2-nitrophenyl 4-O-β-D-galactopyranosyl-β-D-glucopyranoside | 17691-05-3

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: 2-nitrophenyl 4-O-β-D-galactopyranosyl-β-D-glucopyranoside
• 英文别名: 2-Nitrophenyl 4-O-I(2)-D-galactopyranosyl-I(2)-D-glucopyranoside；(2S,3R,4S,5R,6R)-2-[(2R,3S,4R,5R,6S)-4,5-dihydroxy-2-(hydroxymethyl)-6-(2-nitrophenoxy)oxan-3-yl]oxy-6-(hydroxymethyl)oxane-3,4,5-triol
• CAS: 17691-05-3
• 化学式: C₁₈H₂₅NO₁₃
• 分子量: 463.395
• InChiKey: CYCLRDYAFVRUDE-MUKCROHVSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  -3.4
• 重原子数：
  32.0
• 可旋转键数：
  7.0
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.67
• 拓扑面积：
  221.67
• 氢给体数：
  7.0
• 氢受体数：
  13.0

反应信息

• 作为产物：
  描述：

  lactose octaacetate 在 甲醇 、 氢溴酸 、 sodium methylate 、 四丁基硫酸氢铵 、 sodium carbonate 作用下， 以 二氯甲烷 、 溶剂黄146 为溶剂， 反应 3.0h， 生成 2-nitrophenyl 4-O-β-D-galactopyranosyl-β-D-glucopyranoside
  参考文献：
  名称：

  Aryl O- and S-galactosides and lactosides as specific inhibitors of human galectins-1 and -3: Role of electrostatic potential at O-3

  摘要：

  Phase transfer catalyzed reaction was used for the high yielding synthesis of aryl 1-thio-beta-D-galacto- and lacto-pyranosides carrying a panel of substituents on the phenyl groups. Best galectin-1 inhibitors were simple p-nitrophenyl thiogalactoside 5a for the monosaccharide and o-nitrophenyl thiolactoside 6f or napthylsulfonyl lactoside 8c, both being 20 times better relative to natural ligands. Relative inhibitory properties as low as 2500 and 40 mu M were observed, respectively. The electronic effects of the lactoside aglycons directly influenced the electrostatic potential at O-3, which was associated with the inhibitory potencies against galectin-1. (C) 2006 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.bmcl.2005.12.010