(+/-)-p-nitrophenyl N-(benzyloxycarbonyl)-α-aminooctanoate | 112139-11-4

• 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: (+/-)-p-nitrophenyl N-(benzyloxycarbonyl)-α-aminooctanoate
• 英文别名: (4-nitrophenyl) 2-(phenylmethoxycarbonylamino)octanoate
• CAS: 112139-11-4
• 化学式: C₂₂H₂₆N₂O₆
• 分子量: 414.458
• InChiKey: WMGOBQVEHBPCSL-UHFFFAOYSA-N

物化性质

• 熔点：
  80-81 °C
• 沸点：
  584.3±45.0 °C(Predicted)
• 密度：
  1.203±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  4.77
• 重原子数：
  30.0
• 可旋转键数：
  11.0
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.36
• 拓扑面积：
  107.77
• 氢给体数：
  1.0
• 氢受体数：
  6.0

反应信息

• 作为反应物：
  描述：

  (+/-)-p-nitrophenyl N-(benzyloxycarbonyl)-α-aminooctanoate 、 尿嘧啶多氧菌素 C 生成 (2S)-2-[[(2S)-2-aminooctanoyl]amino]-2-[(2R,3S,4R,5R)-5-(2,4-dioxopyrimidin-1-yl)-3,4-dihydroxyoxolan-2-yl]acetic acid
  参考文献：
  名称：

  KHARE, R. K.;BECKER, JEFFREY M.;NAIDER, FRED R., J. MED. CHEM., 31,(1988) N 3, 650-656

  摘要：

  DOI：
• 作为产物：
  描述：

  2-溴正辛酸 在 ammonium hydroxide 、 sodium hydroxide 、 N,N'-二环己基碳二亚胺 作用下， 以 四氢呋喃 为溶剂， 反应 190.0h， 生成 (+/-)-p-nitrophenyl N-(benzyloxycarbonyl)-α-aminooctanoate
  参考文献：
  名称：

  Synthesis and anticandidal properties of polyoxin L analogs containing .alpha.-amino fatty acids

  摘要：

  Analogues of polyoxin L containing amino acids with saturated fatty acid like side chains were synthesized from the benzyloxycarbonyl-protected alpha-amino fatty acid p-nitrophenyl ester and uracil polyoxin C. Transfer hydrogenolysis using palladium black and formic acid gave diastereomeric, dipeptidyl polyoxin L analogues containing alpha-aminooctanoic acid (3), alpha-aminododecanoic acid (4), or alpha-aminohexadecanoic acid (5) as the amine terminal residue in 40-60% yield. Diastereomers of 3 and 5 were resolved by using high-performance liquid chromatography on a reversed-phase column and designated as 3a, 3b and 5a, 5b. Analogues 3-5 were excellent inhibitors of chitin synthetase from Candida albicans; 4, the best inhibitor, had an ID50 of 0.5 microM. The L,L diastereomers of 3 and 5 were 1-2 orders of magnitude more potent chitin synthetase inhibitors than their D,L homologues. None of the synthetic polyoxin L analogues inhibited transport of trimethionine, but 3a, 4, and 5b caused decreases of 71%, 87%, and 83%, respectively, in the initial rate of uptake of dileucine. Compounds 3-5 were significantly more stable to peptidase degradation than polyoxin L analogues containing naturally occurring alpha-amino acids. Compound 4 inhibited growth of C. albicans in culture at 40-80 micrograms/mL. All other analogues were less potent antifungals. The results suggest that synthetic polyoxins can be designed to have increased affinity for a peptide transport system and to have increased stability against intracellular degradation in C. albicans.

  DOI：

  10.1021/jm00398a027