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Some Features of Phosphorylation and Benzoylation of Pyridoxal Imidazolidines

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Abstract

The reactions of pyridoxal imidazolidines with diphenylchlorophosphine oxide, depending on the substituents nature in the imidazolidine ring, resulted in the formation of new salt-like tricyclic structures or a bisalt structure based on N,N′-dibenzylethylenediamine and diphenylphosphinic acid. The benzoylation of pyridoxal imidazolidines also led to decomposition of the imidazolidine fragment with the formation of dibenzoylated N,N′-dimethylethylenediamine.

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REFERENCES

  1. Speck, U., Patent US 5288716, 1994. USA.

  2. Müller, I.B., Wu, F., Bergmann, B., Knöckel, J., Walter, R.D., Gehring, H., and Wrenger, C., PLoS One, 2009, vol. 4, p. 4406. https://doi.org/10.1371/journal.pone.0004406

    Article  CAS  Google Scholar 

  3. Brokamp, R., Bergmann, B., Müller, I.B., and Bienz, S., Bioorg. Med. Chem., 2014, vol. 22, p. 1832. https://doi.org/10.1016/j.bmc.2014.01.057

    Article  CAS  PubMed  Google Scholar 

  4. Zhuravel, I.O., Kovalenko, S.M., Ivachtchenko, A.V., Balakin, K.V., and Kazmirchuk, V.V., Bioorg. Med. Chem. Lett., 2005, vol. 15, p. 5483. https://doi.org/10.1016/j.bmcl.2005.08.081

    Article  CAS  PubMed  Google Scholar 

  5. Heidari, A., Noshiranzadeh, N., Haghi, F., and Bikas, R., Microb. Pathogenesis, 2017, vol. 112, p. 103. https://doi.org/10.1016/j.micpath.2017.09.043

    Article  CAS  Google Scholar 

  6. Pereira, M.B., Fontana, L.A., Siqueira, J.D., Auras, B.L., Da Silva, M.P., Neves, A., Gabriel, P., Terenzi, H., Iglesias, B.A., and Back, D.F., Inorg. Chim. Acta, 2018, vol. 469, p. 561. https://doi.org/10.1016/j.ica.2017.09.063

    Article  CAS  Google Scholar 

  7. Kesel, A.J., Bioorg. Med. Chem., 2003, vol. 11, p. 4599. https://doi.org/10.1016/S0968-0896(03)00500-5

    Article  CAS  PubMed  PubMed Central  Google Scholar 

  8. Garay, R.P., Nazaret, C., Diez, J., Etienne, A., Bourgain, R., and Braquet, P., Biochem. Pharmacol., 1984, vol. 33, p. 2013. https://doi.org/10.1016/0006-2952(84)90567-7

    Article  CAS  PubMed  Google Scholar 

  9. Page, J., Page, K., and Cornett, G., US Patent EP 1951264, 2008.

  10. Bagrov, A.Y., Dmitrieva, R.I., Dorofeeva, N.A., Fedorova, O.V., Lopatin, D.A., Lakatta, E.G., and Droy-Lefaix, M.T., J. Hypertens., 2000, vol. 18. 209. https://doi.org/10.1097/00004872-200018020-00012

  11. Heyl, D., Luz, E., Harris, S.A., and Folkers, K., J. Am. Chem. Soc., 1951, vol. 73, p. 3430. https://doi.org/10.1021/ja01151a125

    Article  CAS  Google Scholar 

  12. Kibardina, L.K., Trifonov, A.V., Burilov, A.R., Pudovik, M.A., Dobrynin, A.B., and Pudovik, E.M., Russ. J. Org. Chem., 2015, vol. 51, p. 1510. https://doi.org/10.1134/S1070428015100280

    Article  CAS  Google Scholar 

  13. Kibardina, L.K., Chumakova, L.V., Gazizov, A.S., Burilov, A.R., and Pudovik, M.A., Synthesis, 2015, vol. 47, p. 721. https://doi.org/10.1055/s-0034-1378684

