New enantiomerically pure 1,2,4-trioxepanes 10a,b/11a,b were synthesized from d-glucose. Their conformational behavior was studied by low-temperature NMR and substantiated by DFT calculations. On evaluation of in vitro antimalarial activity, the adamantyl derivative 11b showed IC50 values in the low micromolar range, particularly against the W2 chloroquine-resistant Plasmodium falciparum strain (IC50 = 0.15 ± 0.12 μM).
D-glucose-derived 1,2,4-trioxepanes: synthesis, conformational study, and antimalarial activity / D.P. Sonawane, Y. Corbett, D.D. Dhavale, D. Taramelli, C. Trombini, A. Quintavalla, M. Lombardo. - In: ORGANIC LETTERS. - ISSN 1523-7060. - 17:16(2015 Aug 21), pp. 4074-4077. [10.1021/acs.orglett.5b01996]
D-glucose-derived 1,2,4-trioxepanes: synthesis, conformational study, and antimalarial activity
Y. CorbettSecondo
;D. Taramelli;
2015
Abstract
New enantiomerically pure 1,2,4-trioxepanes 10a,b/11a,b were synthesized from d-glucose. Their conformational behavior was studied by low-temperature NMR and substantiated by DFT calculations. On evaluation of in vitro antimalarial activity, the adamantyl derivative 11b showed IC50 values in the low micromolar range, particularly against the W2 chloroquine-resistant Plasmodium falciparum strain (IC50 = 0.15 ± 0.12 μM).
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