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Synthesis of new aminomethylated phosphaneoflavonoid derivatives

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Abstract

Phosphaneoflavonoids interact with paraformaldehyde and amines in the Mannich reaction forming new aminomethylated derivatives. The structure of all synthesized compounds was established using 1H, 13C, and 31P NMR spectroscopy, IR spectroscopy, mass spectrometry, and by using elemental analysis data. Biological tests have shown that 4-[2,4-dihydroxy-5-(morpholinylmethyl)phenyl]-2-hydroxy-5,7,8-trimethyl-3,4-dihydrobenzo[e][1,2]oxaphosphinine-2-oxide (2a) and 4-[2,4-dihydroxy-3-methyl-5-(morpholinylmethyl)phenyl]-2-hydroxy-5,7,8-trimethyl-3,4-dihydrobenzo[e][1,2]oxaphosphinine-2-oxide (2b) in relation to cell lines of cervical carcinoma (M-HeLa) and adenocarcinoma of the duodenum (HuTu 80) exhibit moderate activity IC50 of 100±8.2 and 96.7±7.6 µmol L−1, respectively. These compounds turned out to be less toxic in relation to normal cells in comparison with 5-fluorouracil.

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Authors and Affiliations

  1. A. E. Arbuzov Institute of Organic and Physical Chemistry, Russian Academy of Sciences, Federal Research Center Kazan Scientific Center of the Russian Academy of Sciences, 8 ul. Acad. Arbuzova, 420088, Kazan, Russian Federation

    A. V. Zalaltdinova, V. V. Sennikova, Yu. M. Sadykova, A. S. Gazizov, A. D. Voloshina, S. K. Amerkhanova, A. R. Burilov & M. A. Pudovik

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  1. A. V. Zalaltdinova
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  2. V. V. Sennikova
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  3. Yu. M. Sadykova
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  4. A. S. Gazizov
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  5. A. D. Voloshina
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  6. S. K. Amerkhanova
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  7. A. R. Burilov
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  8. M. A. Pudovik
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Corresponding author

Correspondence to A. R. Burilov.

Additional information

The authors of the work express their gratitude to the Collective Spectro-Analytical Center for Physical and Chemical Studies of the Structure, Properties, and Composition of Substances and Materials of the Federal Research Center “Kazan Scientific Center of the Russian Academy of Sciences” for technical support of the studies.

No human or animal subjects were used in this research.

The authors declare no competing interests.

Published in Russian in Izvestiya Akademii Nauk. Seriya Khimicheskaya, Vol. 72, No. 7, pp. 1606–1611, July, 2023.

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Zalaltdinova, A.V., Sennikova, V.V., Sadykova, Y.M. et al. Synthesis of new aminomethylated phosphaneoflavonoid derivatives. Russ Chem Bull 72, 1606–1611 (2023). https://doi.org/10.1007/s11172-023-3940-9

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  • DOI: https://doi.org/10.1007/s11172-023-3940-9

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