(6R,7S)-7-[[4-[5-[[5-[5-[acetyl(hydroxy)amino]pentylamino]-3-carboxy-3-hydroxy-5-oxopentanoyl]amino]pentyl-hydroxyamino]-4-oxobutanoyl]amino]-3-chloro-8-oxo-1-azabicyclo[4.2.0]oct-2-ene-2-carboxylic acid

• 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,7S)-7-[[4-[5-[[5-[5-[acetyl(hydroxy)amino]pentylamino]-3-carboxy-3-hydroxy-5-oxopentanoyl]amino]pentyl-hydroxyamino]-4-oxobutanoyl]amino]-3-chloro-8-oxo-1-azabicyclo[4.2.0]oct-2-ene-2-carboxylic acid
• 化学式: C₃₀H₄₅ClN₆O₁₃
• 分子量: 733.173
• InChiKey: JYBDISMOBNWDSA-YFWNFPKUSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  -2.9
• 重原子数：
  50
• 可旋转键数：
  22
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.67
• 拓扑面积：
  284
• 氢给体数：
  8
• 氢受体数：
  13

反应信息

• 作为产物：
  描述：

  5-(N-叔丁氧羰基氨基)-1-戊醇 在 palladium on activated charcoal 吡啶 、 盐酸 、 sodium hydroxide 、 potassium dihydrogenphosphate 、 氢气 、 1-羟基苯并三唑一水物 、 盐酸-N-乙基-Nˊ-(3-二甲氨基丙基)碳二亚胺 、 三乙胺 、 三苯基膦 、 三氟乙酸 、 锌 、 偶氮二甲酸二乙酯 作用下， 以 四氢呋喃 、 二氯甲烷 、 氯仿 、 N,N-二甲基甲酰胺 、 乙腈 为溶剂， 反应 67.5h， 生成 (6R,7S)-7-[[4-[5-[[5-[5-[acetyl(hydroxy)amino]pentylamino]-3-carboxy-3-hydroxy-5-oxopentanoyl]amino]pentyl-hydroxyamino]-4-oxobutanoyl]amino]-3-chloro-8-oxo-1-azabicyclo[4.2.0]oct-2-ene-2-carboxylic acid
  参考文献：
  名称：

  Synthesis of novel citrate-based siderophores and siderophore-.beta.-lactam conjugates. Iron transport-mediated drug delivery systems

  摘要：

  The synthesis of analogs of arthrobactin (5), a microbial iron chelator, and its imide 8 are described. The differentially protected citric acid residue 31 served as the key intermediate in making conjugates having a generalized structure 14 with two representative carbacephalosporin units, 15 and 16. Both conjugates, 49 and 51, showed antibiotic activity, while conjugate 51 obtained from beta-lactam 16 bearing a phenylglycyl side chain was shown to be more effective.

  DOI：

  10.1021/jo00079a007

文献信息

• Synthesis of novel citrate-based siderophores and siderophore-.beta.-lactam conjugates. Iron transport-mediated drug delivery systems
  作者：Arun Ghosh、Marvin J. Miller

  DOI：10.1021/jo00079a007

  日期：1993.12

  The synthesis of analogs of arthrobactin (5), a microbial iron chelator, and its imide 8 are described. The differentially protected citric acid residue 31 served as the key intermediate in making conjugates having a generalized structure 14 with two representative carbacephalosporin units, 15 and 16. Both conjugates, 49 and 51, showed antibiotic activity, while conjugate 51 obtained from beta-lactam 16 bearing a phenylglycyl side chain was shown to be more effective.