Parallel synthesis of a library of symmetrically- and dissymmetrically- disubstituted imidazole-4,5-dicarboxamides bearing amino acid esters

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

Research output: Contribution to journalArticlepeer-review

7 Scopus citations
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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.

Original languageEnglish
Pages (from-to)352-363
Number of pages12
JournalMolecules
Volume14
Issue number1
DOIs
StatePublished - Jan 2009

Scopus Subject Areas

  • Analytical Chemistry
  • Chemistry (miscellaneous)
  • Molecular Medicine
  • Pharmaceutical Science
  • Drug Discovery
  • Physical and Theoretical Chemistry
  • Organic Chemistry

Keywords

  • Drug discovery
  • Heterocyclic scaffold
  • Imidazole
  • NIH roadmap

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