Skip to main content
Log in

Synthesis and Modification of Isothiocyanate Derivatives of Maleopimaric and Dihydroquinopimaric Acids

  • Published:
Russian Journal of Organic Chemistry Aims and scope Submit manuscript

Abstract

The reaction of maleopimaric and dihydroquinopimaric acid chlorides with potassium thiocyanate gave the corresponding acyl isothiocyanates which were treated with primary amines and L-amino acid methyl esters to afford new diterpenoid thiourea derivatives.

This is a preview of subscription content, log in via an institution to check access.

Access this article

Price excludes VAT (USA)
Tax calculation will be finalised during checkout.

Instant access to the full article PDF.

Scheme

Similar content being viewed by others

REFERENCES

  1. Faustino, C., Neto, I., Fonte, P., and Macedo, A., Curr. Pharm. Des., 2018, vol. 24, p. 4362. https://doi.org/10.2174/1381612825666190112162817

    Article  CAS  PubMed  Google Scholar 

  2. Hou, W., Zhang, G., Luo Zhi, Li Di, Ruan, H., Ruan, B.H., Su, L., and Xu, H., Bioorg. Med. Chem. Lett., 2017, vol. 27, p. 5382. https://doi.org/10.1016/j.bmcl.2017.11.014

    Article  CAS  PubMed  Google Scholar 

  3. González, M.A., Correa-Royero, J., Agudelo, L., Mesa, A., and Betancur-Galvis, L., Eur. J. Med. Chem., 2009, vol. 44, p. 2468. https://doi.org/10.1016/j.ejmech.2009.10.010

    Article  CAS  PubMed  Google Scholar 

  4. Sepúlveda, B., Astudillo, L., Rodríguez, J.A., Yáfiez, T., Theoduloz, C., and Schmeda-Hirschmann, G., Pharm. Res., 2005, vol. 52, p. 429. https://doi.org/10.1016/j.phrs.2005.06.004

    Article  CAS  Google Scholar 

  5. Kazakova, O.B., Smirnova, I.E., Tkhu, H.D.T., Nguen, T.T., Apryshko, G.N., Zhukova, O.S., Medvedeva, N.I., Nazyrov, T.I., Tret’yakova, E.V., Chudov, I.V., Ismagilova, A.F., Suponitsky, K.Yu., Kazakov, D.V., Safarov, F.E., and Tolstikov, G.A., Russ. J. Bioorg. Chem., 2013, vol. 39, p. 202. https://doi.org/10.1134/S1068162013020088

    Article  CAS  Google Scholar 

  6. Justino, G.A.C., Correia, C.F., Mira, L., Dos Santos, R.M.B., Simones, J.A.M., Silva, A.M., Santos, C.L., and Gigante, B.R., J. Agric. Food Chem., 2006, vol. 54, p. 342. https://doi.org/10.1021/jf052062k

    Article  CAS  PubMed  Google Scholar 

  7. Tolstikov, G.A., Tolstikova, T.G., Shul’ts, E.E., Tolstikov, S.E., and Khvostov, M.V., Smolyanye kisloty khvoinykh Rossii. Khimiya, farmakologiya (Rosin Acids from Russian Coniferous Plants. Chemistry and Pharmacology), Novosibirsk: GEO, 2011.

  8. Kazakova, O.B., Tret’yakova, E.V., Smirnova, I.E., Spirikhin, L.V., Tolstikov, G.A., Chudov, I.V., Bazekin, G.V., and Ismagilova, A.F., Russ. J. Bioorg. Chem., 2010, vol. 36, p. 257. https://doi.org/10.1134/S1068162010020160

    Article  CAS  Google Scholar 

  9. Tretyakova, E.V., Smirnova, I.E., Salimova, E.V., Pashkova, T.M., Kartashova, O.L., Odinokov, V.N., and Parfenova, L.V., Russ. J. Bioorg. Chem., 2017, vol. 43, p. 317. https://doi.org/10.1134/S1068162017020169

    Article  CAS  Google Scholar 

  10. Tretyakova, E.V., Smirnova, I.E., Salimova, E.V., and Odinokov, V.N., Bioorg. Med. Chem., 2015, vol. 23, p. 6543. https://doi.org/10.1016/j.bmc.2015.09.006

