N-Acetyl-N-(4-aminophenyl)glycine | 119656-43-8

• 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-Acetyl-N-(4-aminophenyl)glycine
• 英文别名: Nα-acetyl-(4-aminophenyl)-(D)glycine；Nα-acetyl-(4-aminophenyl)-L-glycine；p-amino-D-N-acetylphenylglycine；[Acetyl-(4-amino-phenyl)-amino]-acetic acid；2-(N-acetyl-4-aminoanilino)acetic acid
• CAS: 119656-43-8
• 化学式: C₁₀H₁₂N₂O₃
• 分子量: 208.217
• InChiKey: KSNBINLJAHGAQM-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  0.2
• 重原子数：
  15
• 可旋转键数：
  3
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.2
• 拓扑面积：
  83.6
• 氢给体数：
  2
• 氢受体数：
  4

反应信息

• 作为产物：
  描述：

  N-Acetyl-N-(4-nitrophenyl)glycine 在 palladium on activated charcoal 氢气 作用下， 以 乙醇 为溶剂， 反应 1.0h， 以52%的产率得到N-Acetyl-N-(4-aminophenyl)glycine
  参考文献：
  名称：

  Synthesis and in vitro aldose reductase inhibitory activity of compounds containing an N-acylglycine moiety

  摘要：

  A number of N-benzoylglycines (6), N-acetyl-N-phenylglycines (7), N-benzoyl-N-phenylglycines (8), and tricyclic N-acetic acids (9-12) were synthesized as analogues of the N-acylglycine-containing aldose reductase inhibitors alrestatin and 2-oxoquinoline-1-acetic acid. Derivatives of 6, which represent ring-simplified analogues of alrestatin, are very weak inhibitors of aldose reductase obtained from rat lens, producing 50% inhibition only at concentrations exceeding 100 microM. Compounds of series 7 were designed as ring-opened analogues of the 2-oxoquinolines. While these derivatives are more potent than compounds of series 6 (IC50S of 6-80 microM), they are less active than the corresponding 2-oxoquinolines. Analogues of series 8 were designed as hybrid structures of both alrestatin and the 2-oxoquinoline-1-acetic acids. These compounds are substantially more potent than compounds of series 6 and 7 and display inhibitory activities comparable to or greater than alrestatin or the 2-oxoquinolines (IC50S of 0.1-10 microM). Of the rigid analogues of 8, the most potent derivative is benzoxindole (12) with an IC50 of 0.67 microM, suggesting that fusion of the two aromatic rings of 8 in a coplanar conformation may optimize affinity for aldose reductase in this series.

  DOI：

  10.1021/jm00125a017

文献信息

• Cytoprotective derivatives useful in ischemic diseases, their preparation and compositions containing them
  申请人：ITALFARMACO S.p.A.

  公开号：EP0230037B1

  公开（公告）日：1991-03-06
• J. MED. CHEM., 32,(1989) N, C. 1033-1038
  作者：

  DOI：——

  日期：——
• US3953439A
  申请人：——

  公开号：US3953439A

  公开（公告）日：1976-04-27
• US4013764A
  申请人：——

  公开号：US4013764A

  公开（公告）日：1977-03-22
• US4018921A
  申请人：——

  公开号：US4018921A

  公开（公告）日：1977-04-19