N-[8-(4-benzyloxyphenoxy)-1-octyl]-2-amino-3-phenylpropionamide | 519186-22-2

• 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-[8-(4-benzyloxyphenoxy)-1-octyl]-2-amino-3-phenylpropionamide
• 英文别名: (2S)-2-amino-3-phenyl-N-[8-(4-phenylmethoxyphenoxy)octyl]propanamide
• CAS: 519186-22-2
• 化学式: C₃₀H₃₈N₂O₃
• 分子量: 474.643
• InChiKey: PISUYIMQJYZMBE-LJAQVGFWSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  6.3
• 重原子数：
  35
• 可旋转键数：
  16
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.37
• 拓扑面积：
  73.6
• 氢给体数：
  2
• 氢受体数：
  4

反应信息

• 作为反应物：
  描述：

  N-[8-(4-benzyloxyphenoxy)-1-octyl]-2-amino-3-phenylpropionamide 在 三乙胺 、 三氟乙酸 、 mercury dichloride 作用下， 以 二氯甲烷 、 N,N-二甲基甲酰胺 为溶剂， 反应 3.5h， 生成 (2S)-2-(diaminomethylideneamino)-3-phenyl-N-[8-(4-phenylmethoxyphenoxy)octyl]propanamide
  参考文献：
  名称：

  Antibacterial Nicotinamide Adenine Dinucleotide Synthetase Inhibitors:  Amide- and Ether-Linked Tethered Dimers with α-Amino Acid End Groups

  摘要：

  Tethered dimers incorporating natural alpha-amino acid end groups were synthesized, including examples in which the previously reported esterase-sensitive ester linker was replaced with more stable amide or ether linkers. These compounds remained effective both as inhibitors of NAD synthetase and as potent antibacterial agents for Gram-positive strains. Studies on nonspecific effects, including detergent properties and promiscuous inhibition, suggested little contribution to observed activities.

  DOI：

  10.1021/jm061349l
• 作为产物：
  描述：

  BOC-L-苯丙氨酸 在 4-二甲氨基吡啶 、 盐酸-N-乙基-Nˊ-(3-二甲氨基丙基)碳二亚胺 、 三乙胺 、 三氟乙酸 作用下， 以 二氯甲烷 为溶剂， 反应 12.5h， 生成 N-[8-(4-benzyloxyphenoxy)-1-octyl]-2-amino-3-phenylpropionamide
  参考文献：
  名称：

  Antibacterial Nicotinamide Adenine Dinucleotide Synthetase Inhibitors:  Amide- and Ether-Linked Tethered Dimers with α-Amino Acid End Groups

  摘要：

  Tethered dimers incorporating natural alpha-amino acid end groups were synthesized, including examples in which the previously reported esterase-sensitive ester linker was replaced with more stable amide or ether linkers. These compounds remained effective both as inhibitors of NAD synthetase and as potent antibacterial agents for Gram-positive strains. Studies on nonspecific effects, including detergent properties and promiscuous inhibition, suggested little contribution to observed activities.

  DOI：

  10.1021/jm061349l