    Article  CAS  PubMed  Google Scholar 

  11. Tretyakova, E.V., Salimova, E.V., Parfenova, L.V., Yunusbaeva, M.M., Dzhemileva, L.U., D’yakonov, V.V., and Dzhemilev, U.M., Anticancer Agents Med. Chem., 2019, vol. 19, p. 1172. https://doi.org/10.2174/1871520619666190404100846

    Article  CAS  PubMed  Google Scholar 

  12. Kazakova, O.B., Tret’yakova, E.V., Kukovinets, O.S., Tolstikov, G.A., Nazyrov, T.I., Chudov, I.V., and Ismagilova, A.F., Russ. J. Bioorg. Chem., 2010, vol. 36, p. 762. https://doi.org/10.1134/S1068162010060130

    Article  CAS  Google Scholar 

  13. Tret’yakova, E.V., Smirnova, I.E., Kazakova, O.B., Yavorskaya, N.P., Golubeva, I.S., Zhukova, O.S., Pugacheva, R.B., Apryshko, G.N., and Poroikov, V.V., Bioorg. Med. Chem., 2014, vol. 22, p. 6481. https://doi.org/10.1016/j.bmc.2014.09.030

    Article  CAS  Google Scholar 

  14. Kovaleva, K., Oleshko, O., Mamontova, E., Yarovaya, O., Zakharova, O., Zakharenko, A., Kononova, A., Dyrkheeva, N., Cheresiz, S., Pokrovsky, A., Lavrik, O., and Salakhutdinov, N., J. Nat. Prod., 2019, vol. 82, p. 2443. https://doi.org/10.1021/acs.jnatprod.8b01095

    Article  CAS  PubMed  Google Scholar 

  15. Huang, X.-Ch., Wang, M., Pan, Y.-M., Tian, X.-Y., Wang, H.-Sh., and Zhang, Y., Bioorg. Med. Chem. Lett., 2013, vol. 23, p. 5283. https://doi.org/10.1016/j.bmcl.2013.08.005

    Article  CAS  PubMed  Google Scholar 

  16. Huang, X.-Ch., Wang, M., Pan, Y.-M., Yao, G.-Y., Wang, H.-Sh., Tian, X.-Y., Qin, J.-K., and Zhang, Y., Eur. J. Med. Chem., 2013, vol. 69, p. 508. https://doi.org/10.1016/j.ejmech.2013.08.055

    Article  CAS  PubMed  Google Scholar 

  17. Huang, X., Huang, R., Liao, Z., Pan, Y., Gou, Sh., and Wang, H., Eur. J. Med. Chem., 2016, vol. 108, p. 381. https://doi.org/10.1016/j.ejmech.2015.12.008

    Article  CAS  PubMed  Google Scholar 

  18. Tret’yakova, E.V., Russ. J. Org. Chem., 2021, vol. 57, p. 391. https://doi.org/10.1134/S1070428021030106

    Article  Google Scholar 

  19. Flekhter, O.B., Smirnova, I.E., Tret’yakova, E.V., Tolstikov, G.A., Savinova, O.V., and Boreko, E.I., Russ. J. Bioorg. Chem., 2009, vol. 35, p. 385. https://doi.org/10.1134/S1068162009030157

    Article  CAS  Google Scholar 

  20. Herz, W., Blakstone, R.C., and Nair, M.G., J. Org. Chem., 1967, vol. 32, p. 2292.

    Google Scholar 

  21. Zalkov, L.U., Ford, R.A., and Cutney, J.P., J. Org. Chem., 1962, vol. 27, p. 3535.

    Article  Google Scholar 

Download references

Funding

This study was performed in the framework of state assignment no. AAAA-A20-120012090023-8.

Author information

Authors and Affiliations

Authors

Corresponding author

Correspondence to E. V. Tret’yakova.

Ethics declarations

The author declares no conflict of interest.

Additional information

Translated from Zhurnal Organicheskoi Khimii, 2021, Vol. 57, No. 6, pp. 852–859 https://doi.org/10.31857/S0514749221060070.

Rights and permissions

Reprints and permissions

About this article

Check for updates. Verify currency and authenticity via CrossMark

Cite this article

Tret’yakova, E.V. Synthesis and Modification of Isothiocyanate Derivatives of Maleopimaric and Dihydroquinopimaric Acids. Russ J Org Chem 57, 930–935 (2021). https://doi.org/10.1134/S1070428021060075

Download citation

  • Received:

  • Revised:

  • Accepted:

  • Published:

  • Issue Date:

  • DOI: https://doi.org/10.1134/S1070428021060075

Keywords:

Navigation