methyl 6-thio-6-[2'-(butanoic acid)]-β-D-glucopyranoside

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: methyl 6-thio-6-[2'-(butanoic acid)]-β-D-glucopyranoside
• 英文别名: 2-((2S,3S,4S,5R,6R)-3,4,5-Trihydroxy-6-methoxy-tetrahydro-pyran-2-ylmethylsulfanyl)-butyric acid；2-[[(2S,3S,4S,5R,6R)-3,4,5-trihydroxy-6-methoxyoxan-2-yl]methylsulfanyl]butanoic acid
• 化学式: C₁₁H₂₀O₇S
• 分子量: 296.342
• InChiKey: RWSHSVFVUKQBMI-ISYCEEAWSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  -0.7
• 重原子数：
  19
• 可旋转键数：
  6
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.91
• 拓扑面积：
  142
• 氢给体数：
  4
• 氢受体数：
  8

反应信息

• 作为产物：
  描述：

  甲基 Β-D-吡喃葡萄糖苷 在 吡啶 、 sodium hydroxide 、 乙酸肼 、 三乙胺 作用下， 以 甲醇 、 N,N-二甲基甲酰胺 、 丙酮 为溶剂， 反应 86.0h， 生成 methyl 6-thio-6-[2'-(butanoic acid)]-β-D-glucopyranoside
  参考文献：
  名称：

  Synthesis and Biological Evaluation of Sialylmimetics as Rotavirus Inhibitors

  摘要：

  Rotaviruses cause severe gastroenteritis in infants and are estimated to be responsible for over 600 000 deaths annually, primarily in developing countries. The development of potential inhibitors of this virus is therefore of great interest, particularly since the safety and efficacy of rotaviral vaccines has recently been questioned. This study describes the synthesis of a variety of compounds that can be considered as mimetics of N-acetylneuraminic acid thioglycosides and the subsequent in vitro biological evaluation of these sialylmimetics as inhibitors of rotaviral infection. Our results show that readily accessible carbohydrate-based compounds have the potential to act as inhibitors of rotaviral replication in vitro, presumably through inhibition of the rotaviral adhesion process.

  DOI：

  10.1021/jm0100887

文献信息

• Synthesis and Biological Evaluation of Sialylmimetics as Rotavirus Inhibitors
  作者：Ashmath Fazli、Susan J. Bradley、Milton J. Kiefel、Clare Jolly、Ian H. Holmes、Mark von Itzstein

  DOI：10.1021/jm0100887

  日期：2001.9.1

  Rotaviruses cause severe gastroenteritis in infants and are estimated to be responsible for over 600 000 deaths annually, primarily in developing countries. The development of potential inhibitors of this virus is therefore of great interest, particularly since the safety and efficacy of rotaviral vaccines has recently been questioned. This study describes the synthesis of a variety of compounds that can be considered as mimetics of N-acetylneuraminic acid thioglycosides and the subsequent in vitro biological evaluation of these sialylmimetics as inhibitors of rotaviral infection. Our results show that readily accessible carbohydrate-based compounds have the potential to act as inhibitors of rotaviral replication in vitro, presumably through inhibition of the rotaviral adhesion process.