Abstract
Hydroxyl- and chloroethyl derivatives of neomenthane- and isobornanethiol in yields of to 80% were synthesized. They served as the basis for the preparation of new bis-sulfides with diacetone-protected galacto- and fructopyranose fragments in yields up to 98%. The bis-sulfides synthesized were screened for membrane protective and antioxidant properties in a model cell system (in vitro) based on their ability to inhibit the H2O2-induced hemolysis of erythrocytes and retard the oxyhemoglobin oxidation.
This is a preview of subscription content, log in via an institution to check access.
Similar content being viewed by others
Abbreviations
- AAPH:
-
2,2-azo-bis(amidinopropane) dihydrochloride
- TBAI:
-
tetrabutylammonium iodide
References
Balsells, J., Moyano, A., Pericas, M.A., and Riera, A., Tetrahedron: Asymmetry, 1997, vol. 8, pp. 1575–1580.
Ghirardello, M., Oberg, K., Staderini, S., Renaudet, O., Berthet, N., Dumy, P., Hed, Y., Marra, A., Malkoch, M., and Dondoni, A., J. Polym. Sci., Part A: Polym. Chem., 2014, vol. 52, pp. 2422–2433
Titov, D.V., Gening, M.L., Tsvetkov, Yu.E., and Nifant’ev, N.E., Usp. Khim., 2014, vol. 83, pp. 523–554.
Tiwari, V.K., Singh, B.K., Chaturvedi, V., Manju, Y.K., Srivatava, A.K., Sinha, S., Gaikwad, A., and Tripathi, R.P., Indian J. Org. Chem., 2007, vol. 3, pp. 84–96.
Hinou, H., Sun, X.-L., and Ito, Y., Org. Chem., 2003, vol. 68, pp. 5602–5613.
Ovchinnikova, L.P., Rotskaya, U.N., Vasyunina, E.A., Sinitsina, O.I., Kandalintseva, N.V., Prosenko, A.E., and Nevinskii, G.A., Russ. J. Bioorg. Chem., 2009, vol. 35, pp. 379–384.
Terakh, E.I., Kandalintseva, N.V., Nikulina, V.V., Pinko, P.I., and Prosenko, A.E., Neftekhimiya, 2004, vol. 44, pp. 237–240.
Pestova, S.V., Sudarikov, D.V., Rubtsova, S.A., and Kutchin, A.V., Russ. J. Org. Chem., 2013, vol. 49, pp. 366–373.
Pestova, S.V., Izmest’ev, E.S., Rubtsova, S.A., and Kuchin, A.V., Russ. J. Org. Chem., 2014, vol. 50, pp. 670–677.
Pestova, S.V., Izmest’ev, E.S., Shevchenko, O.G., Rubtsova, S.A., and Kuchin, A.V., Rus. Chem. Bull., 2015, vol. 64, no. 3, pp. 723–731.
Miki, M., Tamai, H., Mino, M., Yamamoto, Y., and Niki, E., Arch. Biochem. Biophys., 1987, vol. 258, pp. 373–380.
Snow, A.W. and Foos, E.E., Synthesis, 2003, vol. 4, pp. 509–512.
Demakova, M.Ya., Sudarikov, D.V., Rubtsova, S.A., Slepukhin, P.A., and Kuchin, A.V., Chem. Nat. Compd., 2012, vol. 47, pp. 899–902.
Volynskii, N.P., Perepelitchenko, L.I., and Zegel’man, L.A., Izv. AN SSSR. Ser. Khim., 1987, vol. 11, pp. 2506–2508.
Lunau, N., Seelhorst, K., Kahl, S., Tscherch, K., Stacke, C., Rohn, S., Thiem, J., Hahn, U., and Meier, C., Chem.-Eur. J., 2013, vol. 19, pp. 17379–17390.
Daniellou, R. and Le Narvor, C., Adv. Synth. Catal., 2005, vol. 347, pp. 1863–1868.
Garegg, P.J. and Samuelsson, B., J. Chem. Soc., Perkin Trans., 1980, vol. 1, pp. 2866–2869.
Goodwin, C.J., Carbohydr. Res., 1989, vol. 195, pp. 150–152.
Martins, A.M.A., D’Accorso, N.B., and Thiel, I.M.E., J. Heterocycl. Chem., 1996, vol. 33, pp. 1339–1343.
Carchon, G., Chre’tien, F., and Chapleur, Y., Tetrahedron Lett., 2003, vol. 44, pp. 5715–5718.
Takebayashi, J., Chen, J., and Tai, A., Advanced Protocols in Oxidative Stress II, in Methods in Molecular Biology, Armstrong, D., Ed., New York: Humana Press, 2010, vol. 594, pp. 287–296.
Berg, J.M., Kamp, J.A.F., Lubin, B.H., Roelofsen, B., and Kuypers, F.A., Free Radical Biol. Med., 1992, vol. 12, pp. 487–498.
Author information
Authors and Affiliations
Corresponding author
Additional information
Original Russian Text © S.V. Pestova, E.S. Izmest’ev, O.G. Shevchenko, S.A. Rubtsova, A.V. Kuchin, 2017, published in Bioorganicheskaya Khimiya, 2017, Vol. 43, No. 3, pp. 301–310.
Rights and permissions
About this article
Cite this article
Pestova, S.V., Izmest’ev, E.S., Shevchenko, O.G. et al. Synthesis and membrane protective activity of bis-sulfides derived from monoterpenoids and monosaccharides. Russ J Bioorg Chem 43, 302–310 (2017). https://doi.org/10.1134/S1068162017030141
Received:
Accepted:
Published:
Issue Date:
DOI: https://doi.org/10.1134/S1068162017030141