(6R,7R)-7-[2-[(4-Ethyl-2,3-dioxo-piperazine-1-carbonyl)-amino]-2-(4-hydroxy-phenyl)-acetylamino]-3-(1-methyl-1H-tetrazol-5-ylsulfanylmethyl)-8-oxo-5-thia-1-aza-bicyclo[4.2.0]oct-2-ene-2-carboxylic acid benzhydryl ester | 74769-05-4

• 分子结构分类: 有机化合物 - 有机酸及其衍生物 - 羧酸及其衍生物
• 英文名称: (6R,7R)-7-[2-[(4-Ethyl-2,3-dioxo-piperazine-1-carbonyl)-amino]-2-(4-hydroxy-phenyl)-acetylamino]-3-(1-methyl-1H-tetrazol-5-ylsulfanylmethyl)-8-oxo-5-thia-1-aza-bicyclo[4.2.0]oct-2-ene-2-carboxylic acid benzhydryl ester
• CAS: 74769-05-4
• 化学式: C₃₈H₃₇N₉O₈S₂
• 分子量: 811.899
• InChiKey: CDLXXCNYYAPGHO-UETNQTCHSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.14
• 重原子数：
  57.0
• 可旋转键数：
  12.0
• 环数：
  7.0
• sp3杂化的碳原子比例：
  0.29
• 拓扑面积：
  209.26
• 氢给体数：
  3.0
• 氢受体数：
  14.0

反应信息

• 作为反应物：
  描述：

  (6R,7R)-7-[2-[(4-Ethyl-2,3-dioxo-piperazine-1-carbonyl)-amino]-2-(4-hydroxy-phenyl)-acetylamino]-3-(1-methyl-1H-tetrazol-5-ylsulfanylmethyl)-8-oxo-5-thia-1-aza-bicyclo[4.2.0]oct-2-ene-2-carboxylic acid benzhydryl ester 在 silica gel 、 苯甲醚 、 三氟乙酸 作用下， 以 甲醇 、 二氯甲烷 、 氯仿 为溶剂， 反应 5.0h， 生成 (6R,7R)-7-{2-(4-Carbamoyloxy-phenyl)-2-[(4-ethyl-2,3-dioxo-piperazine-1-carbonyl)-amino]-acetylamino}-3-(1-methyl-1H-tetrazol-5-ylsulfanylmethyl)-8-oxo-5-thia-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：

  头孢哌酮杂质B 、 二苯基重氮甲烷 以 甲醇 、 二氯甲烷 为溶剂， 反应 2.0h， 以74%的产率得到(6R,7R)-7-[2-[(4-Ethyl-2,3-dioxo-piperazine-1-carbonyl)-amino]-2-(4-hydroxy-phenyl)-acetylamino]-3-(1-methyl-1H-tetrazol-5-ylsulfanylmethyl)-8-oxo-5-thia-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