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Pyridoxal: A New Alkylating Agent in Reactions with Phenols and Polyphenols

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Abstract

A possibility to use pyridoxal as an alkylating agent in the reactions of electrophilic mono-, di-, and trisubstitution in the aromatic core of various phenols and polyphenols was demonstrated for the first time. New types of hydroxyl-containing aromatic aldehydes containing vitamin B6 fragment were obtained, and the conditions for their synthesis were optimized.

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References

  1. Heyl, D., Luz, E., Harris, S.A., and Folkers, K., J. Am. Chem. Soc., 1948, vol. 70, p. 3669. doi 10.1021/ja01191a038

    Article  CAS  PubMed  Google Scholar 

  2. Heyl, D., Luz, E., Harris, S.A., and Folkers, K., J. Am. Chem. Soc., 1948, vol. 70, p. 3429. doi 10.1021/ja01190a061

    Article  CAS  PubMed  Google Scholar 

  3. Heyl, D., Luz, E., Harris, S.A., and Folkers, K., J. Am. Chem. Soc., 1952, vol. 74, p. 414. doi 10.1021/ja01122a038

    Article  CAS  Google Scholar 

  4. Metzler, D.E., Ikawa, M., and Snell, E.E., J. Am. Chem. Soc., 1954, vol. 76, p. 648. doi 10.1021/ja01632a004

    Article  CAS  Google Scholar 

  5. Fogle, E.J., Liu, W., Woon, S.T., Keller, J.W., and Toney, M.D., Biochemistry, 2005, vol. 44, p. 16392. doi 10.1021/bi051475b

    Article  CAS  PubMed  Google Scholar 

  6. Sun, S. and Toney, M.D., Biochemistry, 1999, vol. 38, p. 4058. doi 10.1021/bi982924t

    Article  CAS  PubMed  Google Scholar 

  7. Watanabe, A., Yosimura, T., Mikami, B., Hayashi, H., Kagamiyama, H., and Esaki, N., J. Biol. Chem., 2002, vol. 277, p. 19166. doi 10.1074/jbc.m201615200

    Article  CAS  PubMed  Google Scholar 

  8. Major, D.T. and Gao, J., J. Am. Chem. Soc., 2006, vol. 128, no. 50, p. 16345. doi 10.1021/ja066334r

    Article  CAS  PubMed  Google Scholar 

  9. Christen, P. and Metzler, D.E., Transaminases, New York: Wiley, 1985, 643 р.

    Google Scholar 

  10. Hayashi, H., Mizuguch, H., Miyahara, I., Islam, M.M., Ikushiro, H., Nakajima, Y., Hirotsu, K., and Kagamiyama, H., Biochim. Biophys. Acta, 2003, vol. 1647, p. 103. doi 10.1016/s1570-9639(03)00068-2

    Article  CAS  PubMed  Google Scholar 

  11. Liu, W., Peterson, P.E., Langston, J.A., Jin, X., Zhou, X., Fisher, A.J., and Toney, M.D., Biochemistry, 2005, vol. 44, no. 8, p. 2982. doi 10.1021/bi048657a

    Article  CAS  PubMed  Google Scholar 

  12. Korytnuyk, W. and Bauk, B., J. Med. Chem., 1970, vol. 13, p. 187. doi 10.1021/jm00296a005

    Article  Google Scholar 

  13. Kibardina, L.K., Trifonov, A.V., Dobrynin, A.B., Burilov, A.R., and Pudovik, M.A., Heteroatom Chem., 2016, vol. 27, p. 221. doi 10.1002/hc.21319

    Article  CAS  Google Scholar 

  14. Eliot, A.C. and Kirsch, J.F., Annu. Rev. Biochem., 2004, vol. 73, p. 383. doi 10.1146/annurev.biochem. 73.011303.074021

    Article  CAS  PubMed  Google Scholar 

  15. Toney, M.D., Arch. Biochem. Biophys., 2005, vol. 433, p. 279. doi 10.1016/j.abb.2004.09.037

    Article  CAS  PubMed  Google Scholar 

  16. Gutsche, C.D., Calixarenes, Cambridge: Royal Society of Chemistry, 2008.

    Google Scholar 

  17. Kibardina, L.K., Gasisov, A.S., Burilov, A.R., and Pudovik, M.A., Synthesis, 2015, vol. 47, p. 721. doi 10.1055/s-0034-1378684

    CAS  Google Scholar 

  18. 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, p. 209. doi 10.1097/00004872-200018020-00012

    Article  CAS  PubMed  Google Scholar 

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

    Article  CAS  PubMed  Google Scholar 

  20. Middleton, E., Jr., Kandaswami, C., and Theoharides, T.C., Pharmacol. Rev., 2000, vol. 52, p. 673. doi 0031-6997/00/5204-0673$03.00/0

    CAS  Google Scholar 

  21. Nishino, H., Murakoshi, M., Mou, X.Y., Wada, S., Masuda, M., Ohsaka, Y., Satomi, Y., and Jinno, K., Oncology, 2005, vol. 69, p. 38. doi 10.1159/000086631

    Article  CAS  PubMed  Google Scholar 

  22. Brigelius-Flohe, R. and Traber, M.G., FASEB J., 1999, vol. 13, p. 1145. doi 10.1096/fasebj.13.10.1145

    Article  CAS  PubMed  Google Scholar 

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Authors and Affiliations

  1. Arbuzov Institute of Organic and Physical Chemistry, FRC Kazan Scientific Center of the Russian Academy of Sciences, ul. Akademika Arbuzova 8, Kazan, Tatarstan, 420088, Russia

    L. K. Kibardina, A. V. Trifonov, A. R. Burilov, A. S. Gazizov & M. A. Pudovik

  2. Kazan National Research Technological University, Kazan, Tatarstan, Russia

    A. V. Trifonov

Authors
  1. L. K. Kibardina
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  2. A. V. Trifonov
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  3. A. R. Burilov
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  4. A. S. Gazizov
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  5. M. A. Pudovik
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Corresponding author

Correspondence to L. K. Kibardina.

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Dedicated to the 110th anniversary of M.I. Kabachnik’s birth

Original Russian Text © L.K. Kibardina, A.V. Trifonov, A.R. Burilov, A.S. Gazizov, M.A. Pudovik, 2018, published in Zhurnal Obshchei Khimii, 2018, Vol. 88, No. 9, pp. 1486–1492.

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Kibardina, L.K., Trifonov, A.V., Burilov, A.R. et al. Pyridoxal: A New Alkylating Agent in Reactions with Phenols and Polyphenols. Russ J Gen Chem 88, 1832–1837 (2018). https://doi.org/10.1134/S1070363218090116

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  • DOI: https://doi.org/10.1134/S1070363218090116

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