N-(2,3,4,6-tetra-O-acetyl-1-deoxy-β-D-galactopyranosyl)-3-(3-methoxy-4-acetoxyphenyl)-2-propenamide | 1202010-90-9

• 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: N-(2,3,4,6-tetra-O-acetyl-1-deoxy-β-D-galactopyranosyl)-3-(3-methoxy-4-acetoxyphenyl)-2-propenamide
• 英文别名: [(2R,3S,4S,5R,6R)-3,4,5-triacetyloxy-6-[[(E)-3-(4-acetyloxy-3-methoxyphenyl)prop-2-enoyl]amino]oxan-2-yl]methyl acetate
• CAS: 1202010-90-9
• 化学式: C₂₆H₃₁NO₁₃
• 分子量: 565.531
• InChiKey: SZXJPXNRZORQCC-CCHZORGASA-N

计算性质

• 辛醇/水分配系数(LogP)：
  1
• 重原子数：
  40
• 可旋转键数：
  15
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.46
• 拓扑面积：
  179
• 氢给体数：
  1
• 氢受体数：
  13

反应信息

• 作为产物：
  描述：

  阿魏酸 在 草酰氯 、 sodium carbonate 、 sodium hydroxide 作用下， 以 二氯甲烷 、 水 、 N,N-二甲基甲酰胺 为溶剂， 反应 49.5h， 生成 N-(2,3,4,6-tetra-O-acetyl-1-deoxy-β-D-galactopyranosyl)-3-(3-methoxy-4-acetoxyphenyl)-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