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Developing the Optimal Synthetic Schem for the Potential Nootropic Drug GZK-111, N-Phenylacetylglycyl-L-Proline Ethyl Ester

  • DRUG SYNTHESIS METHODS AND MANUFACTURING TECHNOLOGY
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Pharmaceutical Chemistry Journal Aims and scope

The optimal synthetic scheme for the potential nootropic drug GZK-111 (N-phenylacetylglycyl-L-proline ethyl ester) was developed. Three synthetic schemes were tested, each of which included the following steps: 1) esterification of L-proline; 2) preparation of N-phenylacetylglycine; 3) formation of the peptide bond. Esterification of proline per Brenner and preparation of N-phenylacetylglycine via acylation of glycine with phenylacetyl chloride under Schotten—Baumann conditions were used in all synthetic schemes. Three methods for forming the peptide bond between N-phenylacetylglycine and the proline ester were tried (mixed anhydride under Anderson conditions, activated benzotriazole ester, and activated succinimide ester methods) and showed that the mixed anhydride method was optimal, giving a total yield of 42%.

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Authors and Affiliations

  1. V. V. Zakusov State Institute of Pharmacology, Russian Academy of Medical Sciences, 8 Baltiiskaya St, Moscow, 125315, Russia

    E. A. Kuznetsova, K. N. Kolyasnikova, A. K. Golubyatnikova, A. G. Rebeko & T. A. Gudasheva

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  1. E. A. Kuznetsova
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  2. K. N. Kolyasnikova
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  3. A. K. Golubyatnikova
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  4. A. G. Rebeko
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  5. T. A. Gudasheva
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Correspondence to T. A. Gudasheva.

Additional information

Translated from Khimiko-Farmatsevticheskii Zhurnal, Vol. 54, No. 6, pp. 10 – 10, June, 2020.

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Kuznetsova, E.A., Kolyasnikova, K.N., Golubyatnikova, A.K. et al. Developing the Optimal Synthetic Schem for the Potential Nootropic Drug GZK-111, N-Phenylacetylglycyl-L-Proline Ethyl Ester. Pharm Chem J 54, 642–646 (2020). https://doi.org/10.1007/s11094-020-02251-6

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  • DOI: https://doi.org/10.1007/s11094-020-02251-6

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