or GalNAc moieties linked to flexible spacers for an optimal spatial interaction with the binding site of the ASGP-R. The final constructs were selectively endocytosed by HepG2 cells derived from parenchymal liver cells-the major human liver cell type-in a process that was visualized with the aid of fluorescence microscopy. Furthermore, the internalization was analyzed with flow cytometry, which showed the process to be receptor-mediated and selective. The compounds described in this work could serve as valuable tools for studying hepatic endocytosis, and are suited as carriers for site-specific drug delivery to the liver. (C) 2008 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.bmc.2008.03.017
• 作为产物：
  描述：

  N-{tris[13-acetoxy-2,6,10-trioxatridecyl]methyl}-4-(benzyloxycarbonylamino)butyramide 在 sodium methylate 作用下， 以 甲醇 为溶剂， 反应 4.0h， 以90%的产率得到4-(benzyloxycarbonylamino)-N-{tris[13-hydroxy-2,6,10-trioxatridecyl]methyl}butyramide
  参考文献：
  名称：

  Trivalent, Gal/GalNAc-containing ligands designed for the asialoglycoprotein receptor

  摘要：

  A series of novel, fluorescent ligands designed to bind with high affinity and specificity to the asialoglycoprotein receptor (ASGP-R) has been synthesized and tested on human liver cells. The compounds bear three non-reducing, beta-linked Gal or GalNAc moieties linked to flexible spacers for an optimal spatial interaction with the binding site of the ASGP-R. The final constructs were selectively endocytosed by HepG2 cells derived from parenchymal liver cells-the major human liver cell type-in a process that was visualized with the aid of fluorescence microscopy. Furthermore, the internalization was analyzed with flow cytometry, which showed the process to be receptor-mediated and selective. The compounds described in this work could serve as valuable tools for studying hepatic endocytosis, and are suited as carriers for site-specific drug delivery to the liver. (C) 2008 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.bmc.2008.03.017