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Synthesis of [2+1] Conjugates of Betulic Acid with α,ω-Diols

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Abstract

Three synthetic approaches to [2+1] conjugates of betulic acid with α,ω-diols have been tested. The best results have been obtained in the reaction of betulic acid with α,ω-dibromides in the presence of potassium carbonate in DMF.

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REFERENCES

  1. Poumale, H.M.P., Amadou, D., Shiono, Y., Deccaux, G., Kapche, W.F., and Ngadjui, B.T., Asian J. Chem., 2011, vol. 23, p. 525.

    CAS  Google Scholar 

  2. Ryu, S.Y., Lee, C.K., Ahn, J.W., Lee, S.H., and Zee, O.P., Arch. Pharm. Res., 1993, vol. 16, p. 339. https://doi.org/10.1007/BF02977528

    Article  CAS  Google Scholar 

  3. Flekhter, O.B., Nigmatullina, L.R., Baltina, L.A., Karachurina, L.T., Galin, F.Z., Zarudii, F.S., Tolstikov, G.A., Boreko, E.I., Pavlova, N.I., Nikolaeva, S.N., and Savinova, O.V., Pharm. Chem. J., 2002, vol. 36, p. 484. https://doi.org/10.1023/A:1021844705853

    Article  CAS  Google Scholar 

  4. Mukherjee, R., Jaggi, M., Rajendran, P., Siddiqui, M.J.A., Srivastava, S.K., Vardhan, A., and Burman, A.C., Bioorg. Med. Chem. Lett., 2004, vol. 14, p. 2181. https://doi.org/10.1016/j.bmcl.2004.02.044

    Article  CAS  PubMed  Google Scholar 

  5. Kim, J.Y., Koo, H.-M., and Kim, D.S.H.L., Bioorg. Med. Chem. Lett., 2001, vol. 11, p. 2405. https://doi.org/10.1016/S0960-894X(01)00460-7

    Article  CAS  PubMed  Google Scholar 

  6. Tolstikov, G.A., Flekhter, O.B., Shultz, E.E., Baltina, L.A., and Tolstikov, A.G., Chem. Sustainable Develop., 2005, vol. 13, p. 1.

    Article  CAS  Google Scholar 

  7. Xiong, J., Kashiwada, Y., Chen, C.-H., Qian, K., Morris-Natschke, S.L., Lee, K.-H., and Takaishi, Y., Bioorg. Med. Chem., 2010, vol. 18, p. 6451. https://doi.org/10.1016/j.bmc.2010.06.092

    Article  CAS  PubMed  PubMed Central  Google Scholar 

  8. Pokrovsky, A.G., Plyasunova, O.A., Ilyicheva, T.N., Borisova, O.A., Fedyuk, N.V., Petrenko, N.I., Petukhova, V.Z., Shults, E.E., and Tolstikov, G.A., Chem. Sustainable Develop., 2001, vol. 9, p. 485.

    Google Scholar 

  9. Bębenek, E., Chrobak, E., Wietrzyk, J., Kadela, M., Chrobak, A., Kusz, J., Książek, M., Jastrzębska, M., and Boryczka, S., J. Mol. Struct., 2016, vol. 1106, p. 210. https://doi.org/10.1016/j.molstruc.2015.10.102

    Article  CAS  Google Scholar 

  10. Urban, M., Sarek, J., Tislerova, I., Dzubak, P., and Hajduch, M., Bioorg. Med. Chem., 2005, vol. 13, p. 5527. https://doi.org/10.1016/j.bmc.2005.07.011

    Article  CAS  PubMed  Google Scholar 

  11. Jie, Y., CN Patent no. CN 101519423B, 2011.

  12. Sczepek, R., Nitsche, C., Heller, L., Siewert, B., Schãfer, R., Flemming, F., Otgonbayar, C., and Csuk, R., Mediterranean J. Chem., 2015, vol. 4, p. 126. https://doi.org/10.13171/mjc.4.3.2015.05.26.14.18/csuk

    Article  CAS  Google Scholar 

  13. Leunis, J.-C. and Couche, E., WO Patent Appl. no. WO2007101873 A3, 2006.

  14. Popov, S.A., Semenova, M.D., Baev, D.S., Sorokina, I.V., Zhukova, N.A., Frolova, T.S., Tolstikova, T.G., Shults, E.E., and Turks, M., Steroids, 2019, vol. 150, p. 108443. https://doi.org/10.1016/j.steroids.2019.108443

    Article  CAS  PubMed  Google Scholar 

  15. Kogay, T.I., Svirskaya, N.M., Ivanchenko, N.M., and Kuznetsova, B.N., Zh. Sibir. Fed. Univer. Khim., 2014, vol. 7, p. 79.

