N-phenylaacetyl-L-proplyl-γ-aminobutylic acid methyl ester

• 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-phenylaacetyl-L-proplyl-γ-aminobutylic acid methyl ester
• 英文别名: methyl 4-[[(2S)-1-(2-phenylacetyl)pyrrolidine-2-carbonyl]amino]butanoate
• 化学式: C₁₈H₂₄N₂O₄
• 分子量: 332.4
• InChiKey: WDYFHWXRBFKADG-HNNXBMFYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  1.4
• 重原子数：
  24
• 可旋转键数：
  8
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.5
• 拓扑面积：
  75.7
• 氢给体数：
  1
• 氢受体数：
  4

反应信息

• 作为产物：
  描述：

  N-苯乙酰基-S-脯氨酸 在 N-甲基吗啉 作用下， 以 氯仿 、 N,N-二甲基甲酰胺 为溶剂， 反应 1.53h， 生成 N-phenylaacetyl-L-proplyl-γ-aminobutylic acid methyl ester
  参考文献：
  名称：

  Synthesis and antiamnesic activity of a series of N-acylprolyl-containing dipeptides

  摘要：

  Esters and amides of a series of N-acylprolyl-containing dipeptides were synthesized. It was established that these substances possess the ability to prevent memory decline evoked by maximal electroshock (MES) in a passive avoidance step-through paradigm. These N-acylprolyl-containing dipeptides were designed as analogues of pyroglutamyl-containing dipeptides, which we previously demonstrated to be highly active nootropics. Among the structure-activity relationships explored were the effect of N-acyl-substitution size, C-terminal substitution and the nature of the second amino acid. The optimal N-acyl moiety was the N-phenyl-acetyl group, while the optimal C-terminal substitution-esters were those derived from low alkyl alcohols. The optimal second amino acids were Asp, Glu or their fragments, Gly, beta-Ala, GABA. Compound 1 (N-phenylacetylprolylglycine ethyl ester) was selected for further evaluation in impaired cognitive functions. It was supposed that esters and unsubstituted amides of N-acylprolylglycines are prodrugs,which convert to the bioactive cyclo-(Pro-Gly) by virtue of enzymatic or chemical lability within the body.

  DOI：

  10.1016/0223-5234(96)80448-x

文献信息

• Synthesis and antiamnesic activity of a series of N-acylprolyl-containing dipeptides
  作者：TA Gudasheva、TA Voronina、RU Ostrovskaya、GG Rozantsev、NI Vasilevich、SS Trofimov、EV Kravchenko、AP Skoldinov、SB Seredenin

  DOI：10.1016/0223-5234(96)80448-x

  日期：1996.1

  Esters and amides of a series of N-acylprolyl-containing dipeptides were synthesized. It was established that these substances possess the ability to prevent memory decline evoked by maximal electroshock (MES) in a passive avoidance step-through paradigm. These N-acylprolyl-containing dipeptides were designed as analogues of pyroglutamyl-containing dipeptides, which we previously demonstrated to be highly active nootropics. Among the structure-activity relationships explored were the effect of N-acyl-substitution size, C-terminal substitution and the nature of the second amino acid. The optimal N-acyl moiety was the N-phenyl-acetyl group, while the optimal C-terminal substitution-esters were those derived from low alkyl alcohols. The optimal second amino acids were Asp, Glu or their fragments, Gly, beta-Ala, GABA. Compound 1 (N-phenylacetylprolylglycine ethyl ester) was selected for further evaluation in impaired cognitive functions. It was supposed that esters and unsubstituted amides of N-acylprolylglycines are prodrugs,which convert to the bioactive cyclo-(Pro-Gly) by virtue of enzymatic or chemical lability within the body.