methyl 6-[3-(3-methoxy-4-acetoxyphenyl)propenamido]-6-deoxy-α-D-galactopyranoside | 1202010-98-7

• 分子结构分类: 有机化合物 - 苯丙烷和聚酮 - 肉桂酸及其衍生物
• 英文名称: methyl 6-[3-(3-methoxy-4-acetoxyphenyl)propenamido]-6-deoxy-α-D-galactopyranoside
• 英文别名: [2-methoxy-4-[(E)-3-oxo-3-[[(2R,3R,4S,5R,6S)-3,4,5-trihydroxy-6-methoxyoxan-2-yl]methylamino]prop-1-enyl]phenyl] acetate
• CAS: 1202010-98-7
• 化学式: C₁₉H₂₅NO₉
• 分子量: 411.409
• InChiKey: DSQIAOKYCLQVIO-GCPWNBSASA-N

计算性质

• 辛醇/水分配系数(LogP)：
  -0.2
• 重原子数：
  29
• 可旋转键数：
  8
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.47
• 拓扑面积：
  144
• 氢给体数：
  4
• 氢受体数：
  9

反应信息

• 作为反应物：
  描述：

  methyl 6-[3-(3-methoxy-4-acetoxyphenyl)propenamido]-6-deoxy-α-D-galactopyranoside 、 乙酸酐 在 吡啶 、 4-二甲氨基吡啶 、 三乙胺 作用下， 反应 12.0h， 以74.4%的产率得到methyl 2,3,4-tri-O-acetyl-6-[3-(3-meoxy-4-acetoxyphenyl)propenamido]-6-deoxy-α-D-galactopyranoside
  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：

  阿魏酸 在 1-羟基苯并三唑 、 盐酸-N-乙基-Nˊ-(3-二甲氨基丙基)碳二亚胺 、 sodium hydroxide 作用下， 以 水 、 N,N-二甲基甲酰胺 为溶剂， 反应 25.5h， 生成 methyl 6-[3-(3-methoxy-4-acetoxyphenyl)propenamido]-6-deoxy-α-D-galactopyranoside
  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