[(1S,2S,4R,6R)-2-(3-methylbutoxy)-5-oxo-3,7-dioxabicyclo[4.1.0]heptan-4-yl]methyl 2,2-dimethylpropanoate | 1310543-13-5

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 二氧环庚烷
• 英文名称: [(1S,2S,4R,6R)-2-(3-methylbutoxy)-5-oxo-3,7-dioxabicyclo[4.1.0]heptan-4-yl]methyl 2,2-dimethylpropanoate
• CAS: 1310543-13-5
• 化学式: C₁₆H₂₆O₆
• 分子量: 314.379
• InChiKey: GPOYEWFSYVGECW-SAXRGWBVSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.5
• 重原子数：
  22
• 可旋转键数：
  8
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.88
• 拓扑面积：
  74.4
• 氢给体数：
  0
• 氢受体数：
  6

反应信息

• 作为产物：
  描述：

  isoamyl-6-O-trimethylacetyl-2,3-dideoxy-α-D-glycero-hex-2-enopyranosid-4-ulose 在 双氧水 、 sodium hydroxide 作用下， 以 甲醇 、 水 为溶剂， 反应 0.5h， 以39%的产率得到[(1S,2S,4R,6R)-2-(3-methylbutoxy)-5-oxo-3,7-dioxabicyclo[4.1.0]heptan-4-yl]methyl 2,2-dimethylpropanoate
  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.