1,3,4,6-Tetra-O-acetyl-2-desoxy-2-propionamido-β-D-glucose | 111239-82-8

• 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-desoxy-2-propionamido-β-D-glucose
• 英文别名: 1,3,4,6-tetra-O-acetyl-2-deoxy-2-N-propanoyl-β-D-glucopyranose
• CAS: 111239-82-8
• 化学式: C₁₇H₂₅NO₁₀
• 分子量: 403.386
• InChiKey: CREWSAARWKDFND-LMHBHQSJSA-N

物化性质

• 沸点：
  539.7±50.0 °C(Predicted)
• 密度：
  1.27±0.1 g/cm3(Temp: 20 °C; Press: 760 Torr)(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  -0.4
• 重原子数：
  28.0
• 可旋转键数：
  7.0
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.71
• 拓扑面积：
  143.53
• 氢给体数：
  1.0
• 氢受体数：
  10.0

反应信息

• 作为反应物：
  描述：

  1,3,4,6-Tetra-O-acetyl-2-desoxy-2-propionamido-β-D-glucose 在 盐酸 作用下， 以 乙酸酐 、 溶剂黄146 为溶剂， 生成 3,4,6-Tri-O-acetyl-1-chlor-2-propionamido-1,2-didesoxy-α-D-glucose
  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：

  1,3,4,6-四-O-乙酰基-2-氨基-2-脱氧-Β-D-葡萄糖盐酸盐 、 丙酰氯 在 三乙胺 作用下， 以 二氯甲烷 为溶剂， 生成 1,3,4,6-Tetra-O-acetyl-2-desoxy-2-propionamido-β-D-glucose
  参考文献：
  名称：

  糖基化萘二甲酰亚胺衍生物作为Hex1抑制剂的高效和选择性昆虫β- N-乙酰己糖胺酶的合成，优化和评价

  摘要：

  昆虫几丁质β- ñ -acetylhexosaminidase OfHex1，从农业害虫玉米螟（螟），被认为是绿色农药设计的潜在目标。在这项研究中，合理的分子设计和优化导致了合成15r（K i = 5.3μM ）和15y（K i = 2.7μM）的化合物，它们对OfHex1的活性优于先前报道的先导化合物。化合物15r和15y对OfHex1的选择性都高于人β- N-乙酰基己糖胺酶B（HsHexB）和人O-GlcNAcase（hOGA）。此外，为了研究糖基化萘二甲酰亚胺对OfHex1效力的基础，进行了分子对接和分子动力学模拟，以研究可能的结合模式。此外，在体内高效OfHex1抑制效力目标化合物的生物活性进行测定对桃蚜，小菜蛾，和亚洲玉米螟。这项工作表明，糖基化萘二甲酰亚胺可以进一步开发为针对OfHex1的潜在害虫控制和管理剂。

  DOI：

  10.1021/acs.jafc.9b02281