    Article  CAS  Google Scholar 

  14. Naskar, S., Butcher, R.J., and Chattopadhyay, S.K., Inorg. Chim. Acta, 2010, vol. 363, p. 404. https://doi.org/10.1016/j.ica.2009.11.007

    Article  CAS  Google Scholar 

  15. Sharif, Sh., Schagen, D., Toney, M.D., and Limbach, H.H., J. Am. Chem. Soc., 2007, vol. 129, p. 4440. https://doi.org/10.1021/ja066240h

    Article  CAS  PubMed  Google Scholar 

  16. Kibardina, L.K., Trifonov, A.V., Dobrynin, A.B., Pudovik, M.A., and Burilov, A.R., Mendeleev Commun., 2018, vol. 28, p. 551. https://doi.org/10.1016/j.mencom.2018.09.035

    Article  CAS  Google Scholar 

  17. Nakagawa, K., Yoshimura, I., Sueda, N., and Fukawa, H., Agric. Biol. Chem., 1977, vol. 41, p. 1431. https://doi.org/10.1271/bbb1961.41.1431

    Article  CAS  Google Scholar 

  18. Hongping, B. and Houyuan, Z., China Patent CN101525330 (A), 2009.

  19. Kibardina, L.K., Bagautdinova, R.H., Dobrynin, A.B., Burilov, A.R., Pudovik, M.A., Trifonov, A.V., and Pudovik, E.M., Russ. J. Gen. Chem., 2016, vol. 86, p. 607. https://doi.org/10.1134/S1070363216030178

    Article  CAS  Google Scholar 

  20. Karlsson, S., Liljefors, T., and Sandström, J., Acta Chem. Scand. (B), 1977, vol. 31, p. 399. https://doi.org/10.3891/acta.chem.scand.31b-0399

    Article  Google Scholar 

  21. Bauer, L., J. Am. Chem. Soc., 1956, vol. 78, p. 1945. https://doi.org/10.1021/ja01590a049

    Article  CAS  Google Scholar 

  22. Sheldrick, G.M., SADABS. Bruker AXS Inc., Madison, USA, 1997.

  23. Altomare, A., Cascarano, G., Giacovazzo, C., and Viterbo, D., Acta Crystallogr. (A), 1991, vol. 47, p. 744. https://doi.org/10.1107/S0108767391006566

    Article  Google Scholar 

  24. Sheldrick, G.M., SHELX-97. Programs for Crystal Structure Analysis (Release 97-2). University of Göttingen, 1997, vol. 1, 2.

  25. Farrugia, L.J., J. Appl. Crystallogr., 1999, vol. 32, p. 837. https://doi.org/10.1107/S0021889899006020

    Article  CAS  Google Scholar 

  26. APEX2 (Version 2.1), SAINTPlus. Data Reduction and Correction Program (Version 7.31A), Bruker Advanced X-ray Solutions, Bruker AXS Inc., Madison, Wisconsin, USA, 2006.

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ACKNOWLEDGMENTS

The authors are grateful to the Collective Spectro-Analytical Center for Physicochemical Research 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.

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Authors and Affiliations

  1. Arbuzov Institute of Organic and Physical Chemistry, FRC Kazan Scientific Center, Russian Academy of Sciences, 420088, Kazan, Russia

    L. K. Kibardina, A. V. Trifonov, A. B. Dobrynin, M. A. Pudovik & A. R. Burilov

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  1. L. K. Kibardina
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  2. A. V. Trifonov
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  3. A. B. Dobrynin
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  4. M. A. Pudovik
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  5. A. R. Burilov
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Correspondence to A. V. Trifonov.

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Additional information

Translated from Zhurnal Obshchei Khimii, 2021, Vol. 91, No. 9, pp. 1382–1389 https://doi.org/10.31857/S0044460X21090092.

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Kibardina, L.K., Trifonov, A.V., Dobrynin, A.B. et al. Some Features of Phosphorylation and Benzoylation of Pyridoxal Imidazolidines. Russ J Gen Chem 91, 1667–1673 (2021). https://doi.org/10.1134/S1070363221090097

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  • DOI: https://doi.org/10.1134/S1070363221090097

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