Synthesis and toxicity of substituted-1,4-naphthoquinones

Nancy Elvira Martinez Rey, University of Texas at El Paso


Naphthoquinones and their derivatives have been identified to have a broad range of biological activity. Recently, we reported the synthesis of solid-supported Fischer carbenes and their microwave-assisted Dötz benzannulation reaction producing substituted-1,4-naphthoquinones in moderate to good yields; however, this reaction is highly regioselective for the 5-substituted-1,4-naphthoquinones and limits a thorough investigation of the steric and electronic factors. In order to increase diversity and functionality around the naphthoquinone core we have utilized microwave-assisted transition metal catalyzed Miyaura-Suzuki cross-coupling reactions to synthesize 2,5-disubstituted-1,4-naphthoquinones in moderate to good yields. This novel methodology employs the use of solid supported reagents and scavengers to increase the production of the naphthoquinones with a simple purification process. The optimization and the synthesis of the small library of 2-substituted-1,4-naphthoquinones is obtained. The Suzuki cross coupling reaction was not successful when utilizing 5-acetoxy-2-halide-1,4-naphthoquinones. Furthermore, the viability study of 2,5-disubstituted-1,4-naphthoquinones has demonstrated that the toxicity of the naphthoquinone moiety is modified by changing the functional groups and the mechanisms of cell death is yet to be established.

Subject Area

Cellular biology|Organic chemistry

Recommended Citation

Martinez Rey, Nancy Elvira, "Synthesis and toxicity of substituted-1,4-naphthoquinones" (2008). ETD Collection for University of Texas, El Paso. AAI1456755.