N-Carbobenzoxy-L-alanyl-L-alanyl-D,L-2-<<4-(aminosulfonyl)phenyl>amino>glycine | 118597-54-9

• 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-Carbobenzoxy-L-alanyl-L-alanyl-D,L-2-<<4-(aminosulfonyl)phenyl>amino>glycine
• 英文别名: N-Carbobenzoxy-L-alanyl-L-alanyl-D,L-2-{[4-(aminosulfonyl)phenyl]amino}glycine
• CAS: 118597-54-9
• 化学式: C₂₂H₂₇N₅O₈S
• 分子量: 521.551
• InChiKey: FDQDXVCDBITKQG-QPKCZYJBSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  0.09
• 重原子数：
  36.0
• 可旋转键数：
  11.0
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.27
• 拓扑面积：
  206.02
• 氢给体数：
  6.0
• 氢受体数：
  8.0

反应信息

• 作为反应物：
  描述：

  N-Carbobenzoxy-L-alanyl-L-alanyl-D,L-2-<<4-(aminosulfonyl)phenyl>amino>glycine 在 palladium on activated charcoal 氢气 作用下， 以 甲醇 为溶剂， 反应 3.0h， 生成 L-Alanyl-L-alanyl-L-2-<<4-(aminosulfonyl)phenyl>amino>glycine 、 L-Alanyl-L-alanyl-L-2-<<4-(aminosulfonyl)phenyl>amino>glycine
  参考文献：
  名称：

  Portage transport of sulfanilamide and sulfanilic acid

  摘要：

  Sulfanilic acid, in contrast to sulfanilamide, has poor in vitro antibacterial activity. Paradoxically, it has been shown to be a more effective inhibitor than sulfanilamide of dihydropteroic acid synthase. In order to circumvent the presumed permeability barrier to sulfanilic acid, advantage was taken of the technique of portage transport. Derivatives of the compound were prepared in which it was linked via its primary amino group to the alpha-carbon of glycine residues in di- and tripeptides. L-Alanyl-L-alanyl-L-2-[(4-sulfophenyl)amino]glycine proved to be 207 times more potent than sulfanilic acid and 8 times more active than either sulfanilamide or L-alanyl-L-alanyl-L-2-[[4-(aminosulfonyl)-phenyl]amino]glycine when tested against Escherichia coli. These findings confirm that the weak in vitro activity of sulfanilic acid is due to its limited ability to penetrate the bacterial membrane. They also emphasize the ability of portage transport to reveal therapeutic capability that had been attenuated by poor drug permeation.

  DOI：

  10.1021/jm00123a034
• 作为产物：
  描述：

  Cbz-(S)-alanyl-(2R,S)-acetoxyglycine benzyl ester 在 palladium on activated charcoal 4 A molecular sieve 、 氢气 、 三乙胺 作用下， 以 甲醇 、 N,N-二甲基甲酰胺 为溶剂， 5.0~25.0 ℃ 、344.73 kPa 条件下， 反应 6.0h， 生成 N-Carbobenzoxy-L-alanyl-L-alanyl-D,L-2-<<4-(aminosulfonyl)phenyl>amino>glycine
  参考文献：
  名称：

  Portage transport of sulfanilamide and sulfanilic acid

  摘要：

  Sulfanilic acid, in contrast to sulfanilamide, has poor in vitro antibacterial activity. Paradoxically, it has been shown to be a more effective inhibitor than sulfanilamide of dihydropteroic acid synthase. In order to circumvent the presumed permeability barrier to sulfanilic acid, advantage was taken of the technique of portage transport. Derivatives of the compound were prepared in which it was linked via its primary amino group to the alpha-carbon of glycine residues in di- and tripeptides. L-Alanyl-L-alanyl-L-2-[(4-sulfophenyl)amino]glycine proved to be 207 times more potent than sulfanilic acid and 8 times more active than either sulfanilamide or L-alanyl-L-alanyl-L-2-[[4-(aminosulfonyl)-phenyl]amino]glycine when tested against Escherichia coli. These findings confirm that the weak in vitro activity of sulfanilic acid is due to its limited ability to penetrate the bacterial membrane. They also emphasize the ability of portage transport to reveal therapeutic capability that had been attenuated by poor drug permeation.

  DOI：

  10.1021/jm00123a034