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Synthesis, Antiaggregant, and Antioxidant Activity of 2-{[1-iso-butyl-3-methyl-7-(thietanyl-3)xanthin-8-yl]thio}acetic Acid Salts

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Pharmaceutical Chemistry Journal Aims and scope

8-Bromo-1-iso-butyl-3-methyl-7-(thietanyl-3)xanthine (II) was synthesized by alkylation of 8-bromo-3-methyl-7-(thietanyl-3)xanthine (I) with isobutyl bromide. Nucleophilic substitution of II with thioglycolic acid gave 2{[1-iso-butyl-3-methyl-7-(thietanyl-3)xanthin-8-yl]thio}acetic acid (III). A series of water-soluble salts of 2{[1-iso-butyl-3-methyl-7-(thietanyl-3)xanthin-8-yl]thio}acetic acid (IVa-h) were synthesized by reaction of III with organic and inorganic bases. Compounds possessing antiaggregant activity on the level of acetylsalicylic acid were found among salts IV. All obtained compounds except for IVa and IVc suppressed lipid peroxidation less than ascorbic acid. However, all synthesized compounds suppressed generation of reactive oxygen species by phagocytes, in contrast to ascorbic acid.

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References

  1. D. T. Schmidt, N. Watson, G. Dent, et al., Br. J. Pharmacol., 131(8), 1607 – 1618 (2000).

    Article  CAS  Google Scholar 

  2. S. Cappelletti, P. Daria, G. Sani, and M. Aromatario, Curr. Neuropharmacol., 13(1), 71 – 88 (2015).

    Article  CAS  Google Scholar 

  3. P. J. Barnes, Am. J. Respir. Crit. Care Med., 188(8), 901 – 906 (2013).

    Article  CAS  Google Scholar 

  4. M. D. Mashkovskii, Drugs [in Russian], Novaya Volna, Umerenkov, Moscow (2014).

  5. A. V. Gulevskaya and A. F. Pozharskii, Khim. Geterotsikl. Soedin., 27(1), 1 – 23 (1991).

    Google Scholar 

  6. D. A. Babkov, A. N. Geisman, A. L. Khandazhinskaya, and M. S. Novikov, Usp. Khim., 85(3), 308 – 334 (2016).

    Article  CAS  Google Scholar 

  7. N. Singh, A. K. Shreshtha, M. S. Thakur, and S. Patra, Heliyon, 4(10), e00829 (2018).

    Article  Google Scholar 

  8. A. A. Spasov, F. A. Khaliullin, D. A. Babkov, et al., Khim.-farm. Zh., 51(7), 13 – 19 (2017).

    Google Scholar 

  9. R. Baetta and A. Corsini, Drugs, 71(11), 1441 – 1467 (2011).

    Article  CAS  Google Scholar 

  10. S. H. Havale and P. Manojit, Bioorg. Med. Chem., 17, 1783 – 1802 (2009).

    Article  CAS  Google Scholar 

  11. F. A. Khaliullin, Yu. V. Shabalina, G. G. Davlyatova, and L. A. Valeeva, Khim-farm. Zh., 51(12), 3 – 6 (2017).

    Google Scholar 

  12. L. A. Valeeva, G. G. Davlyatova, Yu. V. Shabalina, et al., Khim.-farm. Zh., 50(6), 8 – 11 (2016).

  13. A. Swierczek, E. Wyska, K. Pociecha, et al., Xenobiotica, 49(10), 1209 – 1220 (2019).

    Article  CAS  Google Scholar 

  14. Yu. V. Shabalina, F. A. Khaliullin, A. A. Spasov, et al., Khim-farm. Zh., 47(3), 27 – 29 (2013).

    Google Scholar 

  15. F. A. Khaliullin, Yu. V. Shabalina, A. V. Samorodov, et al., Khim.-farm. Zh., 52(1), 29 – 32 (2018).

  16. Yu. V. Shabalina, A. V. Samorodov, F. A. Khaliullin, et al., Med. Vestn. Bashk., 12(6), 63 – 67 (2017).

    Google Scholar 

  17. F. A. Khaliullin, Yu. V. Shabalina, A. V. Samorodov, et al., Med. Vestn. Bashk., 11(5), 140 – 144 (2016).

    Google Scholar 

  18. A. V. Samorodov, F. Kh. Kamilov, F. A. Khaliullin, et al., Vopr. Biol., Med. Farm. Khim., No. 8, 10 – 17 (2016).

  19. J. A. Schroeder, J. D. Ruta, J. S. Gordon, et al., Behav. Pharmacol., 23(3), 310 – 314 (2012).

    Article  CAS  Google Scholar 

  20. Y. Usachev and A. Verkhratsky, Cell Calcium, 17(3), 197 – 206 (1995).

    Article  CAS  Google Scholar 

  21. Q. Huai, H. Wang, and W. Zhang, Proc. Natl. Acad. Sci. USA, 101(26), 9624 – 9629 (2004).

    Article  CAS  Google Scholar 

  22. T. P. Geisbuhler, T. L. Shwager, and H. D. Ervin, Biochem. Pharmacol., 63(11), 2055 – 2062 (2002).

    Article  CAS  Google Scholar 

  23. V. B. Bhat and K. M. Madyastha, Biochem. Biophys. Res. Commun., 288(5), 1212 – 1217 (2001).

    Article  CAS  Google Scholar 

  24. S. Constantin, F. G. Lupascu, M. Apotrosoaei, et al., Chem. Cent. J., 11(12), (2017).

  25. F. G. Lupascu, O. M. Dragostin, L. Foia, et al., Molecules, 18(8), 9684 – 9703 (2013).

    Article  CAS  Google Scholar 

  26. F. A. Khaliullin, V. A. Kataev, and Yu. V. Strokin, Khim. Geterotsikl. Soedin., No. 4, 516 – 518 (1991).

  27. A. N. Mironov (ed.), Handbook for Preclinical Drug Trials [in Russian], Vol. 1, Grif i K, Moscow (2012), pp. 453 – 458.

    Google Scholar 

  28. R. R. Farkhutdinov and S. I. Tevdoradze, Methods for Studying Chemiluminescence of Biological Material in a KhL-003 Chemiluminometer. Methods for Evaluating Antioxidant Activity of Biologically Active Compounds [in Russian], RUDN, Moscow (2005), pp. 147 – 154.

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Authors and Affiliations

  1. Bashkir State Medical University, Ministry of Health of the Russian Federation, Ufa, Bashkortostan, 450008, Russia

    F. A. Khaliullin, Zh. K. Mamatov, G. A. Timirkhanova & A. V. Samorodov

  2. Izhevsk State Medical Academy, Ministry of Health of the Russian Federation, Izhevsk, 426034, Russia

    L. I. Bashirova

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  1. F. A. Khaliullin
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  2. Zh. K. Mamatov
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  3. G. A. Timirkhanova
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  4. A. V. Samorodov
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  5. L. I. Bashirova
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Correspondence to F. A. Khaliullin.

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Translated from Khimiko-Farmatsevticheskii Zhurnal, Vol. 54, No. 9, pp. 9 – 14, September, 2020.

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Khaliullin, F.A., Mamatov, Z.K., Timirkhanova, G.A. et al. Synthesis, Antiaggregant, and Antioxidant Activity of 2-{[1-iso-butyl-3-methyl-7-(thietanyl-3)xanthin-8-yl]thio}acetic Acid Salts. Pharm Chem J 54, 891–896 (2020). https://doi.org/10.1007/s11094-020-02293-w

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  • DOI: https://doi.org/10.1007/s11094-020-02293-w

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