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

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 ring...

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Bibliographic Details
Published in:RSC advances 2015-01, Vol.5 (2), p.1244-1261
Main Authors: Castro, MaAngeles, Gamito, Ana Ma, Tangarife-Castano, Veronica, Roa-Linares, Vicky, Miguel del Corral, Jose Ma, Mesa-Arango, Ana C, Betancur-Galvis, Liliana, Francesch, Andres M, San Feliciano, Arturo
Format: Article
Language:English
Subjects:
Biological
Derivatives
Fungi
Imidazole
Pyrazines
Pyrroles
Quinoxalines
Synthesis
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Summary: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 sub(50) antineoplastic values remained under mu M levels for AQs, while the heterocyclic derivatives showed antifungal MIC values in the low mu g mL super(-1) range against yeasts and filamentous fungi. Only few compounds displayed a discrete non-selective antiherpetic activity in the mu g mL super(-1) range.
ISSN:2046-2069
2046-2069
DOI:10.1039/c4ra11726c