Avendaño, Carmen and López-Alvarado, Pilar and Pérez, José María and Alonso, Miguel Ángel and Pascual-Alfonso, Eva and Ruiz-Serrano, Miriam and Menéndez, J. Carlos (2024) Structure-Antitumor Activity Relationships of Aza- and Diaza-Anthracene-2,9,10-Triones and Their Partially Saturated Derivatives. Molecules, 29 (2). p. 489. ISSN 1420-3049
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Abstract
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.
Item Type: | Article |
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Subjects: | Euro Archives > Multidisciplinary |
Depositing User: | Managing Editor |
Date Deposited: | 22 Jan 2024 06:51 |
Last Modified: | 22 Jan 2024 06:51 |
URI: | http://publish7promo.com/id/eprint/4360 |