(2R,3S,6S)-6-(isopentyloxy)-2-((4-pentyl-1H-1,2,3-triazol-1-yl)methyl)-3,6-dihydro-2H-pyran-3-ol | 1620905-27-2

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 吡喃
• 英文名称: (2R,3S,6S)-6-(isopentyloxy)-2-((4-pentyl-1H-1,2,3-triazol-1-yl)methyl)-3,6-dihydro-2H-pyran-3-ol
• CAS: 1620905-27-2
• 化学式: C₁₈H₃₁N₃O₃
• 分子量: 337.462
• InChiKey: MBSDRFNHGFRTMS-KSZLIROESA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.72
• 重原子数：
  24.0
• 可旋转键数：
  10.0
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.78
• 拓扑面积：
  69.4
• 氢给体数：
  1.0
• 氢受体数：
  6.0

反应信息

• 作为反应物：
  描述：

  (2R,3S,6S)-6-(isopentyloxy)-2-((4-pentyl-1H-1,2,3-triazol-1-yl)methyl)-3,6-dihydro-2H-pyran-3-ol 在 戴斯-马丁氧化剂 作用下， 以 二氯甲烷 为溶剂， 反应 4.0h， 以57%的产率得到(2S,6R)-2-(3-methylbutoxy)-6-[(4-pentyltriazol-1-yl)methyl]-2H-pyran-5-one
  参考文献：
  名称：

  Synthesis of 2,3,6-trideoxy sugar triazole hybrids as potential new broad spectrum antimicrobial agents

  摘要：

  Here, we describe a molecular hybridization inspired design and synthesis of novel 6-triazolyl 2,3,6-trideoxy sugars as promising new broad-spectrum antimicrobial agents using click chemistry in key step. These compounds showed MIC between 0.39 and 50 μg/mL against different native and resistant bacteria and fungi with no toxicity. Among them, compound 29 was the most active molecule with MIC 0.78 μg/mL against Staphylococcus aureus and Klebsiella pneumoniae and 3.12 μg/mL against methicillin- and vancomycin-resistant S. aureus. Compound 26 was the most potent anti-fungal candidate with MIC 0.39 μg/mL against Trichophyton mentagrophytes. Compound 46 was found to be promising with broad-spectrum activity against both bacterial and fungal strains. The bioinformatic studies involving bacteria's protein co-crystals prompted penicillin binding protein-2 as the most likely target of these compounds.

  DOI：

  10.1016/j.ejmech.2014.06.048
• 作为产物：
  描述：

  在 sodium azide 、 copper(ll) sulfate pentahydrate 、 sodium ascorbate 作用下， 以 水 、 N,N-二甲基甲酰胺 、 叔丁醇 为溶剂， 反应 3.0h， 生成 (2R,3S,6S)-6-(isopentyloxy)-2-((4-pentyl-1H-1,2,3-triazol-1-yl)methyl)-3,6-dihydro-2H-pyran-3-ol
  参考文献：
  名称：

  Synthesis of 2,3,6-trideoxy sugar triazole hybrids as potential new broad spectrum antimicrobial agents

  摘要：

  Here, we describe a molecular hybridization inspired design and synthesis of novel 6-triazolyl 2,3,6-trideoxy sugars as promising new broad-spectrum antimicrobial agents using click chemistry in key step. These compounds showed MIC between 0.39 and 50 μg/mL against different native and resistant bacteria and fungi with no toxicity. Among them, compound 29 was the most active molecule with MIC 0.78 μg/mL against Staphylococcus aureus and Klebsiella pneumoniae and 3.12 μg/mL against methicillin- and vancomycin-resistant S. aureus. Compound 26 was the most potent anti-fungal candidate with MIC 0.39 μg/mL against Trichophyton mentagrophytes. Compound 46 was found to be promising with broad-spectrum activity against both bacterial and fungal strains. The bioinformatic studies involving bacteria's protein co-crystals prompted penicillin binding protein-2 as the most likely target of these compounds.

  DOI：

  10.1016/j.ejmech.2014.06.048