Organic Letters · 2003 · 37 citations · 18 references
PharmacyMedicinal ChemistryPharmacologyDrug DesignDrug DiscoverySynthetic Medicinal ChemistryAmino Acid ChemistryAntibacterial AgentsAntibacterial PharmacologyAntimicrobial PeptidesPeptide ChemistryPeptide Drug DiscoveryNovel Antibacterial AgentsPeptide ConjugatesPeptide Medicinal ChemistryPeptide-drug ConjugatesQuinoline ChemistryQuinoline SynthesisSolid-phase Organic SynthesisSolid-phase Peptide Synthesis
[reaction: see text] A synthesis of 4,8-disubstituted 2-phenylquinoline amino acids is reported with the incorporation of one example into a peptide by solid-phase synthesis. The phenylquinoline-containing peptide binds an RNA target with nanomolar affinity (K(D) = 208 nM). The strategy can be used to prepare a variety of 2-substituted quinoline amino acids for alteration of affinity in intercalator peptides. Since quinolones represent an important class of antibacterials, these compounds may be useful in the discovery of new antibacterial agents.
18