N-α-(benzyloxycarbonyl)-N-ε-octanoyllysine p-nitrophenyl ester | 100566-81-2

• 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: N-α-(benzyloxycarbonyl)-N-ε-octanoyllysine p-nitrophenyl ester
• CAS: 100566-81-2
• 化学式: C₂₈H₃₇N₃O₇
• 分子量: 527.618
• InChiKey: KZMAMWJTHWXFCO-VWLOTQADSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  5.44
• 重原子数：
  38.0
• 可旋转键数：
  17.0
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.46
• 拓扑面积：
  136.87
• 氢给体数：
  2.0
• 氢受体数：
  7.0

反应信息

• 作为反应物：
  描述：

  N-α-(benzyloxycarbonyl)-N-ε-octanoyllysine p-nitrophenyl ester 在 钯 N-甲基吗啉 、 甲酸 、 二异丙胺 作用下， 以 甲醇 、 二甲基亚砜 、 N,N-二甲基甲酰胺 为溶剂， 反应 35.0h， 生成 (S)-[(S)-2-((S)-2-Benzyloxycarbonylamino-6-octanoylamino-hexanoylamino)-6-octanoylamino-hexanoylamino]-[(2R,3S,4R,5R)-5-(2,4-dioxo-3,4-dihydro-2H-pyrimidin-1-yl)-3,4-dihydroxy-tetrahydro-furan-2-yl]-acetic acid
  参考文献：
  名称：

  Synthesis and biological evaluation of dipeptidyl and tripeptidyl polyoxin and nikkomycin analogs as anticandidal prodrugs

  摘要：

  Nine analogues (1-5, 9-12) of the peptidyl nucleoside antibiotics nikkomycin and polyoxin were synthesized and tested for their biological properties against different strains of the pathogenic yeast Candida albicans. The tripeptidyl series of analogues (1-5) was designed to behave as prodrugs, releasing a toxic moiety upon enzymatic hydrolysis inside the cell. The dipeptidyl series (9-12) was designed as double-targeted drugs, being themselves toxic and releasing a toxic amino acid upon hydrolysis. All the analogues were prepared by coupling suitably protected amino acid p-nitrophenyl esters to 1-(5'-amino-5'-deoxy-alpha-D-allofuranuronosyl)uracil (UPOC) or the corresponding polyoxins and nikkomycins, with subsequent removal of the protecting group. Improved coupling yields were observed when DMSO was used as the solvent. Products were purified with use of reversed-phase HPLC and, in one case, diastereomeric products (compound 11) were resolved by using this procedure. One of the tripeptidyl nikkomycins behaved as a prodrug but none of the compounds, as measured by in vitro testing, proved more effective than nikkomycin as an anticandidal agent.

  DOI：

  10.1021/jm00105a026