Abstract
| Original language | English |
|---|---|
| Pages (from-to) | 445-451 |
| Number of pages | 6 |
| Journal | MedChemComm |
| Volume | 5 |
| Issue number | 4 |
| DOIs | |
| Publication status | Published - 2014 |
| MoE publication type | A1 Journal article-refereed |
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Heterocycle-fused lupane triterpenoids inhibit Leishmania donovani amastigotes. / Haavikko, R; Nasereddin, A; Sacerdoti-Sierra, N; Kopelyanskiy, D; Alakurtti, Sami; Tikka, M; Jaffe, C L; Yli-Kauhaluoma, J (Corresponding Author).
In: MedChemComm, Vol. 5, No. 4, 2014, p. 445-451.Research output: Contribution to journal › Article › Scientific › peer-review
TY - JOUR
T1 - Heterocycle-fused lupane triterpenoids inhibit Leishmania donovani amastigotes
AU - Haavikko, R
AU - Nasereddin, A
AU - Sacerdoti-Sierra, N
AU - Kopelyanskiy, D
AU - Alakurtti, Sami
AU - Tikka, M
AU - Jaffe, C L
AU - Yli-Kauhaluoma, J
PY - 2014
Y1 - 2014
N2 - 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
AB - 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
U2 - 10.1039/c3md00282a
DO - 10.1039/c3md00282a
M3 - Article
VL - 5
SP - 445
EP - 451
JO - MedChemComm
JF - MedChemComm
SN - 2040-2503
IS - 4
ER -