title: Library of 1,4-disubstituted 1,2,3-triazole analogs of oxazolidinone RNA-binding agents.
abstract: The design and synthesis of small molecules that target RNA is immensely important in antibacterial therapy. We had previously reported on the RNA binding of a series of 4,5-disubstituted 2-oxazolidinones that bind to a highly conserved bulge region of bacterial RNA. This biological target T box antitermination system, which is found mainly in Gram-positive bacteria, regulates the expression of several amino acid related genes. In an effort to amplify our library, we have prepared a library of 1,4-disubstituted 1,2,3-triazole analogs that entails an isosteric replacement of the oxazolidinone nucleus. The synthesis of the new analogs was enhanced via copper(I) catalysis of an azide and alkyne cycloaddition reaction. A total of 108 1,4-disubstituted 1,2,3-triazole compounds have been prepared. All compounds were evaluated as RNA binding agents.
authors.affiliation: Department of Chemistry and Biochemistry, Ohio University, Athens, Ohio 45701, USA.
authors.forename: George
authors.initials: G
authors.lastname: Acquaah-Harrison
authors.forename: Shu
authors.initials: S
authors.lastname: Zhou
authors.forename: Jennifer V
authors.initials: JV
authors.lastname: Hines
authors.forename: Stephen C
authors.initials: SC
authors.lastname: Bergmeier
mesh_terms: D000900:Anti-Bacterial Agents / Q000138:chemical synthesis / Q000737:chemistry / Q000494:pharmacology*; D001665:Binding Sites; D020650:Combinatorial Chemistry Techniques; D018360:Crystallography, X-Ray; D015195:Drug Design; D006094:Gram-Positive Bacteria / Q000187:drug effects; D008958:Models, Molecular; D015394:Molecular Structure; D023303:Oxazolidinones / Q000138:chemical synthesis / Q000737:chemistry / Q000494:pharmacology*; D012329:RNA, Bacterial / Q000737:chemistry / Q000187:drug effects*; D054852:Small Molecule Libraries; D013237:Stereoisomerism; D014230:Triazoles / Q000138:chemical synthesis / Q000737:chemistry / Q000494:pharmacology*
chemical_list: D000900:Anti-Bacterial Agents; D023303:Oxazolidinones; D012329:RNA, Bacterial; D054852:Small Molecule Libraries; D014230:Triazoles