1-Cyclopropyl-7-[4-[4-[5-[[4-[4-[(2,3-dihydroxybenzoyl)amino]butyl-[3-[(2,3-dihydroxybenzoyl)amino]propyl]amino]-4-oxobutanoyl]amino]pentyl-hydroxyamino]-4-oxobutanoyl]piperazin-1-yl]-6-fluoro-4-oxoquinoline-3-carboxylic acid | 1432743-65-1

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 喹啉及其衍生物
• 英文名称: 1-Cyclopropyl-7-[4-[4-[5-[[4-[4-[(2,3-dihydroxybenzoyl)amino]butyl-[3-[(2,3-dihydroxybenzoyl)amino]propyl]amino]-4-oxobutanoyl]amino]pentyl-hydroxyamino]-4-oxobutanoyl]piperazin-1-yl]-6-fluoro-4-oxoquinoline-3-carboxylic acid
• 英文别名: 1-cyclopropyl-7-[4-[4-[5-[[4-[4-[(2,3-dihydroxybenzoyl)amino]butyl-[3-[(2,3-dihydroxybenzoyl)amino]propyl]amino]-4-oxobutanoyl]amino]pentyl-hydroxyamino]-4-oxobutanoyl]piperazin-1-yl]-6-fluoro-4-oxoquinoline-3-carboxylic acid
• CAS: 1432743-65-1
• 化学式: C₅₁H₆₃FN₈O₁₄
• 分子量: 1031.1
• InChiKey: AGYYPQVEJWMVCI-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.4
• 重原子数：
  74
• 可旋转键数：
  26
• 环数：
  6.0
• sp3杂化的碳原子比例：
  0.45
• 拓扑面积：
  310
• 氢给体数：
  9
• 氢受体数：
  17

反应信息

• 作为产物：
  描述：

  Benzyl 7-[4-[4-[5-[[4-[4-[[2,3-bis(phenylmethoxy)benzoyl]amino]butyl-[3-[[2,3-bis(phenylmethoxy)benzoyl]amino]propyl]amino]-4-oxobutanoyl]amino]pentyl-phenylmethoxyamino]-4-oxobutanoyl]piperazin-1-yl]-1-cyclopropyl-6-fluoro-4-oxoquinoline-3-carboxylate 在 palladium 10% on activated carbon 、 氢气 作用下， 以 甲醇 、 乙酸乙酯 为溶剂， 反应 24.0h， 以51%的产率得到1-Cyclopropyl-7-[4-[4-[5-[[4-[4-[(2,3-dihydroxybenzoyl)amino]butyl-[3-[(2,3-dihydroxybenzoyl)amino]propyl]amino]-4-oxobutanoyl]amino]pentyl-hydroxyamino]-4-oxobutanoyl]piperazin-1-yl]-6-fluoro-4-oxoquinoline-3-carboxylic acid
  参考文献：
  名称：

  Biscatecholate–Monohydroxamate Mixed Ligand Siderophore–Carbacephalosporin Conjugates are Selective Sideromycin Antibiotics that Target Acinetobacter baumannii

  摘要：

  Chemical syntheses and biological evaluation of biscatecholate-monohydroxamate mixed ligand sideromycins utilizing the carbacephalosporin beta-lactam antibiotic loracarbef and the fluoroquinolone antibiotic ciprofloxacin are described. The mixed ligand beta-lactam sideromycin (1b) had remarkably selective and extremely potent antibacterial activity against the Gram-negative pathogen Acinetobacter baumannii ATCC 17961 (MIC = 0.0078 mu M). The antibacterial activity of the beta-lactam sideromycin was inversely related to the iron(III) concentration in the testing media and was antagonized by the presence of the competing parent siderophore. These data suggested that active transport of the mixed ligand beta-lactam sideromycin across the outer cell membrane of A. baumannii via siderophore-uptake pathways was responsible for the selective and potent antibacterial activity.

  DOI：

  10.1021/jm400265k

文献信息

• Biscatecholate–Monohydroxamate Mixed Ligand Siderophore–Carbacephalosporin Conjugates are Selective Sideromycin Antibiotics that Target Acinetobacter baumannii
  作者：Timothy A. Wencewicz、Marvin J. Miller

  DOI：10.1021/jm400265k

  日期：2013.5.23

  Chemical syntheses and biological evaluation of biscatecholate-monohydroxamate mixed ligand sideromycins utilizing the carbacephalosporin beta-lactam antibiotic loracarbef and the fluoroquinolone antibiotic ciprofloxacin are described. The mixed ligand beta-lactam sideromycin (1b) had remarkably selective and extremely potent antibacterial activity against the Gram-negative pathogen Acinetobacter baumannii ATCC 17961 (MIC = 0.0078 mu M). The antibacterial activity of the beta-lactam sideromycin was inversely related to the iron(III) concentration in the testing media and was antagonized by the presence of the competing parent siderophore. These data suggested that active transport of the mixed ligand beta-lactam sideromycin across the outer cell membrane of A. baumannii via siderophore-uptake pathways was responsible for the selective and potent antibacterial activity.