    CAS  Google Scholar 

  16. Lee, K.-H. and Morris-Natschke, S.L., Pure Appl. Chem., 1999, vol. 71, p. 1045. https://doi.org/10.1351/pac199971061045

    Article  CAS  Google Scholar 

  17. Kaledin, V.I., Zhukova, N.A., Grek, O.R., Tolstikova, T.G., Popova, N.A., Nikolin, V.P., Sorokina, I.V., and Pozdnyakova, S.V., J. Clin. Experim. Med., 2005, p. 53.

  18. Vedernikov, D.N. and Roshchin, V.I., Russ. J. Bioorg. Chem., 2012, vol. 38, p. 762. https://doi.org/10.1134/S1068162012070229

    Article  CAS  Google Scholar 

  19. Yakovleva, M.P., Vydrina, V.A., Sayakhov, R.R., and Ishmuratov, G.Yu., Chem. Nat. Compd., 2018, vol. 54, p. 795. https://doi.org/10.1007/s10600-018-2479-8

    Article  CAS  Google Scholar 

  20. Barycza, B., PL Patent no. PL 232662, 2019.

  21. Li, J., Chang, L.-C., Hsieh, K.-Y., Hsu, P.-L., Capuzzi, S.J., Zhang, Y.-C., Li, K.-Po, Morris-Natschke, S.L., Goto, M., and Lee, K.-H., Bioorg. Med. Chem. Lett., 2019, vol. 27, p. 2871. https://doi.org/10.1016/j.bmc.2019.05.016

    Article  CAS  Google Scholar 

  22. Kazakova, O.B., Giniyatullina, G.V., Tolstikov, G.A., Kataev, V.E., and Musin, R.Z., Russ. J. Bioorg. Chem., 2009, vol. 35, p. 645. https://doi.org/10.1134/S1068162009050173

    Article  CAS  Google Scholar 

  23. Nader, N.P., Marziyeh, B., Ertan, Ş., and Tuncay, T., J. Iran. Chem. Soc., 2014. https://doi.org/10.1007/s13738-014-0415-9

  24. Callies, O., Sánchez-Cañete, M.P., Gamarro, F., Jiménez, I.A., Castanys, S., and Bazzocchi, I., J. Med. Chem., 2016, vol. 59, p. 1880. https://doi.org/10.1021/acs.jmedchem.5b01429

    Article  CAS  PubMed  Google Scholar 

  25. Neises, B. and Steglich, W., Angew. Chem. Int. Ed., 1978, vol. 17, p. 522. https://doi.org/10.1002/anie.197805221

    Article  Google Scholar 

  26. Boden, E.P. and Keck, G.E., J. Org. Chem., 1985, vol. 50, p. 2394. https://doi.org/10.1021/jo00213a044

    Article  CAS  Google Scholar 

  27. Popov, S., Steroids, 2020, vol. 162, p. 108698. https://doi.org/10.1016/j.steroids.2020.108698

    Article  CAS  PubMed  Google Scholar 

  28. Liu, J.-H., Zhu, Z.-F., Tang, J., Jiang, A.-Q., Hua, L.-F., and Chen, L., Chin. Chem. Lett., 2015, vol. 26, p. 759. https://doi.org/10.1016/j.cclet.2015.04.002

    Article  CAS  Google Scholar 

  29. Gordon, A. and Ford, R., Sputnik khimika, Moscow: Mir, 1976.

  30. Petrenko, N.I., Elantseva, N.V., Petukhova, V.Z., Shakirov, M.M., Shul’ts, E.E., and Tolstikov, G.A., Chem. Nat. Compd., 2002, vol. 38, p. 331. https://doi.org/10.1023/A:1021621907515

    Article  CAS  Google Scholar 

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Funding

This work was financially supported by the Russian Academy of Sciences, in the framework of the “Basic Principlesof Chemistry”, topic no. 8 “Chemo-, Regio-, and Stereoselective Transformations of Terpenoids, Steroids, and Lipids in the Directed Synthesis of Low-Molecular-Weight Bioregulators” (State Reg. no. AAAA-A17-117011910023-2, 2017), using the equipment of the “Chemistry” Center for Collective Use, Ufa Institute of Chemistry, Russian Academy of Sciences, and the “Agidel” Regional Center for Collective Use, Ufa Federal Research Center, Russian Academy of Sciences.

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Correspondence to M. P. Yakovleva.

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Translated from Zhurnal Organicheskoi Khimii, 2021, Vol. 57, No. 11, pp. 1624–1632 https://doi.org/10.31857/S0514749221110082.

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Yakovleva, M.P., Vydrina, V.A., Sayakhov, R.R. et al. Synthesis of [2+1] Conjugates of Betulic Acid with α,ω-Diols. Russ J Org Chem 57, 1861–1867 (2021). https://doi.org/10.1134/S1070428021110087

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