(6R,7S)-3-Methyl-8-oxo-7-(2-trifluoromethylsulfanyl-acetylamino)-5-oxa-1-aza-bicyclo[4.2.0]oct-2-ene-2-carboxylic acid benzhydryl ester | 75676-01-6

• 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: (6R,7S)-3-Methyl-8-oxo-7-(2-trifluoromethylsulfanyl-acetylamino)-5-oxa-1-aza-bicyclo[4.2.0]oct-2-ene-2-carboxylic acid benzhydryl ester
• CAS: 75676-01-6
• 化学式: C₂₄H₂₁F₃N₂O₅S
• 分子量: 506.502
• InChiKey: HEGZEFLHLSENMW-XMSQKQJNSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.53
• 重原子数：
  35.0
• 可旋转键数：
  7.0
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.29
• 拓扑面积：
  84.94
• 氢给体数：
  1.0
• 氢受体数：
  6.0

反应信息

• 作为反应物：
  描述：

  (6R,7S)-3-Methyl-8-oxo-7-(2-trifluoromethylsulfanyl-acetylamino)-5-oxa-1-aza-bicyclo[4.2.0]oct-2-ene-2-carboxylic acid benzhydryl ester 在 苯甲醚 、 三氟乙酸 作用下， 以 二氯甲烷 为溶剂， 反应 1.75h， 以61%的产率得到(6R,7S)-3-Methyl-8-oxo-7-(2-trifluoromethylsulfanyl-acetylamino)-5-oxa-1-aza-bicyclo[4.2.0]oct-2-ene-2-carboxylic acid
  参考文献：
  名称：

  1-Oxacephalosporins: enhancement of .beta.-lactam reactivity and antibacterial activity

  摘要：

  The effect of replacement of sulfur in the cephem nucleus by oxygen upon the beta-lactamase stability, infrared carbonyl frequency of the beta-lactam ring, and antibacterial activity was investigated. The replacement reduced the stability of beta-lactam compounds to beta-lactamases, increased the IR frequencies, and enhanced the intrinsic antibacterial activity against bacterial strains without beta-lactamase. The instability of 1-oxacephalosporins to beta-lactamases, in other words, high reactivity to the enzymes, seemed to be due to the enhanced chemical reactivity of their beta-lactam rings which was indicated by their higher IR beta-lactam carbonyl frequencies. Based on a view that acylation of the enzyme by beta-lactam compounds occurred in both cases of beta-lactamase hydrolysis and target enzyme inhibition, the suggestion was made that one of the factors which conferred the higher intrinsic antibacterial activity on 1-oxacephalosporins was their high reactivity to the target enzyme(s), as was the case with beta-lactamases.

  DOI：

  10.1021/jm00133a018
• 作为产物：
  描述：

  7-Amino-3-methyl-1-oxadethia-cephem-4-carbonsaeure-benzhydrylester 、 succinimino trifluoromethylthioacetate 以 N,N-二甲基甲酰胺 为溶剂， 反应 18.0h， 以96%的产率得到(6R,7S)-3-Methyl-8-oxo-7-(2-trifluoromethylsulfanyl-acetylamino)-5-oxa-1-aza-bicyclo[4.2.0]oct-2-ene-2-carboxylic acid benzhydryl ester
  参考文献：
  名称：

  1-Oxacephalosporins: enhancement of .beta.-lactam reactivity and antibacterial activity

  摘要：

  The effect of replacement of sulfur in the cephem nucleus by oxygen upon the beta-lactamase stability, infrared carbonyl frequency of the beta-lactam ring, and antibacterial activity was investigated. The replacement reduced the stability of beta-lactam compounds to beta-lactamases, increased the IR frequencies, and enhanced the intrinsic antibacterial activity against bacterial strains without beta-lactamase. The instability of 1-oxacephalosporins to beta-lactamases, in other words, high reactivity to the enzymes, seemed to be due to the enhanced chemical reactivity of their beta-lactam rings which was indicated by their higher IR beta-lactam carbonyl frequencies. Based on a view that acylation of the enzyme by beta-lactam compounds occurred in both cases of beta-lactamase hydrolysis and target enzyme inhibition, the suggestion was made that one of the factors which conferred the higher intrinsic antibacterial activity on 1-oxacephalosporins was their high reactivity to the target enzyme(s), as was the case with beta-lactamases.

  DOI：

  10.1021/jm00133a018