N-phenylacetyl-L-prolylglycine amide

• 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-phenylacetyl-L-prolylglycine amide
• 英文别名: (2S)-N-(2-amino-2-oxoethyl)-1-(2-phenylacetyl)pyrrolidine-2-carboxamide
• 化学式: C₁₅H₁₉N₃O₃
• 分子量: 289.334
• InChiKey: VVBQBGPCKVFRQC-LBPRGKRZSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  0.1
• 重原子数：
  21
• 可旋转键数：
  5
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.4
• 拓扑面积：
  92.5
• 氢给体数：
  2
• 氢受体数：
  3

反应信息

• 作为产物：
  描述：

  N-(1-(苯基乙酰基)-L-脯氨酰)甘氨酸乙酯 在 氨 作用下， 以 甲醇 为溶剂， 以95%的产率得到N-phenylacetyl-L-prolylglycine amide
  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

• [EN] BIOLOGICALLY ACTIVE N-ACYLPROLYLDIPEPTIDES HAVING ANTIAMNESTIC, ANTIHYPOXIC AND ANOREXIGENIC EFFECTS<br/>[FR] N-ACYLPROLYLDIPEPTIDES BIOLOGIQUEMENT ACTIFS, PRESENTANT DES EFFETS ANTIAMNESIQUES, ANTIHYPOXIE ET ANOREXIGENES
  申请人：RUSSIAN-AMERICAN INSTITUTE FOR NEW DRUG DEVELOPMENT

  公开号：WO1993021216A1

  公开（公告）日：1993-10-28

  (EN) A novel class of substances of N-acylprolyldipeptides, which possess psychotropic activity and particularly facilitate learning and memory are described. The N-acylprolyldipeptides of the invention have formula (1), wherein R1 = (C4-C5) alkyl, cycloalkyl, aralkyl, or aryl; R2 = H1 (C1-C4) alkyl, carbamidoalkyl, or carbalkoxyalkyl; R3 = NH2, NH(alkyl), N(alkyl)2, OH, or alkoxy; and n = 0-3, preferably 0-2.(FR) L'invention se rapporte à une nouvelle catégorie de substances à base de N-acylprolyldipeptides, qui présentent une activité psychotrope et facilitent particulièrement l'apprentissage tout en développant la mémoire. Les N-acylprolyldipeptides de l'invention répondent à la formule (1), dans laquelle R1 = (C4-C5) alkyle, cycloalkyle, aralkyle ou aryle; R2 = H1 (C1-C4) alkyle, carbamidoalkyle ou carbalcoxyalkyle; R3 = NH2, NH(alkyl), N(alkyl)2, OH ou alcoxy; et n = 0-3, de préférence 0-2.
• 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.