7β-<(N⁵-acetyl-N⁵-hydroxy-L-ornithyl)-(N⁵-acetyl-N⁵-hydroxy-L-ornithyl)-(N⁵-acetyl-N⁵-hydroxy-L-ornithyl)-(D-(4-hydroxy)phenylglycyl)amino>-3-chloro-1-carba-3-cephem-4-carboxylic acid | 124620-50-4

• 分子结构分类: 有机化合物 - 碳氢化合物衍生物
• 英文名称: 7β-<(N⁵-acetyl-N⁵-hydroxy-L-ornithyl)-(N⁵-acetyl-N⁵-hydroxy-L-ornithyl)-(N⁵-acetyl-N⁵-hydroxy-L-ornithyl)-(D-(4-hydroxy)phenylglycyl)amino>-3-chloro-1-carba-3-cephem-4-carboxylic acid
• 英文别名: 7β-<(N⁵-acetyl-N⁵-hydroxy-L-ornithyl-N⁵-acetyl-N⁵-hydroxy-L-ornithyl-N⁵-acetyl-N⁵-hydroxy-L-ornithyl-D-4-hydroxyphenylglycyl)amino>-1-carba-3-chloro-3-cephem-4-carboxylic acid；(6R,7S)-7-[[(2R)-2-[[(2S)-5-[acetyl(hydroxy)amino]-2-[[(2S)-5-[acetyl(hydroxy)amino]-2-[[(2S)-5-[acetyl(hydroxy)amino]-2-aminopentanoyl]amino]pentanoyl]amino]pentanoyl]amino]-2-(4-hydroxyphenyl)acetyl]amino]-3-chloro-8-oxo-1-azabicyclo[4.2.0]oct-2-ene-2-carboxylic acid
• CAS: 124620-50-4
• 化学式: C₃₇H₅₂ClN₉O₁₄
• 分子量: 882.325
• InChiKey: ODLIZIGZSPLLOX-BJSMOIIYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  -4.7
• 重原子数：
  61
• 可旋转键数：
  22
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.54
• 拓扑面积：
  342
• 氢给体数：
  10
• 氢受体数：
  15

反应信息

• 作为产物：
  描述：

  4-nitrobenzyl 7β-<5-acetyl-N⁵-(benzyloxy)-N²-(benzyloxycarbonyl)-L-ornithyl-N⁵-acetyl-N⁵-(benzyloxy)-L-ornithyl-N⁵-acetyl-N⁵-(benzyloxy)-L-ornithyl-D-4-(benzyloxy)phenylglycyl>amino>-1-carba-3-chloro-3-cephem-4-carboxylate 在 palladium on activated charcoal 盐酸 、 氢气 作用下， 以 水 、 N,N-二甲基甲酰胺 为溶剂， 反应 24.0h， 生成 7β-<(N⁵-acetyl-N⁵-hydroxy-L-ornithyl)-(N⁵-acetyl-N⁵-hydroxy-L-ornithyl)-(N⁵-acetyl-N⁵-hydroxy-L-ornithyl)-(D-(4-hydroxy)phenylglycyl)amino>-3-chloro-1-carba-3-cephem-4-carboxylic acid
  参考文献：
  名称：

  N5-乙酰基-N5-羟基-L-鸟氨酸衍生的铁载体-头孢菌素β-内酰胺偶联物：铁转运介导的药物递送。

  摘要：

  DOI：

  10.1021/jm00164a001

文献信息

• N5-Acetyl-N5-hydroxy-L-ornithine-derived siderophore-carbacephalosporin .beta.-lactam conjugates: iron transport mediated drug delivery
  作者：E. Kurt Dolence、Albert A. Minnick、Marvin J. Miller

  DOI：10.1021/jm00164a001

  日期：1990.2
• Synthesis and siderophore and antibacterial activity of N5-acetyl-N5-hydroxyl-L-ornithine derived siderophore-.beta.-lactam conjugates: iron transport mediated drug delivery
  作者：E. Kurt Dolence、Albert A. Minnick、Chia En Lin、Marvin J. Miller、Shelley M. Payne

  DOI：10.1021/jm00107a014

  日期：1991.3

  N5-Acetyl-N5-hydroxy-L-ornithyl-N5-acetyl-N5-hydroxy-L-ornithyl-N5-acetyl-N5-hydroxy-L-ornithine, the functionally instrumental component of the albomycins and ferrichromes, has been incorporated as a ''carrier'' substructure into both carbacephalosporin and oxamazin type beta-lactam antibiotics. The previously synthesized protected version of this tripeptide (14) was coupled with various beta-lactam analogues 17, 19, 24, and 25 to give protected conjugates 21, 22, 26, and 27. Final deprotection by hydrogenolysis provided the deprotected siderophore-beta-lactam antibiotic conjugates 1-4. The growth-promoting ability of each has been evaluated using either the siderophore-deficient mutant Shigella flexneri SA 100 or S. flexneri SA240 (SA 100 iucD:Tn5). Measurement of the growth-promoting activity using two isogenic Escherichia coli strains differing only in the presence or absence of fhuA (hydroxamate ferrichrome receptor) suggests uptake by the hydroxamate iron-transport system. The antibacterial activity of these conjugates has been investigated, and the potential for use of the ferrichrome iron-transport system as a means of drug delivery is discussed.