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Synthesis and Hypoglycemic Activity of Aryl(Hetaryl)Propenoic Cyanopyrrolidine Amides

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Abstract

A series of amides based on (2S)-cyanopyrrolidine and α, β-unsaturated aryl- and hetarylcarboxylic acids have been synthesized. The dependence of the hypoglycemic activity of compounds on the structure of the aromatic fragment has been studied in the oral glucose tolerance test in mice. Amides based on (E)-3-phenylprop-2-enoic and (E)-3-(4-methoxyphenyl)prop-2-enoic acids and (2S)-cyanopyrrolidine have been shown to significantly reduce blood glucose levels in mice. The observed hypoglycemic effect at a dose of 10 mg/kg is comparable to the effect of hypoglycemic drug vildagliptin.

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ACKNOWLEDGMENTS

The authors thank the Chemical Research Center for Collective Use of the Siberian Branch of the Russian Academy of Sciences for carrying out spectral and analytical measurements.

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Authors and Affiliations

  1. Vorozhtsov Novosibirsk Institute of Organic Chemistry, Siberian Branch of the Russian Academy of Sciences, 630090, Novosibirsk,, Russia

    S. O. Kuranov, M. E. Blokhin, S. A. Borisov, M. V. Khvostov, O. A. Luzina & N. F. Salakhutdinov

  2. Novosibirsk State University, 630090, Novosibirsk,, Russia

    M. E. Blokhin, M. V. Khvostov & N. F. Salakhutdinov

Authors
  1. S. O. Kuranov
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  2. M. E. Blokhin
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  3. S. A. Borisov
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  4. M. V. Khvostov
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  5. O. A. Luzina
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  6. N. F. Salakhutdinov
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Correspondence to S. O. Kuranov.

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The authors state that there is no conflict of interests.

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Translated by A. Levina

Abbreviations: GTT, glucose tolerance test; DPP-4, dipeptidyl peptidase-4; DM-2, type 2 diabetes mellitus; GLP-1, glucagon-like peptide-1; GIP, glucose-dependent insulinotropic polypeptide.

Corresponding author: fax: (383) 330 9752; e-mail: s.o.kuranov@chemomsu.ru.

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Kuranov, S.O., Blokhin, M.E., Borisov, S.A. et al. Synthesis and Hypoglycemic Activity of Aryl(Hetaryl)Propenoic Cyanopyrrolidine Amides. Russ J Bioorg Chem 45, 374–380 (2019). https://doi.org/10.1134/S1068162019050078

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