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Parallel Synthesis of an Imidazole-4,5-dicarboxamide Library Bearing Amino Acid Esters and Alkanamines
Department of Chemistry and Biochemistry, The University of Tulsa, 800 South Tucker Drive, Tulsa, OK 74104, USA
* Author to whom correspondence should be addressed.
Received: 20 November 2008; in revised form: 11 December 2008 / Accepted: 12 December 2008 / Published: 15 December 2008
Abstract: The imidazole-4,5-dicarboxylic acid scaffold is readily derivatized with amino acid esters and alkanamines to afford compounds with intramolecularly hydrogen bonded conformations that mimic substituted purines and therefore are hypothesized to be potential inhibitors of kinases through competitive binding to the ATP site. In this work, a total of 126 dissymmetrically disubstituted imidazole-4,5-dicarboxamides with amino acid ester and alkanamide substituents 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
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MDPI and ACS Style
Solinas, R.; DiCesare, J.C.; Baures, P.W. Parallel Synthesis of an Imidazole-4,5-dicarboxamide Library Bearing Amino Acid Esters and Alkanamines. Molecules 2008, 13, 3149-3170.
Solinas R, DiCesare JC, Baures PW. Parallel Synthesis of an Imidazole-4,5-dicarboxamide Library Bearing Amino Acid Esters and Alkanamines. Molecules. 2008; 13(12):3149-3170.
Solinas, Rosanna; DiCesare, John C.; Baures, Paul W. 2008. "Parallel Synthesis of an Imidazole-4,5-dicarboxamide Library Bearing Amino Acid Esters and Alkanamines." Molecules 13, no. 12: 3149-3170.