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Design, Synthesis, and Cytotoxicity of Semisynthetic Betulinic Acid-1,2,4-Oxadiazole Amide Derivatives

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Abstract

Biological activity of betulinic acid derivatives containing a 1,2,4-oxadiazole ring prompted us to synthesize betulinic acid-1,2,4-oxadiazole amide derivatives 14–25 starting with the amide coupling reaction of betulinic acid 1 and (3-aryl-1,2,4-oxadiazol-5-yl)methanamines 2–13. The products were tested for cytotoxicity on three human cancer cell lines in vitro. All tested compounds demonstrated high activity. The structures of the synthesized compounds were elucidated from IR, NMR and mass spectra.

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References

  1. Wang, C.M., Chen, H.T., Wu, Z.Y., Jhan, Y.L., Shyu, C.L., and Chou, C.H., Molecules, 2016, vol. 21, p. 139. doi 10.3390/molecules21020139

    Article  Google Scholar 

  2. Tsai, J.C., Peng, W.H., Chiu, T.H., Lai, S.C., and Lee, C.Y., Am. J. Chinese Med., 2011, vol. 39, p. 943. doi 10.1142/S0192415X11009329

    Article  CAS  Google Scholar 

  3. Govdi, A.I., Sokolova, N.V., Sorokina, I.V., Baev, D.S., Tolstikova, T.G., Mamatyuk, V.I., and Nenajdenko, V.G., Med. Chem. Comm., 2015, vol. 6, p. 230. doi 10.1039/C4MD00236A

    Article  CAS  Google Scholar 

  4. Safe, H.S., Prather, L.P., Brents, K.L., Chadalapaka, G., and Jutooru, I., Curr. Med. Chem. Anticancer Agents, 2012, vol. 12, p. 1211.

    Article  CAS  Google Scholar 

  5. Li, J., Goto, M., Yang, X., Morris-Natschke, S.L., Huang, L., Chen, C.H., and Lee, K.H., Bioor. Med. Chem. Lett., 2016, vol. 26, p. 68. doi 10.1016/j.bmcl.2015.11.029

    Article  CAS  Google Scholar 

  6. Pisha, E., Chai, H., Lee, I.S., Chagwedera, T.E., Farnsworth, N.R., Cordell, G.A., Beecher, C.W., Fong, H.H., Kinghorn, A.D., Brown, D.M., and Wani, M.C., Nat. Med., 1995, vol. 1, p. 1046.

    Article  CAS  Google Scholar 

  7. Eiznhamer, D.A. and Xu, Z.Q., Drugs, 2004, vol. 7, p. 359.

    CAS  Google Scholar 

  8. Shintyapina, A.B., Shults, E.E., Petrenko, N.I., Uzenkova, N.V., and Tolstikov, G.A., Bioorg. Chem., 2007, vol. 33, p. 579. doi 10.1134/S1068162007060076

    Article  CAS  Google Scholar 

  9. Jeong, H.J., Chai, H.B., Park, S.Y., and Kim, D.S.H.L., Bioorg. Med. Chem. Lett., 1999, vol. 9, p. 1201.

    Article  CAS  Google Scholar 

  10. Kim, J.Y., Koo, H.M., and Kim, D.S.H.L., Bioorg. Med. Chem. Lett., 2001, vol. 11, p. 2405. doi 10.1016/2Fj.bmcl.2011.12.102

    Article  CAS  Google Scholar 

  11. Kumar, V., Rani, N., Aggarwal, P., Sanna, V.K., Singh, A.T., Jaggi, M., Joshi, N., Sharma, P.K., Irchhaiya, R., and Burman, A.C., Bioorg. Med. Chem. Lett., 2008, vol. 18, p. 5058. doi 10.1016/j.bmcl.2008.08.003

    Article  CAS  Google Scholar 

  12. Clitherow, J.W., Beswick, P., Irving, W.J., Scopes, D.I.C., Barnes, J.C., Clapham, J., Brown, J.D., Evans, D.J., and Hayes, A.G., Bioorg. Med. Chem. Lett., 1996, vol. 6, p. 833.

    Article  CAS  Google Scholar 

  13. Zhang, H.E., Kasibhatla, S., Kuemmerle, J., Kemnitzer, W., and Cai, S.X., J. Med. Chem., 2005, vol. 48, p. 5215. doi 10.1016/0960-894X(96)00122-9

    Article  CAS  Google Scholar 

  14. Nicolaides, D.N., Fylaktakidou, K.C., and Litinas, K.E., Eur. J. Med. Chem., 1998, vol. 33, p. 715. doi 10.1016/S0223-5234(98)80030-5 p

    Article  CAS  Google Scholar 

  15. Chimirri, A., Grasso, S., Montforte, A.M., Rao, A., and Zappala, M., Farmaco, 1996, vol. 51, p. 125.

    CAS  Google Scholar 

  16. Kumar, D., Patel, G., Johnson, E.O., and Shah, K., Bioorg. Med. Chem. Lett., 2009, vol. 19, p. 2739. doi 10.1016/j.bmcl.2009.03.172

    Article  CAS  Google Scholar 

  17. Luthman, K., Borg, S., and Hacksell, U., Methods Mol. Med., 1999, vol. 23, p. 1. doi 10.1385/0-89603-517-4:1

    CAS  Google Scholar 

  18. Borg, S., Vollinga, R.C., Laborre, M., Payza, K., Terenius, L., and Lut, K., J. Med. Chem., 1999, vol. 42, p. 4331. doi 10.1021/jm990229t

    Article  CAS  Google Scholar 

  19. Genet, C., Strehle, A., and Schimdt, C., J. Med. Chem., 2010, vol. 53, p. 178. doi 10.1021/jm900872z

    Article  CAS  Google Scholar 

  20. Packiarajan, M., Christine, G., Ferreira, M., Hong, S.P., and White, A.D., Bioorg. Med. Chem. Lett., 2012, vol. 22, p. 5658. doi 10.1016/j.bmcl.2012.06.094

    Article  CAS  Google Scholar 

  21. Zhao, Q., Liu, S., and Li, Y., J. Agric. Food Chem., 2009, vol. 57, p. 2849.

    Article  CAS  Google Scholar 

  22. Mosmann, T., J. Immunol. Method., 1983, vol. 65, p. 55.

    Article  CAS  Google Scholar 

  23. Rahbari, R., Sheahan, T., Modes, V., and Badge, R.M., Biotech., 2009, vol. 46, p. 277. doi 10.2144/000113089

    Article  CAS  Google Scholar 

  24. Scherer, W.F., Syverton, J.T., and Gey, G.O., J. Exp. Med., 1953, vol. 97, p. 695.

    Article  CAS  Google Scholar 

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Authors and Affiliations

  1. Department of Chemistry, Faculty of Science, Osmania University, Hyderabad, 500007, India

    C. Krishna & G. L. D. Krupadanam

  2. Department of Pharmacy, Faculty of Technology, Osmania University, Hyderabad, 500007, India

    M. V. Bhargavi

Authors
  1. C. Krishna
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  2. M. V. Bhargavi
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  3. G. L. D. Krupadanam
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Correspondence to C. Krishna.

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The text was submitted by the authors in English.

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Krishna, C., Bhargavi, M.V. & Krupadanam, G.L.D. Design, Synthesis, and Cytotoxicity of Semisynthetic Betulinic Acid-1,2,4-Oxadiazole Amide Derivatives. Russ J Gen Chem 88, 312–318 (2018). https://doi.org/10.1134/S1070363218020196

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  • DOI: https://doi.org/10.1134/S1070363218020196

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