[(2S,4aR,6S,7R,8S,8aR)-6-[[(2S,4aR,6S,7R,8R,8aS)-8-benzoyloxy-7-hydroxy-2-phenyl-4,4a,6,7,8,8a-hexahydropyrano[3,2-d][1,3]dioxin-6-yl]sulfanyl]-8-hydroxy-2-phenyl-4,4a,6,7,8,8a-hexahydropyrano[3,2-d][1,3]dioxin-7-yl] benzoate | 1093376-86-3

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: [(2S,4aR,6S,7R,8S,8aR)-6-[[(2S,4aR,6S,7R,8R,8aS)-8-benzoyloxy-7-hydroxy-2-phenyl-4,4a,6,7,8,8a-hexahydropyrano[3,2-d][1,3]dioxin-6-yl]sulfanyl]-8-hydroxy-2-phenyl-4,4a,6,7,8,8a-hexahydropyrano[3,2-d][1,3]dioxin-7-yl] benzoate
• CAS: 1093376-86-3
• 化学式: C₄₀H₃₈O₁₂S
• 分子量: 742.801
• InChiKey: UBHKZFDRBUFAQN-ISKZEYJBSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  4.9
• 重原子数：
  53
• 可旋转键数：
  10
• 环数：
  8.0
• sp3杂化的碳原子比例：
  0.35
• 拓扑面积：
  174
• 氢给体数：
  2
• 氢受体数：
  13

反应信息

• 作为产物：
  描述：

  bis-(4,6-O-benzylidene-β-D-galactopyranosyl)sulfane 、 苯甲酰氯 以 吡啶 为溶剂， 反应 3.0h， 以22%的产率得到bis-(3-O-benzoyl-4,6-O-benzylidene-β-D-galactopyranosyl)sulfane
  参考文献：
  名称：

  Galectin-Inhibitory Thiodigalactoside Ester Derivatives Have Antimigratory Effects in Cultured Lung and Prostate Cancer Cells

  摘要：

  Aromatic 3,3'-diesters of thiodigalactoside were synthesized in a rapid three-step sequence from commercially available thiodigalactoside and evaluated as inhibitors of cancer- and immunity-related galectins. For each of galectins-1, -3, -7, and -9N-terminal domain, aromatic 3,3'-diesters of thiodigalactoside were found to have affinities in the low micromolar range, which represents a 7-70 fold enhancement over thiodigalactoside itself. No significant improvement was found for galectin-8 N-terminal domain. Two of the compounds were selected for testing in cell Culture and were shown to have potent antimigratory effects oil human PC-3 prostate and human A549 nonsmall-cell lung cancer cells.

  DOI：

  10.1021/jm801077j

文献信息

• Galectin-Inhibitory Thiodigalactoside Ester Derivatives Have Antimigratory Effects in Cultured Lung and Prostate Cancer Cells
  作者：Tamara Delaine、Ian Cumpstey、Laurent Ingrassia、Marie Le Mercier、Paul Okechukwu、Hakon Leffler、Robert Kiss、Ulf J. Nilsson

  DOI：10.1021/jm801077j

  日期：2008.12.25

  Aromatic 3,3'-diesters of thiodigalactoside were synthesized in a rapid three-step sequence from commercially available thiodigalactoside and evaluated as inhibitors of cancer- and immunity-related galectins. For each of galectins-1, -3, -7, and -9N-terminal domain, aromatic 3,3'-diesters of thiodigalactoside were found to have affinities in the low micromolar range, which represents a 7-70 fold enhancement over thiodigalactoside itself. No significant improvement was found for galectin-8 N-terminal domain. Two of the compounds were selected for testing in cell Culture and were shown to have potent antimigratory effects oil human PC-3 prostate and human A549 nonsmall-cell lung cancer cells.