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Parallel Synthesis of a Library of Symmetrically- and Dissymmetrically-disubstituted Imidazole-4,5-dicarboxamides Bearing Amino Acid Esters

Department of Chemistry and Biochemistry, The University of Tulsa, 800 South Tucker Drive, Tulsa, Oklahoma, USA
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Molecules 2009, 14(1), 352-363; https://doi.org/10.3390/molecules14010352
Received: 20 November 2008 / Revised: 7 January 2009 / Accepted: 12 January 2009 / Published: 13 January 2009
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 1H-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. View Full-Text
Keywords: Imidazole; NIH Roadmap; Heterocyclic scaffold; Drug discovery Imidazole; NIH Roadmap; Heterocyclic scaffold; Drug discovery
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MDPI and ACS Style

Solinas, R.; DiCesare, J.C.; Baures, P.W. Parallel Synthesis of a Library of Symmetrically- and Dissymmetrically-disubstituted Imidazole-4,5-dicarboxamides Bearing Amino Acid Esters. Molecules 2009, 14, 352-363. https://doi.org/10.3390/molecules14010352

AMA Style

Solinas R, DiCesare JC, Baures PW. Parallel Synthesis of a Library of Symmetrically- and Dissymmetrically-disubstituted Imidazole-4,5-dicarboxamides Bearing Amino Acid Esters. Molecules. 2009; 14(1):352-363. https://doi.org/10.3390/molecules14010352

Chicago/Turabian Style

Solinas, Rosanna, John C. DiCesare, and Paul W. Baures. 2009. "Parallel Synthesis of a Library of Symmetrically- and Dissymmetrically-disubstituted Imidazole-4,5-dicarboxamides Bearing Amino Acid Esters" Molecules 14, no. 1: 352-363. https://doi.org/10.3390/molecules14010352

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