2026-06-26T10:33:39Zhttps://docta.ucm.es/rest/oai/request

oai:docta.ucm.es:20.500.14352/1038022025-03-18T12:34:27Zcom_20.500.14352_14col_20.500.14352_15

Avendaño López, María Carmen López-Alvarado Gutiérrez, María Pilar Pérez, José María Alonso, Miguel Ángel Pascual Alfonso, Eva Ruiz Serrano, Miriam Menéndez Ramos, José Carlos 2024-05-08T09:37:34Z 2024-05-08T09:37:34Z 2024-01-18 Avendaño 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/molecules29020489 10.3390/molecules29020489 https://hdl.handle.net/20.500.14352/103802 1420-3049 https://www.mdpi.com/1420-3049/29/2/489 The 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. eng http://creativecommons.org/licenses/by/4.0/ open access Attribution 4.0 International Structure-antitumor activity relationships of Aza- and Diaza-Anthracene-2,9,10-Triones and their partially saturated derivativer journal article