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Specific features of phase transfer catalytic glycosylation of aromatic hydroxy acids

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Abstract

Reactions of peracetylated α-D-glucosaminyl chloride with isomeric hydroxybenzoic and 1-hydroxy-2-naphthoic acids in a solid phase transfer system of potassium carbonate-acetonitrile were studied. It was found that the nature of carboxylic acids, lipophilicity of the phase transfer catalyst, and reaction temperatures affected the reaction composition and product yields. The O-β-glycosyl esters of ortho-hydroxyaromatic acids were first found to form anomeric 1,2-cis derivatives in the presence of potassium carbonate. The structures of the synthesized compounds were confirmed by 1H NMR spectroscopy. As was shown in vivo experiments, the analgesic activities of glycosyl esters of salicylic acid and peracetylated 2-carboxyphenylglucosaminide were comparable with that of aspirin.

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Abbreviations

15C5:

15-crown-5

PT:

phase transfer

[3.3] DB18C6:

[3.3]-dibenzo-18-crown-6

PTC:

phase transfer catalysis

References

  1. Hongu, M., Saito, K., and Tsujihara, K., Synth. Commun., 1999, vol. 29, pp. 2775–2781.

    Article  CAS  Google Scholar 

  2. Wang, Y., Li, L., Wang, Q., and Li, Yu., Synth. Commun., 2001, vol. 31, pp. 3423–3427.

    Article  CAS  Google Scholar 

  3. Rothermel, J. and Faillard, H., Carbohydr. Res., 1990, vol. 196, pp. 29–40.

    Article  PubMed  CAS  Google Scholar 

  4. Ngameni, B., Patnam, R., Sonna, P., Ngadjui, B.T., Roy, R., and Abegaz, B.M., ARKIVOC, 2008, vol. 6, pp. 152–159. www.arkat-usa.org

