title: Parallel synthesis of a library of symmetrically- and dissymmetrically-disubstituted imidazole-4,5-dicarboxamides bearing amino acid esters.
abstract: The imidazole-4,5-dicarboxylic acid scaffold is readily derivatized with amino acid esters to afford symmetrically- and dissymmetrically-disubstituted imidazole-4,5-dicarboxamides with intramolecularly hydrogen bonded conformations that predispose the presentation of amino acid pharmacophores. In this work, a total of 45 imidazole-4,5-dicarboxamides bearing amino acid esters were prepared by parallel synthesis. The library members were purified by column chromatography on silica gel and the purified compounds characterized by LC-MS with LC detection at 214 nm. A selection of the final compounds was also analyzed by (1)H-NMR spectroscopy. The analytically pure final products have been submitted to the Molecular Library Small Molecule Repository (MLSMR) for screening in the Molecular Library Screening Center Network (MLSCN) as part of the NIH Roadmap.
authors.affiliation: Department of Chemistry and Biochemistry, The University of Tulsa, 800 South Tucker Drive, Tulsa, OK 74104, USA. rosannasolinas@yahoo.it
authors.forename: Rosanna
authors.initials: R
authors.lastname: Solinas
authors.forename: John C
authors.initials: JC
authors.lastname: DiCesare
authors.forename: Paul W
authors.initials: PW
authors.lastname: Baures
mesh_terms: D000577:Amides / Q000138:chemical synthesis / Q000737:chemistry; D000596:Amino Acids / Q000737:chemistry*; D002853:Chromatography, Liquid / Q000379:methods; D020650:Combinatorial Chemistry Techniques; D015195:Drug Design; D004952:Esters / Q000737:chemistry*; D006860:Hydrogen Bonding; D007093:Imidazoles / Q000138:chemical synthesis / Q000737:chemistry; D013058:Mass Spectrometry / Q000379:methods; D015394:Molecular Structure; D019906:Nuclear Magnetic Resonance, Biomolecular
chemical_list: D000577:Amides; D000596:Amino Acids; D004952:Esters; D007093:Imidazoles