(2S,6R)-6-(hydroxymethyl)-2-isopentyloxy-2H-pyran-5-one | 1310542-88-1

• 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-(hydroxymethyl)-2-isopentyloxy-2H-pyran-5-one
• 英文别名: (2S,6R)-6-(hydroxymethyl)-2-(3-methylbutoxy)-2H-pyran-5-one
• CAS: 1310542-88-1
• 化学式: C₁₁H₁₈O₄
• 分子量: 214.262
• InChiKey: UEFKJSLDEOVFNL-MNOVXSKESA-N

计算性质

• 辛醇/水分配系数(LogP)：
  1.6
• 重原子数：
  15
• 可旋转键数：
  5
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.73
• 拓扑面积：
  55.8
• 氢给体数：
  1
• 氢受体数：
  4

反应信息

• 作为反应物：
  描述：

  (2S,6R)-6-(hydroxymethyl)-2-isopentyloxy-2H-pyran-5-one 在 吡啶 、 sodium tetrahydroborate 、 sodium azide 、 copper(ll) sulfate pentahydrate 、 cerium(III) chloride heptahydrate 、 sodium ascorbate 作用下， 以 乙醇 、 二氯甲烷 、 水 、 N,N-二甲基甲酰胺 、 叔丁醇 为溶剂， 反应 4.0h， 生成 (2R,3S,6S)-2-((1H-1,2,3-triazol-1-yl)methyl)-6-(isopentyloxy)-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
• 作为产物：
  描述：

  乙酰化葡萄烯糖 在 甲醇 、 manganese(IV) oxide 、 碘 、 sodium methylate 作用下， 以 四氢呋喃 、 氯仿 为溶剂， 反应 1.5h， 生成 (2S,6R)-6-(hydroxymethyl)-2-isopentyloxy-2H-pyran-5-one
  参考文献：
  名称：

  2,3-Dideoxy hex-2-enopyranosid-4-uloses as promising new anti-tubercular agents: Design, synthesis, biological evaluation and SAR studies

  摘要：

  The alarming resurgence of tuberculosis (TB) underlines the urgent need for development of new and potent anti-TB drugs. Towards this goal we herein report the design and synthesis of 2,3-dideoxy hex-2-enopyranosid-4-uloses as promising new anti-tubercular agents. These easily accessible, small molecules were found to exhibit in vitro activity against Mycobacterium tuberculosis H37Rv in a MIC range of 0.78 mu g/mL to 25 mu g/mL. A detailed SAR study on these hex-2-enopyranosid-4-uloses led to the identification of compound 5g (5007-724) which on the basis of low MIC (0.78 mu g/mL-M. tuberculosis H37Rv; 1.56 mu g/mL-MDR, SDR strains of M. tuberculosis; 0.78 mu g/mL-inhibition of intracellular replication of M. tuberculosis) and SI value of 13.5 has been identified as a promising lead molecule. (C) 2011 Elsevier Masson SAS. All rights reserved.

  DOI：

  10.1016/j.ejmech.2011.03.002

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.
• 2,3-Dideoxy hex-2-enopyranosid-4-uloses as promising new anti-tubercular agents: Design, synthesis, biological evaluation and SAR studies
  作者：Mohammad Saquib、Irfan Husain、Smriti Sharma、Garima Yadav、Vipul K. Singh、Sandeep K. Sharma、Priyanka Shah、Mohammad Imran Siddiqi、Brijesh Kumar、Jawahar Lal、Girish K. Jain、Brahm S. Srivastava、Ranjana Srivastava、Arun K. Shaw

  DOI：10.1016/j.ejmech.2011.03.002

  日期：2011.6

  The alarming resurgence of tuberculosis (TB) underlines the urgent need for development of new and potent anti-TB drugs. Towards this goal we herein report the design and synthesis of 2,3-dideoxy hex-2-enopyranosid-4-uloses as promising new anti-tubercular agents. These easily accessible, small molecules were found to exhibit in vitro activity against Mycobacterium tuberculosis H37Rv in a MIC range of 0.78 mu g/mL to 25 mu g/mL. A detailed SAR study on these hex-2-enopyranosid-4-uloses led to the identification of compound 5g (5007-724) which on the basis of low MIC (0.78 mu g/mL-M. tuberculosis H37Rv; 1.56 mu g/mL-MDR, SDR strains of M. tuberculosis; 0.78 mu g/mL-inhibition of intracellular replication of M. tuberculosis) and SI value of 13.5 has been identified as a promising lead molecule. (C) 2011 Elsevier Masson SAS. All rights reserved.