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Synthesis and Cytotoxic Activity of 5-Benzoylhexahydropyrimidine Derivatives

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Abstract

The reaction of ethyl benzoylacetate with formaldehyde and natural amino acid ester hydrochlorides in acetate buffer (AcONa/AcOH, pH 4.0) at room temperature afforded 41–61% of new 5-benzoylhexahydropyrimidine derivatives. The synthesized compounds were evaluated for their in vitro cytotoxic activity against normal (HEK293) and tumor cell lines (Jurkat, HepG2). T-Lymphoblastic leukemia Jurkat cells turned out to be most sensitive to the examined hexahydropyrimidine derivatives. Ethyl 5-benzoyl-1,3-bis[2-ethoxy-1-(4-hydroxybenzyl)-2-oxoethyl]hexahydropyrimidine-5-carboxylate showed the highest cytotoxic activity against all tested cell lines.

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ACKNOWLEDGMENTS

The spectral studies were performed using the facilities of the Chemistry joint center (Ufa Institute of Chemistry, Ufa Federal Research Center, Russian Academy of Sciences).

Funding

This study was performed in the framework of state assignment to Ufa Institute of Chemistry, Ufa Federal Research Center, Russian Academy of Sciences (project no. AAAA- A20-120012090031-3).

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Authors and Affiliations

  1. Ufa Institute of Chemistry, Ufa Federal Research Center, Russian Academy of Sciences, 450054, Ufa, Russia

    D. R. Kireeva & V. A. Dokichev

  2. Institute of Biochemistry and Genetics, Ufa Federal Research Center, Russian Academy of Sciences, 450054, Ufa, Russia

    Z. R. Zileeva & D. V. Ishmetova

Authors
  1. D. R. Kireeva
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  2. Z. R. Zileeva
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  3. D. V. Ishmetova
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  4. V. A. Dokichev
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Corresponding author

Correspondence to D. R. Kireeva.

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The authors declare no conflict of interest.

Additional information

Translated from Zhurnal Organicheskoi Khimii, 2021, Vol. 57, No. 7, pp. 1036–1041 https://doi.org/10.31857/S0514749221070156.

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Kireeva, D.R., Zileeva, Z.R., Ishmetova, D.V. et al. Synthesis and Cytotoxic Activity of 5-Benzoylhexahydropyrimidine Derivatives. Russ J Org Chem 57, 1180–1183 (2021). https://doi.org/10.1134/S1070428021070204

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