(S)-4-(Benzoyloxy-methyl-carbamoyl)-2-[(S)-2,6-bis-(2,3-diacetoxy-benzoylamino)-hexanoylamino]-butyric acid benzyl ester | 452303-69-4

• 分子结构分类: 有机化合物 - 有机酸及其衍生物 - 羧酸及其衍生物
• 英文名称: (S)-4-(Benzoyloxy-methyl-carbamoyl)-2-[(S)-2,6-bis-(2,3-diacetoxy-benzoylamino)-hexanoylamino]-butyric acid benzyl ester
• CAS: 452303-69-4
• 化学式: C₄₈H₅₀N₄O₁₆
• 分子量: 938.942
• InChiKey: HNJBGNWXEIFTLY-UWXQCODUSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  4.33
• 重原子数：
  68.0
• 可旋转键数：
  21.0
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.29
• 拓扑面积：
  265.41
• 氢给体数：
  3.0
• 氢受体数：
  16.0

反应信息

• 作为反应物：
  描述：

  (S)-4-(Benzoyloxy-methyl-carbamoyl)-2-[(S)-2,6-bis-(2,3-diacetoxy-benzoylamino)-hexanoylamino]-butyric acid benzyl ester 在 palladium on activated charcoal N-甲基吗啉 、 氢气 、 氯甲酸异丁酯 作用下， 以 四氢呋喃 为溶剂， 反应 2.75h， 生成 N-{2-[N²,N⁶-bis(2,3-diacetoxybenzoyl)-L-lysyl]amino-4-[(N-benzyloxy-N-methyl)-carbamoyl]-L-n-butanoyl}ampicillin sodium salt
  参考文献：
  名称：

  New synthetic siderophores and Their β-Lactam conjugates based on diamino acids and dipeptides

  摘要：

  Linking of siderophores to antibiotics improves the penetration and therefore increases the antibacterial activity of the antibiotics. We synthesized the acylated catecholates and hydroxamates as siderophore components for antibiotic conjugates to reduce side effects of unprotected catecholate and hydroxamate moieties. In this paper, we report on bis- and tris-catecholates and mixed catecholate hydroxamates based on diamino acids or dipeptides. These compounds were active as siderophores in a growth promotion assay under iron limitation. Most of the conjugates with beta-lactams showed high in vitro activity against Gram-negative bacteria especially Pseudomonas acruginosa, Escherichia coli, Klebsiella pneumoniae, Serratia mareeseems and Stenotrophomonas maltophilia. The compounds with enhanced antibacterial activity use active iron uptake routes to penetrate the bacterial outer membrane barrier, demonstrated by assays with mutants deficient in components of the iron transport system. Correlation between chemical structure and biological activity was studied. (C) 2002 Published by Elsevier Science Ltd.

  DOI：

  10.1016/s0968-0896(02)00044-5
• 作为产物：
  描述：

  2,3-diacetoxybenzoyl chloride 在 N-甲基吗啉 、 碳酸氢钠 、 氯甲酸异丁酯 作用下， 以 四氢呋喃 为溶剂， 反应 6.5h， 生成 (S)-4-(Benzoyloxy-methyl-carbamoyl)-2-[(S)-2,6-bis-(2,3-diacetoxy-benzoylamino)-hexanoylamino]-butyric acid benzyl ester
  参考文献：
  名称：

  New synthetic siderophores and Their β-Lactam conjugates based on diamino acids and dipeptides

  摘要：

  Linking of siderophores to antibiotics improves the penetration and therefore increases the antibacterial activity of the antibiotics. We synthesized the acylated catecholates and hydroxamates as siderophore components for antibiotic conjugates to reduce side effects of unprotected catecholate and hydroxamate moieties. In this paper, we report on bis- and tris-catecholates and mixed catecholate hydroxamates based on diamino acids or dipeptides. These compounds were active as siderophores in a growth promotion assay under iron limitation. Most of the conjugates with beta-lactams showed high in vitro activity against Gram-negative bacteria especially Pseudomonas acruginosa, Escherichia coli, Klebsiella pneumoniae, Serratia mareeseems and Stenotrophomonas maltophilia. The compounds with enhanced antibacterial activity use active iron uptake routes to penetrate the bacterial outer membrane barrier, demonstrated by assays with mutants deficient in components of the iron transport system. Correlation between chemical structure and biological activity was studied. (C) 2002 Published by Elsevier Science Ltd.

  DOI：

  10.1016/s0968-0896(02)00044-5