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

doi:10.3390/molecules14010352

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Molecules 2009, 14(1), 352-363; doi:10.3390/molecules14010352

Article

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

Rosanna Solinas, John C. DiCesare and Paul W. Baures*

Department of Chemistry and Biochemistry, The University of Tulsa, 800 South Tucker Drive, Tulsa, Oklahoma, USA

* Author to whom correspondence should be addressed.

Received: 20 November 2008; in revised form: 7 January 2009 / Accepted: 12 January 2009 / Published: 13 January 2009

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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 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.

Keywords: Imidazole; NIH Roadmap; Heterocyclic scaffold; Drug discovery

Supplementary Files

Supplementary File 1:
Supporting Information: Tables S1-S2, Figures S1-S26 (PDF, 4691 KB)
Supplementary File 2:
Supporting Information: Figures S27-S46 (PDF, 4640 KB)
Supplementary File 3:
Supporting Information: Figures S47-S80 (PDF, 6202 KB)

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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.

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.

Chicago/Turabian Style

Solinas, Rosanna; DiCesare, John C.; Baures, Paul W. 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.

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