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Synthesis and properties of fluorinated uracils as promising drugs for medicine

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Abstract

5-Fluorouracil is a well-known and widely used drug in medical practice for the treatment of cancer. However, there is no analytical review in the literature on the synthesis of 5-fluorouracil and its prodrugs, the properties of these compounds and the factors affecting their metabolism. In the present mini review, we made an attempt to summarize and analyze available material on these issues.

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References

  1. G. M. Blackburn, M. J. Gait, D. Loakes, D. M. Williams, Nucleic Acids in Chemistry and Biology, Royal Society of Chemistry, Cambridge, 2006, 470 p.

    Google Scholar 

  2. C. Heidelberger, F. J. Ansfield, Cancer Res., 1963, 23, 1226.

    CAS  PubMed  Google Scholar 

  3. H. Luellmann, K. Mohr, A. Ziegler, D. Bieger, Color Atlas of Pharmacology, 2nd ed., Thieme, Stuttgart—New York, 2000, 368 pp.

    Google Scholar 

  4. S. L. Guturov, N. N. Semenov, E. I. Zagrekova, Rus. Med. Zhurn. [Russ. Med. J.], 2001, 9, No. 22, 1017 (in Russian).

    Google Scholar 

  5. A. V. Semakov, A. A. Blinkov, G. P. Gaenko, A. G. Vostrova, J. G. Molotkovsky, Russ. J. Bioorg. Chem., 2013, 39, 299; DOI: https://doi.org/10.1134/S1068162013030138.

    Article  CAS  Google Scholar 

  6. Yu. I. Murinov, S. A. Grabovskii, N. N. Kabal’nova, Russ. Chem. Bull., 2019, 68, 946; DOI: https://doi.org/10.1007/s11172-019-2505-4.

    Article  CAS  Google Scholar 

  7. E. N. Knyazev, S. V. Nikulin, A. Yu. Khristichenko, T. N. Gerasimenko, O. V. Kindeeva, V. A. Petrov, G. A. Belyakova, D. V. Maltseva, Russ. Chem. Bull., 2019, 68, 2344; DOI: https://doi.org/10.1007/s11172-019-2709-7.

    Article  CAS  Google Scholar 

  8. J.-P. Bégué, D. Bonnet-Delpon, Bioorganic and Medicinal Chemistry of Fluorine, Wiley, Hoboken, 2008, 365 pp.

    Book  Google Scholar 

  9. A. Tressaud, G. Haufe, Fluorine and Health. Molecular Imaging, Biomedical Materials and Pharmaceuticals, Elsevier, Amsterdam, 2008, p. 553–778.

    Google Scholar 

  10. P. Kirsch, Modern Fluoroorganic Chemistry: Synthesis, Reactivity, Applications; Wiley-VCH, Weinheim, 2013, 320 pp.

    Book  Google Scholar 

  11. R. Duschinsky, E. Pleven, C. Heidelberger, J. Am. Chem. Soc., 1957, 79, 4559; DOI: https://doi.org/10.1021/ja01573a087.

    Article  CAS  Google Scholar 

  12. R. Duschinsky, T. Gabriel, W. Tautz, A. L. Nussbaum, M. Hoffer, E. Grunberg, J. H. Burchenal, J. J. Fox, Nucleosides, 1967, 37, 47.

    Google Scholar 

  13. Medicinal Chemistry of Nucleic Acids, Eds L.-H. Zhang, L. Xi, J. Chattopadhyaya, Wiley, Hoboken, 2011, 456 pp.

    Google Scholar 

  14. S. Hironao, Yu. Iida, K. Ikawa, Yo. Sawama, Ya. Monguchi, Yu. Kitade, Yo. Maki, H. Inoue, K. Hirota, Molecules, 2012, 17, 6519; DOI: https://doi.org/10.3390/molecules17066519.

    Article  Google Scholar 

  15. J. Shelton, X. Lu, J. A. Hollenbaugh, J. Hyun. Ch. Franck, A. Raymond, F. Schinazi, Chem. Rev., 2016, 23, 14379; DOI: https://doi.org/10.1021/acs.chemrev.6b00209.

    Article  Google Scholar 

  16. A. A. Markovich, V. A. Gorbunova, Rus. Med. Zhurn. [Russ. Med. J.], 2006, No. 14, 1016 (in Russian).

  17. K. Ohkura, T. Sugaoi, M. Takahashi, K.-i. Seki, Heterocycles, 2007, 72, 691; DOI: https://doi.org/10.3987/COM-06-S(K)54.

    Article  CAS  Google Scholar 

  18. Y. Shibamoto, L. Zhou, H. Hatta, M. Mori, Si. Nishimoto, Jpn. J. Cancer Res., 2000, 91, 433; DOI: https://doi.org/10.1111/j.1349-7006.2000.tb00963.x.

    Article  CAS  Google Scholar 

  19. C. Liu, J. Wang, Y. Xie, H. Chen, MedChemComm, 2017, 8, 385–389; DOI: https://doi.org/10.1039/C6MD00536E.

    Article  CAS  Google Scholar 

  20. D. E. Metzler, Biochemistry: the Chemical Reactions of Living Cell, Elsevier, New York, 1980, Vol. 1, 940 pp.

    Google Scholar 

  21. I. B. Chernikova, S. L. Khursan, L. V. Spirikhin, M. S. Yunusov, Russ. Chem. Bull., 2013, 62, 2445; DOI: https://doi.org/10.1007/s11172-013-0354-0.

