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Synthesis and antitubercular activity of first glucuronosyl phosphates and amidophosphates containing polymethylene chains

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Abstract

Novel phosphorylated glycolipids based on glucuronic acid have been synthesized and shown to inhibit M. Tuberculosis H37Rv in vitro at a minimum inhibitory concentration of 12.5 μg/mL.

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References

  1. King, C.D., Rios, G.R., Green, M.D., and Tephly, T.R., Curr. Drug Metab., 2000, vol. 1, p. 143.

    Article  CAS  Google Scholar 

  2. Stachulski, A.V. and Meng, X., Nat. Prod. Rep., 2013, vol. 30, p. 806.

    Article  CAS  Google Scholar 

  3. Stachulski, A.V. and Jenkins, G.V., Nat. Prod. Rep., 1998, vol. 15, p. 173.

    Article  CAS  Google Scholar 

  4. Wadouachi, A. and Kovensky, J., Molecules, 2011, vol. 16, p. 3933.

    Article  CAS  Google Scholar 

  5. Andreeva, O.V., Sharipova, R.R., Garifullin, B.F., Strobykina, I.Yu., and Kataev, V.E., Chem. Nat. Compd., 2015, vol. 51, p. 689.

    Article  CAS  Google Scholar 

  6. Andreeva, O.V., Sharipova, R.R., Strobykina, I.Yu., Kravchenko, M.A., Strobykina, A.S., Voloshina, A.D., Musin, R.Z., and Kataev, V.E., Russ. J. Org. Chem., 2015, vol. 51, p. 1324.

    Article  CAS  Google Scholar 

  7. Garifullin, B.F., Strobykina, I.Yu., Sharipova, R.R., Kravchenko, M.A., Andreeva, O.V., Bazanova, O.B., and Kataev, V.E., Carbohydr. Res., 2016, vol. 431, p. 15.

    Article  CAS  Google Scholar 

  8. Tietze, L.F., Schuster, H.J., Schmuck, K., Schuberth, I., and Alves, F., Bioorg. Med. Chem., 2008, vol. 16, p. 6312.

    Article  CAS  Google Scholar 

  9. El Alaoui, A., Schmidt, F., Monneret, C., and Florent, J.-C., J. Org. Chem., 2006, vol. 71, p. 9628.

    Article  CAS  Google Scholar 

  10. Gauthier, C., Legault, J., Rondeau, S., and Pichette, A., Tetrahedron Lett., 2009, vol. 50, p. 988.

    Article  CAS  Google Scholar 

  11. Renoux, B., Legigan, T., Bensalma, S., Chadeneau, C., Muller, J.-M., and Papot, S., Org. Biomol. Chem., 2011, vol. 9, p. 8459.

    Article  CAS  Google Scholar 

  12. Greimel, P., Lapeyre, M., Nagatsuka, Y., Hirabayashi, Y., and Ito, Y., Bioorg. Med. Chem., 2008, vol. 16, p. 7210.

    Article  CAS  Google Scholar 

  13. Chen, C., Liu, B., Xu, Y., Utkina, N., Zhou, D., Danilov, L., Torgov, V., Veselovsky, V., and Feng, L., Carbohydr. Res., 2016, vol. 430, p. 36.

    Article  CAS  Google Scholar 

  14. Brockhausen, I., Larsson, E.A., and Hindsgaul, O., Bioorg. Med. Chem. Lett., 2008, vol. 18, p. 804.

    Article  CAS  Google Scholar 

  15. Vinnikova, A.N., Torgov, V.I., Utkina, N.S., Veselovsky, V.V., Druzhinina, T.N., Wang, S., Brockhausen, I., and Danilov, L.L., Russ. J. Bioorg. Chem., 2015, vol. 41, p. 105.

    Article  CAS  Google Scholar 

  16. Vinnikova, A.N., Demirova, K.A., Druzhinina, T.N., and Veselovsky, V.V., Russ. Chem. Bull., Int. Ed., 2015, vol. 64, p. 202.

    Article  CAS  Google Scholar 

  17. Sevrain, C.M., Haelters, J.-P., Chantôme, A., Couthon-Gourvès, H., Gueguinou, M., Potier-Cartereau, M., Vandier, C., and Jaffrès, P.-A., Org. Biomol. Chem., 2013, vol. 11, p. 4479.

    Article  CAS  Google Scholar 

  18. Hardre, R., Khaled, A., Willemetz, A., Dupre, T., Moore, S., Gravier-Pelletier, C., and Le Merrer, Y., Bioorg. Med. Chem. Lett., 2007, vol. 17, p. 152.

    Article  CAS  Google Scholar 

  19. Li, N.S., Scharf, L., Adams, E.J., and Piccirilli, J.A., J. Org. Chem., 2013, vol. 78, p. 5970.

    Article  CAS  Google Scholar 

  20. Wolucka, B.A., FEBS J., 2008, vol. 275, p. 2691.

    Article  CAS  Google Scholar 

  21. Smellie, I.A., Bhakta, S., Sim, E., and Fairbanks, A.J., Org. Biomol. Chem., 2007, vol. 5, p. 2257.

    Article  CAS  Google Scholar 

  22. Cheng, T.C., Roffler, S.R., Tzou, S.C., Chuang, K.H., Su, Y.C., Chuang, C.H., Kao, C.H., Chen, C.S., Harn, I.H., Liu, K.Y., Cheng, T.L., and Leu, Y.L., J. Am. Chem. Soc., 2012, vol. 134, p. 3103.

    Article  CAS  Google Scholar 

  23. Johgkees, S.A.K. and Withers, S.G., J. Am. Chem. Soc., 2011, vol. 133, p. 19334.

    Article  Google Scholar 

  24. Pilgrim, W. and Murphy, P.V., J. Org. Chem., 2010, vol. 75, p. 6747.

    Article  CAS  Google Scholar 

  25. Donahue, M.G. and Johnston, J.N., Bioorg. Med. Chem. Lett., 2006, vol. 16, p. 5602.

    Article  CAS  Google Scholar 

  26. Young, R.W., J. Am. Chem. Soc., 1952, vol. 74, p. 1672.

    Article  CAS  Google Scholar 

  27. Pannecoucke, X., Schmitt, G., and Luu, B., Tetrahedron, 1994, vol. 50, p. 6569.

    Article  CAS  Google Scholar 

  28. Donald, P.R., Tuberculosis, 2010, vol. 90, p. 279.

    Article  CAS  Google Scholar 

  29. Bollenback, G.N., Long, J.W., Benjamin, D.G., and Lindquist, J.A., J. Am. Chem. Soc., 1955, vol. 77, p. 3310.

    Article  CAS  Google Scholar 

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Correspondence to V. E. Kataev.

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Original Russian Text © E.S. Izmest’ev, O.V. Andreeva, R.R. Sharipova, M.A. Kravchenko, B.F. Garifullin, I.Yu. Strobykina, V.E. Kataev, V.F. Mironov, 2017, published in Zhurnal Organicheskoi Khimii, 2017, Vol. 53, No. 1, pp. 56–61.

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Izmest’ev, E.S., Andreeva, O.V., Sharipova, R.R. et al. Synthesis and antitubercular activity of first glucuronosyl phosphates and amidophosphates containing polymethylene chains. Russ J Org Chem 53, 51–56 (2017). https://doi.org/10.1134/S1070428017010092

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  • DOI: https://doi.org/10.1134/S1070428017010092

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