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Synthesis, Molecular Docking, and Biological Activity of Antimetabolites Based on Uracils and 5-Substituted 2,6-Dimethylpyrimidin-4(3H)-ones

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Abstract

5-Substituted 2,4-dimethyl-1,6-dihydropyrimidin-6-ones reacted with aromatic aldehydes to give 5-substituted 2-[(E)-2-arylethenyl]pyrimidin-6-ones, and the reaction of 5-(4-fluorobenzyl)-2,6-dimethylpyrimi­din-4(3H)-one with 4-fluorobenzaldehyde produced 5-(4-fluorobenzyl)-2,6-bis[(E)-2-(4-fluorophenyl)ethenyl]­pyrimidin-4(3H)-one. Uracil and 5-fluorouracil were alkylated with 2-(chloromethyl)-4-methoxybenzaldehyde, and the resulting 3-[2,4-dioxo- and 5-fluoro-2,4-dioxo-1,2,3,4-tetrahydropyrimidin-1-yl)methyl]-4-methoxy­benz­aldehydes were condensed with 5-substituted 2,4-dimethyl-1,6-dihydropyrimidin-6-ones to obtain 1-(5-{(E)-2-[5-(butyl, arylmethyl)-4-methyl-6-oxo-1,6-dihydropyrimidin-2-yl]ethenyl}-2-methoxybenzyl)­uracil, -5-fluorouracil, and -5-bromouracil. The synthesized compounds were evaluated for their antibacterial, antitumor, and anti-monoaminoxidase activities, and their molecular docking to some biological targets was performed.

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Fig. 1.

CONFLICT OF INTEREST

The authors declare the absence of conflict of interest.

Notes

  1. Hereinafter, primed locants refer to the substituent at position 5 of the pyrimidine ring, and double-primed locants, to the substituent at position 2.

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Funding

This work was supported by ongoing institutional funding. No additional grants to carry out or direct this particular research were obtained.

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Authors and Affiliations

  1. Scientific Technological Center of Organic and Pharmaceutical Chemistry, National Academy of Sciences of Armenia, 0014, Yerevan, Armenia

    A. A. Harutyunyan, A. S. Sumbatyan, H. A. Panosyan, A. S. Grigoryan, H. M. Stepanyan & R. E. Muradyan

  2. Scientific and Production Center “Armbiotechnology,” National Academy of Sciences of Armenia, 0056, Yerevan, Armenia

    A. A. Hambardzumyan

Authors
  1. A. A. Harutyunyan
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  2. A. S. Sumbatyan
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  3. A. A. Hambardzumyan
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  4. H. A. Panosyan
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  5. A. S. Grigoryan
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  6. H. M. Stepanyan
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  7. R. E. Muradyan
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Corresponding authors

Correspondence to A. A. Harutyunyan or A. A. Hambardzumyan.

Additional information

Translated from Zhurnal Organicheskoi Khimii, 2023, Vol. 59, No. 9, pp. 1179–1192 https://doi.org/10.31857/S0514749223090082.

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Harutyunyan, A.A., Sumbatyan, A.S., Hambardzumyan, A.A. et al. Synthesis, Molecular Docking, and Biological Activity of Antimetabolites Based on Uracils and 5-Substituted 2,6-Dimethylpyrimidin-4(3H)-ones. Russ J Org Chem 59, 1511–1522 (2023). https://doi.org/10.1134/S1070428023090087

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