1,3,4,6-tetra-O-acetyl-2-deoxy-2-N-butanoyl-β-D-glucopyranose | 111270-21-4

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: 1,3,4,6-tetra-O-acetyl-2-deoxy-2-N-butanoyl-β-D-glucopyranose
• 英文别名: 1,3,4,6-Tetra-O-acetyl-2-desoxy-2-butyramido-β-D-glucose；[(2R,3S,4R,5R,6S)-3,4,6-triacetyloxy-5-(butanoylamino)oxan-2-yl]methyl acetate
• CAS: 111270-21-4
• 化学式: C₁₈H₂₇NO₁₀
• 分子量: 417.413
• InChiKey: WXTMNEIVBVUCNI-JVNHZCFISA-N

计算性质

• 辛醇/水分配系数(LogP)：
  0.9
• 重原子数：
  29
• 可旋转键数：
  12
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.72
• 拓扑面积：
  144
• 氢给体数：
  1
• 氢受体数：
  10

反应信息

• 作为反应物：
  描述：

  1,3,4,6-tetra-O-acetyl-2-deoxy-2-N-butanoyl-β-D-glucopyranose 在 盐酸 、 sodium methylate 作用下， 以 甲醇 、 乙酸酐 、 溶剂黄146 、 丙酮 为溶剂， 生成 2-butyramido-2-deoxy-β-D-glucopyranosyl N,N-dimethyldithiocarbamate
  参考文献：
  名称：

  Synthesis and evaluation of anti-tubercular activity of new dithiocarbamate sugar derivatives

  摘要：

  The present study was undertaken to optimize the anti-tubercular activity of 2-acetamido-2-deoxy-beta-D-glucopyranosyl N,N-dimethyldithiocarbamate (OCT313, Glc-NAc-DMDC), a lead compound previously reported by us. Structural modifications of OCT313 included the replacements of the DMDC group at C-1 by pyrrolidine dithiocarbamate (PDTC) and the acetyl group at C-2 by either propyl, butyl, benzyl or oleic acid groups. The antimycobacterial activities of these derivatives were evaluated against Mycobacterium tuberculosis (MTB). Glc-NAc-pyrrolidine dithiocarbamate (OCT313HK, Glc-NAc-PDTC) exhibited the most potent anti-tubercular activity with the minimal inhibitory concentration (MIC) of 6.25-12.5 mu g/ml. The antibacterial activity of OCT313HK was highly specific to MTB and Mycobacterium bovis BCG, but not against Mycobacterium avium, Mycobacterium smegmatis, Staphylococcus aureus or Escherichia coli. Importantly, OCT313HK was also effective against MTB clinical isolates, including multidrug-resistant (MDR) and extensively drug-resistant (XDR) strains. Interestingly, OCT313HK was exerted the primary bactericidal activity, and it was also exhibited the bacteriolytic activity at high concentrations. We next investigated whether the mycobacterial monooxygenase EthA, a common activator of thiocarbamide-containing antitubercular drugs, also activated OCT313HK. Contrary to our expectations, the anti-tubercular activity of dithiocarbamate sugar derivatives and dithiocarbamates were not dependent on ethA expression, in contrast to thiocarbamide-containing drugs. Overall, this study presents OCT313HK as a novel and potent compound against MTB, particularly promising to overcome drug resistance. (C) 2010 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.bmcl.2010.12.084
• 作为产物：
  描述：

  2-氨基-2-脱氧葡萄糖盐酸盐 在 吡啶 、 sodium 作用下， 以 甲醇 为溶剂， 反应 11.25h， 生成 1,3,4,6-tetra-O-acetyl-2-deoxy-2-N-butanoyl-β-D-glucopyranose
  参考文献：
  名称：

  Synthesis and characterization of N-acyl-tetra-O-acyl glucosamine derivatives

  摘要：

  利用吡啶作为催化剂，通过酰化反应从葡萄糖胺盐酸盐（GlcN·HCl）合成了新型1,3,4,6-四-O-酰基-N-酰基-D-葡萄糖胺衍生物。首次合成了一种含有酮洛芬的四-O-乙酰基葡萄糖胺衍生物，酮洛芬是一种具有镇痛和退热作用的无菌性抗炎药物（NSAID）。通过NMR谱图分析，α:β-异构体的比例表明，含有O-酰基的五酰基-D-葡萄糖胺衍生物和N-乙酰化的葡萄糖胺均为α-异构体。同时，酮洛芬的中间体和葡萄糖结合物均为β-异构体。

  DOI：

  10.1039/c3ra46007j