N-phenylacetyl-L-prolylglycine methylamine

• 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 methylamine
• 英文别名: N-phenylacetyl-L-prolylglycine N-methylamide；(2S)-N-[2-(methylamino)-2-oxoethyl]-1-(2-phenylacetyl)pyrrolidine-2-carboxamide
• 化学式: C₁₆H₂₁N₃O₃
• 分子量: 303.361
• InChiKey: INRIVMRLLOCBOJ-ZDUSSCGKSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  0.5
• 重原子数：
  22
• 可旋转键数：
  5
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.44
• 拓扑面积：
  78.5
• 氢给体数：
  2
• 氢受体数：
  3

反应信息

• 作为反应物：
  描述：

  N-isovaleryl-L-prolylglycine ethyl ester 、 N-phenylacetyl-L-prolyl-L-valine ethyl ester 、 N-benzoyl-L-prolyl-L-valine ethyl ester 、 N-benzoyl-L-prolyl-β-alanine ethyl ester 、 N-benzoyl-L-prolyl-β-alanine amide 、 N-benzoyl-L-prolylglycine amide 、 N-phenylacetyl-L-prolylglycine methylamine 、 N-phenylacetyl-L-prolylglycine dimethylamide 生成 N-benzoyl-L-prolylglycine ethyl ester
  参考文献：
  名称：

  Methods for restoring cognitive function following systemic stress

  摘要：

  本发明提供了用于治疗与全身性压力相关的认知衰退的方法。

  公开号：

  US20020187977A1
• 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 甲醇 、 氯仿 、 N,N-二甲基甲酰胺 为溶剂， 反应 1.53h， 生成 N-phenylacetyl-L-prolylglycine methylamine
  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

• METHODS FOR RESTORING COGNITIVE FUNCTION FOLLOWING SYSTEMIC STRESS
  申请人：Saegis Pharmaceuticals

  公开号：EP1372620A2

  公开（公告）日：2004-01-02
• US5439930A
  申请人：——

  公开号：US5439930A

  公开（公告）日：1995-08-08
• [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.
• [EN] METHODS FOR RESTORING COGNITIVE FUNCTION FOLLOWING SYSTEMIC STRESS<br/>[FR] METHODES PERMETTANT DE RETABLIR LA FONCTION COGNITIVE SUITE A UN STRESS SYSTEMIQUE
  申请人：DAVID PHARMACEUTICALS

  公开号：WO2002074293A2

  公开（公告）日：2002-09-26

  The invention provides methods for treating cognitive decline that is associated with systemic stress.
• 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.