2",3",4",6"-tetra-O-acetyl-β-d-galactopyranosyl-(1→4)-2',3',6'-tri-O-acetyl-1-thio-β-d-glucopyranosyl-(5-nitro-2-pyridyl) sulfoxide | 1448822-47-6

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: 2",3",4",6"-tetra-O-acetyl-β-d-galactopyranosyl-(1→4)-2',3',6'-tri-O-acetyl-1-thio-β-d-glucopyranosyl-(5-nitro-2-pyridyl) sulfoxide
• CAS: 1448822-47-6
• 化学式: C₃₁H₃₈N₂O₂₀S
• 分子量: 790.71
• InChiKey: BRGRJRPRDALXQR-DSVOIVARSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  -0.28
• 重原子数：
  54.0
• 可旋转键数：
  14.0
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.61
• 拓扑面积：
  284.89
• 氢给体数：
  0.0
• 氢受体数：
  21.0

反应信息

• 作为产物：
  描述：

  1',2',3',6',2,3,4,6-octa-O-acetyl-β-D-lactose 在 potassium pyrosulfite 、 氢溴酸 、 potassium carbonate 、 间氯过氧苯甲酸 作用下， 以 二氯甲烷 、 氯仿 、 溶剂黄146 、 丙酮 为溶剂， 生成 2",3",4",6"-tetra-O-acetyl-β-d-galactopyranosyl-(1→4)-2',3',6'-tri-O-acetyl-1-thio-β-d-glucopyranosyl-(5-nitro-2-pyridyl) sulfoxide
  参考文献：
  名称：

  Synthesis and antiviral activity of a novel glycosyl sulfoxide against classical swine fever virus

  摘要：

  A novel compound-2 '',3 '',4 '',6 ''-tetra-O-acetyl-beta-D-galactopyranosyl-(1 -> 4)-2',3',6'-tri-O-acetyl-1-thio-beta-D-glucopyranosyl-(5-nitro-2-pyridyl) sulfoxide-designated GP6 was synthesized and assayed for cytotoxicity and in vitro antiviral properties against classical swine fever virus (CSFV) in this study. We showed that the examined compound effectively arrested CSFV growth in swine kidney cells (SK6) at a 50% inhibitory concentration (IC50) of 5 +/- 0.12 mu g/ml without significant toxicity for mammalian cells. Moreover, GP6 reduced the viral E2 and E-rns glycoproteins expression in a dose-dependent manner. We have excluded the possibility that the inhibitor acts at the replication step of virus life cycle as assessed by monitoring of RNA level in cells and culture medium of SK6 cells after single round of infection as a function of GP6 treatment. Using recombinant E-rns and E2 proteins of classical swine fever virus produced in baculovirus expression system we have demonstrated that GP6 did not influence glycoprotein production and maturation in insect cells. In contrast to mammalian glycosylation pathway, insect cells support only the ER-dependent early steps of this process. Therefore, we concluded that the late steps of glycosylation process are probably the main targets of GP6. Due to the observed antiviral effect accompanied by low cytotoxicity, this inhibitor represents potential candidate for the development of antiviral agents for anti-flavivirus therapy. Further experiments are needed for investigating whether this compound can be used as a safe antiviral agent against other viruses from unrelated groups. (C) 2014 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.bmc.2014.03.027