    Article  Google Scholar 

  5. Grabley, S., Garies, M., Bockers, W., and Thiem, J., Synthesis, 1992, vol. 27, pp. 1078–1080.

    Article  Google Scholar 

  6. Demetzos, C., Skaltsounis, A.-L., Tillequin, F., and Koch, M., Carbohydr. Res., 1990, vol. 207, pp. 131–137.

    Article  PubMed  CAS  Google Scholar 

  7. Du, Y., Wei, G., and Linhardt, R.J., J. Org. Chem., 2004, vol. 69, pp. 2206–2209.

    Article  PubMed  CAS  Google Scholar 

  8. Alluis, B. and Dangles, O., Helvetica Chimica Acta, 2001, vol. 84, pp. 1133–1156.

    Article  CAS  Google Scholar 

  9. Du, Y., Wei, G., and Linhardt, R.J., Tetrahedron Lett., 2003, vol. 44, pp. 6887–6890.

    Article  CAS  Google Scholar 

  10. Borowiecka, J. and Michalska, M., Synthesis, 1994, no. 7, pp. 709–713.

    Google Scholar 

  11. Borowiecka, J. and Stańczak, A., IlFarmaco, 2001, vol. 56, pp. 257–262.

    Article  CAS  Google Scholar 

  12. Tanaka, S., Hayakawa, K., Umetani, Y., and Tabata, M., Phytochemistry, 1990, vol. 29, pp. 1555–1558.

    Article  CAS  Google Scholar 

  13. Kawano, T., Tanaka, S., Kadono, T., and Muto, S., Z. Naturforsc., 2004, vol. 59c, pp. 684–692.

    Google Scholar 

  14. Strachan, R.G., Ruyle, W.V., Shen, T.Y., and Hirschmann, R., J. Org. Chem., 1966, vol. 31, pp. 507–509.

    Article  CAS  Google Scholar 

  15. Hennig, J., Malamy, J., Grynkiewicz, G., Indulski, J., and Klessig, D.F., Plant J., 1993, vol. 4, pp. 593–600.

    Article  PubMed  CAS  Google Scholar 

  16. Xue, L., Sun, G., and Gao, J., Huaxuefongbao = Chemistry, 1994, no. 1, pp. 30–32. (Ros. Chem. Zh., 1994, 24E18).

    Google Scholar 

  17. Hanessian, S., Mascitti, V., Lu, P.-P., and Ishida, H., Synthesis, 2002, no. 14, pp. 1959–1968.

    Google Scholar 

  18. Samczewska, G. and Borowiecka, J., Acta Poloniae Pharm. Drug Res., 1999, vol. 56, pp. 361–366.

    CAS  Google Scholar 

  19. Grynkiewicz, G., Szeja, W., and Boryski, J., Acta Poloniae Pharm. Drug Res., 2008, vol. 65, pp. 655–676.

    CAS  Google Scholar 

  20. Kuryanov, V.O., Chupakhina, T.A., Zemlyakov, A.E., Kotlyar, S.A., Kamalov, G.L., and Chirva, V.Ya., Russ. J. Bioorg. Chem., 2001, vol. 27, pp. 385–389.

    Article  CAS  Google Scholar 

  21. Chupakhina, T.A., Kur’yanov, V.O., Chirva, V.Ya., Grigorash, R.Ya., Kotlyar, S.A., and Kamalov, G.L., Russ. J. Bioorg. Chem., 2004, vol. 30, pp. 301–303.

    Article  CAS  Google Scholar 

  22. Kuryanov, V.O., Katsev, A.M., Chupakhina, T.A., and Chirva, V.Ya., Zh. Org. Farm. Khim., 2009, vol. 7, pp. 30–40.

    CAS  Google Scholar 

  23. Kuryanov, V.O., Chupakhina, T.A., Shapovalova, A.A., Katsev, A.M., and Chirva, V.Ya., Russ. J. Bioorg. Chem., 2011, vol. 37, pp. 231–239

    Article  CAS  Google Scholar 

  24. Kuryanov, V.O., Chupakhina, T.A., and Chirva, V.Ya., Zh. Org. Farm. Khim., 2009, vol. 7, pp. 57–63.

    CAS  Google Scholar 

  25. Kuryanov, V.O., Chupakhina, T.A., Shishkin, O.V., Shishhkina, S.V., and Chirva, V.Ya., Russ. J. Bioorg. Chem., 2008, vol. 34, pp. 730–738.

    Article  CAS  Google Scholar 

  26. Caram, S.M. and Shen, K.F., Brain Res., 2001, vol. 888, pp. 75–82.

    Article  Google Scholar 

  27. Mashkovskii, M.D., Lekarstvennye sredstva. Posobie dlya vrachei: (Drugs: Manual for Doctors), Moscow: Novaya volna, 2002.

    Google Scholar 

  28. Metody issledovaniya uglevodov (Methods of Carbohydrate Research), Khorlin, A.Ya., Ed., Moscow: Mir, 1975, pp. 221–224.

    Google Scholar 

  29. Kuryanov, V.O., Chupakhina, T.A., Kotlyar, S.A., and Chirva, V.Ya., Zh. Org. Farm. Kh?m., 2007, vol. 5, pp. 44–48.

    CAS  Google Scholar 

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Authors and Affiliations

  1. Vernadsky Tauric National University, pr. Akademika Vernadskogo 4, Simferopol, 95007, Ukraine

    T. A. Chupakhina, A. A. Astrakhantseva & V. O. Kuryanov

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  1. T. A. Chupakhina
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  2. A. A. Astrakhantseva
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  3. V. O. Kuryanov
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Correspondence to V. O. Kuryanov.

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Original Russian Text © T.A. Chupakhina, A.A. Astrakhantseva, V.O. Kuryanov, 2013, published in Bioorganicheskaya Khimiya, 2013, Vol. 39, No. 3, pp. 346–352.

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Chupakhina, T.A., Astrakhantseva, A.A. & Kuryanov, V.O. Specific features of phase transfer catalytic glycosylation of aromatic hydroxy acids. Russ J Bioorg Chem 39, 306–311 (2013). https://doi.org/10.1134/S1068162013030059

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  • DOI: https://doi.org/10.1134/S1068162013030059

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