New 1,4-anthracenedione derivatives with fused heterocyclic rings: synthesis and biological evaluation

Abstract

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. GI₅₀ 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.