7-<2-(2-aminothiazol-4-yl)-2-<(Z)-(1-carboxy-1-methylethoxy)imino>acetamido>-3-<(3,4-dihydroxyphenyl)methyl>ceph-3-em-4-carboxylic acid | 113886-58-1

• 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: 7-<2-(2-aminothiazol-4-yl)-2-<(Z)-(1-carboxy-1-methylethoxy)imino>acetamido>-3-<(3,4-dihydroxyphenyl)methyl>ceph-3-em-4-carboxylic acid
• 英文别名: 7-{2-(2-aminothiazol-4-yl)-2-[(Z)-(1-carboxy-1-methylethoxy)imino]acetamido}-3-[(3,4-dihydroxyphenyl)methyl]ceph-3-em-4-carboxylic acid；(6R,7R)-7-[[(2Z)-2-(2-amino-1,3-thiazol-4-yl)-2-(2-carboxypropan-2-yloxyimino)acetyl]amino]-3-[(3,4-dihydroxyphenyl)methyl]-8-oxo-5-thia-1-azabicyclo[4.2.0]oct-2-ene-2-carboxylic acid
• CAS: 113886-58-1
• 化学式: C₂₃H₂₃N₅O₉S₂
• 分子量: 577.596
• InChiKey: ZXLKOJZRNKSKLQ-CDOVDWRASA-N

物化性质

• 密度：
  1.76±0.1 g/cm3(Temp: 20 °C; Press: 760 Torr)(predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  0.7
• 重原子数：
  39.0
• 可旋转键数：
  9.0
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.3
• 拓扑面积：
  224.97
• 氢给体数：
  6.0
• 氢受体数：
  12.0

反应信息

• 作为产物：
  描述：

  7-氨基头孢烷酸 在 苯磺酰胺 、 三氟化硼乙醚 、 三氟乙酸 作用下， 以 乙腈 为溶剂， 反应 3.0h， 生成 7-<2-(2-aminothiazol-4-yl)-2-<(Z)-(1-carboxy-1-methylethoxy)imino>acetamido>-3-<(3,4-dihydroxyphenyl)methyl>ceph-3-em-4-carboxylic acid
  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