7-amino-3-<2-(ethoxycarbonyl)-3-(3-bromo-4,5-dihydroxyphenyl)-3-oxopropyl>ceph-3-em-4-carboxylic acid | 141613-35-6

• 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: 7-amino-3-<2-(ethoxycarbonyl)-3-(3-bromo-4,5-dihydroxyphenyl)-3-oxopropyl>ceph-3-em-4-carboxylic acid
• 英文别名: 7-amino-3-[2-(ethoxycarbonyl)-3-(3-bromo-4,5-dihydroxyphenyl)-3-oxopropyl]ceph-3-em-4-carboxylic acid；(6R,7R)-7-amino-3-[2-(3-bromo-4,5-dihydroxybenzoyl)-3-ethoxy-3-oxopropyl]-8-oxo-5-thia-1-azabicyclo[4.2.0]oct-2-ene-2-carboxylic acid
• CAS: 141613-35-6；141613-36-7
• 化学式: C₁₉H₁₉BrN₂O₈S
• 分子量: 515.338
• InChiKey: NXQJLJVQHOPKRI-ZNGJCICASA-N

计算性质

• 辛醇/水分配系数(LogP)：
  1.19
• 重原子数：
  31.0
• 可旋转键数：
  7.0
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.37
• 拓扑面积：
  167.46
• 氢给体数：
  4.0
• 氢受体数：
  9.0

反应信息

• 作为反应物：
  描述：

  7-amino-3-<2-(ethoxycarbonyl)-3-(3-bromo-4,5-dihydroxyphenyl)-3-oxopropyl>ceph-3-em-4-carboxylic acid 在 三乙胺 、 三氟乙酸 作用下， 以 N,N-二甲基甲酰胺 为溶剂， 反应 4.0h， 生成 7-<2-(2-aminothazol-4-yl)-2-<(Z)-(1-carboxy-1-methylethoxy)imino>acetamido>-3-<3-(3-bromo-4,5-dihydroxyphenyl)-2-(ethoxycarbonyl)-3-oxopropyl>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
• 作为产物：
  描述：

  3-溴-4,5-二甲氧基苯甲醛 在 jones reagent 、 三氟化硼乙醚 、 水 、 三溴化硼 、 sodium hydride 、 溶剂黄146 作用下， 以 四氢呋喃 、 二氯甲烷 、 丙酮 为溶剂， 反应 8.33h， 生成 7-amino-3-<2-(ethoxycarbonyl)-3-(3-bromo-4,5-dihydroxyphenyl)-3-oxopropyl>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