(2S,3R)-3-benzenesulfinyl-2-hydroxyheptanoic acid (tetrahydropyran-2-yloxy)amide | 285572-44-3

• 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,3R)-3-benzenesulfinyl-2-hydroxyheptanoic acid (tetrahydropyran-2-yloxy)amide
• 英文别名: (2S,3R)-3-(benzenesulfinyl)-2-hydroxy-N-(oxan-2-yloxy)heptanamide
• CAS: 285572-44-3
• 化学式: C₁₈H₂₇NO₅S
• 分子量: 369.482
• InChiKey: NKLHOTCHJHONPU-AYNYANHRSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.4
• 重原子数：
  25
• 可旋转键数：
  9
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.61
• 拓扑面积：
  104
• 氢给体数：
  2
• 氢受体数：
  6

反应信息

• 作为反应物：
  描述：

  (2S,3R)-3-benzenesulfinyl-2-hydroxyheptanoic acid (tetrahydropyran-2-yloxy)amide 在 acidic Amberlyst IR₁₅ 作用下， 以 甲醇 、 二氯甲烷 、 水 为溶剂， 反应 72.0h， 以63%的产率得到(2S,3R)-3-Benzenesulfinyl-2-hydroxy-heptanoic acid hydroxyamide
  参考文献：
  名称：

  Hydroxamic Acid Derivatives as Potent Peptide Deformylase Inhibitors and Antibacterial Agents

  摘要：

  Low-molecular-weight beta-sulfonyl- and beta-sulfinylhydroxamic acid derivatives have been synthesized and found to be potent inhibitors of Escherichia coli peptide deformylase (PDF). Most of the compounds synthesized and tested displayed antibacterial activities that cover several pathogens found in respiratory tract infections, including Chlamydia pneumoniae, Mycoplasma pneumoniae, Haemophilus influenzae, and Moraxella catarrhalis. The potential of these compounds as antibacterial agents is discussed with respect to selectivity, intracellular concentrations in bacteria, and potential for resistance development.

  DOI：

  10.1021/jm000018k
• 作为产物：
  描述：

  (2S,3S)-2,3-epoxyheptan-1-ol 在 ruthenium(IV) oxide 、 aluminum oxide 、 sodium periodate 、 lithium perchlorate 、 1-羟基苯并三唑 、 2-(Phenylsulfonyl)-3-phenyloxaziridin 、 N,N'-羰基二咪唑 作用下， 以 二氯甲烷 、 水 、 乙腈 为溶剂， 反应 24.0h， 生成 (2S,3R)-3-benzenesulfinyl-2-hydroxyheptanoic acid (tetrahydropyran-2-yloxy)amide
  参考文献：
  名称：

  Hydroxamic Acid Derivatives as Potent Peptide Deformylase Inhibitors and Antibacterial Agents

  摘要：

  Low-molecular-weight beta-sulfonyl- and beta-sulfinylhydroxamic acid derivatives have been synthesized and found to be potent inhibitors of Escherichia coli peptide deformylase (PDF). Most of the compounds synthesized and tested displayed antibacterial activities that cover several pathogens found in respiratory tract infections, including Chlamydia pneumoniae, Mycoplasma pneumoniae, Haemophilus influenzae, and Moraxella catarrhalis. The potential of these compounds as antibacterial agents is discussed with respect to selectivity, intracellular concentrations in bacteria, and potential for resistance development.

  DOI：

  10.1021/jm000018k

文献信息

• Hydroxamic Acid Derivatives as Potent Peptide Deformylase Inhibitors and Antibacterial Agents
  作者：Christian Apfel、David W. Banner、Daniel Bur、Michel Dietz、Takahiro Hirata、Christian Hubschwerlen、Hans Locher、Malcolm G. P. Page、Wolfgang Pirson、Gérard Rossé、Jean-Luc Specklin

  DOI：10.1021/jm000018k

  日期：2000.6.1

  Low-molecular-weight beta-sulfonyl- and beta-sulfinylhydroxamic acid derivatives have been synthesized and found to be potent inhibitors of Escherichia coli peptide deformylase (PDF). Most of the compounds synthesized and tested displayed antibacterial activities that cover several pathogens found in respiratory tract infections, including Chlamydia pneumoniae, Mycoplasma pneumoniae, Haemophilus influenzae, and Moraxella catarrhalis. The potential of these compounds as antibacterial agents is discussed with respect to selectivity, intracellular concentrations in bacteria, and potential for resistance development.