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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
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Molecules 2008, 13(12), 3149-3170; https://doi.org/10.3390/molecules13123149
Received: 20 November 2008 / Revised: 11 December 2008 / Accepted: 12 December 2008 / Published: 15 December 2008
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. View Full-Text
Keywords: Imidazole; NIH Roadmap; Heterocyclic scaffold; Drug discovery Imidazole; NIH Roadmap; Heterocyclic scaffold; Drug discovery
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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.

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