7-<2-(2-aminothiazol-4-yl)-2-<(Z)-(1-carboxy-1-methylethoxy)imino>acetamido>-3-<<amino>methyl>ceph-3-em-4-carboxylic acid | 141613-49-2

• 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-<<amino>methyl>ceph-3-em-4-carboxylic acid
• 英文别名: (6R,7R)-7-[[(2Z)-2-(2-amino-1,3-thiazol-4-yl)-2-(2-carboxypropan-2-yloxyimino)acetyl]amino]-3-[[[2-[(2-methylpropan-2-yl)oxycarbonylamino]acetyl]amino]methyl]-8-oxo-5-thia-1-azabicyclo[4.2.0]oct-2-ene-2-carboxylic acid
• CAS: 141613-49-2
• 化学式: C₂₄H₃₁N₇O₁₀S₂
• 分子量: 641.683
• InChiKey: MOLLPYFJSGVUFL-SOCQYBPFSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  -0.31
• 重原子数：
  43.0
• 可旋转键数：
  11.0
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.5
• 拓扑面积：
  251.94
• 氢给体数：
  6.0
• 氢受体数：
  13.0

反应信息

• 作为反应物：
  描述：

  7-<2-(2-aminothiazol-4-yl)-2-<(Z)-(1-carboxy-1-methylethoxy)imino>acetamido>-3-<<amino>methyl>ceph-3-em-4-carboxylic acid 在 三氟乙酸 作用下， 以 N,N-二甲基甲酰胺 为溶剂， 反应 0.5h， 生成 (6R,7R)-7-{2-(2-Amino-thiazol-4-yl)-2-[(Z)-1-carboxy-1-methyl-ethoxyimino]-acetylamino}-3-{[2-(3,4-diacetoxy-5-bromo-benzoylamino)-acetylamino]-methyl}-8-oxo-5-thia-1-aza-bicyclo[4.2.0]oct-2-ene-2-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：

  (6R,7R)-7-{2-(2-Amino-thiazol-4-yl)-2-[(Z)-1-tert-butoxycarbonyl-1-methyl-ethoxyimino]-acetylamino}-3-azidomethyl-8-oxo-5-thia-1-aza-bicyclo[4.2.0]oct-2-ene-2-carboxylic acid 在 镍 N-羟基丁二酰亚胺 、 氢气 、 三乙胺 、 N,N'-二环己基碳二亚胺 、 三氟乙酸 作用下， 以 水 为溶剂， 反应 6.0h， 生成 7-<2-(2-aminothiazol-4-yl)-2-<(Z)-(1-carboxy-1-methylethoxy)imino>acetamido>-3-<<amino>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