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 | 1432743-67-3

• 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: 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
• CAS: 1432743-67-3
• 化学式: C₉₃H₉₉FN₈O₁₄
• 分子量: 1571.85
• InChiKey: KSMPVEQKZWDWBY-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  12.8
• 重原子数：
  116
• 可旋转键数：
  44
• 环数：
  12.0
• sp3杂化的碳原子比例：
  0.31
• 拓扑面积：
  244
• 氢给体数：
  3
• 氢受体数：
  17

反应信息

• 作为反应物：
  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
• 作为产物：
  描述：

  O-benzyl-ciprofloxacin hydrochloride 、 trocCl 在 盐酸 、 4-二甲氨基吡啶 、 1,2-二氯乙烷 、 N,N-二异丙基乙胺 作用下， 以 氯仿 、 二氯甲烷 为溶剂， 反应 28.0h， 以52%的产率得到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
  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