2-{[5-(Acetyl-benzyloxy-amino)-pentylcarbamoyl]-methyl}-2-hydroxy-succinic acid 1-tert-butyl ester 4-(4-nitro-phenyl) ester | 153492-07-0

• 分子结构分类: 有机化合物 - 苯类化合物 - 苯酚酯
• 英文名称: 2-{[5-(Acetyl-benzyloxy-amino)-pentylcarbamoyl]-methyl}-2-hydroxy-succinic acid 1-tert-butyl ester 4-(4-nitro-phenyl) ester
• 英文别名: 1-O-tert-butyl 4-O-(4-nitrophenyl) 2-[2-[5-[acetyl(phenylmethoxy)amino]pentylamino]-2-oxoethyl]-2-hydroxybutanedioate
• CAS: 153492-07-0
• 化学式: C₃₀H₃₉N₃O₁₀
• 分子量: 601.654
• InChiKey: RYTHRNDQISZSSK-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.9
• 重原子数：
  43
• 可旋转键数：
  18
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.47
• 拓扑面积：
  177
• 氢给体数：
  2
• 氢受体数：
  10

反应信息

• 作为反应物：
  描述：

  2-{[5-(Acetyl-benzyloxy-amino)-pentylcarbamoyl]-methyl}-2-hydroxy-succinic acid 1-tert-butyl ester 4-(4-nitro-phenyl) ester 在 palladium on activated charcoal 盐酸 、 氢气 作用下， 以 氯仿 、 N,N-二甲基甲酰胺 、 乙腈 为溶剂， 反应 24.0h， 生成 (6R,7S)-7-[[(2R)-2-[[4-[5-[[5-[5-[acetyl(hydroxy)amino]pentylamino]-3-carboxy-3-hydroxy-5-oxopentanoyl]amino]pentyl-hydroxyamino]-4-oxobutanoyl]amino]-2-phenylacetyl]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
• 作为产物：
  描述：

  枸橼酸叔-丁酯 在 N,N'-二环己基碳二亚胺 作用下， 以 氯仿 、 乙腈 为溶剂， 反应 5.5h， 生成 2-{[5-(Acetyl-benzyloxy-amino)-pentylcarbamoyl]-methyl}-2-hydroxy-succinic acid 1-tert-butyl ester 4-(4-nitro-phenyl) ester
  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