[(2S,6R)-4-[(R)-(2,4-dinitrophenyl)-hydroxy-methyl]-2-isopentyloxy-5-oxo-2H-pyran-6-yl]methyl acetate | 1310543-04-4

• 分子结构分类: 有机化合物 - 苯类化合物 - 苯和取代衍生物
• 英文名称: [(2S,6R)-4-[(R)-(2,4-dinitrophenyl)-hydroxy-methyl]-2-isopentyloxy-5-oxo-2H-pyran-6-yl]methyl acetate
• 英文别名: [(2S,6R)-4-[(R)-(2,4-dinitrophenyl)-hydroxymethyl]-2-(3-methylbutoxy)-5-oxo-2H-pyran-6-yl]methyl acetate
• CAS: 1310543-04-4
• 化学式: C₂₀H₂₄N₂O₁₀
• 分子量: 452.418
• InChiKey: OZFKQDVJUGFFCB-CEXWTWQISA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.7
• 重原子数：
  32
• 可旋转键数：
  9
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.5
• 拓扑面积：
  174
• 氢给体数：
  1
• 氢受体数：
  10

反应信息

• 作为产物：
  描述：

  (2S,6R)-6-(hydroxymethyl)-2-isopentyloxy-2H-pyran-5-one 在 吡啶 、 四氯化钛 、 四丁基碘化铵 作用下， 以 二氯甲烷 为溶剂， 生成 [(2S,6R)-4-[(R)-(2,4-dinitrophenyl)-hydroxy-methyl]-2-isopentyloxy-5-oxo-2H-pyran-6-yl]methyl acetate
  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

• 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.