Avendaño López, María CarmenLópez-Alvarado Gutiérrez, María PilarPérez, José MaríaAlonso, Miguel ÁngelPascual Alfonso, EvaRuiz Serrano, MiriamMenéndez Ramos, José Carlos2024-05-082024-05-082024-01-18Avendaño C, López-Alvarado P, Pérez JM, Alonso MÁ, Pascual-Alfonso E, Ruiz-Serrano M, et al. Structure-antitumor activity relationships of Aza- and diaza-anthracene-2,9,10-triones and their partially saturated derivatives. Molecules [Internet]. 2024;29(2):489. Available from: http://dx.doi.org/10.3390/molecules2902048910.3390/molecules29020489https://hdl.handle.net/20.500.14352/1038022024 Descuento MDPIThe 1,8-Diazaanthracene-2,9,10-triones, their 5,8-dihydro derivatives, and 1,8-diazaanthracene-2,7,9,10-tetraones, structurally related to the diazaquinomycin family of natural products, were synthesized in a regioselective fashion employing Diels-Alder strategies. These libraries were studied for their cytotoxicity in a variety of human cancer cell lines in order to establish structure-activity relationships. From the results obtained, we conclude that some representatives of the 1,8-diazaanthracene-2,9,10-trione framework show potent and selective cytotoxicity against solid tumors. Similar findings were made for the related 1-azaanthracene-2,9,10-trione derivatives, structurally similar to the marcanine natural products, which showed improved activity over their natural counterparts. An enantioselective protocol based on the use of a SAMP-related chiral auxiliary derived was developed for the case of chiral 5-substituted 1,8-diazaanthracene-2,9,10-triones, and showed that their cytotoxicity was not enantiospecific.engAttribution 4.0 Internationalhttp://creativecommons.org/licenses/by/4.0/journal article1420-3049https://www.mdpi.com/1420-3049/29/2/489open access615.011Azaanthracene-2,9,10-trionesDiazaanthracene-2,9,10-trionesHetero Diels–Alder reactionsAntitumor activityDiazaquinomycinsMarcaninesQuímica farmaceútica2390 Química Farmacéutica