(2S,6R)-6-[[4-(1-adamantylmethoxymethyl)triazol-1-yl]methyl]-2-(3-methylbutoxy)-2H-pyran-5-one | 1620905-62-5

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 吡喃
• 英文名称: (2S,6R)-6-[[4-(1-adamantylmethoxymethyl)triazol-1-yl]methyl]-2-(3-methylbutoxy)-2H-pyran-5-one
• CAS: 1620905-62-5
• 化学式: C₂₅H₃₇N₃O₄
• 分子量: 443.586
• InChiKey: FTKLQKPBDWVNOK-OUOOCPCMSA-N

物化性质

• 沸点：
  590.137±60.00 °C(Press: 760.00 Torr)(predicted)
• 密度：
  1.333±0.14 g/cm3(Temp: 25 °C; Press: 760 Torr)(predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  3.7
• 重原子数：
  32
• 可旋转键数：
  10
• 环数：
  6.0
• sp3杂化的碳原子比例：
  0.8
• 拓扑面积：
  75.5
• 氢给体数：
  0
• 氢受体数：
  6

反应信息

• 作为产物：
  描述：

  1-金刚烷甲醇 在 copper(ll) sulfate pentahydrate 、 sodium hydride 、 戴斯-马丁氧化剂 、 sodium ascorbate 作用下， 以 四氢呋喃 、 二氯甲烷 、 水 、 叔丁醇 为溶剂， 反应 28.0h， 生成 (2S,6R)-6-[[4-(1-adamantylmethoxymethyl)triazol-1-yl]methyl]-2-(3-methylbutoxy)-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

文献信息

• Synthesis of 2,3,6-trideoxy sugar triazole hybrids as potential new broad spectrum antimicrobial agents
  作者：Smriti Sharma、Mohammad Saquib、Saroj Verma、Nripendra N. Mishra、Praveen K. Shukla、Ranjana Srivastava、Yenamandra S. Prabhakar、Arun K. Shaw

  DOI：10.1016/j.ejmech.2014.06.048

  日期：2014.8

  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.