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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King, C.D., Rios, G.R., Green, M.D., and Tephly, T.R., Curr. Drug Metab., 2000, vol. 1, p. 143.
Stachulski, A.V. and Meng, X., Nat. Prod. Rep., 2013, vol. 30, p. 806.
Stachulski, A.V. and Jenkins, G.V., Nat. Prod. Rep., 1998, vol. 15, p. 173.
Wadouachi, A. and Kovensky, J., Molecules, 2011, vol. 16, p. 3933.
Andreeva, O.V., Sharipova, R.R., Garifullin, B.F., Strobykina, I.Yu., and Kataev, V.E., Chem. Nat. Compd., 2015, vol. 51, p. 689.
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.
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.
Tietze, L.F., Schuster, H.J., Schmuck, K., Schuberth, I., and Alves, F., Bioorg. Med. Chem., 2008, vol. 16, p. 6312.
El Alaoui, A., Schmidt, F., Monneret, C., and Florent, J.-C., J. Org. Chem., 2006, vol. 71, p. 9628.
Gauthier, C., Legault, J., Rondeau, S., and Pichette, A., Tetrahedron Lett., 2009, vol. 50, p. 988.
Renoux, B., Legigan, T., Bensalma, S., Chadeneau, C., Muller, J.-M., and Papot, S., Org. Biomol. Chem., 2011, vol. 9, p. 8459.
Greimel, P., Lapeyre, M., Nagatsuka, Y., Hirabayashi, Y., and Ito, Y., Bioorg. Med. Chem., 2008, vol. 16, p. 7210.
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.
Brockhausen, I., Larsson, E.A., and Hindsgaul, O., Bioorg. Med. Chem. Lett., 2008, vol. 18, p. 804.
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.
Vinnikova, A.N., Demirova, K.A., Druzhinina, T.N., and Veselovsky, V.V., Russ. Chem. Bull., Int. Ed., 2015, vol. 64, p. 202.
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.
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.
Li, N.S., Scharf, L., Adams, E.J., and Piccirilli, J.A., J. Org. Chem., 2013, vol. 78, p. 5970.
Wolucka, B.A., FEBS J., 2008, vol. 275, p. 2691.
Smellie, I.A., Bhakta, S., Sim, E., and Fairbanks, A.J., Org. Biomol. Chem., 2007, vol. 5, p. 2257.
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.
Johgkees, S.A.K. and Withers, S.G., J. Am. Chem. Soc., 2011, vol. 133, p. 19334.
Pilgrim, W. and Murphy, P.V., J. Org. Chem., 2010, vol. 75, p. 6747.
Donahue, M.G. and Johnston, J.N., Bioorg. Med. Chem. Lett., 2006, vol. 16, p. 5602.
Young, R.W., J. Am. Chem. Soc., 1952, vol. 74, p. 1672.
Pannecoucke, X., Schmitt, G., and Luu, B., Tetrahedron, 1994, vol. 50, p. 6569.
Donald, P.R., Tuberculosis, 2010, vol. 90, p. 279.
Bollenback, G.N., Long, J.W., Benjamin, D.G., and Lindquist, J.A., J. Am. Chem. Soc., 1955, vol. 77, p. 3310.
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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