(6R,7R)-3-(3,4-Diacetoxy-5-bromo-benzoyloxymethyl)-8-oxo-7-(2-thiophen-2-yl-acetylamino)-5-thia-1-aza-bicyclo[4.2.0]oct-2-ene-2-carboxylic acid benzhydryl ester | 141613-32-3

• 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: (6R,7R)-3-(3,4-Diacetoxy-5-bromo-benzoyloxymethyl)-8-oxo-7-(2-thiophen-2-yl-acetylamino)-5-thia-1-aza-bicyclo[4.2.0]oct-2-ene-2-carboxylic acid benzhydryl ester
• 英文别名: benzhydryl (6R,7R)-3-[(3,4-diacetyloxy-5-bromobenzoyl)oxymethyl]-8-oxo-7-[(2-thiophen-2-ylacetyl)amino]-5-thia-1-azabicyclo[4.2.0]oct-2-ene-2-carboxylate
• CAS: 141613-32-3
• 化学式: C₃₈H₃₁BrN₂O₁₀S₂
• 分子量: 819.708
• InChiKey: SVCKFLQMLOAEFP-RRTCDKLQSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  5.75
• 重原子数：
  53.0
• 可旋转键数：
  12.0
• 环数：
  6.0
• sp3杂化的碳原子比例：
  0.21
• 拓扑面积：
  154.61
• 氢给体数：
  1.0
• 氢受体数：
  12.0

反应信息

• 作为反应物：
  描述：

  (6R,7R)-3-(3,4-Diacetoxy-5-bromo-benzoyloxymethyl)-8-oxo-7-(2-thiophen-2-yl-acetylamino)-5-thia-1-aza-bicyclo[4.2.0]oct-2-ene-2-carboxylic acid benzhydryl ester 在 吡啶 、 1,3-丁二醇 、 五氯化磷 作用下， 以 二氯甲烷 为溶剂， 反应 3.75h， 生成 diphenylmethyl 7-<2-(2-aminothiazol-4-yl)-2-<<(Z)-1-(tert-butoxycarbonyl)-1-methylethoxy>imino>acetamido>-3-<<(3-bromo-4,5-diacetoxybenzoyl)oxy>methyl>ceph-3-em-4-carboxylate
  参考文献：
  名称：

  Synthesis and structure-activity relationships of cephalosporins with C-3' catechol-containing residues

  摘要：

  Cephalosporins with new catechol substituents at C-3' have been synthesized, including novel compounds with C-3' carbon-carbon bonds. Many of these compounds have high potency against Gram-negative bacteria, in particular against resistant strains like Pseudomonas aeruginosa. Structure-activity relationships are discussed in terms of their dependence on the pK(a) of the C-3' catechol and also in terms of steric and conformational factors of the C-3' substituent. The best overall properties were found in compounds with a bulky and/or conformationally restricted acidic C-3' catechol.

  DOI：

  10.1021/jm00092a014
• 作为产物：
  描述：

  diphenylmethyl 7β-(2-thienylacetamido)-3-(hydroxymethyl)-cephem-4-carboxylate 、 3-bromo-4,5-diacetoxybenzoyl chloride 在 4-二甲氨基吡啶 、 三乙胺 作用下， 以 二氯甲烷 为溶剂， 反应 0.17h， 以100%的产率得到(6R,7R)-3-(3,4-Diacetoxy-5-bromo-benzoyloxymethyl)-8-oxo-7-(2-thiophen-2-yl-acetylamino)-5-thia-1-aza-bicyclo[4.2.0]oct-2-ene-2-carboxylic acid benzhydryl ester
  参考文献：
  名称：

  Synthesis and structure-activity relationships of cephalosporins with C-3' catechol-containing residues

  摘要：

  Cephalosporins with new catechol substituents at C-3' have been synthesized, including novel compounds with C-3' carbon-carbon bonds. Many of these compounds have high potency against Gram-negative bacteria, in particular against resistant strains like Pseudomonas aeruginosa. Structure-activity relationships are discussed in terms of their dependence on the pK(a) of the C-3' catechol and also in terms of steric and conformational factors of the C-3' substituent. The best overall properties were found in compounds with a bulky and/or conformationally restricted acidic C-3' catechol.

  DOI：

  10.1021/jm00092a014