    Article  CAS  Google Scholar 

  22. I. B. Chernikova, S. L. Khursan, L. V. Spirikhin, M. S. Yunusov, Chem. Heterocycl. Compd., 2015, 51, 568; DOI: https://doi.org/10.1007/s10593-015-1737-y.

    Article  CAS  Google Scholar 

  23. I. B. Chernikova, M. S. Yunusov, Russ. Chem. Bull., 2020, 69, 2159; DOI: https://doi.org/10.1007/s11172-020-3015-0.

    Article  CAS  Google Scholar 

  24. I. B. Chernikova, L. V. Spirikhin, M. F. Abdullin, M. S. Yunusov, Chem. Nat. Compd., 2017, 53, 1141; DOI: https://doi.org/10.1007/s10600-017-2218-6.

    Google Scholar 

  25. T. B. Lozeron, M. P. Gordon, T. Gabriel, W. Tautz, R. Duschinsky, Biochemistry, 1964, 3, 1844; DOI: https://doi.org/10.1021/bi00900a009.

    Article  CAS  Google Scholar 

  26. S. A. Giller, R. A. Zhuk, M. Yu. Lidak, Dokl. Akad. Nauk SSSR [Dokl. USSR Acad. Sci.], 1967, 176, 332 (in Russian).

    CAS  PubMed  Google Scholar 

  27. O. Miyashita, K. Matsumura, H. Shimadzu, N. Hashimoto, Chem. Pharm. Bull., 1981, 29, 3181. DOI: https://doi.org/10.1248/cpb.29.3181.

    Article  CAS  Google Scholar 

  28. I. B. Chernikova, S. L. Khursan, M. Yu. Eropkin, M. S. Yunusov, Pharm. Chem. J., 2019, 53, 108; DOI: https://doi.org/10.1007/s11094-019-01962-9.

    Article  CAS  Google Scholar 

  29. I. B. Chernikova, M. S. Yunusov, A. G. Mustaphin, Russ. Chem. Bull., 2020, 69, 114; DOI: https://doi.org/10.1007/s11172-020-2731-9.

    Article  CAS  Google Scholar 

  30. R. B. Diasio, B. E. Harris, Clin. Pharmacokinet., 1989, 16, 215; DOI: https://doi.org/10.2165/00003088-198916040.

    Article  CAS  Google Scholar 

  31. Y. Isobe, M. Tobe, Y. Inoue, M. Isobe, M. Tsuchiya, H. Hayashi, Bioorg. Med. Chem., 2003, 11, 4933; DOI: https://doi.org/10.1016/j.bmc.2003.09.012.

    Article  CAS  Google Scholar 

  32. J. P. Henderson, J. Byun, J. Takeshita, J. W. Heinecke, J. Biol. Chem., 2003, 278, 23522; DOI: https://doi.org/10.1074/jbc.M303928200.

    Article  CAS  Google Scholar 

  33. J. Takeshita, J. Byun, T. Q. Nhan, D. K. Pritchard, S. Pennathur, S. M. Schwartz, A. Chait, J. W. Heinecke, J. Biol. Chem., 2006, 281, 3096; DOI: https://doi.org/10.1074/jbc.M509236200.

    Article  CAS  Google Scholar 

  34. O. S. Tee, S. Banerjee, Can. J. Chem., 1979, 57, 626; DOI: https://doi.org/10.1139/v79-101.

    Article  CAS  Google Scholar 

  35. I. B. Chernikova, M. S. Yunusov, Izv. Ufimsk. Nauchn. Tsentra RAN [Bull. Ufa Sci. Center of RAS], 2020, No. 1, 45; DOI: https://doi.org/10.31040/2222-8349-2020-0-1-45-49 (in Russian).

  36. I. B. Chernikova, M. S. Yunusov, Vestn. Bashkirsk. Un-ta [Bull. Bashkir. Univ.], 2021, 26, 605; DOI: https://doi.org/10.33184/bulletin-bsu-2021.3.11 (in Russian).

    Article  Google Scholar 

  37. V. G. Kasradze, I. B. Ignatyeva, R. A. Khusnutdinov, K. Yu. Suponitskii, M. Yu. Antipin, M. S. Yunusov, Chem. Heterocycl. Compd., 2012, 48, 1018; DOI: https://doi.org/10.1007/s10593-012-1094-z.

    Article  CAS  Google Scholar 

  38. I. B. Chernikova, L. V. Spirikhin, A. N. Lobov, M. S. Yunusov, Chem. Nat. Compd., 2017, 53, 714; DOI: https://doi.org/10.1007/s10600-017-2097-x.

    Article  CAS  Google Scholar 

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Correspondence to I. B. Chernikova.

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Dedicated to Academician of the Russian Academy of Sciences O. M. Nefedov on the occasion of his 90th birthday.

Published in Russian in Izvestiya Akademii Nauk. Seriya Khimicheskaya, No. 1, pp. 1–5, January, 2022.

The work was carried out in the framework of the Russian state assignment to the Ufa Institute of Chemistry of the Ufa Federal Research Centre of the Russian Academy of Sciences “Synthesis of biologically active heterocyclic and terpenoid compounds” (Research theme AAAA-A20-120012090026-9, Registration number 0246-2019-0027).

No human or animal subjects were used in this research.

The authors declare no competing interests.

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Chernikova, I.B., Yunusov, M.S. Synthesis and properties of fluorinated uracils as promising drugs for medicine. Russ Chem Bull 71, 1–5 (2022). https://doi.org/10.1007/s11172-022-3370-0

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  • DOI: https://doi.org/10.1007/s11172-022-3370-0

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