Vega Pérez, José ManuelPalo Nieto, CarlosVega Holm, MargaritaGóngora Vargas, PurificaciónCalderón Montaño, José ManuelCalderón Montaño, José ManuelBurgos Morón, EstefaníaLópez Lázaro, MiguelIglesias Guerra, Fernando2025-01-282025-01-282013-12Vega Pérez, J.M., Palo Nieto, C., Vega Holm, M., Góngora Vargas, P., Calderón Montaño, J.M., Calderón Montaño, J.M.,...,Iglesias Guerra, F. (2013). Aziridines from alkenyl-β-D-galactopyranoside derivatives: Stereoselective synthesis and in vitro selective anticancer activity. European Journal of Medicinal Chemistry, 70, 380-392. https://doi.org/10.1016/j.ejmech.2013.10.020.0223-52341768-3254https://hdl.handle.net/11441/167745A series of new aziridines β-D-galactopyranoside derivatives were synthesized from alkenyl β-D-galactopyranosides employing Sharpless conditions. The structures of the compounds were established by 1H NMR, 13C NMR, MS, HRMS and elemental analysis. The stereoselectivity of the reaction and the structural requirements of the alkenyl precursor for improving diastereoisomeric excesses of the direct aziridination reaction were also studied. The new compounds were subjected to a preliminary screening for cytotoxic activity against human lung cancer cells vs. human non-malignant lung cells. Terminal aziridine derivatives showed activity and, most notably, selectivity. One of the most active and selective compounds was also evaluated against breast cancer cells, melanoma cells, and non-malignant cells from the same origin. Its cytotoxic activity was similar to that of the positive controls, displaying a highly selective cytotoxic activity against both types of cancer cells.application/pdf50 p.engAttribution-NonCommercial-NoDerivatives 4.0 Internationalhttp://creativecommons.org/licenses/by-nc-nd/4.0/Aziridine carbohydrate derivativeCancerSelective cytotoxic activityStereoselective synthesisinfo:eu-repo/semantics/articleinfo:eu-repo/semantics/openAccesshttps://doi.org/10.1016/j.ejmech.2013.10.020