N-[5-(Acetyl-benzyloxy-amino)-pentyl]-2-{[5-(acetyl-benzyloxy-amino)-pentylcarbamoyl]-methyl}-2-hydroxy-succinamic acid tert-butyl ester | 153492-05-8

• 分子结构分类: 有机化合物 - 脂质和类脂质分子 - 脂肪酰基
• 英文名称: N-[5-(Acetyl-benzyloxy-amino)-pentyl]-2-{[5-(acetyl-benzyloxy-amino)-pentylcarbamoyl]-methyl}-2-hydroxy-succinamic acid tert-butyl ester
• 英文别名: Tert-butyl 4-[5-[acetyl(phenylmethoxy)amino]pentylamino]-2-[2-[5-[acetyl(phenylmethoxy)amino]pentylamino]-2-oxoethyl]-2-hydroxy-4-oxobutanoate
• CAS: 153492-05-8
• 化学式: C₃₈H₅₆N₄O₉
• 分子量: 712.884
• InChiKey: HKDOFCBCSRONQA-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3
• 重原子数：
  51
• 可旋转键数：
  25
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.55
• 拓扑面积：
  164
• 氢给体数：
  3
• 氢受体数：
  9

反应信息

• 作为反应物：
  描述：

  N-[5-(Acetyl-benzyloxy-amino)-pentyl]-2-{[5-(acetyl-benzyloxy-amino)-pentylcarbamoyl]-methyl}-2-hydroxy-succinamic acid tert-butyl ester 在 palladium on activated charcoal 氢气 、 三氟乙酸 作用下， 以 四氢呋喃 、 二氯甲烷 、 水 为溶剂， 反应 3.5h， 生成 4-[5-(乙酰基-羟基氨基)戊基氨基]-2-[2-[5-(乙酰基-羟基氨基)戊基氨基]-2-氧代乙基]-2-羟基-4-氧代丁酸
  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：

  1-氨基-5-[乙酰基(苄氧基)氨基]戊烷 、 2-Hydroxy-1,2,3-propanetricarboxylic acid 2-tert-butyl 1,3-bis(p-nitrophenyl) triester 以 氯仿 、 乙腈 为溶剂， 反应 2.0h， 以94%的产率得到N-[5-(Acetyl-benzyloxy-amino)-pentyl]-2-{[5-(acetyl-benzyloxy-amino)-pentylcarbamoyl]-methyl}-2-hydroxy-succinamic acid tert-butyl 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

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.