Heterocycle-fused lupane triterpenoids inhibit Leishmania donovani amastigotes

R Haavikko, A Nasereddin, N Sacerdoti-Sierra, D Kopelyanskiy, Sami Alakurtti, M Tikka, C L Jaffe, J Yli-Kauhaluoma (Corresponding Author)

    Research output: Contribution to journalArticleScientificpeer-review

    35 Citations (Scopus)

    Abstract

    The synthesis of heterocyclic betulin derivatives and their activity against Leishmania donovani is reported. Betulonic acid was used as a versatile intermediate. Several different fused heterocycles were introduced at the 2,3-position of the lupane skeleton including isoxazole, pyrazine, pyridine, indole and pyrazole rings. Also the 28-position was modified. Three compounds, 5, 8 and 25, showed low micromolar activity with IC50 values of 13.2, 4.3 and 7.2 µM, respectively. Compound 8 showed the best activity and selectivity, and its activity was tested on infected macrophages using a concentration, 5 µM, where no macrophage toxicity was exhibited. Interestingly, the activity of compound 8 on axenic amastigotes and Leishmania-infected macrophages was similar
    Original languageEnglish
    Pages (from-to)445-451
    Number of pages6
    JournalMedChemComm
    Volume5
    Issue number4
    DOIs
    Publication statusPublished - 2014
    MoE publication typeA1 Journal article-refereed

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  • Cite this

    Haavikko, R., Nasereddin, A., Sacerdoti-Sierra, N., Kopelyanskiy, D., Alakurtti, S., Tikka, M., Jaffe, C. L., & Yli-Kauhaluoma, J. (2014). Heterocycle-fused lupane triterpenoids inhibit Leishmania donovani amastigotes. MedChemComm, 5(4), 445-451. https://doi.org/10.1039/c3md00282a