Synthesis and nootropic activity of pyrrolidino[1,2-a]diazacycloalkanes

Gudasheva, T. A.; Vasilevich, N. I.; Ostrovskaya, R. U.; Трофимов, С. С.; Воронина, Т. А.; Сколдинов, А. П.; Rozantsev, G. G.

doi:10.1007/bf02219346

Cited by 11 publications

(7 citation statements)

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“…The design of peptides improving cognitive function is based on the hypothesis on the role of oligopeptides containing an endogenous pyrrolidine-carbonic amino acid (pyroglutamic acid or proline) as the ligands of pitative recognition sites for piracetam [1,10]. The study of synthetic pyroglutamine-containing dipeptides with various natural amino acids showed that these compounds improve cognitive function in experimental animals [3].…”

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confidence: 99%

Dipeptide preparation Noopept prevents scopolamine-induced deficit of spatial memory in BALB/c mice

2007

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The effect of original nootropic preparation Noopept on learning and long-term memory was studied with BALB/c mice. Scopolamine (1 mg/kg) impaired long-term memory trace, while Noopept (0.5 mg/kg) had no significant effect. Noopept completely prevented the development of cognitive disorders induced by scopolamine (blockade of muscarinic cholinergic receptors). Our results confirmed the presence of choline-positive effect in dipeptide piracetam analogue Noopept on retrieval of learned skill of finding a submerged platform (spatial memory). We conclude that the effectiveness of this drug should be evaluated in patients with Alzheimer's disease.

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confidence: 99%

Dipeptide preparation Noopept prevents scopolamine-induced deficit of spatial memory in BALB/c mice

2007

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“…CPG was synthesized as described elsewhere [2] with the following constants: melting point 199-Institute of Pharmacology, Russian Academy of Medical Sciences. Moscow…”

Section: Methodsmentioning

confidence: 99%

New endogenous dipeptide cycloprolyl-glycine is similar to piracetam by its mnemotropic selectivity

et al. 1999

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The effects of endogenous dipeptide cycloprolyl-glycine on learning and memory in the model of postconvulsive retrograde amnesia of passive avoidance response in rats depended on the administration schedule. The dipeptide prevented retrograde amnesia, when injected prior to learning, had no effect after postlearning administration, and aggravated amnesia, when injected immediately before retrieval. These data suggest that cycloprolyl-glycine is similar to the standard nootropic piracetam by its mnemotropic activity.

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“…We designed and synthesized a number of active linear N -acylproline-containing dipeptides with the common formulae R—CO— Pro—AAR—X (R-CO is acyl, AAR is amino acid residue, X is a functional group such as NH 2 , OMe, OEt) [13-15] and a cyclic dipeptide, cycloprolylglycine ( cyclo (Pro—Gly)). The last one was coincided topologically with Piracetam most exactly; therefore cyclo(Pro-Gly) represents another possible endogenous prototype of Piracetam [16]. After a SAR analysis and consequent design, N -phenylacetyl-L-propylglycine ethyl ester was selected as the most active and technologically available compound for the subsequent development as a medicine.…”

Section: Noopept a Dipeptide Nootropic Drugmentioning

confidence: 99%

Novel Technologies for Dipeptide Drugs Design and their Implantation

Gudasheva

Ostrovskaya

Середенин

2018

CPD

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The article is an overview of author’s data obtained in the framework of the project “The Creation of dipeptide preparations” at the V.V. Zakusov Institute of Pharmacology, Moscow, Russia. Advantages of dipeptides over longer peptides consist in that they are orally active owing to higher sta-bility and ability to penetrate biological barriers due to the presence of specific ATP–dependent trans-porters in enterocytes and blood-brain barrier. Two original approaches for dipeptide drugs design have been developed. Both of them are based on the idea of a leading role of central dipeptide fragment of the peptide chain beta-turn in the peptide-receptor interaction. The first approach, named “peptide drug-based design” represents the transformation of known nonpeptide drug into its dipeptide topological analog. The latter usually corresponds to a beta-turn of some regulatory peptide. The second approach represents the design of tripeptoide mimetic of the beta-turn of regulatory peptide or protein. The results of the studies, which led to the discovery of endogenous prototypes of the known non-peptide drugs piracetam and sulpiride, are presented herein. The paper discusses the process, based on the above-mentioned principles, that was used in designing of nontoxic, orally available, highly effective dipeptide drugs: nootropic noopept, dipeptide analog of piracetam; antipsychotic dilept, neurotensin tripeptoid analog; selective anxiolytic GB-115, tripeptoid analog of CCK-4, and potential neuroprotector GK-2, homodimeric dipeptide analog of NGF.

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Synthesis and nootropic activity of pyrrolidino[1,2-a]diazacycloalkanes

Cited by 11 publications

References 9 publications

Dipeptide preparation Noopept prevents scopolamine-induced deficit of spatial memory in BALB/c mice

Dipeptide preparation Noopept prevents scopolamine-induced deficit of spatial memory in BALB/c mice

New endogenous dipeptide cycloprolyl-glycine is similar to piracetam by its mnemotropic selectivity

Novel Technologies for Dipeptide Drugs Design and their Implantation

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