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