(6R-trans)-3-<<<<4-(3-carboxy-1-cyclopropyl-6-fluoro-1,4-dihydro-4-oxo-7-quinolinyl)-1-piperazinyl>carbonyl>oxy>methyl>-7-<(cyanoacetyl)amino>-8-oxo-5-thia-1-azabicyclo<4.2.0>oct-2-ene-2-carboxylic acid | 135312-09-3

• 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-trans)-3-<<<<4-(3-carboxy-1-cyclopropyl-6-fluoro-1,4-dihydro-4-oxo-7-quinolinyl)-1-piperazinyl>carbonyl>oxy>methyl>-7-<(cyanoacetyl)amino>-8-oxo-5-thia-1-azabicyclo<4.2.0>oct-2-ene-2-carboxylic acid
• 英文别名: (6R-trans)-3-[({[4-(3-carboxy-1-cyclopropyl-6-fluoro-1,4-dihydro-4-oxo-7-quinolinyl)-1-piperazinyl]carbonyl}oxy)methyl]-7-[(cyanoacetyl)amino]-8-oxo-5-thia-1-azabicyclo[4.2.0]oct-2-ene-2-carboxylic acid；(6R,7R)-3-[[4-(3-carboxy-1-cyclopropyl-6-fluoro-4-oxoquinolin-7-yl)piperazine-1-carbonyl]oxymethyl]-7-[(2-cyanoacetyl)amino]-8-oxo-5-thia-1-azabicyclo[4.2.0]oct-2-ene-2-carboxylic acid
• CAS: 135312-09-3
• 化学式: C₂₉H₂₇FN₆O₉S
• 分子量: 654.633
• InChiKey: NSSFTUUULHHLIU-ATIYNZHBSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  1.4
• 重原子数：
  46
• 可旋转键数：
  9
• 环数：
  6.0
• sp3杂化的碳原子比例：
  0.41
• 拓扑面积：
  226
• 氢给体数：
  3
• 氢受体数：
  14

反应信息

• 作为产物：
  描述：

  吉非替尼中间体3 、 (6R-trans)-7-amino-3-<<<<4-(3-carboxy-1-cyclopropyl-6-fluoro-1,4-dihydro-4-oxo-7-quinolinyl)-1-piperazinyl>carbonyl>oxy>methyl>-8-oxo-5-thia-1-azabicyclo<4.2.0>oct-2-ene-2-carboxylic acid trifluoroacetic acid salt 在 三乙胺 作用下， 以 二氯甲烷 为溶剂， 反应 3.0h， 以65%的产率得到(6R-trans)-3-<<<<4-(3-carboxy-1-cyclopropyl-6-fluoro-1,4-dihydro-4-oxo-7-quinolinyl)-1-piperazinyl>carbonyl>oxy>methyl>-7-<(cyanoacetyl)amino>-8-oxo-5-thia-1-azabicyclo<4.2.0>oct-2-ene-2-carboxylic acid
  参考文献：
  名称：

  Dual-action cephalosporins: cephalosporin 3'-quinolone carbamates

  摘要：

  A series of cephalosporins has been prepared in which the 3'-position was linked to the nitrogen of the antibacterial quinolone ciprofloxacin through a carbamate function. Like the ester-linked and quaternary-linked dual-action cephalosporins reported earlier, these carbamate-linked compounds exhibited a broad antibacterial spectrum derived from both cephalosporin-like and quinolone-like activities, suggesting a dual mode of action. Studies to elucidate details of the mechanism of action have been inconclusive. Ciprofloxacin liberated as a consequence of bacterial enzyme-mediated reactions may contribute to the second mode of action, although some evidence indicates that the intact carbamate-linked bifunctional molecules may possess intrinsically both beta-lactam and quinolone activities.

  DOI：

  10.1021/jm00113a026