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).

Sonawane, D.P., Corbett, Y., Dhavale, D.D., Taramelli, D., Trombini, C., Quintavalla, A., et al. (2015). D-Glucose-Derived 1,2,4-Trioxepanes: Synthesis, Conformational Study, and Antimalarial Activity. ORGANIC LETTERS, 17(16), 4074-4077 [10.1021/acs.orglett.5b01996].

D-Glucose-Derived 1,2,4-Trioxepanes: Synthesis, Conformational Study, and Antimalarial Activity

TROMBINI, CLAUDIO;QUINTAVALLA, ARIANNA;LOMBARDO, MARCO
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).
2015
Sonawane, D.P., Corbett, Y., Dhavale, D.D., Taramelli, D., Trombini, C., Quintavalla, A., et al. (2015). D-Glucose-Derived 1,2,4-Trioxepanes: Synthesis, Conformational Study, and Antimalarial Activity. ORGANIC LETTERS, 17(16), 4074-4077 [10.1021/acs.orglett.5b01996].
Sonawane, D P; Corbett, Y; Dhavale, D D; Taramelli, D; Trombini, C; Quintavalla, A; Lombardo, M
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Utilizza questo identificativo per citare o creare un link a questo documento: https://hdl.handle.net/11585/516078
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