bis-{3-deoxy-3-[4-(phenyl)-1H-1,2,3-triazol-1-yl]-β-D-galactopyranosyl} sulfane | 1421638-24-5

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: bis-{3-deoxy-3-[4-(phenyl)-1H-1,2,3-triazol-1-yl]-β-D-galactopyranosyl} sulfane
• 英文别名: (2S,3R,4S,5R,6R)-2-[(2S,3R,4S,5R,6R)-3,5-dihydroxy-6-(hydroxymethyl)-4-(4-phenyltriazol-1-yl)oxan-2-yl]sulfanyl-6-(hydroxymethyl)-4-(4-phenyltriazol-1-yl)oxane-3,5-diol
• CAS: 1421638-24-5
• 化学式: C₂₈H₃₂N₆O₈S
• 分子量: 612.663
• InChiKey: KPVDZDWKPRUGKK-MQFIMZJJSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  0
• 重原子数：
  43
• 可旋转键数：
  8
• 环数：
  6.0
• sp3杂化的碳原子比例：
  0.43
• 拓扑面积：
  227
• 氢给体数：
  6
• 氢受体数：
  13

反应信息

• 作为产物：
  描述：

  bis-{2,4,6-tri-O-acetyl-3-deoxy-3-[4-(phenyl)-1H-1,2,3-triazol-1-yl]-β-D-galactopyranosyl}sulfane 在 甲醇 、 sodium methylate 作用下， 反应 2.5h， 以9 mg的产率得到bis-{3-deoxy-3-[4-(phenyl)-1H-1,2,3-triazol-1-yl]-β-D-galactopyranosyl} sulfane
  参考文献：
  名称：

  Tuning the Preference of Thiodigalactoside- and Lactosamine-Based Ligands to Galectin-3 over Galectin-1

  摘要：

  Inhibitors for galectin-1 and -3 were synthesized from thiodigalactoside and lactosamine by derivatization of the galactose C3. Introduction of 4-phenyl-1H-1,2,3-triazol-1-yl substituents at the thiodigalactoside C3 by CuAAC, targeting arginine-arene interactions, increased the affinity to 13 nM but yielded little selectivity. The builder 4-(4-phenoxypheny1)-1H-1,2,3-triazol-1-yl substituent, however, increased the preference for galectin-3 over galectin-1 to more than 200-fold. Modeling showed more arginine-arene interactions for galectin-3 than for galectin-1. Introducing 4-phenoxyaryl groups on lactosamine had a similar effect.

  DOI：

  10.1021/jm301677r

文献信息

• Tuning the Preference of Thiodigalactoside- and Lactosamine-Based Ligands to Galectin-3 over Galectin-1
  作者：Hilde van Hattum、Hilbert M. Branderhorst、Ed E. Moret、Ulf J. Nilsson、Hakon Leffler、Roland J. Pieters

  DOI：10.1021/jm301677r

  日期：2013.2.14

  Inhibitors for galectin-1 and -3 were synthesized from thiodigalactoside and lactosamine by derivatization of the galactose C3. Introduction of 4-phenyl-1H-1,2,3-triazol-1-yl substituents at the thiodigalactoside C3 by CuAAC, targeting arginine-arene interactions, increased the affinity to 13 nM but yielded little selectivity. The builder 4-(4-phenoxypheny1)-1H-1,2,3-triazol-1-yl substituent, however, increased the preference for galectin-3 over galectin-1 to more than 200-fold. Modeling showed more arginine-arene interactions for galectin-3 than for galectin-1. Introducing 4-phenoxyaryl groups on lactosamine had a similar effect.