New 1,4-anthracenedione derivatives with fused heterocyclic rings: synthesis and biological evaluationElectronic supplementary information (ESI) available: 13C NMR data and complete assignments for the 1H and 13C NMR signals are included together with HMQC and HMBC spectra for several separated regioisomers. Complementary antifungal, antiviral and Vero cytotoxicity data for all the compounds tested. See DOI: 10.1039/c4ra11726c

• Main Authors: Castro, Ma. Ángeles, Gamito, Ana Ma, Tangarife-Castaño, Verónica, Roa-Linares, Vicky, Miguel del Corral, José Ma, Mesa-Arango, Ana C, Betancur-Galvis, Liliana, Francesch, Andrés M, San Feliciano, Arturo
• Format: Journal Article
• Language: English
• Published: 04.12.2014
• ISSN: 2046-2069
• DOI: 10.1039/c4ra11726c

Several terpenylquinones derived from 1,4-anthracenedione (1,4-anthracenequinone, AQ) have been prepared by addition or substitution nucleophilic reactions and further transformed into extended polycyclic systems, which mainly kept the 1,4-quinone moiety fused to different nitrogen-heterocyclic rings (pyrrole, imidazole, pyrazine or quinoxaline) into the structure. The compounds synthesized were evaluated for their antineoplastic, antifungal and antiviral activities. GI 50 antineoplastic values remained under μM levels for AQs, while the heterocyclic derivatives showed antifungal MIC values in the low μg mL −1 range against yeasts and filamentous fungi. Only few compounds displayed a discrete non-selective antiherpetic activity in the μg mL −1 range. New 1,4-anthracenediones bearing fused-heterocycle rings were synthesized and evaluated as cytotoxics, antifungals and antivirals. Some of them showed GI 50 at the μM level.