methyl 3-deoxy-3-(4-methylbenzamido)-1-thio-β-D-galactopyranoside | 1018903-36-0

• 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)-1-thio-β-D-galactopyranoside
• 英文别名: N-[(2R,3R,4S,5R,6S)-3,5-dihydroxy-2-(hydroxymethyl)-6-(methylsulfanyl)oxan-4-yl]-4-methylbenzamide；N-[(2R,3R,4S,5R,6S)-3,5-dihydroxy-2-(hydroxymethyl)-6-methylsulfanyloxan-4-yl]-4-methylbenzamide
• CAS: 1018903-36-0
• 化学式: C₁₅H₂₁NO₅S
• 分子量: 327.401
• InChiKey: MYAWDXDLUZEXBG-KDBYPZKRSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  0.8
• 重原子数：
  22
• 可旋转键数：
  4
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.53
• 拓扑面积：
  124
• 氢给体数：
  4
• 氢受体数：
  6

反应信息

• 作为产物：
  描述：

  methyl 3-deoxy-4,6-O-(4-methoxybenzylidene)-3-(4-methylbenzamido)-1-thio-β-D-galactopyranoside 在 Dowex 50 作用下， 以 甲醇 、 二氯甲烷 、 水 为溶剂， 反应 20.0h， 以60%的产率得到methyl 3-deoxy-3-(4-methylbenzamido)-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