methyl 3-deoxy-3-(4-methylbenzamido)-2-O-(O-benzyl-phospho)-1-thio-β-D-galactopyranoside | 1018903-32-6

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: methyl 3-deoxy-3-(4-methylbenzamido)-2-O-(O-benzyl-phospho)-1-thio-β-D-galactopyranoside
• 英文别名: Methyl 2-O-[(S)-(Benzyloxy)(Hydroxy)phosphoryl]-3-Deoxy-3-{[(4-Methylphenyl)carbonyl]amino}-1-Thio-Beta-D-Galactopyranoside；benzyl [(2S,3R,4S,5R,6R)-5-hydroxy-6-(hydroxymethyl)-4-[(4-methylbenzoyl)amino]-2-methylsulfanyloxan-3-yl] hydrogen phosphate
• CAS: 1018903-32-6
• 化学式: C₂₂H₂₈NO₈PS
• 分子量: 497.506
• InChiKey: IDAWZVIHHBVHNS-QWPXSNKBSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  1.7
• 重原子数：
  33
• 可旋转键数：
  9
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.41
• 拓扑面积：
  160
• 氢给体数：
  4
• 氢受体数：
  9

反应信息

• 作为产物：
  描述：

  在 溶剂黄146 作用下， 反应 4.5h， 生成 methyl 3-deoxy-3-(4-methylbenzamido)-2-O-(O-benzyl-phospho)-1-thio-β-D-galactopyranoside
  参考文献：
  名称：

  Arginine Binding Motifs: Design and Synthesis of Galactose-Derived Arginine Tweezers as Galectin-3 Inhibitors

  摘要：

  Anionic O2 derivatives of methyl 3-deoxy-3-(4-methylbenzamido)-1-thio-beta-D-galactopyranoside have been synthesized as inhibitors against galectin-3. The sulfate, H-phosphonate, and benzyl phosphate derivatives showed an increased affinity as compared to the parent unsubstituted galactopyranoside. Modeling revealed arginine-144 being pinched by the C3 benzamide and O2 anionic substituents in that the benzamide stacked face-to-face and the anionic O2 substituent ion-paired with the guanidinium moiety.

  DOI：

  10.1021/jm701266y