1,3,6-tri-O-acetyl-4-O-(2,3,4,6-tetra-O-acetyl-β-D-galactopyranosyl)-2-amino-2-deoxy-β-D-glucopyranose p-toluenesulfonate | 1476786-56-7

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: 1,3,6-tri-O-acetyl-4-O-(2,3,4,6-tetra-O-acetyl-β-D-galactopyranosyl)-2-amino-2-deoxy-β-D-glucopyranose p-toluenesulfonate
• CAS: 1476786-56-7
• 化学式: C₇H₈O₃S*C₂₆H₃₇NO₁₇
• 分子量: 807.781
• InChiKey: WVAJACRPQJYPJR-KWRWQIAXSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  -0.19
• 重原子数：
  55.0
• 可旋转键数：
  12.0
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.61
• 拓扑面积：
  292.18
• 氢给体数：
  2.0
• 氢受体数：
  20.0

反应信息

• 作为反应物：
  描述：

  1,3,6-tri-O-acetyl-4-O-(2,3,4,6-tetra-O-acetyl-β-D-galactopyranosyl)-2-amino-2-deoxy-β-D-glucopyranose p-toluenesulfonate 、 3,4-dimethoxy-cinnamoyl chloride 在 sodium carbonate 作用下， 以 二氯甲烷 、 水 为溶剂， 反应 12.0h， 以58.4%的产率得到N-[1,3,6-tri-O-acetyl-4-O-(2,3,4,6-tetra-O-acetyl-β-D-galactopyranosyl)-2-amino-2-deoxy-β-D-glucopyranosyl]-3-(3,4-dimethoxyphenyl)-2-propenamide
  参考文献：
  名称：

  Synthesis and anti-angiogenetic activity evaluation of N-(3-aryl acryloyl)aminosaccharide derivatives

  摘要：

  In order to find novel potent inhibitors for signal pathways of FGF/FGFR, nineteen N-(3-aryl acryloyl)aminosaccharide derivatives were designed and synthesized based on the binding sites of FGF and oligosaccharides of heparin. Their structures were confirmed by IR, H-1 NMR, C-13 NMR, MS and elemental analysis. The nineteen target compounds were evaluated for biological activity against HUVEC cell. In vitro assays showed that compound 10s (IC50 = 5.3 mu M) exhibited comparable inhibitory effects on endothelial cell growth with topotecan (IC50 = 2.7 mu M). Compound 10s (10 mu g/egg) also showed obvious anti-angiogenetic activity in the in vivo chicken chorio allantoic membrane (CAM) assay, and the potency was similar to topotecan (10 mu g/egg). (C) 2013 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.carres.2013.08.022
• 作为产物：
  描述：

  O-(2,3,4,6-tetra-O-acetyl-β-D-galactopyranosyl)-(1->4)-3,6-di-O-acetyl-2-azido-2-deoxy-α-D-glucopyranosyl bromide 在 palladium 10% on activated carbon 、 mercury(II) diacetate 、 氢气 作用下， 以 四氢呋喃 为溶剂， 反应 23.0h， 生成 1,3,6-tri-O-acetyl-4-O-(2,3,4,6-tetra-O-acetyl-β-D-galactopyranosyl)-2-amino-2-deoxy-β-D-glucopyranose p-toluenesulfonate
  参考文献：
  名称：

  Synthesis and anti-angiogenetic activity evaluation of N-(3-aryl acryloyl)aminosaccharide derivatives

  摘要：

  In order to find novel potent inhibitors for signal pathways of FGF/FGFR, nineteen N-(3-aryl acryloyl)aminosaccharide derivatives were designed and synthesized based on the binding sites of FGF and oligosaccharides of heparin. Their structures were confirmed by IR, H-1 NMR, C-13 NMR, MS and elemental analysis. The nineteen target compounds were evaluated for biological activity against HUVEC cell. In vitro assays showed that compound 10s (IC50 = 5.3 mu M) exhibited comparable inhibitory effects on endothelial cell growth with topotecan (IC50 = 2.7 mu M). Compound 10s (10 mu g/egg) also showed obvious anti-angiogenetic activity in the in vivo chicken chorio allantoic membrane (CAM) assay, and the potency was similar to topotecan (10 mu g/egg). (C) 2013 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.carres.2013.08.022