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Natural-Product Hybrids: Design, Synthesis, and Biological Evaluation of Quinone-Annonaceous Acetogenins
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2000
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Combinatorial ChemistryEngineeringQuinone SubunitOrganic ChemistryDiversity Oriented SynthesisBiosynthesisBiochemistryNadh Ubiquinone OxidoreductaseDiversity-oriented SynthesisPharmacologyNatural Product SynthesisNatural-product HybridsEnantioselective SynthesisBiomolecular EngineeringNatural SciencesMitochondrial MembranesSynthetic BiologySynthetic ChemistryDrug Discovery
Replacement of the butyrolactone unit of the natural products with a quinone subunit has resulted in the synthesis of natural-product hybrids of quinone–mucocin (1). These compounds, which are combined from partial structures of annonaceous acetogenins and ubiquinone, are very potent inhibitors of complex I (an NADH ubiquinone oxidoreductase) from mitochondrial membranes.