1027016-69-8Relevant academic research and scientific papers
New dipeptides containing thiazolidine-4-carboxylic acid derivatives: Synthesis and characterization using NMR techniques and X-ray data
Pellegrini, Nadia,Refouvelet, Bernard,Crini, Gregorio,Blacque, Olivier,Kubicki, Marek M.,Robert, Jean-Francois
, p. 950 - 955 (1999)
New dipeptides, structural analogues of known immunomodulating agents, were prepared by stereospecific condensation between 2-substituted thiazolidine-4-carboxylate esters with N-substituted L-proline or L- thiaproline. The structure of these compounds has been elucidated by combination of NMR methods and X-ray analysis. In addition, NMR measurements on dipeptides indicated the presence of S-cis and S-trans conformers around the amide bonds.
Synthesis and antiamnesic activity of a series of N-acylprolyl-containing dipeptides
Gudasheva,Voronina,Ostrovskaya,Rozantsev,Vasilevich,Trofimov,Kravchenko,Skoldinov,Seredenin
, p. 151 - 157 (2007/10/03)
Eaters 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-acylsubstitution 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, β-Ala, GABA. Compound 1 (N-phenylacetylprolylglycine ethyl eater) was selected for further evalution 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.
