p-nitrobenzyl (7S,6R)-7-(2-thienylacetamido)-3-carbomethoxy-1-carba-1-dethia-3-cephem-4-carboxylate | 127132-80-3

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 内酰胺类
• 英文名称: p-nitrobenzyl (7S,6R)-7-(2-thienylacetamido)-3-carbomethoxy-1-carba-1-dethia-3-cephem-4-carboxylate
• CAS: 127132-80-3
• 化学式: C₂₃H₂₁N₃O₈S
• 分子量: 499.501
• InChiKey: QOFGZKNWPKWAGI-MJGOQNOKSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  1.86
• 重原子数：
  35.0
• 可旋转键数：
  8.0
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.3
• 拓扑面积：
  145.15
• 氢给体数：
  1.0
• 氢受体数：
  9.0

反应信息

• 作为反应物：
  描述：

  p-nitrobenzyl (7S,6R)-7-(2-thienylacetamido)-3-carbomethoxy-1-carba-1-dethia-3-cephem-4-carboxylate 在 盐酸 、 锌 作用下， 以 N,N-二甲基甲酰胺 为溶剂， 反应 2.0h， 以30%的产率得到(7S,6R)-7-(2-thienylacetamido)-3-carbomethoxy-1-carba-1-dethia-3-cephem-4-carboxylic acid
  参考文献：
  名称：

  Comparative reactivity of 1-carba-1-dethiacephalosporins with cephalosporins

  摘要：

  Nine matched pairs of cephalosporins and their 1-carba-1-dethiacephalosporin analogues have been compared with regard to microbiological activity, beta-lactam carbonyl infrared absorption, and aqueous stability. In general the microbiological activity of the pairs of compounds were very similar across a broad range of bacteria. The infrared absorption bands for the beta-lactam carbonyls of the pairs indicated a general trend for the 1-carba-1-dethiacephalosporins to absorb at lower frequencies than the corresponding cephalosporins. All of the 1-carba-1-dethiacephalosporins did however present a striking stability enhancement over their cephalosporin counterparts at pH = 10 or 11 in water. This marked contrast of MIC similarity with the observed differences in chemical reactivity clearly demonstrates hydroxide ion catalyzed hydrolysis is not a good model for transpeptidase activity unless the compounds comprise a limited domain of structural type.

  DOI：

  10.1021/jm00168a019
• 作为产物：
  描述：

  p-nitrobenzyl (7S,6R)-7-(phenoxyacetamido)-3-{[(trifluoromethyl)sulfonyl]oxy}-1-carba-1-dethia-3-cephem-4-carboxylate 在 2,6-二甲基吡啶 、 双(乙腈)氯化钯(II) 、 五氯化磷 、 三乙胺 、 lithium chloride 作用下， 以 N,N-二甲基甲酰胺 为溶剂， 反应 22.5h， 生成 p-nitrobenzyl (7S,6R)-7-(2-thienylacetamido)-3-carbomethoxy-1-carba-1-dethia-3-cephem-4-carboxylate
  参考文献：
  名称：

  Comparative reactivity of 1-carba-1-dethiacephalosporins with cephalosporins

  摘要：

  Nine matched pairs of cephalosporins and their 1-carba-1-dethiacephalosporin analogues have been compared with regard to microbiological activity, beta-lactam carbonyl infrared absorption, and aqueous stability. In general the microbiological activity of the pairs of compounds were very similar across a broad range of bacteria. The infrared absorption bands for the beta-lactam carbonyls of the pairs indicated a general trend for the 1-carba-1-dethiacephalosporins to absorb at lower frequencies than the corresponding cephalosporins. All of the 1-carba-1-dethiacephalosporins did however present a striking stability enhancement over their cephalosporin counterparts at pH = 10 or 11 in water. This marked contrast of MIC similarity with the observed differences in chemical reactivity clearly demonstrates hydroxide ion catalyzed hydrolysis is not a good model for transpeptidase activity unless the compounds comprise a limited domain of structural type.

  DOI：

  10.1021/jm00168a019