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Amides of substituted 3-(pteridin-6-yl)propanoic acids: synthesis, spectral characteristics, and cytotoxic activity

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Chemistry of Heterocyclic Compounds Aims and scope

A heterocyclization reaction of 5,6-diamino-1-methyluracil and 2-oxopentanedioic acid was used in this study to synthesize 3-(1-methyl-2,4,7-trioxo-1,2,3,4,7,8-hexahydropteridin-6-yl)propanoic acid, intramolecular cyclization of which led to the formation of a tricyclic lactone, namely, 1-methyl-6,7-dihydro-2H-pyrano[3,2-g]pteridine-2,4,8-(1H,3H)-trione. Reactions of the latter with N-nucleophiles gave a series of amides – structural analogs of antifolates. The structure and identity of the synthesized compounds were confirmed by IR spectroscopy, 1H and 13C NMR spectroscopy, LC-MS analysis, and mass spectrometry. It was established that the synthesized compounds showed cytotoxic effects against human hepatocellular carcinoma (HepG2) cells and may be of interest for further studies of their antitumor activity against other cell lines.

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Authors and Affiliations

  1. Zaporizhzhya State Medical University, 26 Mayakovs’koho Ave., Zaporizhzhia, 69035, Ukraine

    Maxim S. Kazunin, Oleksii Yu. Voskoboynik & Sergiy I. Kovalenko

  2. National University of Pharmacy, Laboratory of Morphofunctional Research, 12 Kulikovska St., Kharkiv, 61000, Ukraine

    Oksana M. Shatalova & Ludmila N. Maloshtan

Authors
  1. Maxim S. Kazunin
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  2. Oleksii Yu. Voskoboynik
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  3. Oksana M. Shatalova
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  4. Ludmila N. Maloshtan
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  5. Sergiy I. Kovalenko
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Correspondence to Sergiy I. Kovalenko.

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Translated from Khimiya Geterotsiklicheskikh Soedinenii, 2019, 55(4/5), 408–415

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Kazunin, M.S., Voskoboynik, O.Y., Shatalova, O.M. et al. Amides of substituted 3-(pteridin-6-yl)propanoic acids: synthesis, spectral characteristics, and cytotoxic activity. Chem Heterocycl Comp 55, 408–415 (2019). https://doi.org/10.1007/s10593-019-02473-x

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  • DOI: https://doi.org/10.1007/s10593-019-02473-x

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